Chapters View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
The Wicked Witch of The School(Principal Cinch)
It was a quiet monday after you got done with lunch. You typically don’t eat much and would spend the rest of the lunch period outside drinking a water, minding your own business while listening to your Black Sabbath playlist. While doing your routine of post-lunch relaxation, you began to reflect on what happened last friday. Losing your virginity and with the hot-as-hell dean of the school, you smile with a smug sense of accomplishment that you finally became a real man. Sadly, you couldn’t brag about it because shagging with staff is a taboo, despite you being 18 and the one who initiated the whole thing. It’ll have to be a secret between you and Cadence… or so you hope.
As you were jamming to Paranoid, you saw your friend Ignacio approaching, trying to speak to you but you couldn’t hear a single word because of how loud you had the volume. After a bit of seeing him gesturing you to remove your earbuds, you do so and finally heard what he was saying.
“Yo Calc, what happened yesterday?” Ignacio asked with a puzzled look. “I tried calling you after I got home but you never answered.” You trust Ignacio like a brother, but he has a tendency to be a bit of a blabbermouth. One hint of your affair with Dean Cadence last week and he’ll possibly blab about it, getting you and Cadence into trouble. So, you had to play it cool and tell your half-true cover story.
“I… was busy getting my stuff packed to go when Dean Cadence caught me just as I was about to leave.” You saw Ignacio giving a look of surprise. “I explained my case and she decided to give me a detention rather than suspending me. Also, my phone was outta juice and I couldn’t find an outlet anywhere. I do apologize.” Then and there, Ignacio gave you a neutral look, leaving you uncertain at first whether or not he bought your story. Then, his face switched to that of one that says “Eh, Alright.”, relieving you of your worries... for now.
“So, what was it you wanted to tell me about last week?”
“Well Calc, we have that thing today at the football field. They already brought the water balloons and whatnot. We're just waiting on you now.” Since the seniors were set to graduate in a month, Dean Cadence has authorized them to have a day where they can engage in whatever activity that's school appropriate. Since a good ol’ fashioned water balloon fight was harmless, they were given permission to do so as long as it doesn't get out of hand.
“Ok let's go. We better hope the wicked witch of the school doesn't kill us over this.” You remarked.
“Eh, who gives a shit.” Words like that would do little against Principal Cinch’s wrath, should it ever be invoked. Many of the students of the school liken her to a drill sergeant, only more calculating and cold hearted. She cares more for her reputation and that of the school's than the personal happiness of the students, running it like a tight ship. Students would do well to not piss her off lest they suffer a horrid punishment only she could devise.
After a few minutes walking, you and Ignacio reached the green football field where two groups of senior students were ready for one hell of a moment in their senior year. Once you were with your group, you grab an armful of water grenades and stood with your teammates, ready for battle. As you eagerly waited of the cue, Ignacio walked to the front, pointing his open hand at the opposing team before yelling:
“Attaaaaaaccckk!” Then, as if it were from a play rehearsal, both sides threw their water balloons toward each other, drenching each other in a hailstorm of water and rubber. Splat after splat, the area around the football field became filled with a symphony of water splashing, laughing and swearing. You threw balloon after balloon, managing to hit a few as they threw a several in your direction, only managing to get your legs as you evaded their assault. Then, you locked eyes with the leader of the enemy team, an opportunity to get them where it hurts. You take your last big water bomb and took aim before throwing with glee unbound.
“Stick this up your pipe and smoke it.” You muttered as you turned to your comrades, jumping and cheering with glee as you heard a loud splat.
“HELL YEAH! WHO'S YOUR DADDY?! HUH? WHO'S YOUR DADDY?!” Your cheers were stopped by the progressive shocked expression being directed towards you. You looked at them with a confused expression as you wondered what has them scared. “What? Do I have something on my face?”
They nodded no, still keeping their fearful expressions.
“Is there someone behind me?”
They nodded yes.
“Does that person look angry?”
They nodded yes once again. However, one of your teammates managed to break the silence and said “Turn around.”.
Obliging his request, you slowly turned your body around and come face to face with something you hoped never to see. Standing before you was Principal Cinch herself, hands on her hips, drenched in water, and angry with the fury of 100 wound up pitbull terriers, held back only by her sheer willpower. This was the last thing you wanted to do, especially to her. You could run but knowing how angry she was, she would grab your shirt collar before you could move a single leg muscle. The pure experience of fear kept you in place and even your facial expression didn’t change at all, even as you try to say something.
“Well… fuck.” That was all you could mutter before Cinch grabbed you by your wrist and looked at you with the meanest expression imaginable.
“You... are in a lot of trouble, mister.” She snarled as she dragged you with her back towards the main building while Ignacio and the rest of the seniors looked on with worry.
“Well… there he goes, the end of the road.” Ignacio whispered as he saw you getting dragged off by Principal Cinch. As you were being dragged through the halls of CPA, you were momentarily distracted from your fear by a sight that you didn’t expect but nonetheless mesmerizing. As Cinch was leading you to your office, you couldn’t help but notice her giving her hips some noticeable sway as she walked, making her firm yet thick rear hypnotizing with every bounce. You didn’t expect this from someone who was noticeably older than Dean Cadence. It was amazing to you that someone at the age of 40 kept her form so perky yet graceful. Just the mere thought and sight of her jiggling made one thought dance in your mind:
“Dat Ass!”
… complete with a developing boner. Staring briefly down in horror, you had focus all your energy towards stopping your half-chub from developing into a full-on hard-on, fearing what Cinch would do if she were to find out. You were able to stop it... for now. After a few more minutes of walking, you arrived at her office and she gets you to sit on the chair in front of her desk, briefly walking behind you to shut the blinds on the door, locking it, and flipping the sign to say “Busy”. After shutting the window blinds and dimming the lights, she walks in front of you with a slightly less angry frown.
“Now Mr. Calculus,” Cinch started with her usual authoritative tone. “ I’m very disappointed in you. The behavior you exhibited was completely unbecoming of what is expected of all students and the reputation that this school is known for.”
“I’m sorry, ma’am.” You said softly. “We were given permission to do this. We’re going to clean up afterwards.”
“NO EXCUSES!” Cinch snapped at you, stopping your train of thought. “Now, because of your stunt, I have to change my soaking attire. When I get back, I’ll have your punishment decided.” Just like that, she left for the other room, leaving you to ponder in fear of what will become of you. As you did, you got up and stared out through the window, fearing the worst case scenario of suspension. Being suspended meant you had to answer to your parent to which they’ll chew you out so hard that your ears would be ringing for months. Standing and sighing, you failed to notice the door to the other room creaking open.
“I thought I told you to stay put, you naughty deviant.” You had little time to process what you just heard before you felt a soft, squishy presence against your back while a pair of hands slowly rub all over your chest. “You should know by now that rebellious students turn me on and when I get turned on, I can get uncontrollably... horny.” The sound of the voice was unmistakable. Principal Cinch was fondling your chest as she took a whiff of your musky scent, moaning in ecstasy. Looking in the mirror next to you, you saw that she was in nothing but her bra and panties. You were caught completely off guard, never expecting this to happen, save for a phone call to your parents. However, you managed to get the courage to jump out of your speechless state and ask her why.
“W-w-what are you d-doing?” You stuttered
“I've heard that you have quite the body for sensual pleasure.” Cinch moaned as she sunk one hand down towards your crotch, cupping your erection in her hand. “I just had to try it for myself.” The sensation was overwhelming, slow yet arousing, like she had the most sexual experience out of all the staff in CPA.
“What?! H-h-how?!” You wondered how she knew of your performance with Cadence since she made such a statement. You began to ponder if somehow Ignacio might've caught wind of it or something else you didn't count on. Then, she brought her mouth close to your ear and whispered:
“Just because Cadence and I are co-workers doesn't mean we never talk outside of school. Why, me and her are good friends and she talked to me Sunday night about how you ravaged her senseless. Just thinking about every detail she told me is enough to make me feel wet down there.” Just as she kissed the nape of your neck, she undid your belt and zipper, pulling down your jeans and underwear, allowing your member to stand free and uncovered.
“Hmmm, quite the tool you have there.” Cinch purred as she rubbed her sizeable breasts against your back, gripping your bare cock in her hand. You were speechless as to how she was so good as she slowly yet sensually stroked the length of your penis. But, you were more speechless to the fact that Cadence was the one who told Cinch about your experience with her and now she wanted a piece of what’s between your legs. While the handjob was not as fast paced as your masturbation sessions, you still felt the same rate of pressure buildup. The kissing of your neck, the rubbing of her breasts on your back, and the handjob she was giving you is indicative of her having been with someone in the past and she knew how to please him in this way. As you feel the pressure build up in your crotch, it took all of your willpower not to cum early. You wanted to impress her since you were getting laid with her. Sadly, your capacity to withstand those urges eventually wore out when she bit your neck, sending shivers down your spine and to your crotch.
“Oh god, holy shit!” You grunted as you orgasmed, sending rope upon rope of your hot seed at the wall in front of you. You’ve never felt this good when you usually jack off but that… that was heaven. As you became lost in your post orgasmic bliss, you were turned around by Principal Cinch to see that her lacy bra and panties were on the floor behind her revealing her mature yet perky naked form to you. You were amazed that some woman at the age of forty was able to keep a body that luscious. She had mostly shaven pussy, her breast size is more than the average bust size of the female students but not as big as Cadence’s, and her ass… HER ASS was a sight to behold. It was pretty big but not too big, the right size for a booty.
“I honestly don’t think it’s fair if I’m the only one who’s nude.” You were too quick to notice when she, with one careful maneuver, quickly removed your shirt. “And your shoes and pants too, student.” Complying with her orders, you kicked of the aforementioned clothing leaving nothing on and letting your erection develop once more as Cinch embraced you with your respective nether parts touching, filling you with so much pleasure.
“Cadence told me how good of a kisser you are. Please, do prove it.” Just as you about to let a word out, you principal plants her lips on yours, invading your mouth with her tongue. Just like with Cadence, as Cinch opened her mouth, you invaded her's with your own tongue, pressing your body further against her as your shaft came into contact with her moist, wet nether lips. You enjoyed every moment of the kiss as she walked the both of you to her chair and seating you on it. For a time, you became lost in the kiss’s rapturous feeling before Cinch broke it to get some air.
“Hmmm, I wonder how it tastes.” Cinch breathly moaned as she stared hungrily at your raging boner, licking her lips. “How about I have a little taste.” Just then, she snaked her moist tongue along the length of your member, slowly and methodically. You were paralyzed at the sensation of receiving quit a blowjob, especially from the principal of all people. Normally in a normal fantasy such as this, one would imagine ploughing some hot language teacher but this takes it a level beyond. Here you were, sitting naked on the principal's chair, receiving a blowjob from the head of state of this school. Still reeling from the handy that she gave you, you've built up an improved endurance, ready for what she has in store for you. Just as she gave your tip a playful flick with her tongue, she began to take the entirety of your length into her mouth. For a moment, you could’ve sworn that your eyes rolled into the back of your head as she began bobbing her head up and down your shaft.
“Oh fuck, this is amazing.” You grunted as Principal Cinch kept on giving you head. As you tried to lean up, you were met with a quick palm to your face, sending you back into the chair. Taking time to process what she did, you came to a realization: she likes to be the one in charge during sex. You immediately realize that she’s a person that respects strength and authority. To get the upper hand and be the assertive one would bring her pleasure unbound.
However, your presser was soon built pass the threshold that you could tolerate and you soon climaxed in your principal’s mouth. Spurt after spurt of your cum went down Cinch’s throat as she took the whole of your cock into her mouth, desiring to enjoy every last drop of your seed. After a minute of shooting your load, you began to reel from your orgasm as Principal Cinch brought you to the floor, straddling your waist.
“Relax, just enjoy it. That’s an order, student.” As she purred her command, her lower lips made contact with the tip of your spear, almost sending you unto bliss. “Just for that balloon, I’ll be the one on top. If you aimed it somewhere else, things would’ve been different.” Then, you felt her inner walls swallow your pride as she impaled herself on it. Just like with last friday, your dick went deeper and deeper into her tunnel until it poked at the cervical wall, eliciting a pleasured scream from the domineering principal. After catching her breath from the shock, Cinch began hop up and down your shaft. You enjoyed every minute of her ministrations as she continued to bounce and bounce as her tits and ass jiggled with every movement. It was hypnotic for sure but one thought still lingered on your mind. You wanted to take charge... to impress her. You just had to wait for an opportunity to present itself.
Then, it came as Cinch lowered herself onto you where both your chests were touching. She was still gyrating her hips, holding your face in her hands and leaving your arms free. There it was, the opportunity that you’ve waited for. You brought your mouth to her ears and whispered seductively:
“Hey, you wanna hear something naughty?”
“Oh yes, student. What is it?” She moaned. Thinking really quick, you thought of a cool sounding quote from a video game you enjoyed playing.
“Well… Power shifts more quickly than some people think.” Without an extra whisper, you quickly wrapped your arms around her back and roll over, making you the one on top. Cinch was quite surprised to say the least. “Now, you’ve had your fun. It’s my turn now.”
“My word, I’ve never expected this to happen.” Cinch gasped in reply.
“Well, you could’ve never anticipated what I’m about to do to you… Dear.” There, you began plunging and thrusting into her puffy wet caverns. Anticipating that she’ll try to regain her dominance, you hold her arms down by the wrists as you thrust roughly with all the might you could muster while trying to endure as long as possible. Surprisingly, Cinch wrapped her legs around your waist and made no moves to regain her dominance. Come to think of it, the look on her face tells you that she enjoys being rutted that way.
“OH YES!” Cinch yelled with a lustful, hoarse sounding voice. “KEEP FUCKING ME LIKE THIS! PAINT MY WALLS WHITE WITH YOUR CUM!” You kept thrusting and thrusting your cock into her moist love tunnel as much and as long as your stamina permitted, reveling in every moment her inner walls tighten around your member as her orgasm draws near. With a few more pumps, Principal Cinch let out a pleasured yelp as she coats your crotch with her juices, further clamping your dick with in her walls. With a few more thrusts, combined with the wet tightness around your shaft, you blew your entire load into her womb.
“HOLY JESUS, OH FUCK!” You grunted as you blew load after load of your cum into her pussy as her walls milked you for every drop of your seed in your balls. Over the course a minute, you completely emptied every ounce of your cum into her and your orgasm died down, collapsing on to the floor next to the principal you just banged with puddles of ladycum and seed around you both.
“My word,” Cinch said as she cuddles up to you, tracing a finger around your chest. “ It’s been quite a long time since I was satisfied that much. I suppose I have to thank you for this, Calculus.” Still exhausted and in your post-orgasmic bliss, you could only let out a soft and breathy:
“You’re welcome.” As you began to recover, you began to put your clothes back on as Cinch did the same. Her backup attire was a pair of some denim shorts with a Jimi Hendrix t-shirt. You were honestly surprised she had a thing for rock and roll, thinking that a usually uptight person like her would prefer orchestral music. Just as you got your shoes back on, Principal Cinch hands you a slip for a week of detention for every lunch period you had, taking you by surprise.
“What?!” You gasped in shock.
“Don’t worry, it’s only for a week. We’ve got to have a cover so no one finds out about this.” After hearing her explanation, you began to shake your head in agreement. It was a solid cover, so hopefully nobody would suspect anything, save for your friend Ignacio.
“Well now, run along. And remember, we might run into each other again.” With a sultry look, Principal Cinch excused you from her office. Walking towards your locker, you put the detention slip in your pocket and did the combination lock, opening your locker.
“So, how bad was she?” Nearly bumping your head, you turn around to see Ignacio behind you.
“Not really, I told her that I was the one that organized it. Apparently, she appreciates honesty.” You cautiously explained.
“What did she give ya?”
“A weeks detention for my lunch periods.” You calmly stated, hoping your explanation would hold water to him.
“Rrrriiiiggghht.” Ignacio sarcastically quipped. You knew then he suspected something but you hoped he didn’t know of your exploits. As far as you know, you had ‘reasonable’ conversations that narrowly avoided a suspension. There was one upside to it: you never have to tell your parents about your detentions, knowing how they can get. “Anyways, I’ll be off. I’ll see ya next week.”
“Alright. See you then.” As you walked to your car, thoughts of the two MILFs you banged recently made your pride and ego soar through the roof. But, another thought got you as well. Are all these MILFs somehow connected in some way where every MILF talks to one another? You thought about it but immediately cast all those aside and focused on the fact that you got laid for the second week in a row.
“Damn, that’s one hell of an accomplishment.”
Author's Note
Well, here's the 2nd chapter with more to come. I'm really amazed at how well this story blew up from just the 1st chapter alone. That's what keeps me going. Thank you all for the good reception.
P.S.: Try to find a hidden reference in the dialogue.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Naughty, Naughty Teacher(Cheerilee)
“Can’t believe it, Just a few more weeks until I’m outta here for good!” You thought to yourself as you roamed the halls of Crystal Prep towards your next class. Reflecting on the events of the past weeks, You didn’t find it odd that Cadence and Cinch talk to each other outside of school. However, you found it odd that Cadence spoke of your little “affair” with her to Cinch. It made you think of a lot of things but you never put any real consideration towards either possibility. All that mattered to you was getting this last class done for the day. Since there was no school for Thursday and Friday, you took great relief in knowing that it was a half week. “Well, here it is, the last class. I hope my review checks out.”
Your final class for the day was literature, one class you actually liked. When you weren’t out and about or with the swim team, you plunged your nose into many Sci-Fi novels. The most recent one you finished was Starship Troopers by Robert Heinlein. You enjoyed the book and how it explored its themes from the protagonist’s point of view. Your last major project was to read any fictional book and give an oral review of it in front of the class while discussing the themes and your opinions about it.
Normally, your class today would be taught by Ms. Ruby Jubilee but it wasn’t the case for the past two weeks. Despite the events surrounding the Friendship Games last year, Canterlot High and Crystal Prep managed to improve relations between them. As an addition to improved relations, both schools implemented a teacher exchange program where if one teacher was incapacitated, which was the case for Ruby Jubilee due to a broken leg, they would be subbed by another teacher from either school. In place of Ms. Jubilee, your class was being taught by Mrs. Cheerilee.
“Good afternoon, Calculus!” Cheerilee sang as you entered the room. “How are you today?”
“I’m doing alright.” You replied. “ Just Nervous about today’s presentation, that’s all.”
“Don’t be. I’m sure you’ll do fine. Just take a seat, relax and wait for class to start.” Taking her advice, you sat at your usual desk in the middle row. As you got situated, you grabbed your presentation papers and mentally read the entire five page presentation, word by word, paragraph by paragraph. As you read through the entire thing, your eyes began to drift to a sight that wasn’t the papers. It was Mrs. Cheerilee drawing a farewell message on the chalkboard because it was her last day subbing for that class. As she drew out her heartfelt message, you saw her voluptuous rump in full view with a slight peek of her magenta panties.
How you would describe Mrs. Cheerilee from the weeks she subbed for your class left you flabbergasted. She looked to be around Dean Cadence’s age but slightly shorter than her. She was dressed in a nice dress shirt and vest with a green knee-length skirt. As before, her beautifully big rump is something to take one’s glance away for being big while not being too big, the perfect size. The way she had her hair styled, her posture, that enticingly melodic voice of hers would make one thing they’re being seduced by a succubus. It sometimes made you wonder if she had aspirations for becoming a singer. Fortunately, she wasn’t a mean spirit by any means. She always helped you with any assignments you got stuck on, always carrying herself throughout the day with her cheerful disposition. As you felt your erection get hard from the sight, you would normally feel embarrassed and would race to cover your pitched tent. However, you didn’t pay much mind to it. It certainly felt strange to not freak out over getting a boner over such a view. You thought of many reasons but the only one you felt that fit the bill perfectly was your previous sexcapades with the school’s Dean and Principal desensitized you to such a situation.
Snapping you out of your train of thought was the arrival of the other students. One by one, they all poured into the classroom, papers in hand, ready to give their honest review of their favorite novels. After everyone had entered the classroom and attendance was taken, Cheerilee gave her spiel reminding everyone about today’s assignment and a short speech thanking the whole class for being good students. Once all that was said and done, she called up students to the front of the room to give their oral review. One by one, each of your classmates gave their thoughts about the books they’ve read. One review that you thought was interesting was Twilight Sparkle’s review and discussion of Larry Niven’s Ringworld. As time went by while you were waiting for your turn, a vision snapped into your mind’s view.
It was a daydream of You and Cheerilee, on the floor, naked, and furiously making out while you fondled her CC-cupped breasts. Each vision of every kiss, tit massage, and grinding your erect shaft against her wet flower made your pants feel tighter as your boner starts to pitch its tent. As your daydream dragged on, you began to hear a voice get louder and louder before it jolted you from your wet dream. You saw Cheerilee looking at you with a slightly frustrated expression.
“Calculus, It’s your turn.” Cheerilee said. Your eyes jolted from side to side, seeing the entire class glare at you. As you got up from your desk, you noticed that your penis is still erect, making a slightly noticeable bulge in your pants. At that point, you ceased giving a damn and walked to the front of the class with your covered member constricted by your jeans. Clearing your throat and sitting at the podium., you began to read through your five page review while keeping a calm demeanor. The only visual cue of your nervousness were a few beads of sweat dripping down your head.
“...and that’s why I think Starship Troopers is a good book for any fan of sci-fi, regardless of what they’ll think of the political undertones of the story.” After you handed your packet off to Cheerilee, the class gave the usual round of applause they gave to everyone else while you walked back to your desk. Hearing the end of school bell ring, the students began to walk out with their backpacks in tow. You prepared to walk out when you heard a feminine voice callout to you.
“Calculus, can I see you after class?” Not wanting to dig yourself a deeper hole, you obliged her request as she watched the last of the students leave from her, sitting back down at your seat. You had no clue as to what she wanted with you. Did she want to talk to you about your assignment? Did she want to read you the riot act about your daydreaming episode? Either possibility made you quake slightly in your seat. Nevertheless, you kept a stiff upper lip to the best of your abilities. Deciding to break the silence, you decided to ask her the question.
“Mrs. Cheerilee, why are you keeping me behind? Was it something I did? My assignment?”
“Well, no.” Cheerilee answered with an increasing hitch in her voice. “You did good on your assignment. I wanted to talk to about you slee-ping in class again. This was the third time I-I-I caught you doing it. W-W-Was it because you aren’t getting enough sleep?” You always had a good night’s sleep. All you did was let your mind drifted towards thoughts you never wanted to reveal.
“Uhhh, no.” You nervously responded. “I just let my mind wander off, that’s all”
“Well… *eeep* You should be more ffffocused next time. I k-kept you h-here so we could sort this thing out.” There she was, like shark to blood in the water, she was on to you. But, due to your previous escapades with Cadence and Cinch, you’ve gotten used to the thought of some cougar wanting to pounce on you. Though she wasn’t readily implying it, you mentally and physically prepared yourself for that outcome. Cheerilee stood up and walked to the door, locking it and closed its blinds before dimming the lights. Then, she walked towards you with a rather seductive sway in her hips and sat on top of the desk in front of yours.
“I believe our little… one on one conversation can remedy this.” Cheerilee said with bedroom eyes. Then, it happened, the one thing to make your shaft hard as granite. Cheerilee opened her legs, revealing her magenta colored panties. It was the same tantalizing sight as before but something else caught your eyes. There was a dark spot down the middle of the clothing with a barely visible stream of wetness running down her thighs. It was an all too familiar sight for you as told you she was incredibly aroused. Even the musky scent had hit your nose with the force of a backhand. You knew how this was going to end: sex… sex as always.
“Come closer, Calculus.” Cheerilee said with a sultry tone. “I know you want to.” With a smooch on the air, she broke your hesitation. Without another thought crossing your mind, you got up and rushed to her, wrapping your arms around her back and ass, delivering a passionate kiss upon her lips. This kiss wasn’t fueled by lust but frustration from the project you did. For an entire week, you wrote a page, feeling worried that you might not get a good grade. Now, you channeled your frustration to your sex drive and began furiously making out with your substitute teacher. You broke the kiss to allow the both of you the breathe.
“H-How are you this good?” Cheerilee stuttered, catching her breath.
“Wanna know a secret?” You asked to which she nodded. Slowly, you brought your mouth to her ear.
“I’ve done this before with Dean Cadence and Principal Cinch.” You whispered. Judging by the surprise on her face, she was both shocked and aroused by your revelation. Smirking a mischievous grin, you brought your lips close to hers but never touching. “And Cheerilee, you’re in for one wild ride.”
“We’ll see about that.” Cheerilee purred as you pressed your lips against hers while picking her up from the desk. You kissed and kissed with heightened passion, wrestling her tongue with hers as you walked her to the teachers desk. Pushing stuff off the desk and seating her on it, you resumed your assault upon her mouth. However, Cheerilee upped the ante by wrapping her legs around your waist, pusing your crotch closer to her honeypot. Though you wore heavy jeans, the warm wet juices of her aroused vagina seeped through the denim, making you more aroused than ever. Holding her closer, you began dry humping her as your loins tighten in your jeans. With every bump of your veiled package against her vulva, you felt surges of ecstacy down your spine. As your humping got more forceful, the desk shook with your movements until you stopped when you heard the sound of metal and plastic clanking against the tiled floor.
Looking at the object, it appeared to be a thin cylindrical object with a blunt tip at the end. From the flat end, a cord ran down to a small pad with a dial on it that had ten settings. You’ve seen enough porn to know what it was: a vibrator. It was still wet with the fluids from Cheerilee’s pussy. That explained the hitches in her voice as she grilled you on daydreaming. However, this gave you the opportunity to enact a fantasy you only got to witness in a porno. Picking it up, you began to make your fantasy real.
“Well, well, well, looks like some teacher has been rather…” In the midst of your seduction, you brought the vibrator to her eyes view, making her jolt in nervousness. “...naughty.”
“Wh-Www-what will you do to me?” She gasped as you grabbed her arms, looking her in the eyes with a lustful glare.
“Assume the position, ma’am.”
“What?!”
“Do it!” You firmly snapped. Moving away from her, you saw Cheerilee leaning over the desk on her stomach, grabbing the opposite end of it. Walking towards the chalkboard, you got hold of a long ruler. Holding it in your hands, you walked back to your horny teacher, getting down on your knees and pulling her skirt down along with her panties. Now, her bare pussy and ass is in full view. As much as you wanted to whip your dong out and ravage her, doggy style, all that had to wait. Getting up of her knees, hearing the nervous panting from Cheerilee, you took the Vibrator in hand, turning it to level 4 and rubbed it along her wet slit. She moaned and moaned, yelped and gasped as you brushed the sex toy along her moist and puffy folds. Cranking the vibrator’s intensity up another level, you inserted it into her love canal, leaving it in there to her perverted pleasure. Reaching down, you picked up the ruler and held it to where she can see it.
Wh -What A-AHHHHHNNNN are you going to do ww-w-wwith that?!” Cheerilee stuttered as you firmly gripped it in hand. Raising it up in the air, you smirked like a madman.
“This.” With speed, you brought the ruler down flat on her plump posterior. The sound of a hard slap along with a short loud moan from her signified that she enjoyed it, something you never thought she did.
“My gosh,” Cheerilee panted. “Please do it again! Harder!” Heeding her words, you brought the ruler down again with a little more force than last time. Each and every time you did it, she begged for you to do it harder. You kept on spanking your lewd teacher with the ruler several more times until you decided to stop, not wanting to bruise her. You were horny but not without rationality. At that point, feeling incredibly turned on by such a kinky woman, you undid your belt and pulled down your pants and underwear, allowing your member some freedom. Cheerilee looked over shoulder and was caught off guard by the size of your girth. Grabbing her supple buttcheeks in your palms, you slid your shaft in between those luscious cheeks.
“Oh god! Your cock feels so good!” She screamed as you slid your rod along her crack, the both of you reveling in the pleasure of such an erotic move. As you slid and slid, Cheerilee’s moans and gasps increased in frequency and pitch as her orgasm drew near. You felt yourself getting to that point and you upped the intensity of your movements, squeezing her cheeks closer and harder against your cock. You increased your pace as you continued to hump her ass until you reached the top of your climax.
“OH GOD, I’M CUMMING!!!” Cheerilee screamed as she arched her back at the dawn of her orgasm, letting out on pleasured moan that you swore shook the table a bit. With your willpower drained, your shaft shot out rope upon rope of semen upon her back. Increasing the pleasure of your release, you held yourself tightly against her rump as you continued to shoot your loads for for a minute before your orgasm died down. Panting and exhasuted, you leaned against Cheerilee, helping her remove the rest of her garments, shirt and bra. After taking off your shirt, the both of you stood naked in the room and your erection still stood strong. You hungered… craved for more of you substitute teacher. You repositioned yourself in the same position and pulled the still buzzing vibrator out of her dripping wet pussy.
“Please Calculus, Put it in me! Ravage me until you fill me to the brim!” Hearing Cheerilee moan those words while reeling from her orgasm, you positioned the tip of your spear at the entrance of her folds. It felt slick and wet, perfect lubrication for your steel hard dick. Sliding it in, you noticed that it went in without any difficulty. In fact, as it slid inside her love canal, you felt her inner walls constrict around you length. It felt good, really fucking good, so good that your inhibitions had faded away as you began to pound away at her insides, savoring the feeling of her slick vaginal walls squeezing your girth. You thrust and thrust away with complete abandon, not having a care in the world as you fuck such a beautiful MILF.
“OH YES, CALCULUS! FUCK ME! GIVE ME ALL YOUR MIGHT AND MAKE ME YOUR BITCH! PLLEEEEAASSSEE!!!” Thrusting and fondling her CC-cupped breasts, you kept on ravaging her, doggy style, increasing the tempo of thrusting your hips forward. Like all good things such as ice cream, this pleasure is not to last forever as much as you wanted it to. With a one more mighty thrust, you felt her inner walls and hearing her scream like a banshee. The pleasure was too much for you to bear and you let out a loud grunt as you emptied your balls deep into her womb. Shot after shot, you felt your shaft being surrounded by a river of your cum. You kept on thrusting to increase yours and Cheerilee’s pleasure as your respective orgasms began to fade away. Eventually, you both stopped cumming and collapsed onto the floor with her on top.
“Holy shit!” Cheerilee breathed. “How are you this good?!”
“Experience.” You groaned. "Experience, Mrs. Cheerilee.” Desiring some post-coital cuddling, you moved on top of her and held her head in your hands as you gave her a passionate kiss. You and Cheerilee revelled in the lust your tongues lapped around in a sensual dance. Eventually, you had to exit the kiss and get ready to leave, knowing that your parents are likely worried.
“I guess this resolves our earlier issue, Mr. Calculus.” Cheerilee said as she got her panties back on. “Now, I hope Ms. Jubilee won’t see you doing this again.”
“Oh, rest assured, I think this solved it.” You coyly retorted. “It felt like you’ve been wanting it for quite some time.”
“Well, my husband is a busy man, always coming home tired and not having the energy for some fun in the bed.”
“Yeah, that does sound like a real drag.”
“Heh, that’s a big understatement.” As you put a hand on the doorknob, you were turned around by Cheerilee in her bra and panties, giving you a quick passionate kiss. “Now, I do hope we run into each other again. I may have need of your… services once more.” Waving farewell to her, you walked out to the parking lot and your car where, to your surprise, Ignacio was waiting for you.
“Hey Calc, what’s up?” He greeted.
“Nothing much, man. Whatta about you?” You replied.
“Same old, same old.” Just as you opened your car, Ignacio shocked you with something that made you freeze in place. “So, how good did that MILF feel?” You nervously stammered, trying to process you you’ve just heard. How did Ignacio know about your earlier tryst with Cheerilee? Just as you were about to open your mouth, Ignacio pulled out his phone and opened a sound recording of what sounded like a call from your phone number. “You should really be careful and check if you’re buttdialin’ someone.”
He pushed play and the recording was of your little sexcapade with Cheerilee. Every moan, every orgasmic scream, even the sounds of the spanking was recorded. You pulled yout your phone to check the call logs and to your horror, you did indeed buttdial him while you were ravaging some MILF ass. Dropping to the ground in in embarrassment, you cupped your head and sigh in shame as the sound file finished playing.
“So, now it all makes sense. You banged both the Dean, the Principal, and now Ms. Jubilee’s temporary replacement. I’ve suspected it since that one friday when Cinch busted you.” Ignacio said as he began pressing on his phone’s touch screen.
“Ignacio?”
“What? If you’re wondering, I just deleted the file. No worries.” You were surprised at what Ignacio did. You thought for sure that he was going to put the file on the internet. Paranoid as you might seem at times, the thought always seemed to scare you. “I gotta say, I’m actually quite proud of you getting laid thrice.”
“Well, they all just happened at the spur of the moment.” You said as Ignacio gave you a fist bump. “I just roll with the punches, you know?”
“Like you always do. So, what’s the teacher’s name?”
“Mrs. Cheerilee.” As you gave your answer, you saw Ignacio act so surprised, he nearly fell to the ground.
“Mrs. Cheerilee? As in, one of the teachers from CHS?”
“Yeah, so what?”
“So what? Dude, my brother goes to CHS and he told me that Cheerilee is close friends with the two principals that run the roost there. In fact, Principal Celestia is well liked around these parts and is well acquainted with the local cougars.”
“What are you getting at?” You shakeningly replied, causing Ignacio to come closer to you.
“The local MILFs know each other, talk to each other and hang out on a weekly basis. When Mrs. Cheerilee goes back to Canterlot High, it’s pretty much assured that Celestia will know and word among the town’s MILFs will spread of you. Sooner or later, every cougar will be on the hunt for you… and the thing between your legs.” You began to worry but only slightly. It wasn’t the prospect of banging potential scores of MILFs, the fact that at any moment, you could get caught with your pants down with some of those cases might be literal.
“Aw shit, I kicked the hornets nest in a big way, didn’t I?” You groaned with slight pain in your head.
“Perhaps.” Ignacio said with a slight chuckle. “But hey, man. I count you lucky.”
“How so?” You asked with slight annoyance.
“You’ll be pretty much drowning in pussy. Imagine that, the town’s sexually starved chicks looking forward to to dancing on your pole. You’re so fucking lucky but, to be sure, watch your back. Those cougars can get awfully sneaky.”
“Well okaaayy. I’ll keep one eye open… I guess.” You said as you started the car’s engine and drove off. As you got home, you climbed into bed, exhausted from your fuck session with Cheerilee. Pondering what Ignacio told you, it didn’t seem half bad. MILF after MILF will know about you and want some. Slowly, you began to warm up to that thought as you drifted off to sleep, knowing that you’ll be the topic of discussion among your inner circle.
“To all the MILFs out there, bring it on. I’m Dr. MILFlove and I’m the cure for your horniness.”
Author's Note
Well, Dr. MILFlove has officially risen. Stay tuned for Mrs. Cake's turn. Just a teaser, it'll involve whipped cream, chocolate sauce, and a very horny mature woman with a sweet tooth to match.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Sweet Momma(Mrs. Cup Cake)
“Come on, Calc! We got some baking to do!” Pinkie Pie said as she exited her car.
“Yep, and it’s gonna be one helluva cake to make, Pinks.” You replied as you followed suit. It was hard to imagine that in the weeks before you graduated that you left having done the horizontal hokey-pokey with some of the hot mature babes among Crystal Prep’s staff. It was that one stroke of luck that you left your virginity behind when you kissed the school goodbye. But now, since your one on one time Mrs. Cheerilee, Canterlot’s local population of MILFs and cougars are now on the prowl, looking for a chance to dance upon your pole. Now, your extended inner circle is planning on a huge party and your friend Pinkie Pie, who was organizing the whole show, brought you to her workplace at Sugarcube Corner to bake a huge cake for the party, the biggest that place ever made.
For a small bakery/house deal in the city, business was booming for Sugarcube Corner. Delicious food, creative pastries, it was quite the place for a treat at an affordable price. However, It was also co-ran by one fly MILF.
“Oh, hello Pinkie!” A woman with tall, pink hair greeted as you and Pinkie entered the building. “Brought a friend to help you with the cake, I take it?”
“Absolutely, Mrs. Cake!” Pinkie answered to her boss. “I believe my friendo here will be of great help.” Just as her boss, Mrs. Cake turns to face you, she was caught off guard by your appearance as you gave her a confused look. For a MILF, Mrs. Cake was one thicc woman. She was plump but plump in all the right places. She looked rather sexy for someone her age and weight. Plus the way she carried herself, Mrs. Cake had this motherly aura to her. Just observing her features was enough for your boner to begin rising. But, from your past experiences, you were able control it, like you had a superhuman ability to do so. Snapping back from her shock, Mrs. Cake recomposed herself to yours and Pinkie’s confusion.
“Oh, sorry dearies, my mind wandered off a bit.” Mrs. Cake said as she brushed off her apron. She turns back to her mixing bowl which had a raspberry filling that she was making for the cake. “I’ve already laid out all of the ingredients you’ll need for the batter. Since this is a big cake we’re making, I’ve adjusted the directions to count for the size of it. I’m sure this’ll turn out good.”
“Oh, It will, Mrs. Cake!” Pinkie Pie said cheerfully as you and her began to make the cake batter. Since the party numbered at around 70 seniors that were acquainted with one another, there was a lot prep work and mixing to be done. Egg by egg, cup by cup of flour, and bits of chocolate and some almond flavoring in the batter, the huge bowl almond cake batter was finished. Even though you’ve yet to put it in a pan and bake it, the smell was so enticing. As you were about to work on the frosting, Pinkie’s phone went off and she answers it.
“Heeelllooo?”
“Calc, bad news. Rarity and Fluttershy got into a car accident while driving to crafts store. They’re not terribly hurt but I wish I could say the same for the car.” Pinkie Pie explained to your shock.
“How badly did the car get hit?” You asked.
“Rear ended, with said end hitting a lamp post. The back wheels are gone. Luckily, the front end hardly suffered a scratch.”
“Okay, what do you need me to do?”
“Can you be a buddy and stay here to help Mrs. Cake finish the cake for Friday?” You’ve heard it, Pinkie wants you to stay behind to help a deliciously thick MILF with finishing the rest of the project. You didn’t mind that, but how things can potentially turn out and get in the way of the task at hand. Although, you always were a ‘play things by ear’ sort of person when it came to what transpires during any given day. With your mind agreeing to Pinkie’s proposal, you waved her off as she walked out of the store. Now, It’s just you and the head MILF of the bakery.
“Calculus, ” Mrs. Cake called to you. “Can you be a dear and get started on the buttercream icing and put the cake in the oven, please?”
“Will do.” You replied. After filling the cake tins with the batter and tossing them into the oven, which was large for Sugarcube Corner, you set the temperature and time to bake. “Okay, set the temp for 375 degrees, set bake time for 40 minutes, aaaannnnd we’re good to go.” After all that, you proceeded to get to work on the buttercream icing. As you were mixing the ingredients in the bowl, your thoughts drifted to some rather naughty thoughts Mrs. Cake. In your mind, you imagined motorboating her plump F-Cup breasts, sucking the warm milk from those luscious orbs as you go down on her. And to your surprise, you picture yourself ravaging her in the showers, letting the steam from the hot water conceal you as you hump and fuck her. Talk about adding a literal meaning to the phrase ‘steamy’. As you mix away at the contents of the bowl, pouring in bits of sugar as you go along, you felt a soft and squishy presence against your back, accompanied by a pair of hands gently rubbing your shoulders. It did made you jump slightly not to where it made you twitch. The scent coming from behind was odd but interesting, smelt like pecan pie and cherry turnovers.
“You’re quite the hard worker there, Calculus.” Mrs. Cake cooed as she continued to rub your shoulders in a relaxing way. “I can see why my employee Pinkie likes to bring you in here to help out from time to time.” You couldn’t help but moan in a relaxing way at her massage on your shoulders and the mounds soothing your upper back. It maybe from the lack of sex you’ve had as of your departure from CPA that you’ve been feeling tense.
“Yep, ” You yawned, feeling relaxed and tired from Mrs. Cake’s rubbing. “While I wait for the college to accept me into my prograaamm-ohgodthatfeltgood, I figured I’d do something to occupy my time and earn some money.”
“What program are you going into, deary?”
“Accounting. As a little kid, I’ve always been good with numbers and still am to this day. My folks named me after my grandpa, who was a respected bank accountant and coordinator.”
“Hmmm, all that thinking and hardly any time to relax.” Mrs. Cake moaned as she snaked her arms around your stomach and began to rub her breasts against your back. “Sometimes, It’s good for the brain to relax than to let it run 24/7.”
“Yeah, I guess s-” As a surge of pleasure pulsed through your spine, your arms accidentally hit the handle of the mixing spatula of the icing bowl. You were able to move out of the way in time but the glob of icing managed to splatter all over Mrs. Cake’s shirt. You panicked as you rush to get a towel to clean up your mistake.
“Oh shit! Sorry Mrs. Cake, I truly am!” You said with a sense of worry as you found a towel. As you rushed to Mrs. Cake, she held her hands out, stopping you from getting any closer.
“That’s okay, deary.” Mrs. Cake said as she took the towel from you and tosses it aside. “No use crying over spilled milk.” You saw her walking towards the door and flip the sign to where the ‘Closed’ side can be seen from the other side. She then walked back to you with could be a motherly smile.
“Now, I’m going upstairs to wash up. Go ahead and put the icing in the fridge and wait for the oven alarm. While you’re at it, sit down, relax, and don’t be shy about grabbing a soda if you want.” Mrs. Cake proceeded to walk upstairs, giving a subtle sway of her rump that didn’t elude your sight. Doing as she suggested, you wrapped the icing up and stashed in the fridge, grabbing a soda while kicking back in the seating area.
“Well, time for a little R&R for a change.” You mumbled as you chugged down your drink. Resting your head on the booth nearby, you began to doze, dreaming a rather wet dream.
There you were, in the shower with Mrs. Cake, completely naked as she massages soap into her sizeable titties. With your full might, you swiftly turned her around and began to pound her mercilessly from behind. You grasped those wet, soap orbs in your hands, squeezing and burrowing your fingers into those supple, fleshy mounds. With each thrust into her behind and pleasured moan, it drove your testosterone to new heights as you pounded her faster than before. Before you knew it with the passage of time becoming lost to you, you came into Mrs. Cake’s tight booty, collapsing onto the bathtub floor with her in tow in a comfortable spooning position. There, you cuddled with her for an extended period of time.
*BEEP*
Reeling you from your slumber was the sound of the oven alarm, signaling that the cakes were done baking. You briskly wandered over to the oven and pulled the cakes out, wrapping them with tinfoil before you heard a familiar voice boom from upstairs.
“Calculus, can you come help me, please?” You couldn’t help but sweat a bit when you heard those words from Mrs. Cake. She was practically inviting you to her room. After dusting off your pants, you climbed the stairs. Once at the top, you saw a door has been opened a bit. She had to have been there. You walked toward the door, opening it and beheld a sight that surprised you.
“Why hello there, big boy.” There, on a bed lies Mrs. Cake, completely naked with what looked to be whipped cream sprayed on her from her breasts and all the way down to her vulva. It also looked to be some chocolate sauce was drizzled on the cream as well. The sight was so erotic that you were frozen in place at such a sight. Your sweet tooth began to bark at you to dig in. “You should take your clothes off so they won’t get dirty.”
Obliging her request, you stripped yourself, shirt and all, wandering towards her to claim your prize. You hovered over her, observing the tantalizing and sweet smelling display. Layers of sugar waited for you to devour them.
“Where should I start, Mrs. Cake?” You asked her with renewed focus.
“Start at my breasts, Calculus.” She cooed in a flirting tone. “Make sure to get every last bit.” Propping your knuckles, you brushed your tongue across her left tit, scooping up every conceivable bit cream and chocolate. Mrs. Cake gasped and moaned with every stroke of your tongue upon her breast. It sounded like she hasn’t had any sex in quite a while. Once you saw that was clean, a stroke of curiosity snapped at you. Latching one hand on her melon, you enveloped her nipple with your mouth and began to suck on it. She gasped as you began to suck on her teet. To your surprise, a stream of breast milk had shot out from her nipple. The milk tasted sweet and creamy, kind of like vanilla ice cream. It surprised you even more that she was lactating, seeing as Pinkie told you she gave birth to twins about five months ago.
“How did my milk taste, young man?” Mrs. cake asked with motherly eyes.
“Sweet and creamy, ma’am.” You replied, licking your lips as she brushed your hair in a loving way. “Where are your kids, though?”
“In their room, fast asleep.” She replied. “No need to worry. We have quite a lot of alone time here.” Seeing her sultry eyes piercing your vision, you resumed your work and ate up the cream and chocolate from her other breast. As you worked your tongue down along her stomach, you felt your shaft becoming harder and tighter as you neared her juicy thighs. Gasping and twitching, writhing and moaning, more pleasure that Mrs. Cake had held back for so long was starting to escape like a water balloon filled past its limit that is bound to burst. You licked all the cream around her thighs, saving the last glob on her flower for last. Grabbing her lower legs, you spread them apart, making her blush and her pussy wetter than when you began.
“Wow, this pussy looks sweet.” You seductively growled. “I hope you don’t mind if I snack on it.” Cocking your head back a bit, you practically nosedived right into her vagina, furiously sucking and licking up any cream that you can taste. When no cream was left, you kept eating her out with the same fervor as before. Only that time, you tasted something that was tangy and oddly tasted like oranges and pineapple. Her loud moans pressured you to continue pleasing her.
“OOOOOHHHHHH, FUCK YES, CALCULUS! KEEP EATING ME OUT! MAKE ME FEEL SO FUCKING GOOD! OH FUCK, OH FUCK, OH FUCK, OH YES! OH GOD, I’M ABOUT TO CUM!”
After a few more moments of hungrily licking her vagina, she indeed came. A stream of her lady cum squirted into your mouth, making you suck down the entirety of her orgasm. Mrs. Cake’s orgasm eventually died down after a minute when she laid down and panted in slight exhaustion. You were truly amazed at her stamina and she must’ve gone on without sexual pleasure for so long that you thought was part of the reason she recovered so quickly.
“Holy fuck, that was good.” Mrs. Cake moaned.
“Well, I’m pleasantly surprised you recovered so quickly.” You retorted with a laugh which led to another question. “Why have you been holding back getting pleasured for so long.” With a long and drawn out sigh, Mrs. Cake gave her answer.
“Between taking care of our babies and running the family business, me and my husband never had any time available to have fun. He left yesterday to talk with some people about opening another chain. Though I’m fine with running things here alone, I do miss being sensually caressed by a man.” Those words had touched you somewhat. You felt a shred sympathy for her in that moment. But, lust made you and her blind to everything and never paid those thoughts anymore attention. It was time go back to pleasure city. Getting off her bed, Mrs. Cake examined your erect cock with a grin most mischievous. She then pulled out a can of whipped cream and covered your entire length with the sugary creamy topping, tip and all. All that cream around your shaft felt so cold yet strangely arousing, making you moan slightly, knowing what was going to happen next. But then, Mrs. Cake did something that surprised you by taking a stemless cherry and placing it on the top of your cream coated cock. She then got down on her knees in between your legs, pushing you back onto the bed.
“Now, for all the hard work you’ve done for me, I think it’s time I’ve pleasured you.” She hovered her mouth over the tip of your shaft, nearly enveloping your length in her mouth before taking it away. The teasing drove you wild beyond comprehension as she breathed on it as she bit the cherry while not taking it off. If there was an award for most creative and erotic blowjob, Mrs. Cake would sure as hell take home the gold. She eventually lapped up the small fruit in with her tongue and devoured it. Soon after, She licked along the length of your cock, lapping up all that cream before reaching the tip and giving it a light kiss, making you shiver heavily before she took it all into her mouth.
You were powerless to the point of barely able to move a muscle. Out of all the blowjobs you’ve had, this was the best one you’ve felt by far. The setup, the display, the passion, all of had clicked so well and it was rather sweet, both figuratively and literally. Eventually, your stamina could only take so much before you blew your load into her mouth, making her deepthroat your entire length as she consumed your seed to the last drop. Eventually she removed your shaft from her mouth with a pop sound.
“Wow dearie, your milk tastes salty… yet sweet.” Mrs. Cake remarked as she climbed back onto the bed on her back, spread eagle. “I think it’s time to move on to the centerpiece.”
There it was like before, her pussy laid bare before you with its musky scent inviting you in. You inched your shaft closer to her honeypot, prodding it with your tip which made her moan like lonely wolf. Giving you her begging eyes, you slid your member into her hungry love tunnel.
“HOLY FUCKING SHIT!” Mrs. Cake screamed in sensual pleasure. “I haven’t felt something like this in a while! Please, FUCK ME INTO NEXT WEEK! I BEG YOU!” You felt that no words needed to be said at that point and you began pounding her pussy with total lust. Moaning and panting, Mrs. Cake not only enjoyed the feeling of dick in her pussy, she felt starved from it for so long, her hunger for sex blinded her to everything else, as if everything else in the universe except for you and her didn’t exist. Such sensual pleasure, much carnal bliss being let out, words couldn’t describe how blissful she was. Once again, your curiosity got the better of you and latched your mouth upon her left nipple once again, sucking some more of that sweet and warm milk from her teet.
“Oh fuck yes, suck on my titty! Suck on it, dearie!” Mrs. Cake groaned as her hips began to gyrate with your movements, further enhancing your pleasure as well as hers. The feeling of the breast milk in your mouth and the slickness of her still somewhat tight pussy drove you closer to your climax until it eventually came. Giving a few more mighty jabs at her cervix with your lap howitzer, your spear quivered and shot loads of your cum into her womb. The feeling of your seed flooding her inner walls caused them to clamp down and milk your knob for every drop of it. Eventually like the last couple of times, you were able to reel from your orgasm but quicker than before which shocked you. Mrs. Cake was also not done yet as she climbed off her bed with drips of your cum and hers leaking from her vagina. Her body still craved for more and you didn’t complain one bit, not that you wanted to anyway.
“I feel like getting cleaned in the shower.” Mrs cake said, entering her bathroom and gesturing you to follow. “Feel free to join me, dearie.” Stretching your back and giving your spear a good few tugs to make it erect again, you followed the milf into the shower which was already bellowing steam from the hot water. Opening up the shower stall, you found Mrs. Cake massaging soap into her lusciously big mounds, just like in that dream you had earlier. Seeing you enter, she turns to face you with arms extended and wraps you in a deep hug while giving you a very passionate open mouth kiss. It felt like heaven for the short time you and her made out that way. You eventually broke the kiss and turned her toward the wall lining up your cock with her pussy.
Just then, a thought dawned on you, one born out of curiosity. You’ve yet to try anal with any of the MILFs before that point. You always wondered what it felt like going in through the backdoor. Catching her by surprise, you lined your cock at the entrance of her anus, making her jump and yelp in shock. Her reaction was all the fuel you need to go on ahead and push your glans in her ass. It was a tight fit and it took time to get it all in but you were eventually able to.
“OH WOW!” Mrs. Cake shouted with pained pleasure. “I-I’ve never tried this before and it feels… sooo gooood! Go on, fuck my ass!” You began pounding her ass like a madman at her command. Her anal walls felt extremely tight yet added a lot of pleasure to your already throbbing cock, begging to release its last storm of cum.
“Say my name!” You grunted as you thrusted.
“Calculus!” Mrs. Cake moaned.
“No, not that name!”
“Wh-What would you like me to call you, then?” You stopped thrusting for a brief moment and leaned your mouth to her ear.
“Call me… Dr. MILFlove.” You whispered to her excitement.
“Dr. MILFlove.”
“Louder!”
“Dr. MILFlove!”
“LOUDER!”
“DR. MILFLOVE!”
“LIKE YOU MEAN IT!”
“OH PLEASE, DR. MILFLOVE! PLEASE RAVAGE MY ASS! PLEASE!” With her begging, you firmly grabbed hold of her succulent buns and took a deep breath.
“Well now… THE DOCTOR IS IN!!!” You resumed thrusting in her butt with renewed vigor, powered by your heightened ego. You felt your head getting lighter and lighter and hotter as you continued to hump away at her ass. Eventually, like a nice glass of the finest whiskey, it was not to last forever as the newest sensation eventually made you cum rivers in her tight round booty. Thrusting for a bit more, you let your relaxed state carry you from your orgasm as you and Mrs. Cake collapsed onto the shower floor, cuddling in the spoons position, feeling exhausted from the intense coitus.
“Th-Thank you, Dr. MILFlove.” Mrs. Cake yawned as she schooched in closer, allowing you to embrace her even tighter than before. Feeling the warm wetness of the shower drippin upon your bodies, you eventually drifted off to sleep after you turned off the water, cuddling with the MILF you just banged and feeling a great sense of pride over adding another mature woman to your score.
“Heh, Dr. MILFlove has struck yet again. Come to me at anytime and I also do house calls.”
Author's Note
Well, to anyone who was wondering if I would get around to a chapter where anal sex was involved, your wish has been granted. Anyways, I've had a lot of fun writing this chapter and I thought it would be the one where OC would fully assume his alter ego. Anyways, I'm glad you've enjoyed this story so far and as a reward for all the positive reception and comments, You can vote on who'll be next. I've included a strawpoll link you can use to determine which MILF will be next.
Here's the link, so have at it.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Dungeons & MILFs(Elaina - AKA: Button's Mom)
Last week was one hell of a party. Even to this day, especially after high school, you’re still amazed that Pinkie Pie can throw one hell of a party. In between your job hunts and your scholarly duties, you still managed to keep a stable social life and hang with your friends when time allows it. Even now, as you walk along the streets of suburban Canterlot, you were excited about tonight because your friend Button Mash and his mother are throwing a LAN party with some of his friends and hers. Hours upon hours of scarfing down pizza and soda while playing such great hits as CS:GO, Red Alert 3, Left 4 Dead 2, MvC3 and Smash Bros await you and your mutual friends that want a night to let loose and have fun.
As you were getting closer to Button’s house, your phone vibrated briefly in your pocket. Pulling it out, you saw a text message from Button Mash himself.
“Yo Calculus, Rumble’s rig is on the fritz. From what I can tell, it shouldn’t take me no more than say three hours to get it fixed. Go on ahead to my house and you can help my mom get things squared away. I’ll be there as soon as I can get this machine fixed. Peace!”
You couldn’t help but let off a small chuckle at the situation with Rumble’s “Mjolnir” as he likes to refer to his computer as. Though you and Button Mash went to separate high schools, the both of you attended the same elementary and middle schools. Though he was upset that your parents put you in Crystal Prep, you still kept in regular contact with him. Hell, you attended his graduation party and got him the latest DOOM. He had a substantial knowledge when it came to computers and helped build your first rig. Knowing how long it’ll take him to fix Rumble’s problem, you kept on your course towards his house with your rig in tow.
Eventually, you arrived at his house. It looked well kept and the grass was vibrant green color. Button did mention that his mother had a bit of a green thumb. Walking up to the door, you gave it a few good raps on its surface. After a few seconds, the door opens, revealing a sight that made your heart skip a beat.
“Hello there, Calculus!” Elaina, Button’s Mom, said. “No doubt my little Button told you he was helping a friend, right?” Elaina was, as you would say… a bomb-ass lady. Curvy and bubbly, cheerful and motherly, with a nice long hairdo with a bow at the end, she had her own charm to compliment her looks for a woman that’s nearing 40. Though her husband is the breadwinner of the household, she does a few part-time stuff to make sure her family has money for the fun stuff. Oddly enough, like you and her son, she was a bit of a gamer as well. Who would’ve thought that a mother likes to play video games. Taking a slight cough, you reorient yourself and made eye contact with her.
“Yeah,” You replied. “He texted me about it five minutes ago. He said it’ll be a few hours. He also told me to help you get things squared away.”
“I see.” She replied with a veiled moan. “Well, all we have to do is get the tables in the basement setup and everything else hooked up. It’ll be done faster now that I have an extra pair of hands for help.”
“Okay, let’s get to work then.” With that exchange, you set your rig to rest in the living room and followed Elaina into the basement. However, as you were climbing down the stairs, you noticed she was giving her rear end an added sway with each step. Though you would find it arousing to where it left you frozen in place, your past experiences with some of the older women you’ve known had let your mind numb to such sights. Quickly shaking the sight from memory, you helped Elaina set up the power strips at every outlet you could find. You also had to make sure that the tables would be able to reach them, considering that computers and consoles will be in use. After the power strips were all set, Elaina called to you with a ladder in hand.
“Calculus, can you be a big helper and hold this ladder while I place this router? It’s a bit rickety and it makes me nervous.”
Complying with her request, you meandered over to the ladder and held it in place, allowing her to setup the aforementioned router. For a such a relatively young MILF, Elaina had both a youthful appearance and geeky nature along with the refined curvy features of more older women, a nice combination, one in a million. She wore a white tank-top with a short blue skirt. As she clambered the ladder and fiddled with the wires and velcro, you got a good glimpse of her tan red lacy panties, barely veiling her puffy wet vulva.
The sight… the all too familiar sight made you desire nothing more than to lay her on one of the tables and rut her like a wild beast in heat. But, you’ve felt these thoughts weren’t kosher because she’s your friend’s mother. However, you are Dr. MILFlove and knowing that Elaina is on CHS’s parent-teacher council, she likely knows about your exploits. With yourself on guard, you decide to shift your mind away from such lecherous thoughts and decide to strike up a friendly conversation.
“So Elaina,” You started. “Where’s your husband at?”
“Sparkplug?” She replied “He’s on a business trip in Manhattan, they’re probably gonna make him the regional manager for the GoGoTire chains in this state.”
“Hmmm, sounds like he’ll be one busy man, I take it.”
“Busy, yes. But hey, At least it’ll allow for more wiggle room on the budget side of things. With him gone for a few days, it allowed me to do this sort of party, knowing me and my son’s mutual interests.”
“Vidya games, right?”
“Exactly.”
“Who would’ve thought that an older woman like video games. Interesting.”
“Well hey, I was young at one point, you know.”
“Heh, true, true.”
Elaina then finished setting up the router and cables. From your view, it looked a bit like a kraken made of wiring and circuitry, considering all the ethernet wires were all dangling from the metal box above. With everything setup, there was nothing else to do but wait a few hours for the event to start.
“Well, since just about everything is in place, wanna play some Street Fighter V?” Elaina asked.
“Sounds good, getting a little bored myself.” Following her back up to the living room, you and Elaina sat in front of the television and powered up the ol’ PS4. When you saw her username on the home, you were in shock as you were reminded of an embarrassing defeat. A week ago, you were on an amazing win streak against random players in SFV’s multiplayer. When you got to what would’ve been your 50th win, it was against a player named “MadameKrieg747”, the same username as Elaina. You were barely given any time until she won all two rounds against you. It was a crushing defeat and now… you were in the same room with the person that stole your thunder.
“You.” You growled slightly. “You’re the one who robbed me of my win streak!” Elaina then turned to you with a wry smile.
“So, how embarrassing was it, noob?” She replied with a chuckle.
“It killed an amazing streak I was rocking!” You said as you picked up a controller. “Now, I’m so gonna enjoy this little rematch of ours.”
“Well, try to beat me if you can, WardawgAlpha.” Calling you by your username made your blood bubble with pride and adrenaline as you chose Vega and Elaina chose Cammy. You both decided on a random stage select, wanting to get to the fight, post haste. When the fight began in earnest, you were quick to dodge and counter her attacks, netting you a round of victory. However, almost as if she pulled a clutch, she put you on the defensive the following round which resulted in her victory when the time ran out as she had the most health.
When the tie breaker round began, both you and her brought your respective A-Games and began matching her blow for blow. When there was 30 seconds left on the clock, the both of you had tiny slivers of HP left. One connected attack will decide the victor. Elaina went for a jumping kick. You anticipated she was going to and went for an uppercut. Your hit was the first to land and Elaina’s character was KO’d. Finally, your defeat was avenged.
“Hells Bells!” You shouted as you raised your arms in the air, humming the aforementioned song. Elaina was none too happy about her loss.
“FUCK!!!” She shouted as she, without warning, accidentally slammed a fist down hard onto your balls in impulsive anger. The shock and pain from the blow was so much that it caused you pass out. The only thing you heard as you slipped out of consciousness was Elaina shouting:
“OH SHIT, SORRY!”
When you came to, you found yourself on a bed built for a couple. You immediately figured it to be Elaina’s bedroom. You began to feel a chilly presence develop on your crotch. Lifting your head a bit revealed it to be an ice pack on your genitals, unveiled by your boxers and jeans. Though the pain subsided for the most part, you still felt a bit sore in the sack. But, you’ll work through it and soldier on. About five minutes later, Elaina walks in, looking regretful and apologetic.
“I’m so sorry about that, Calculus.” She said as she sat down on the chair next to you. “I just carried away, didn’t mean to do that.”
“No worries.” You grunted. “People make mistakes, just… watch where you land a fist next time.”
“No worries.” Elaina sang as she moved a hand near your crotch, taking off the chilling bag of ice. “Does it still hurt down there?” She, in a non sexual way, lightly squeezed your nads with her hands. You felt hardly any pain, only the residual soreness.
“Just a bit sore, that’s all.” You moaned as she continued to fondle your sack. Then, you felt a stirring in your loins as she massaged your testicles in a sensual way as opposed to how it was before. The grin she sported was one you’re all too familiar with, the signature smile of a cougar that’s staring at her prey. Eventually, the thightness bloomed into a full-on hard on. You were amazed that you were able to sprout an erection when got punched in the nads so hard.
“Hmmm,” Elaina said as she say your erection, uncovered by clothes of any kind rise and stiffen. “It seems your joystick is a little stiff. Heh, it’s gonna need some…” She then took your tool in hand and looked you seductively in the eyes. “ recalibration.”
“Heh, using double entendres I see.” You chuckled as she began fondling your package, causing you to moan in pleasure. Though it still hurt a bit, the pleasure overrode the still lingering pain in your nuts and kicked your head back to Elaina’s amusement.
“Hmmmm, looks like I’m doing such a good job at taming this monster that I might gain a level after this fight.” She mused as she continued to stroke your shaft with progressive vigor. As cheesy as her double entendres were, you found them oddly arousing, probably because you do a lot of gaming on the side apart for your usual schedule. On top of that, because she had experience with her husband and she’s also a gamer, the whole scene felt like heaven.
“I guess it’s time to activate my limit breaker.” The moment she said that, she began to deepthroat your entire schlong in a slow and sensual manner. You felt immense pleasure from feeling the back of her throat with your shaft while she also massaged your pills. You wanted to give her presumably wet vagina some pleasure but you knew she wouldn’t have any of that. As you looked around, you noticed your foot is within striking distance of her puffy vulva. Smirking a mischievous grin, you used the toes of your right foot and pulled aside the crotch of her panties, soaking wet from her hungry pussy. You rubbed and rubbed your big toe across the length of her folds, causing her to shudder and moan with your cock still in her mouth.
“Oh yeah, baby!” She said, briefly removing your cock. “Keep pleasing the water goddess and you’ll receive her blessing!” More of that gamer talk integrated with her intercourse, she was one sly and hungry minx. It must’ve been months since she had someone rock her world. Resuming her blowing, you upped the tempo of footing her sopping wet vagina. The moans she made vibrated along your length, pushing you closer to your inevitable climax and hers as well. With your blood basically being replaced by pure testosterone at that point, you decided to maneuver your big toe into her wet lower lips. With each insertion, Elaina moaned and gasped with desperation and abandon
“Oh my goodness, my mana is low!” Elaina moaned out as you felt her walls clamp around your big toe, upping the tempo of her blowjob as she orgasmed. You couldn’t withstand it any longer and you busted your load down her gullet. You held onto her head for dear life as you shot loads of ropes of you continued to cum.
“The goddess… of.. the... water temple… is pleased!” Elaina panted as she rolled onto her back next to you on the bed. “Your battle prowess is to be commended.”
“Well then, I do declare myself blessed.” As you said those words, Elaina gets off the bed and stops at the end of it. Those bedroom eyes she gave you… enchanting, mesmerizing, and intoxicating.
“Now, the water goddess shall give you a reward that few mortals dream of.” She then began the most erotic dance you ever saw. It was a mix between what strippers would do at a club and the most erotic belly dance. Her hips gyrated in a hypnotic way as she fondled her E-Cup mounds. Then, she began to slowly hook her fingers on the hem of her tank-top. As she pulled up her top you then got a glimpse at her perky chest pillows, covered by a red bra.
“I see the wayward adventurer enjoys the view.” She said as she raised her arms in the air and began to shake her hips as her skirt started to become loose, falling down and revealing her pantie covered flower. “You have the rare privilege of having a personal audience with a goddess.” Elaina reached her hands behind her back. You heard an audible click and you knew what that meant. She allowed gravity do the rest as you saw her breasts unveiled, puffy nipples and all.
“I know you like what you see, adventurer.” Elaina moaned as she took her tits in hand and massaged them, shaking the pair up and down. There, you’ve felt your loins beginning to tighten as your member became hard once more. Elaina immediately took notice and gently blew on your spear, sending shivers of pleasure down your spine. It was very erotic and sensual to the touch. You reached forward to grab hold of her soft titflesh, only to haf your hand swatted away by hers. “The adventurer should wait for permission to touch the water goddess.”
Hooking her fingers around the hem of her sex-soaked panties, she continued her erotic dance as she slowly but surely slid them off. Just as Elaina was about to reveal her slightly hairy beaver, she crouched down and pulled them back up. For a tease, you found that rather sexy. Your cock tingled with unprecedented lust and want as you want to net another MILF like her to your high score as you call it. Finally, she does away with her panties and tosses them to the side. Her eyes became half-lidded and a lustful smile develops on her face.
“Holy mother fuck, this is intense.” You gasped as she climbed onto the bed like a cat on the prowl, lightly brushing her boobs against your cock. When her eyes met yours, she pulled you in for an open-mouth kiss. It certainly felt weird having sex with one of your friends mothers. But, you being Dr. MILFlove, you couldn’t care less as Elaina broke the kiss. To further tease you, she ground her puffy pussy against your shaft, leaving trails of her warm juices on your length. She continued to do so until the tip of your spear made contact with her lips. However, she just continues to grind her vulva against your tip, further driving you insane as everytime she puts the tip in, she takes it out and grinds it once more.
“I think it’s time for the adventurer to receive his reward.” Elaina moaned as she stopped her grinding. “Now… You may enter the water temple and lay with the water goddess.” She then speared herself on your cock, swallowing your shaft in her love canal. She blushed, you blushed as she brought her mouth to your ear. “Your legend precedes you, Dr. MILFlove.”
Before you could think about her earlier remark, Elaina’s lips made contact with yours as her hips moved her vagina up and down your length. The feeling of her breasts against her chest, her tongue wrestling with yours and her pussy humping your cock, it all indeed felt like a gift from a goddess… a very sexy gamer goddess. The both of you had fuck for about an hour before the inevitable outcome came around.
“I… can feel that… you’re about… to cum!” Elaina said as she took your hands in hers locking both your fingers together, humping with complete abandon. “Go on, unleash your life force into my caves and let it flow!” Even at the doorsteps of her climax, she still kept up with fantasy. You gotta hand it to her being able to think clearly with all of those endorphins flooding her brain. Just as her walls were about to clamp down on your rod, Elaina pulls sits you up and embraces you. She lets out a hoarse moan when her walls lock around your cock and squirts rivers of ladycum allover your crotch, making your shaft quiver and shoot torrents of semen into her womb and making her stomach slightly bulge. After respective orgasms lost their momentum, the both of you collapsed on the bed next to each other.
“Oh wow!” Elaina gasped. “That certainly cured my itch.”
“Glad to be of service, Elaina.” You replied as you climbed on top of her to make out with her furiously. In the midst of your kiss, you heard the faint sound of your phone vibrating. Pulling it out of your pocket, you saw another text from Button.
“Dude, just fixed Rumble’s machine. Will be there in about 20 mins. CYT.”
“Oh shit!” You muttered to which Elaina heard. “Button will be over within 20 minutes!”
“No worries, we’ll take short showers and I can phone in the pizza.” Elaina said as she got off the bed and directed you to her shower room. “You can go first. It’s the least I can thank you for… servicing me.” Giving her a quick wink, you jumped into the hot shower, and began cleansing every trace of your deed from your body, taking extra care to not give your friend any hints of what you did. You could only imagine how awkward the air would be if Button Mash found out that you banged his mom. All in all, you’ve had sex and it was time to play games and scarf down pizza.
“Heh, Time for Dr. MILFlove to relax and play.”
Author's Note
Warning: The Surgeon General has determined that this chapter will contain cheesy video game double entendres.
Anyways, I'm glad y'all like this so far. Show of hands, who wants Milky Way in this story? Ask and ye shall receive.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Hit The Showers(Windy Whistles)
Well, you’ve done it. You’ve conquered your first year of your two-year business and accounting program in college. With summer break having arrived at long last, you had more time for recreational activities that you so enjoy. One such passtime you like is running and jogging. Though it annoyed you that your parents forced you to be on the swim team, it did instill an obsession for physical fitness for you. In your line of work or the one you’ll be going into, it pays to have a healthy body for a fully functional mind. Even though you were no longer on the swim team, you replaced it with running. One of your favorite places to run at was the track at Canterlot High, which was closed for the summer.
“Come on, where are they?” you muttered to yourself as you looked down at your phone’s clock. “Rainbow dash said they’d be here by now.”
Rainbow Dash, oh how could you forget that name. Despite being from opposing schools, that didn’t stop you from hanging out outside of the education system. You first met her while she and her boyfriend Soarin were working out at Planet Fitness. While they were at the bench press station with Soarin spotting her reps, you walked over to them and stuck up a friendly conversation. Eventually, the conversation sparked a friendship between the three of you as Rainbow got done with her exercise. As you began your turn on the station, they were still there and wanted to what you were made of. You managed to bench 40 reps at 200lbs which made your arms feel like jello. From there on, You, Rainbow and Soarin became workout buddies. Though she and Soarin were dating, it didn’t make the friendship between you and Rainbow awkward, considering that you banged Principal Cinch a couple days before meeting her. Then again, you didn’t care about their romance from the get go.
Despite being done with high school, the three of you have this monthly tradition where you all would spend an afternoon running a track, depending on the weather. It was a nice way to stay connected, to do the things you all enjoy. As you were reminiscing on your earlier years, your phone received a text message from Rainbow Dash:
“Soarin won’t be with us today. He has an out-of-state family emergency. Will be there in two minutes.”
Well, the monthly workout will still go on but without the other member of your workout. Normally, the workout would’ve been rescheduled if such a situation came up but for Rainbow Dash to do it anyway sounded odd for sure. You wondered if she was bringing her equally athletic friend Applejack to stand in for Soarin. However, your thoughts were brought to an end when you saw Rainbow’s blue camaro pull up in the parking lot. You then decided to do some last minute leg stretches to stave off any leg cramps before the group workout.
“Heya Calc, sorry we’re late!” Hearing RD’s signature energetically impulsive voice, you turned around to see Rainbow Dash along with an older woman with her. She looked a lot like Rainbow Dash but just slightly taller, older looking and with a different hair color and style than her. At first your instinct thought her to be a sister she didn’t tell you about but you knew she was an only child. The woman runs up to you with the intent of giving a handshake.
“Oh hiiiiiii, you must be Calculus!” She says as she shook your hand. “I’m Windy Whistles, Rainbow Dash’s mom. It’s a pleasure to meet you!”
How you would describe Windy Whistles is this: Rainbow Dash might as well have been a near-perfect clone of her. They both look nearly alike with the spunky can-do attitude to match. However, for a woman her age, she looks relatively young to the effect of looking just slightly older than her daughter. From what you can tell from her breast size, she was a C-Cup, not too big but not too small, decent. She had a nice slender body from working out to the same degree as her daughter and her shorts made her nicely firm and muscular ass stand out, a nice size that would make you happily hotdog those nice buttcheeks.
“Nice to meet you too!” You replied. “What made you wanna workout with us?”
“My little Dash was somewhat annoyed that her boyfriend had to go out of state for an emergency. Being athletic as her in my haydays, I offered to tag along with her. Though she was reluctant at first, she eventually warmed up to the idea.”
“Yeah,” Rainbow Dash scoffed. “I know it feels weird working out with my mother here but I really didn’t want to miss leg day with Soarin MIA.”
“Well, a mother and daughter workout day it is then...” You scoffed as you joined them on the track between them, getting into a starting position. “Plus a friend. Though I’m not on CPA’s swim team, I still treat my fitness like a hobby.”
“Heh, for an egghead like yourself, you sure do work on a body to match.” Rainbow Dash chuckled at your statement.
“Yes,” Windy Whistles agreed “such a combination would make ladies everywhere swarm all over you, Calculus.” Her statement made Rainbow groan in embarrassment.
“MOM!” She shouted. “He’s right next to you!”
“Eh, I really don’t care, Dash.” You shot back with a laugh. “I know I’m somewhat attractive. I can’t help it.”
“Don’t let that get to your head, amigo.”
“I try not to.”
“Well kiddos, are you ready?” Windy Whistles chimed in. You and Dash both look at her and shook your heads in agreement.
With a count of three, the three of you began the sprint, working your legs as fast as they and your respective staminas can take. You were a little faster than Rainbow as you were able to keep a noticeable distance ahead of her with her mother taking the lead but out of your sight. As you were keeping your sprint in perfect tempo, you felt a something smack onto your right buttcheek.
“You gotta keep up, young man!” Windy Whistles sang as she ran ahead of you. It felt weird, not just that she did it, but because she had the audacity to do so in broad daylight in full view of her daughter. You anticipated it was gonna feel awkward when the workout was finished but you didn’t know for sure. All in all, you just wanted to focus on your workout and not skip a beat. For the next three hours, You, Rainbow Dash, and her mother continued the footrace before the setting sun told you that it’s time to stop.
“Holy shit!” You panted as you leaned down, palming your knees. “I’ll hardly get used to the feeling of my lungs burning.”
“Ah, tough it up, big boy.” Windy Whistles wheezed as she patted you on the back. “You’ll get used to it in no time.”
“Yeah,” You shot back “not when I keep upping the intensity. You gave me a run for my money, Ms. Whistles.”
“Heh, It’s funny when you got outclassed by my mother.” Rainbow Dash snarked to your annoyance.
“Yeah Dash, pull the other one.”
After the both of you caught your respective breaths, you all felt relaxed enough to move again with sweat drenching your clothes and bodies.
“Hey Calculus,” Windy Whistles called to you. “How did you get here?”
“I walked here actually.” You replied.
“You must be tired after all the jogging. How about you shower at my house and I’ll take you back to your place afterwards.” You were slightly stunned at Windy Whistles offer, more so in front of her own daughter. Even then, you were much too weak to walk back to your place to really care about that fact. Being grateful towards her offer, you accept it.
“Yeah, that sounds good.” You agreed to her delight.
“Hey Calc, you might wanna be careful around my mom.”
“Why’s that?”
“For starters, I saw how she was checking you out before we got started. Plus, I did see her slap you on the ass.”
“Uhhh, why should this worry me?”
“Because Calc, she’s, how should I put this… frisky. She’s very horny and frequency that she and my father have sex is one of the reasons I moved out. Ugh, the moaning and squeaking of the bed drove me nuts.” You feigned concern at her cautioning but you were no stranger to what she warned about. After all, you’re making yourself known amongst the town’s local MILFs and have no aversion to some ‘fun time’ with them.
“Don’t worry, I’ll be cautious around her.” You assured Dash to her slight relief.
“Okay then.” She said as she walked over to her car with you following her.
For the ten minutes on the road, the car pulled up to Windy’s house. It looked somewhat big but not as you imagined. Climbing out of the car with your duffel bags in hand, You and Windy Whistles walked into her house, still exhausted from the workout. Her living room was decorated with pictures of her daughter, some of them with herself and what looked to be her husband. You couldn’t help but let an amused huff that Rainbow Dash has such supportive parents that hold her in such high regard.
“Calculus, the bathroom is upstairs.” Windy Whistles said as she walked over to said stairs. “Here, I’ll show you where it is.” Following her up the stairs, you arrived at the bathroom at the end of the hall. It had all the usual stuff such a room would always have with the shower and the bath being an all-in-one deal. You walked in, expecting to have the first shot at cleaning up. To your surprise, you heard the door lock latch in place with Windy Whistles standing behind you with an all too familiar look. You were prepared for such an occasion but your stamina was starting to tell you otherwise.
“Mrs. Whistles,” You gasped. “I thought you let me go first.” Windy, however, walked in front of you and began taking off her shirt, revealing… absolutely nothing. There was nothing hiding her bare breasts from your sight, those soft and perky mounds that you like to squish in your hands. You blushed as she took off her shorts along with her panties, revealing a hairless flower that’s either dripping with sweat or from arousal, you couldn’t tell. She then climbed into the shower and turned on the hot water, hosing her entire body.
“What are you still doing standing there?” She asked as you looked her in the eye. “Come on, strip and join me.” Being the horndog you are, you oblige her and stripped off all your clothes and climbed in. Upon entry, you were hit by streams of soothing hot water, relaxing your aching leg muscles. As you stared at the naked form of Rainbow Dash’s mom, she turned around with a confused look on her face. “What’s the matter, Calc?”
“Uhhh, nothing.” You replied, gathering your thoughts. “It just… feels kinda weird being in a shower with my workout friend.” You could tell by the change in her facial expression that she didn’t buy what you said.
“Is that all?” Windy said as she walks over to you with water flowing down her slender figure. “Well, Mrs Cake told me about how you pleasured her like a beast. I know my body is awesome, judging by how you’ve been looking at it.”
“Heh, I guess word did spread more quickly than I realized.”
“Indeed.” She replied, snaking a finger seductively down your chest. “I used this as an opportunity to try you out for myself. However, since you did a good job during your workout, I’ll let you wash me first, front and back.” You were left slightly speechless at her offer. Windy Whistles, Rainbow Dash’s smoking hot mom, wants you to wash her first. You knew from the first time you saw her that you wanted to caress every inch of her hot body. Giving into your carnal desires, you take some body wash and globbed it in your hands and began lathering her arms with the soap.
“Mmmmmm,” She moaned as you went from her shoulders to her arms. “You have quite an amazing touch.” With every massage of her arms, Windy backed further into you until your now rock hard member made contact with her firm ass. It felt good to feel such a thing from an older yet athletic and youthful woman grind against your cock. “Please Dr. MILFlove, feel free to feel the rest of my body.”
With the mentioning of your alter ego, you needed no further persuasion as you moved your soapy hands from her arms to her tits, washing them with the palms of your hands. With every lathering, you felt the bump of her erect nipples against your hands. For some reason, you subconsciously began bumping your crotch against her firm rear end. Your member wanted it and it wanted it badly. However, you wanted her to invite you in for it, considering she brought you here to wash up instead of having to walk home for that.
With the moaning from her tit massage beginning to die down, you had to think of something more erotic and sensual. Keeping your left hand on her right tit, you slowly moved your right hand down her chest and stomach, sensually feeling the subtle hints of her pores on her silky smooth skin. Her breathing and moaning intensified as she felt the soapy and warm wetness of your palm glide across her flat toned tummy. Finally, your hand reached the beginning of her crotch. You balled up your hand with the exception of your index and middle fingers and massaged her crotch with them. Form the increased tempo of her breathing, you could tell she was enjoying this alot.
“D-D-Dr. MILFlove,” Windy Whistles panted in pleasure. “Go ahead, stick that cock between my asscheeks and hotdog me!”
There it happened, the invitation you’ve been longing for ever since you laid eyes on her. Your inner beast compelled you to stick your throbbing erection between her ass and grind like a madman. Briefly adjusting yourself but not taking your hands off of her, you nestled your rod between her firm yet cushiony buns, pulling her closer to as you grind against her ass. She knew that her ass would please you this way and you were doing good pleasing her as well. To you, this type of skin to skin contact was so good and intimate that it felt better than a blowjob. You loved every second of it as you and her moaned into the night without any care in the world. Moving your hand over her vulva, you took it in your hand, palming and massaging it as her screams heightened in volume.
Because you were palming her, you frequently brushed against her sensitive clit as you squeezed and kneaded her wet pussy walls. Soon, you felt the familiar pressure in your balls build up to its peak. You want to cum at the same time as she does to add to the collective pleasure between the two of you. Stopping your palming for a short moment, you took three of your fingers and slid them into her hungry wet sex. She was both surprised and enraptured at your change of tactics that you could’ve swore you saw her eyes roll to the back of her head in pure bliss. Eventually, neither of you could take it anymore as she squirts her juices all over your hand with you emptying your balls all over her back. Ropes upon ropes of your cum splattered onto her back as you held her tighter against you, wanting to hug her tight as you became entranced in orgasmic bliss. As your orgasms subsided, Windy Whistles collapsed onto the bathtub floor wit you following shortly after.
“Wow,” Windy Whistles wheezed, still reeling from her orgasm and wrapping her arms around your neck. “I’m impressed that you have such amazing stamina. You even make me break a sweat.
“The pleasure is all mine.” You said as you prodded her vagina with your still rock hard cock.
“My goodness!” She gasped in amazement. “You’re still hard?!” Looking her square in the eyes, you brought your face closer to her.
“Because… we’ve yet to do the main event.” You said as you touched your her lips with hers, partaking in a passionate kiss. As your tongues wrestled for dominance, Windy’s tongue fought with incredible ferocity. You eventually broke the kiss to breathe some air, knowing that it was time to do.
“Do it,” Windy Whistles begged. “Shove that big cock of yours into my pussy and ravage me like all the others!” The begging sounded hot and sexy. She really wanted to feel your cock inside her. You rolled your hips forward and slowly slid your member into her love tunnel until you were hilted. It felt incredible to be so deep inside Rainbow Dash’s mom that you couldn’t describe what it felt like. Exchanging smiles, the both of you resumed your passionate kissing as you thrust your hips forward, sliding in and out of her vagina. You kissed and fucked Windy Whistles with all your might as the still running shower continued to spray soothing hot water upon your bodies which made rubbing your bodies together all the more easier and pleasurable. In the spur of the moment, you sat yourself and her up and placed your hands on her ass and upper back, pulling the two of you closer as you continued to pump her pussy like you were starved of sex.
You began to feel the impulse of your orgasm on the horizon and you could tell she was there too, judging by how tightly her inner walls gripped around your shaft. You began to pull out, not wanting to risk getting her pregnant. To your shock, she wrapped her legs around your waist. Though she didn’t say anything else, you knew what she meant, what she wanted. As you picked up the tempo of your thrusts, a thought began to course through your mind.
“Holy hell, I can’t believe I’m about to cum inside Rainbow Dash’s mom! I can’t believe it’s happening. Though part of me wants to bail, I’m assuming she’s on birth control. You know what, fuck it. I WANT TO CUM INSIDE RAINBOW DASH’S MOM!!!”
And cum you did. You practically felt the contents of your balls explode inside her womb. The feeling of your hot seed exploding in her insides was enough to push her over the edge and make her orgasm all over your crotch. You held her in a deep hug for a few good minutes before you both collapsed back onto the floor. Breathing and panting and still reeling from your orgasms, you and Windy Whistles engaged in some post coital snuggling with some kissing to top it.
“Wow,” You said, looking at a tired Windy Whistles. “You felt extremely good.”
“I… know!” Windy Whistles breathed. “I’m just one awesome woman! How did you have that much energy after the workout?”
“Just had some leftover drive I guess.”
“Hmmm, It’s amazing that you have so much endurance. It reminds me of how me and my husband do it, but compared to how we just did it, you were slow yet passionate. I love it.”
“I’m glad you do. Speaking of which, where’s your husband?”
“Oh, he’s out with his brother, throwing a wild bachelor party before he gets married. He won’t be home until tomorrow night.”
“Well now, congratulations to his brother.” As you looked around the bathroom, you noticed the clock read 10:07 PM. You were amazed that you and Windy Whistles have been fucking for a little more than three hours. You wanted to pack up, get dressed, and go home but spending all of your energy made that impossible to do so. You let out a yawn as you snuggled back into her arms.
“Hey Calculus, do you want to sleep with me for the night?”
“Well... sure, why not? You agreed without an extra thought. After the both of you climbed out of the shower and dried off, You and Windy Whistles, still completely naked, walked into her bedroom. She climbs onto the bed with you climbing on top of her, looking at her with your own brand of bedroom eyes. You wrapped each other in warming embrace as you pulled the covers over your bodies. Giving her one last kiss, you rested your head on her chest and began to fall asleep. The last thing you remember hearing before you drifted to sleep was:
“I love you… Dr. MILFlove.”
“Heh. Dr. MILFlove, even to this day, you still got game.
Author's Note
Whew, managed to get this one written just in time for Valentines Day(took me 2 days to write it). Well, since one person in the comments wanted to see Windy Whistles as a subject of a chapter, I couldn't help but want to do it. Truth be told, this chapter in particular was inspired by Hit The Showers by Harm's Way, one of my favorite clopfics. So, this is the surprise chapter I was working on in parallel to Chrysalis's Chapter.
Anyways, I hope you enjoy this chapter and the story so far. Happy Late Valentines Day.
P.S.: When I had the O.C. say
"I WANT TO CUM INSIDE RAINBOW DASH'S MOM!!!"
, I actually had planned on that reference to that phrase pertaining to her daughter, seeing as how Windy Whistles is involved.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Candlelit Romance(Chrysalis)
“Fuck a duck!” You groaned. “Don't have the stuff for my cheat day meal!”
It was late October, well into your first semester of your second year in college. Despite being busy with your studies, you kept time aside to keep your body as fit as a fiddle. There are even days where you just want to let loose from your fitness crusade and indulge in the very things that aren't conducive to your regimen. One of these is enjoying the foods that you swore off for your diet.
One such food that you enjoyed was this asian noodle dish that Ignacio's girlfriend made for you two while hanging out last month. It had chow mein noodles with chicken, shrimp, peppers and onion with the whole thing flavored in savory teriyaki with hints of garlic. The first time tasting it felt like heaven made real. Being really polite about it, you asked her for the recipe for the dish which she gladly shared with you. Since today was the day you can try it for yourself, you were especially pissed that you forgot to get what you needed to make it happen. Fortunately for you, you had enough money to go get what you needed.
Taking about ten minutes by car to get to the store, the first thing you recognized was the produce aisle, rife with the fresh vegetables you needed. Grabbing some bags of peppers, onions, garlic and some chillies for an extra kick, you turned your attention to the exotic aisle where the last of the stuff you needed was there, the chow mein noodles and teriyaki. At that point, you could practically smell the dish cooking as if you were making it in that moment. Quickly grabbing the remaining items on your list, you turned back to your cart before you saw a familiar figure, one that you haven’t seen since high school.
“Chrysalis?”
How could you forget the name of Chrysalis? Back in your junior year of CPA, you took her sex-ed class. You recall the first day you took the class that you thought that the teacher would be old person. But to your surprise, Chrysalis stepped in and you almost felt your eyes jump out of your sockets at such a beautiful sight. Wearing a skirt with jeans, her hair long and flowing with the look silk and a nice keyhole sweater, it took all your strength to hide your boner during those classes. It was especially hard to do so when she was giving lessons on reproduction. You were always too nervous to ask a question in that class, let alone ask for help with the homework, she was just too damn sexy. Now, even as you caught a good glimpse of her, she still looked as sexy as she was back then that your ‘past experiences’ hadn’t prepared you for running into her for the first time since Crystal Prep.
“Holy hell, she still is smoking sexy like last time.” You thought to yourself as you pushed your cart to the checkout area. To your annoyance, the lines were rather long. You gotta blame the monthly sales for such an inconvenience. After a brief seven minutes, you got to check out and bag your groceries and leave. “Thank fuck that’s over.” You thought as you felt your stomach rumble with hunger. “Damn, gotta get home quick and cook this thing.”
Driving home, you decided to cut through the residential area where you encountered the least amount of traffic. It certainly felt relaxing to see the summer sun shine brightly through the trees as you move on through. As you approached an intersection, your eyes came across a familiar sight. It was Chrysalis and it looked like she was struggling to unload her van full of groceries. Wanting to use the situation to reconnect with an old teacher you secretly had the hots for, you parked on the boulevard near her house and climbed out, building up your courage.
“Ummm, Chrysalis, do you need some help?” She turns around with a confused look on her face, like she vaguely knows you but not all that well. As she completely turned around, you discovered to your shock that she appeared to be seven months pregnant. It paralyzed your legs in place to see that one of your crushes from high school was bearing a child.
“Yes I do, actually.” She said as she gripped more bags in hand. “But, how do you know my name though?” Taking a gulp of air, you prepared to bring an old memory to light.
“I’m Calculus, I was in your sex-ed class in Crystal Prep.” She crooked an eyebrow, still confused as to who you were. However, you stood out in that class as the nervous one that sat in the back, partially because of how beautiful she was. “I-I-I… *whew* was that nervous kid that sat in the back of class.” From that last statement, her eyes shot open as she remembered who you were.
“Oh yeah, I think I do remember you.” She said as she moved closer to you, putting the bags back in her van. Her bulbous belly was just short of touching yours. But then, she quickly pulled you into a hug, making your bellies touch each other. It felt awkward for sure, being hugged by a pregnant woman in broad daylight but the belly felt warm and oddly relaxing to the touch. “It’s really nice to see you after so long. How have you been?”
“Been doing good.” You replied, breaking from the hug. “Just making my way through the world.” You looked at the van’s trunk. It was full of bags of various stuff from the store, mainly food. You figured she had been there to take advantage of the deals after having been paid. “I actually saw you at the store earlier.”
“Did you now?” She replied “What were you doing there?”
“Just getting some ingredients for a cheat day meal. Been quite a fitness nut.”
“Oh yeah, I can certainly tell.” Chrysalis’s gaze turned back to her groceries with a look of worry and fatigue. “Hey, can you give me a hand with my stuff here?” Your heart beat at the speed of a rabbit. She was inviting you into her home. But then again, your intention was to help her out and allow her body some rest in her current condition. Without a second thought, you grabbed a load of bags and hauled them into her house. It looked cozy and nicely decorated with a fireplace as its centerpiece. She had some really good taste in decor. It took around twenty minutes to get everything put away, even your own stuff which she graciously allowed you to store for the time being. After everything was put away, you joined her on the couch where she was rubbing her belly.
“I was glad you helped me out back there.” Chrysalis said, rubbing her belly. “It wasn’t necessary but I appreciate the offer.”
“Well, I couldn’t have you overworking yourself when you’re this pregnant, Chrysalis.” You said as you found your gaze slowly drifting towards her protruding midsection. “I actually intended on stopping by and saying hello when I saw you at the store.” You grew more nervous as you continued to look on at her belly. The very sight of was oddly hypnotic to you and strangely enough, sexy. You’d never thought that after spending your time having sex with so many mature women that the thought of one being pregnant would make your dick tingle with excitement. However, you failed to notice Chrysalis staring at you with curiosity.
“Ummm, is there something the matter, Calculus?” Her question made you panic as you quickly looked away. You were embarrassed but you were also shocked as the fabled Dr. MILFlove has been left speechless by a pregnant woman. Unexpectedly, she put a hand on your shoulder and you jumped and shivered. “Calculus, are you okay?”
“S-Sorry, Chrysalis.” You stammered. “It was rude of me to stare.”
“You don’t have to be sorry.” She said. “I know my belly can draw a few glances here and there. I don’t mind if you do.”
“Ar-Are you sure?”
“Yeah, I can’t help it if the one growing inside me is making my belly big.”
“True. True.”
You were snapped from your conversation by a rumbling in your stomach followed by the most primal instinct known to man: hunger. Chrysalis was quick to take notice.
“Are you hungry there?” She asked
“Yeah, I was gonna make a noodle dish at my place.” You replied
“I’m going to make dinner here in a little bit. Care to join?”
“What are you making?”
“Hamburgers. Some delicious hamburgers.” You thought hard about what to do. On one hand, you wanted to have that noodle stir fry, on the other hand, you were just hungry and wanted something right away. Your primal desire for sustenance overruled your plans and made you impulsively accept.
“You know what, a hamburger does sound great. I haven’t had one in quite a while.” Your acceptance made Chrysalis smile with joy.
“Excellent. Why don’t you just kick back on the couch while I go make our dinner. Sound good?”
“Okay. Can’t wait to eat something, anything!”
“Oh, I think you’ll enjoy these hamburgers.” Chrysalis said as she retreated into her kitchen. Just as you heard what could be the pan sizzling, you began resting your head against the couch armrest.
As you drifted off to a short nap, you began having a dream of her… Chrysalis. The dream was about you and her, naked, on her bed, embracing each other while passionately making out. After breaking the kiss, you got behind her and locked her in a spoons position. You then began sliding your rock hard cock into her slit and began pumping and pumping into her moist wet sex as you caress her soft belly. Just as you were about to bust a nut in her, you were suddenly jolted awake by the soft slapping of your forehead. When you awoke, you were greeted by a protruding belly and a soft smile.
“Hey Calculus,” Chrysalis sang. “Dinner is ready!” Still choked up from the sight of her tummy inches from your face, you got up and nervously followed her to the dining room. What you saw plated on the table is what would make your mouth water like a waterfall. Two nicely grilled burgers, all topped with some sort of ketchup, some fried shellfish, a few slices of pickle and what looked to be hard boiled eggs on brioche buns, was staring you in the face. On her burger, the shellfish is notably absent, presumably because her condition forbade the consumption of such things, understandable. Part of you wanted to sit down and indulge right away. Being the gentleman you are with the pregnancy being hard on her body, you helped Chrysalis sit down before taking your seat. Both of your meals were served with some juice that smelled like apple and ginger, an amazing combo of flavors.
“So Ms. Chrysalis?” You broke the silence.
“Yes Calculus?” She replied as she took a bite out of her sandwich.
“I know it sounds awkward of me to ask but… who’s the father?” When you saw her cheerful face turn into a frustrated frown, it gave you a sense of guilt for bringing that subject up. It told you that how she got pregnant was something she wasn’t proud of. But, she did explain how it happened.
“I went to a party, made the mistake of getting drunk, one night stand and I later found myself growing a future child in me.” She growled. “Since that asshole doesn’t want to care for it, even though I considered the ‘other option’, I decided in the end to keep the child. I’ve always wanted kids anyway.”
“Yeouch.” You replied, feeling bad for her. “Are you fine rearing a child by yourself?”
“I’ll be alright in the financial side of things. My sister up north told me she’ll lend a hand.” You were amazed at how strong Chrysalis was in a situation like this, raising a child alone. From the time you first met her in school, she always postured herself as strong woman to match her beauty. Though you felt bad she’ll be single mother, her reassurances alleviated your worries. You always admired her for those properties, making her a tie between her and Cadence in terms of your crushes. “Go on, eat your dinner. You don’t want it getting cold now, don’t you?”
Taking the sandwich in your hands, you bit into it, making sure to get at least a bit of everything to get the full flavor. It tasted good, really good, like the most savory meal that’s odd looking but appetizing. Becoming enamored with the flavor, you took another big bite before taking a sip of the juice. It did taste like what it smelled like: apples and ginger.
“How’s the meal?” Chrysalis asked.
“I love it.” You said as you took another bite. “Where did you find out about it?”
“Found it from a video online, oddly enough. It just looked so appetizing.”
“That it is.” As you moved to take another bite, you felt your body getting hotter. At first you thought it was the AC but it felt cool when you walked in and it certainly felt like that outside. Then, your suspicions turned to the meal, wondering if there was something wrong with it. Seeing your slight discomfort, Chrysalis let out a chuckle.
“About the burger,” She started which alarmed you.
“What did you put in them?!” You blurted out in annoyance as the heat began to build up.
“All of the toppings on the burger are natural aphrodisiacs.” It shocked you for a moment but not for long. She was your sex-ed teacher after all and she knew all about how to sexually arouse people. “Oh and the drinks also has a bit of aphrodisiac as well.”
“So, you drugged me?”
“No, at least not with the burger.”
“Then why?”
“I’ve heard about your little sexcapades with some of the women around these parts. Cheerilee was all too happy to tell me.”
“Can’t say I’m surprised that word spreads around.”
“Well, since you’ve done a good job pleasuring a few of my friends, I wanted to treat you to something more… romantic.”
You saw her struggling to get up from her seat. With your gentlemanly instincts kicking in, you rushed to help her up. However, you accidentally found yourself holding her in a loving hug. You were both blushing with a shade of red so deep that it made it look like the color of Pinkie Pie’s hair. You found yourselves slowly leaning into each other as you puckered up for a kiss, only to be denied that pleasure by Chrysalis, holding a finger to your lips with a teasing smile.
“Not just yet.” She said as she left the hug. “I want to set up the scenery a bit.”
“What did you have in mind?” You asked.
“It’s a secret, Calculus. Why don’t you go into the guest room down the hall behind you and wait there. I’ll call you when I’m ready.”
Your excitement was an an all time high as you plopped down on the bed in the guest room. Imagination ran wild as you pondered what Chrysalis would do. The big thing on your mind was finally hooking up with the second of your two crushes from CPA. Desire went to new heights as you imagine groping her nice milk filled titties while passionately making sweet sweet love to her, much more different and much more passionate than the last six times you had sex. Just the thought alone was enough to make your dick erect.
“God damnit.” You mumbled to yourself as you began rubbing your bulge to satisfy that itch for the time being. You for sure knew how this was going to end but in what way was a mystery to you. Since she was your sex-ed teacher, Chrysalis possibly knew every trick in the book when it came to seduction and sex. Hell, you wouldn’t even be surprised if she had a copy of the Kama Sutra. You spent about twenty minutes rubbing your clothed member before a voice called out to you, a voice as smooth as silk.
“Calculus, I’m ready!”
There it was, Chrysalis’s call of seduction. Like you were rehearsing for a play, You walked out of the room to a sight that nearly stopped your already racing heart. There was no light in the living room, save for the lit up fireplace and a few scented candles on various perches. There were rose petals scattered around the floor, all, leading to a figure that was the subject of your earlier fantasy. There was Chrysalis, dressed in a green ball gown that had only a single strap on the back of her neck that kept the top in place. The dress had hugged offered enough support to her belly and breasts. In fact, It made them stand out and the breasts seem bigger than normal. You were left speechless at such a romantic setup.
“Hello there, Calculus.” Chrysalis said as you slowly entered the living room. She had her hair in a bun with enough length to dangle down her back. She then walks seductively towards you, making your spine tingle in anticipation. “I hope you like what I did here.”
“I-I-It looks… nice.” You stuttered to her amusement.
“Your tone gives me enough hint.” She pulls out a remote and presses a button. A few seconds later, some music plays through her room wide speaker system.
The music sounded like jazz, like the slow kind of jazz that romantic couples dance to. As the music entered your ears, her intentions became clear to you. Chrysalis, your old sex-ed teacher wanted to dance with you.
“Come on…” She said with an arm out, gesturing you to come forward. “I know you want to.”
Finally giving into your desires, you walk up to her and wrap one hand around her waist while taking the other one and holding one of hers up. She then rests her free hand on your shoulder as you pull her into you, beginning the dance in earnest. It felt good to finally be that close and that intimate with one of your crushes, despite her being pregnant. In fact, her belly touching yours felt nice, warm, exciting and soft to the touch. You two swayed from side to side as you and Chrysalis danced to the tune of the song. Slow yet sensual, the romance was certainly in the air.
As the song was nearly over, Chrysalis wore the fabled bedroom eyes and leaned in slowly towards your face. Knowing her intent and with your blood still boiling from the aphrodisiacs, you closed the gap between you two and locked your lips with hers, sharing the most intimate kiss you’ve ever had and pulling your bodies close. But, the kiss felt different than last several times you did with any women. It had a feeling that wasn’t of just pure lust; It was of love, pure love, the kind of love one would feel for their significant other. For the first time as Dr. MILFlove, you had found a MILF you can call your ‘favorite’. The kiss lasted until the song ended to which Chrysalis broke it and switched off the music player.
“Wow,” You gasped, still reeling from the romantic experience. “I’ve never felt my heart beat like that apart from working out.”
“That’s called love, Calculus.” She said as she placed a hand over your heart. You blushed harder than before as your heart rate grew faster. “I can tell by your heart that you want me… and you like this.” Taking your hand, she walked you to the couch, directly in front of the fireplace. As you sat down, the both of you looked on at the dancing flames, going in all sorts of weird directions in a mesmerizing dance. Chrysalis then leaned into you as she wrapped her arms around you and rested her head on your shoulders.
“You’ve really went the distance for this, Chrysalis.” You said as you rested an arm on her left shoulder. “I’ve never experienced romance like this before.”
“Well, you’re in for a treat *chuckles*, Dr. MILFlove.”
“I like it when you call me by my nickname, Chrysi.”
“Chrysi, that sounded cute.”
“It’s meant to be.” Upon hearing that, Chrysalis unhooked one of her arms from around you and grabbed your free hand, placing it upon her large belly. It felt strange at first but you warmed up to it, feeling the warmth and life that she grows within her. It was pure intimacy as you sighed and hummed while brushing your hand across the surface of her tummy. However, you wanted to change things up as you knelt down and placed your lips on the belly, giving it a long and loving kiss. Chrysalis seemed to enjoy it, even laughing a few times as you gave it a few light pecks which tickled her. But then, you craved more. You wanted to go all the way with her.
Slowly climbing back on the couch, you hovered over her as you held her in an embrace like the one from the dance and slowly touched her lips with yours. You moved your hands around her body and began to dry hump her as she moaned in your kiss. She enjoyed it, you enjoyed the she fact she does as you began to ramp up the passion. However, you surprised as she pushed you to your back as she climbed over you with a look of hunger in her eyes.
“You know, Dr. MILFlove…” She purred. “With my pregnancy, my hormones are on the fritz and that makes me exceptionally…” She then nibbles your ear for a bit but enough to make you shiver exponentially shiver. “Horny.”
“What do you have in mind then?” You asked to her delight as she climbed off the couch and turned her back toward you. She then fiddled with the dress strap on her back until you heard an audible click. Letting go of it, she lets the fabric fall to the ground which presented you with a sight that made your dick become rock hard with excitement. She was wearing nothing at all, no bra, no panties, not a damn thing. There she was, your old sex-ed teacher, naked and pregnant in front of you. You knew you were going to be in for a good night.
“Your shirt, get rid of it.” Doing as she ordered, you removed your shirt, exposing your toned chest for her to see. She was giving you that hungered look as she started to lick the surface of your chest until she reached the hem of your jeans. She proceeded to unbuckle your belt and unbutton your pants, dragging it and your underwear down, exposing your already hard member for her to see. Judging by the way she looked at it, Chrysalis hungered for your cock and she was going to get it.
She sandwiched your shaft between her milk-swelling breasts and began rocking them up and down your length. Compared to the other titjobs you’ve had before, this was the best you’ve had so far. The feeling of your cock being massaged by her warm milk filled breasts felt like… well, you couldn’t really describe it at all. It felt that good. What she did next is what would be a test of your endurance. She gave a light peck on the tip of your spear, giving it a good few licks before taking it into her mouth. Your stamina was being tested as the combined warmth of her wet mouth and the softness of her mounds began to eat away at your endurance, your willpower not to cum. You badly wanted to explode your load into her mouth but you wanted to enjoy it for as long as you can last and to make her happy. Eventually, your willpower ran out as you couldn’t hold it in any longer but you were able to pull out in time and aimed your cock at her belly. With one good stroke, you shot your semen onto her belly, decorating her rotund tummy with your sticky seed.
After your orgasm subsided, Chrysalis left your side as she began lining up various pillows in front of the chair near the fireplace. Your heart raced in anticipation of being able to mount Chrysalis and fucking her. Chrysalis however, had other plans in store for you.
“Come,” Chrysalis said, patting a hand on the pile of pillows. “Lay back on this.”
“Wouldn’t this be the part where I take the lead?” You sarcastically quip.
“Calculus, You’ve spent so long taking the lead that I think you deserve a rest. Now, come here and lay down. I’ll take the lead.” Heeding her words, you walk over and laid upon the bedding of pillows. Not long after, Chrysalis mounted you, rubbing her dripping wet slit against the tip of your spear, sending shivers throughout all your nerves. She then took your cock and lined it up with her vulva, spearing herself on your length. It felt incredible, a whole new feeling, being inside your crush while she’s pregnant, exotic and erotic.
She then takes your hands in hers as she begins riding your cock. Gradually increasing her pace as she rode your length, Chrysalis leaned closer to you, allowing her belly to rub against yours as she pressed her lips against yours. Abandoning the hand holding, you wrapped your arms around her back as she began riding you harder.
“OH YEEEEESSSSS, DR. MILFLOVE!” Chrysalis loudly moaned as her hips continued to pounce on your dick. “YOU CAN’T IMAGINE HOW LONG I’VE WANTED TO BE FUCKED SINCE THAT DAY!”
“I can certainly tell!” You grunted as you kissed her back. You groaned and moaned as she began going faster than ever, pushing you and her to the edge. Her inner walls began to tighten around your pole as they eagerly desired to milk you for every drop of your cum. Soon, you were at your peak and couldn’t take it anymore.
“Chrysalis, I’m… gonna cum!” You groaned as you held her tight, feeling your orgasm draw closer.
“Go ahead!” Chrysalis breathed. “Fill me up to the brim!” After that, you couldn’t hold it in any longer and busted your life giving seed into her warm vagina. Every pump of your cum sent you and Chrysalis deeper into orgasmic bliss. You held each other tight as you kissed in front of the fireplace. As your orgasm drew to a close, you expected to be tired out of your wits. But oh no, you still had the energy to go a couple another round, same for her.
“Goodness!” Chrysalis sighed in slight exhaustion. “You’re still hard! Care to go for one last round?”
“Yeah,” You panted. “I’m not tapped out yet!”
You sat up as Chrysalis speared herself on your still erect shaft with her back facing you. It was perfect; She sat against you in a position that allows for easy access to fondle her belly and succulent boobs. You groped and grabbed at her breasts and midsection as she rode on you, reverse-cowgirl style. Without any thinking, you kissed up her neck before your lips made contact with hers once more. Both of you were lost in passionate love as you saw an opportunity to take control. You held her tight and laid down on the pillows, going from reverse cowgirl to spoons.
“Spoons?” Chrysalis asked with amusement. “You want to do spoons?”
“Yeah, I thought it would be romantic that way.” You replied.
“Well, don’t stop thrusting, Dr. MILFlove.” With the utterance of your pseudonym, your lust went into overdrive as you lifted one of her legs up and resumed your thrusting. Still buzzed from the aphrodisiacs from your dinner, you still had some energy to spend and spend it on one last fuck you will. Thrusting and pumping your cock in and out of her wet and hungry sex, you grunted with passion and lust as you enjoyed another round of humping another long time crush. You enjoyed every second of being in that position with Chrysalis, a romantic way to top off an evening like this.
Eventually, like the sweetest of candies, all good things must come to an end as your energy burned out, causing you to shoot the last of your load into her hungry pussy. You growled in sheer orgasmic pleasure as you busted your nuts in Chrysalis for the third and final time tonight. You felt like you were in heaven. With your orgasm dying down, you cuddled behind Chrysalis, hugging her from behind as you felt her heartbeat with your hand.
“I hope you liked our little… dance, Calculus.” Chrysalis moaned as she placed her hands on yours. “I know you like to feel my heartbeat. It beats for you.”
“So does mine,” You say as you peck her on the lips. “For you that is.” It’s true, you feel feelings for Chrysalis. However, your identity as Dr. MILFlove would seem to put your heart’s desires into uncertain waters. But then again, you do enjoy the idea of a ‘personal favorite’, a notion you have to keep secret.
“You’d better watch out for my friends, stud.” Chrysalis whispered. “They can be quite the opportunists.”
With her words, you could tell she gave you her blessing to continue with your ‘line of work’. Every MILF in town still wanted a piece of you and you can’t fathom how they’ll react when you chose to settle down with one lucky woman. But then again, you found yourself better at keeping secrets as nervous at times as you can be. Taking a moment to give some thought, you noticed the candles have burned out, saving you the trouble of having to put them out. The fireplace was starting to get that way as well. Leaving Chrysalis’s side for a moment, you fetched a blanket from the nearby couch and draped it over your bodies, rejoining Chrysalis in post coital cuddling.
“Chrysalis,” You started. “Though Dr. MILFlove doesn’t limit him to just one lady,” You gently placed your hand on her belly and held her close once more. “He does have room for a ‘preferred client’.”
“You cheeky stud.” She moaned as she began to fall asleep in your arms. “I might have to take up on that offer in the future.” With her finally asleep, you feel the pull of slumber bearing down on your mind. As your eyes begin to shut close, you rubbed your cheek against hers as you let out one last yawn before you go down for the night, content and satisfied.
“Well, there’s a first. Dr. MILFlove found himself a ‘special ladyfriend’. She’s something special alright. Gotta play this cool though.”
Author's Note
Sorry this took a while to write. I wanted to make this chapter a little longer because I felt that it would be better that way. Also, sorry if the whole pregnancy fetish of this chapter possibly might not be your cup of tea. I came up with it to try something new as per the story description of including some kinks that aren't too gross. Truth be told, I originally planned on releasing this for valentine's day instead of Windy Whistle's chapter. Anyways, I hope you continue to enjoy this story so far. Your feedback is what matters the most.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
One is good...(Celestia & Luna Part 1)
Spring break had arrived and you couldn’t be any happier. It was an excellent time to wind down and relax to vent all the stress from your last semester of college. To top all of that, your job hunting has paid off when you got an entry-level position with the accounting department at the Friendship Games association. You were always good with numbers like such a skill was coded into your genes.
Though the job had fairly decent pay, you took up another job to make ends meet and have some pocket change to whatever you want. You started a small lawn mowing service, giving lawns a quick trim on a client by client basis. You charged a reasonable rate that sounded good to your clients and they were pleased with the results. Today, you were going to your last client for the weekend in some nice part of town, not too fancy but nonetheless cozy and lively.
“Okay, here’s the place.” You muttered to yourself as you parked your car in front of the house. It was a two storied deal with a brick-like finish; rustic yet pleasing. As you unpacked your mower, a feminine figure emerges from the house. She had a perfect hourglass with perfect ass/titties size ratio, four-colored flowing hair and wore a white t-shirt with a pair of purple shorts. You recognized her as Celestia, principal of Canterlot High. You even caught a glimpse of her during the last friendship game you competed in. Immediately as your gaze met hers, she rushed over to give you a hug.
“Oh hey, you’re that one kid from Crystal Prep’s swim team!” Celestia said as she hugged you, planting your head in her breasts. “How have things been for you, uhh-”
“Calculus.” You finished for her, breaking the hug. As much as you liked her pillowy soft breasts, you came here to mow the lawn of your rival high school’s principal and had to keep on task.
“Yeah, right. Sorry about that.” Celestia chuckled as she dusted off your jacket. “So, the only things you really need to do is mow the front and back yard. I have no dogs so there’s no worry for you when you move to the back yard.”
“Thank goodness for that one.” You replied. When you first started the service, you worried that you’d wind up accidentally letting your clients pets loose when you did your work. Though you were careful as humanly possible, you were always cautious about such a thing, lest you get a bad rep. You began to pull the mower out of scrap bed your father lent you, moving it onto the front lawn.
“Well, I have to go back in and take a bath. Meet me inside when you’re done, okay?”
“Will do, it shouldn’t take me too terribly long.”
“Okay, seeya!”
With her retreating back into her house, you revved the engine on the mower and went right to work. The vibrations of the engine coursed through your arms while the scent of freshly clipped grass filled your nostrils. With each pass, your progress became clear as the lawn looked more trim and proper. As you continued to mow, you couldn’t help but think of the titty hug Celestia gave you earlier. Her chest pillows were a solid E-Cup from your view, just right but not any less pleasing. Just thinking of her luscious mounds made your cock become fully erect from the imagery of sticking your member between those warm and soft breasts. As much as you wanted to head inside, whip out your dick and start masturbating, you had to focus on your job. Once you started something, you had to see it to the end.
“Well, front yard is clipped,” You muttered as you looked on at the sight of a beautifully trimmed lawn, inhaling the scent of trimmed grass. “Time to trim the back lawn a bit.” You opened the gate and entered the backyard. There was nothing special about it with the exception of the garage next to the grassy field. It was quite spacious with room for some additions if the city would allow for such things. Wasting not another moment, you got to work and mowed the back lawn, going upwards in a left to right pattern until you reached the fence between Celestia’s lawn and her neighbor’s. After about four minutes of lawn mowing, your job was finished at last and you loaded your mower back onto the scrap bed and hooked it in place.
“Well, another job well done.” You said as you wiped the sweat from your forehead. “Time to ask her about my pay.”
As you enter the house, you couldn’t help but admire the decor she used for the living room. Exotic looking vases and beautiful arrangements of flowers. It looked so beautiful that you could almost stare at the whole display forever. As you looked on, your ears caught the whisper of a sound coming from one of the nearby rooms. You walked down the hall and found the noise getting louder. Eventually, your search brought you to the bathroom door where your heard the splashing of water and a sound as smooth as silk.
Seeing the bathroom door was slightly open, your jaw nearly dropped to the floor at the sight you beheld. Celestia was taking a bath, massaging soap into her tits as she sang. You were amazed that she had the voice of an angel. It was the perfect seduction tool to match her beautiful physical form. Every note she hit was done so perfectly that it made your spine tingle in fascination. Without warning, Celestia began groping her boobs with one hand while another sank into the water and towards her crotch, moaning as she rubbed her submerged slit. To you, this was the straw that broke the camel’s back… or rather made your dick erect once more.
“Oh for fuck’s sake.” You muttered as you started unzipping your pants. “Might as well, I guess.” Rubbing your hard-on, you pulled your pulsating manhood out of your underwear and started stroking your cock at the sight of Celestia’s naked form pleasuring herself in the sudsy bath. Her voice, even while moaning is pure lust given sound. As her moans intensified, you couldn’t help but stroke harder at how hot the display was. You fantasized about stripping naked, diving into the water and fuck her then and there. You so wanted to do so, badly.
“Enjoying the view, Calculus?” You jumped the moment those words reached your ears. How in the world did she manage to see you beating your meat to her? Oddly enough, you kept stroking your shaft as if the very thought of getting caught turned you on. Allowing your mind to recover from the surprise, you stopped stroking, bet kept your erection in your hand.
“I’d be lying if I said I wasn’t.” You remarked as you entered the room, knowing that Celestia didn’t seem to mind. Celestia then turned to face you. Once her gaze met the sight of your lap howitzer, her surprised face turned into one of hunger and lust.
“Well, since your cock is already out, you might as well just strip right now.” Needing no further incentives from her, you quickly took off all of your clothes. Once Celestia saw you completely naked, her lust only grew in intensity. “My my, you have a nice body.”
“Why thank you,” You replied, feeling flattered. “I still kept myself active since high school. It’s actually been a bit of a hobby of mine.”
“I can tell. You know, you look so dirty and sweaty from being out in the sun and mowing my lawns. Why don’t you jump in the tub with me? I can wash your front.” Celestia then spreads her legs and gestures with a finger for you to come over. You couldn’t hardly believe it; the woman you were masturbating to seconds ago had invited you to lie back on her front while she washed yours. Your mind tingled at the very imagery of you being fondled by a woman that could be mistaken for a goddess. Accepting her offer, you climb into the water filled tub, laying your head on her soaking wet breasts. The water felt hot yet soothing. In fact, your aching leg joints from yesterday’s workout started to relax. All in all, it felt good, especially when you’re laying down on a prime example of female beauty.
Celestia then reaches for a scrubber, lathering it with some lavender-scented body wash and began scrubbing your arms. It felt like the most erotic thing you did in a bath since your time with Windy Whistles several months back. Being cleaned like this felt incredibly erotic as a MILF looking so amazing was scrubbing you spotless.
“So, how do you like this?” Celestia purred as she moved to your chest, brushing the scrubber all over your torso.
“Very much.” You shot back. “You certainly have the magic touch there, Celestia.”
“Oh, you flatterer.”
“Well, keep doing what you were doing. It feels great.”
You couldn’t help but relax at Celestia’s arousing method of scrubbing your bare chest. You enjoyed every minute of the nicely-scented soap-lathered scrub ball moving across the surface of your body. You could say it almost feels ticklish to the touch. The one thing that gave you slight pause was Celestia moving her soap covered hand down to your throbbing pecker, gripping it in her slick hands.
“Woah,” You gasped, briefly shaking at the touch. “A surprise to be sure but a welcome one.”
“Did you really expect me not to get a piece of you today?” Celestia quipped with a sly grin.
“I was sorta tipped off to it when you gave my face a tittyhug.”
“Oh, breastman aren’t ya?”
“No preferences. I like every part of the female anatomy.” With that, Celestia began jerking at your cock. You arched your back slightly at such a pleasurable feeling. “And I must say, you’re good with with your hands.”
“Hmmm, I’ll take that as a yes.” Celestia moved her head and yours into position for both of your lips to connect. You couldn’t help but moan in her lips as her tongue invades your mouth and wrestles your tongue into submission. You didn’t want the only one to feel pleasure and you wanted to hear those sweet seductive moans from earlier. Moving your only free hand, you felt around the submerged part of her body until you felt a wet hairy presence. That’s when you knew you found her pussy. You had to admit, from what you felt, she had a perfectly sized bush, not too big nor too small. After feeling around a bit more, you found your prize: her clit and her puffy slit, eagerly waiting to be fondled once more.
“AAAHHNNN!” Celestia moaned as you brushed two fingers across her throbbing clit. “You certainly know how to treat a lady right.”
“Hey, I can’t let myself have all the fun.” You scoffed as you vigorously massaged her love button, hearing those sensual moans escape her. Soon the moans turned to gasps as she quickened the pace of her ministrations on your dick. You feel your balls tighten as they became full of your seed. You wanted to release but you had to endure at least until the beauty upon which you lay was ready for her release.
Thinking quick, you pushed your fingers past her slit and proceeded to fingerbang her with the same vigor as rubbing her clit. In fact, the position your hand was in also allowed for her clit to have some attention, further intensifying her pleasure… and the frequency of her handjob. The both of you moaned from the build up of pleasure as your respective genitals began to throb and pulse with lust, yearning for release. Your grunts and her screaming only increased in volume as the pleasure rendered you incapable of speech.
Eventually, both your respective limits were exceeded and your cock began to throb. Not wanting any of your own spunk in your eyes, you aimed at the wall opposite and painted it white with your cum. Celestia’s inner walls constrict around your fingers as she squirts her juices all over your hands. Though they were both submerged in water, your hand still felt the force of her vagina releasing its fluids.
The water was still fairly hot as you and Celestia recovered from the release of your orgasms. Panting and heaving with exhaustion and sweat, you snaked an arm to the back of her head and planted a loving kiss on her lips.
“Wow,” Celestia breathed, still recovering from her orgasm. “Your reputation definitely precedes you, Dr. MILFlove.”
“*rrrrrraaaooooww* What can I say? I aim to please the foxier ladies.”
“Prove it to me.”
“How?” You asked, feigning confusion. Celestia brings her head to your ears and whispers.
“Take that big fucking cock of yours and ravage me like a beast.” All the hairs on your arms stood up in anticipation for some nice bath sex. You never had sex in a bath before and you find the idea interesting. Turning around, your eyes contact with Celestia’s. Those sparkling royal purple eyes of hers combined with her warm smile made you throw your inhibition out the window, lunging at Celestia and kissing her with sloppy yet passionate pecks on her lips. Eventually, without any guidance, you were able to penetrate her hairy hungry cunt. She moaned as your cock was able to penetrate her warm sex, lubricated by the water. You pushed further in until you were stopped by her cervical barrier.
“OH GOD! YES! THIS IS WHAT I WANT!” Celestia screamed in rapturous pleasure. “PLEASE DR. MILFLOVE, FUCK ME! FUCK MY BRAINS OUT!”
You began pumping in and out of her snuggly warm love tunnel, taking in every bit of pleasure of your cock thrusting deep inside her. With every thrust and lust driven movement, water splashed everywhere, making a huge mess of the bathroom; but, neither of you cared as lust blocked anything else but sex from your minds. You proceeded to engage Celestia in an open mouth tongue kiss, wrestling your tongue with hers like it was one of those pay-per-view wrestling matches you watch with Soarin’ and Rainbow Dash.
“D-Dr. MILFlove,” Celestia moaned out. “I’m a-about t-t-to cum!” You felt the same way as her inner walls started to constrict tightly around your member. It made your balls tremble and pulse with pain as you desired to make this moment last as long as your endurance allowed. “Please, fill me up with your seed.”
“Wait, won’t you get pregnant?” You asked with caution which was turned to worry as her legs wrap around your waist.
“No need to worry, the hot water will kill off the sperm. Besides, I’m already on the pill and so were the others you danced with.” At that point, with her assurance, you felt it was alright to release your thick cum into her womb… and release you did. With every shot of your seed shooting inside her pussy, her moans devolved into pleasured screaming as it triggered an orgasm of her very own. You continued to thrust your hips as you wanted to increase the pleasure for both of you. Soon, your orgasms died down and you and Celestia laid in the tub to recover before managing the strength to leave the tub.
“I suppose we can start talking about your payment.” Celestia said as she dried off her naked body.
“About that, this little session of ours can be considered payment to me.” You replied. Originally, you wanted to ask her for 20 bucks for mowing her lawn, but the sex you just had proved to you to be enough. However, being rather generous today, you wanted to give her some ‘extra service’. Turning to her naked form, you knelt down and scooped her into your arms, bridal style.
“My goodness! You’re no slouch in strength.” Celestia gasped in surprise.
“Well… I’m also no slouch in bed either.” You rushed her to her bedroom which she directed you to. Once there, you rested her on the bed and flipped her on her hands and knees, presenting her plump ass to you in all its glory.
“Please, fuck my pussy like you did before! It’s still not yet satisfied!” Taking position in front of juicy badonkadonk, you thrust your pelvis forward and penetrated her honeypot for the second time. Like last time, it felt great, but no less pleasing than the first time around. You have to admit, you like the doggy-style position. Ramming your crotch against her succulent rear felt rather pleasurable as you thrust forward like you were starved of water for days on end. Every scream, every thrust, and every smack of your pelvis making contact with her butt only served to fuel the horny beast within you. Soon, you felt the all too familiar pressure as cock started to throb.
“You’re about to cum again?” Celestia moaned with amusement. “Give me more of your seed! I want it!” You continued to thrust without any care as you began to shoot more of your sticky seed into her love tunnel as you hilted yourself against her cheeks, grabbing hold of them for dear life as you filled her up again.
Collapsing on the bed with her in tow, you cuddled her in the spoons position as you kissed up her neck before reaching her lips.
“Damn, you felt like a goddess, Celestia.” You said as you continued to grope her.
“You’re trying to deify me, aren’t you?” She moaned back.
“Not necessarily. Just making a truthful remark.”
“I do appreciate honesty.”
As you were about to move in for another kiss, you were stopped and startled by the sounds of door opening and a figure walking in.
“TIA! SISTER, WHAT IN THE FUCK ARE YOU DOING?!”
Author's Note
Dun dun DUUUUUUNNNNN!!! That cliff hanger though. Stay tuned for the next part. It's only gonna get steamier from here on in.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
...But Two is Better(Celestia & Luna Part 2)
You turned around and saw another woman standing in front of the doorway. She was shorter than Celestia and had a similar style of flowing hair but colored two different shades of blue. She did look familiar as you recall her always being next to Celestia during the friendship games. She was none other than Vice-Principal Luna, Celestia’s younger sister and she looked visibly upset.
“Tia, what the ever living hell are you doing?!” Luna screamed again.
“Oh nothing, Luna; Just having some post coital cuddling with a man who just fucked my brains out.” Celestia nonchalantly replied with an innocent smile.
“You know, I could fucking hear you from the entryway! You always were a screamer.”
“Oh please and you’re not?” Things were starting to get heated as you witnessed the two sisters bicker on about trivial issues between them. Gathering your thoughts and calming your mind, you motioned to speak up.
“Ummm, Luna, I do hope we can be reas-”
“QUIET!” Luna snapped at you, stunning you to silence. “You have a lot of nerve to just waltz in here and bang my sister!” Your heart raced as Luna shot you an angry look. She was incredibly pissed off. “You know what else is rude?”
“W-what?” You asked. Then, Luna drew a sinister smirk as she reached for the collar of her magenta dress shirt.
“You started the fun without me.” Her reaction didn’t confuse you much as you thought it would. In fact, it was surprising that she began to strip naked in front of you. Once the very last article of clothing had left her body, her stunning naked form was present in front of you. Her features were a little less than her sister’s but her attitude and hourglass figure made up for it and then some. The one thing that also stood out to you was that her bush was in the shape of a crescent moon. In that moment, you were in awe that you were going to bang two hot MILFs in one sitting. You screamed internally as your excitement reached levels enough for your cock to become erect once more. Fortune truly does favor the bold.
“Oh yes, now we’re talking!” You exclaimed with heightened glee. “Come, there’s plenty of room… on the bed.” Luna then reaches for her purse, pulling out a small pill and a bottle of water, ingesting them both.
“There we go, don’t want any unplanned pregnancies now, do we.” Luna wandered onto the bed, making you sit up. You expected her to pull you into a kiss but, to your surprise, she pushes you down with a palm to your forehead. Laying on the bed, Luna sat between your legs with a commanding smile on her face. You were at her mercy at that point.
“Now, I’m taking the lead, Mr. MILFlove.” Luna then lowers her D-cupped breasts down to your stiff member and sandwiches it between them. You knew right off the bat what was going to happen next when she started to rub those perky mounds up and down your pride.
“Oh lord, *uuunngghh!* how can your breasts feel this great?!” You groaned as Luna continued her ministrations. You got no response, only Luna further increasing the tempo of her titjob. She massaged your cock with her breasts in a variety of ways: up and down, squishing them, and sometimes moving them around independently. All of the various movements of her breasts continued to fill you with a tantalizing rush of pleasure. However, you only felt halfway to your release and the wonder was starting to slow and Luna was aware of it. Removing her breasts, she hovered her mouth over the tip of your spear and breathed her hot breath over it, making you shiver. She then began giving it slow yet sensual pecks that soon grew into light nibbling.
“Holy fuck, this is new and just so much!” You screamed internally as Luna continued to give playful nibbles on your tip. After a few more minutes of your speartip getting gnawed at, she finally takes the whole length in and bobs her head. You slightly arched your back as she got increasingly aggressive with the blowjob. You had to admit she had quite the drive. “Goddamn, she gives really good head!”
Suddenly, you felt pressure on your balls, not the same kind of pressure you would feel when you were about to nut. It was a more forceful and squeezy sensation. Lifting your head up for a bit, you were able to see Luna squeezing and massaging your balls. It felt painful yet oddly pleasing. You didn’t think that having your nads being touched like a stress ball would feel amazing but it did.
You tried your damnedest to hold back the desire to release in her mouth but you could only take so much. As much as you wanted to enjoy the excellent blowjob, you could no longer hold back and released your seed into her mouth. Astoundingly enough, she still continued to suck. The pleasure... it felt paralyzing that she wanted every last drop of your cum. Once the entirety of your load was devoured, Luna removed your dick from her mouth and wiped some excess cum from her chin.
“Mmmm, delicious. How did you like my work?” You couldn’t respond as you were still reeling from your orgasm. “I’ll take your silence as a yes.” You were nearly helpless as Luna straddled your waist and aimed your still erect member at the entrance of her moist and hungry sex.
“I’m impressed that you’re able to keep an erection after I blew you like that. I wonder how good it’ll feel in pussy.” You weren’t able to utter even a whisper as you felt the sensation of Luna’s warm and wet walls devouring your cock as she impaled herself on you. She gasped and moaned as she hilted you deep inside her. So far today, you busted a total four nuts and now a fifth time is inevitable. It was like an endurance round and you couldn’t tell how much you were able to take.
“You’ve had fun with my sister and now it’s my turn.” Luna said as she rests her body on yours while keeping your member in her snatch. She gives you an authoritative smile as she places her hands on both sides of your head. She senses your weariness as gives a humorous chuckle. “Don’t worry, I won’t go hard on you… mostly anyways.”
She then dove in for a furious kiss and began to move her hips up and down your lap howitzer. With the amount of vigor and desire that fueled her movements, you had to wonder if she got around on a frequent basis. Then again, you really didn’t give a shit as she fucked you with the fury of an overly horny Aphrodite. She was forceful but she wasn’t without a modicum of grace as she rode you. She then lifted you into a sitting position as she continued to ride you, holding you tightly as she resumed her tongue wrestling match.
“Oh yeah, baby!” Luna moaned, breaking the kiss. “Your cock does feel exceptionally good. I can see why my dear sis screamed louder than she usually does!” When she resumed the kiss, your eyes drifted for a bit back towards Celestia. From what you were able to see, she was fingering herself and playing with her boobs at the sight of her sister going to town on you. She was clearly turned on by it and that’s what made it hotter for you as well. Still, your endurance could only take so much before you could no longer hold it in and your limit was fast approaching.
“L-Luna, I don’t know how much longer I can last!” You groaned as you neared the inevitable conclusion. She did heed your words alright… by going faster and harder with her ministrations. She really wanted you to release inside her, to paint the walls of her love tunnel a shade of cum white. With a few more forceful jumps, your loins gave in and opened the floodgates as you emptied your hot sticky cum deep inside her. The warmth from your seed was enough to send her over the edge as well. She screamed almost as loud as a banshee, making it amusing that she accused Celestia of being louder. A few minutes of your orgasm passed before the moment died down and you were left flaccid, slipping out of Luna’s snatch.
“Goddamn,” You breathed in exhaustion. “That was incredibly wild!”
“I know.” Luna snickered. “I like to be forward and forceful.”
“Yep, you sure made that abundantly clear.”
Luna then looked at your crotch and noticed your member was flaccid. From the look on her face, she wasn’t satisfied yet and was a little worried. Pondering for a moment, Luna came up with a plan.
“Ummm, Dr. MILFlove, why don’t you go sit on the chair over there while me and my sister have a word, okay?” Still exhausted from the prior experience, you lumbered over to the chair as instructed. Seeing you sit down, Luna motioned for Celestia to sit up and began to whisper in her ear.
“Tia, we have a problem.”
“What's wrong?
“Your friend's umm… equipment there has lost its energy.”
“I can see that.”
“Tia, I’m still horny and I know for damned sure that you’re still that way, too.”
“You do have a point. After all, it was quite a while since either of us saw any kind of action.”
“You know, come to think of it, I do have an idea that might revitalize him.”
“Like what, exactly?”
“Umm, remember the time we were in college and we began to *whew* ‘experiment’ with each other?”
“Luna?! You can’t possibly be suggesting that! That was years ago and what we did was a big taboo!”
“Well, from what I’ve seen in a magazine and possibly a porno or two, men get turned on by that.”
“Be that as it may. It’s still wrong and I regret doing that.”
“Oh please, like you didn’t enjoy what we did.” Celestia pondered for a moment and came to terms with the fact that she did enjoy her and Luna’s little ‘experiments’. As guilty as it made her feel, she found those moments to be pleasurable. Relenting, Celestia agreed to go along with with her sister’s plans.
“Okay, I’m in. What do you have in mind?”
“Just follow my lead, okay?” Celestia nodded in agreement. As you looked on at them, Luna turned to you with half-lidded eyes.
“Dr. MILFlove,” She said. “my sister and I are going to put on a little show for you. Just sit back and enjoy the view.” After she said her piece, Luna wrapped her arms around Celestia, one on her upper back and another around her ass. At that point, both their bodies were tightly against each other, stomach to stomach and breast to breast. Then, they closed the distance between their faces and locked lips in a lust filled kiss.
“Holy shit, this is hot!” You screamed internally as the sisters slowly made out. Their audible moans made your already racing heart beat faster. Just the sight of the two sisters engaging in such an incestious act felt so wrong yet so hot at the same time. Celestia the reached for one of Luna’s titties and began groping it while Luna began to massage her sister’s vulva. The moaning intensified as they got more into it. You had to guess that their ‘experiments’ were something they both enjoyed, due to the naughty nature of whatever they did. As they got deep into it, they fell back down onto the bed and began rubbing their bodies against one another. As they went on, you felt a familiar tight feeling coming from your crotch as your erection was starting to come back.
“I think our guest is starting to become aroused.” Luna remarks, shooting you a glance.
“Let’s take it to the next level, Lulu.” Celestia agreed.
“Heh, I always find it cute that you call me that.” Celestia and Luna then sat up and positioned themselves to where their vulvas were touching, eliciting gasps of pleasure. “It has been a while since we scissored each other.”
“Holy shit! They’re really going to do that! Keep still my ever beating heart!” Alas, your heart couldn’t keep still for a moment as they began to bump their vulvas together, moaning and howling into the air in pure euphoria. Every moan, every scream and every curse only further signified the passion they secretly had for one another, one that stretched beyond the boundaries of being merely sisters. They then resumed their kissing from earlier as they continued to scissor. The ever increasing frequency and volume of their lustful noises told you their orgasms were nigh. They went at it for a few more sweet minutes of erotic sister-on-sister action before their stamina couldn’t let them go any further and let their orgasms loose, staining the bedsheets with their juices. They both collapsed onto the bed once more as they heaved and panted in exhaustion.
“H-H-Holy shit!” Celestia gasped as she wiped sweat from her forehead. “This brings back so many memories!”
“Yeah, we also had a few close calls back then as well.” Luna replied
“Oh yeah, those times especially turned me on. Just the rush of nearly getting caught was so exciting.”
Luna then turned to face you and saw that your member was erect once more. She gives you a sly grin as she turns to Celestia and nods.
“I can see that your stamina has been replenished.” Celestia remarked. “Care to join us again?”
Accepting her invitation, you leapt back on the bed and flat on your back between the lovely sisters. They both gave you smiles as they gave you kisses on your cheeks. You swore you done nearly fainted when they did. Just the thought of being fucked by two hot MILFs at once nearly left you speechless. But then again, you’ve gotten lucky many times before and now it’s about to double.
“So, I’ve heard you’re a breastman.” Luna remarked to which you nod. She chuckled at your silence, finding it cute. “Come Tia, let’s service this man.” Celestia and Luna then hovered over your erect spear with their soft chest pillows and sandwiched it between them. You groaned at the sight and feeling of having two sets of titties was nearly too much for you, but you resolved to endure what they could throw at you. They then began using their breasts to give your dick a most sensual massage. God only knows that an opportunity like this is one in a million for any guy like yourself. They all began taking turns giving licks on your shaft, savoring the drips of precum that began to flow out of your tip. Each lick and rub from their boobs excited you exponentially as you began to grip the bed sheets like you were holding on to them for dear life.
“Holy Jesus, holy fuck! ” You screamed internally. “I can stand one at a time but two at once feels sooooo good! I’m not sure how much longer I can last against this!”
You were right as you were about to reach the peak of your orgasm for the sixth time in a row. When they both were giving your dick a lick, it was the last straw for you as your dick shot your seed up in the air, landing on their tits and faces. Subconsciously, you thrust your hips forward to feel the pleasure in its fullest. Managing to gather enough strength to sit up, you look down at your member and it’s surprisingly still erect. Your body and mind had enough for just one more go before you can consider yourself thoroughly spent.
“Damn, and you’re still not tired yet?” Luna remarked in amusement.
“No worries, I still have enough for just one more round.” You grunted as stretched your back. “So, what’s next on the list of events, ladies?”
Luna and Celestia nodded at each other as they once again embraced one another. This time, they fell down onto the bed with Luna on top.
“Come on, Dr. MILFlove,” Luna called. “Stick that cock of yours between our flowers.” As she began kissing Celestia, you crawled over to them and positioned your still throbbing erection in front of the two wet, puffy and hungry pussies. With one thrust forward, your cock is nestled in between them, making them moan as it brushes against their clits. You can feel them shudder and shake at your thrusts as you hump their cunts. You felt alive, like a wave of pure bliss washing over you, it was godlike. Feeling your drive spur into high gear for one last effort, you pick up the pace of your thrusts as you hold on to both of their hips, much to their delight if their moans and screams are anything to go by.
“Oh god, I think I’m gonna nut again!” You groaned as you felt your last release approach rapidly.
“That’s good! Coat us with your seed!” Celestia moaned.
“Yes, I want feel more of your cum on me! Give us all you got!” Luna cried out. At that point, you gave the last of your strength for the final assault and thrust harder and faster than ever before. After a few more good minutes, your cock throbbed and pulsed as you shot your seed in between the two horny MILFs. It felt exciting to cum between two women, like a dream come true for you. You felt exhausted as your final orgasm of the day was over and you collapsed next to Luna and Celestia with the later crawling to your left side. They began to fondle your chest and give you light pecks on your lips as they rest in your arms.
“Wow, never thought I would end up having two sexy babes like yourselves.” You yawned as exhaustion turned into tiredness.
“Well, after hearing about you, I just had to get a turn.” Celestia sighed.
“Yeah, and I couldn’t just let you have my sister to yourself.” Luna moaned in response.
“Yeah, I’m always open to sharing with my sis. Wouldn’t you agree, Calculus?”
“Yep, I couldn’t agree more.” You yawned as your eyelids began to feel heavy and slumber was about to lure you in. Before you were shut your eyes for the rest of the night, you were able to mutter one phrase:
“Hail to the king, baby.”
Author's Note
Well, here it is, the second part of the long awaited Celestia/Luna threesome. I really had a blast writing this and I hope you also have a blast reading it. Keep up with the ratings and comments because that'll tell me how good of a job I'm doing. Also, Ms. Harshwhinny is up next and that'll mark the beginning of a new story arc. I'm also open to revisiting at least some MILFs later on but not all of them.
Hope you all enjoyed the story so far!
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Sensual Spa Session(Ms. Harshwhinny + Bonus)
Author's Note
Well, here it is, the long awaited 10th chapter of this series of MILFs and Cougars, a milestone. Sorry it took so long for me to get this one out. I got caught up in a bunch of IRL stuff that I had to put this on the back burner for sometime. I'll try my best to keep a consistent writing schedule.
With all that said, enjoy this chapter, ya filthy animals.
Sensual Spa Session(Ms. Harshwhinny + Bonus)
Well, you’ve done it. After years of studying and refining your proficiency with numbers, you were able to land a job at the Canterlot Sports Committee’s accounting department. Spending a year as an intern, management saw fit to bump you up to a junior level accountant position. The pay was a significant improvement from your internship. However, you still felt your natural affinity with math and analyzing data was being underutilized. For one whole year, you languished in your post and cubicle, annoyed at the lack of actual challenging work. But, the pay was great and you get a cubicle with a nice view of the city and the surrounding skyline, a nice bonus.
It was late in the afternoon and you were filling out a few additional forms on your desktop to be sent to upper management. Reports, statistics, digitized paperwork that needed to be filled. With your skill set, you should’ve had some degree of authority by now but it seemed to be based on how long you’ve worked there. With a sigh, you finished up your workload and began to leave before the ringing your cubicle phone grabbed your attention. With an surprised ‘hmph’, you picked it up and answered it.
“Hello?” You asked.
“Mr. Crunch, I request to see you in my office at your earliest convenience.”
From the sound of the voice and the vocabulary, you knew very well it was your boss, Ms. Harshwhinny. From the times you’ve seen her, she carried that intimidating aura of professionalism that would even make Principal Cinch break a sweat. She would be quick to grill one over the slightest of errors that you mentally nicknamed her “The Drill Sergeant” due to how tight a ship she operates in the office. However, she had a body that was very slightly plumper than Mrs. Cake, curvy and very busty. But, your fantasies about bending her over desk and ravaging her like a maniac was overridden by the potential consequences of keeping her waiting.
“Okay, I’ll be there in a second. I was just finishing up my workload for today,” you nervously answered.
“Very well. I’ll be expecting you then.” After that, she hung up. Taking a moment to breathe, you began to ponder what she wanted of you. This was going to be the first time you had a one-on-ne meeting with her. You were nervous about so many things going wrong and reflecting poorly upon you. But, you had to retain a straight face for your own sake as you walked to her office. Opening the door, you were greeted by the sight of your blonde-haired boss, sitting at her desk with a clipboard in hand.
“Ah, Mr. Crunch, I’ve been expecting you.” Harshwhinny said, motioning a hand towards the other chair in her office. “Please take a seat.” Doing as you were instructed, you sat there with a calm expression, hiding your ever racing mind. “So, Mr. Crunch, I trust you’ve had a productive day. Am I correct?”
“Yes ma’am,” you answered, shedding a bead of sweat. “It was quite a lot, but it was nothing I couldn’t handle.”
“Hmmm... well, I suppose that was due to that focused mindset of yours.”
“I agree. But, why did you want to see me?”
“Well, I’ve been looking at your records here and it says you never took a break since you started out as an intern here. I will admit, I appreciate such devotion to your duties, but state law mandates that I give you at least two weeks off.”
“What? I mean, shouldn’t that thing be left up to you?”
Harshwhinny sighed, rubbing the bridge of her nose/ “I know, Mr. Crunch. But, I have to do this or I’ll be hounded by state officials. Do you have anything to do in your freetime?”
“Other than working out, nothing. To be honest, I find comfort in keeping myself busy.” Hearing those words from you, Ms. Harshwhinny thought of an idea that might work, seeing as how you were stressed as of late. But, there was something that drove her thought processes, the one thing that constantly surged in her mind like the deepest of desires.
“Well, I would like to make a proposition, Mr. Crunch.” She started. “I’m going to this spa in the city tomorrow at 8PM and I would like for you to accompany me there.” You were surprised at her suggestion. You’ve never been to a spa before in your life, let alone with your boss. You sat there with a shocked expression, stammering, trying to get a word out. “If it’s an issue about money, Mr. Crunch, I can assure you that I’ll be paying for the both of us.”
“Well, it’s not that.” You replied, breaking your stammering. “I mean, you’re my boss. Doesn’t this seem… unethical?”
“Unethical? Mr. Crunch, it’ll just be a simple massage and steam bath treatment. There’s nothing that would break workplace code about it. We’ll be in separate rooms for the treatment.” For a moment, your worries were diffused but Harshwhinny could tell that you still felt apprehensive from the look on your face. “However, if it will make you more receptive to my offer, you’re free to arrive earlier than me.”
It took you a few moments to render a decision, given the option that Ms. Harshwhinny offered you. The more you thought about it, the more you gravitated towards thinking that it wouldn’t be such a bad idea after all. In all honesty, your mind and body could do with enjoying a week off and having your stiff muscles relaxed away with a good massage. After all, you always thought that a good mind and body go hand in hand.
“Very well, Ms. Harshwhinny,” you said, straightening your tie. “I like the idea. To be honest, my muscles do feel stiff. A massage doesn’t sound like a bad idea.”
“Good,” Harshwhinny deadpanned. “I’ll be expecting to see you there when I arrive. Here’s the address and the time to be there by.” She hands you a notecard with the address of the place and what time to meet her there by. Putting it in your wallet, you shake her hand with the straightest face you’ve ever made, knowing Harshwhinny’s expectations for professionalism. “Oh, Mr. Crunch, I trust that you can find ways to keep yourself entertained for two weeks.”
“Well, I can manage.” With that, you walked out the door and made your way to your car. As you drove home, you began to wonder why she would choose you, a junior-level accountant, to join her for some time at a spa. You suspected her to have an ulterior motive, but her posture and expression didn’t give away any hint to that. You’ll have to wait until the next day to find out.
The Next Day - 7:20 PM
You arrived at the address Ms. Harshwhinny gave you, Canterlot Day Spa. It looked to be a rather nice place but pricey. Given that Harshwhinny is the head of the CSC, she could afford going here about once maybe twice a month. All you want to know is how good the service is, being the first time you’ve done something like that. Walking in, you were greeted by two women who staff the place.
“Hello there!” One of the women greeted with a semi-thick eastern european accent. “Welcome to Canterlot Day Spa. I’m Aloe and over there at the front desk is my sister Lotus. Do you have an appointment set for today?”
“No,” You replied. “I’m waiting on someone who does.”
“Okay, who might that person be?”
“Last name is Harshwhinny.”
“Harshwhinny? Oh, you mean ‘Julia’, right?”
“Julia, hmmm.” You thought. Apart from the interview invitation email, you never became familiar with her on a first name basis. “Yes. She told me to wait for her.”
“Well, her appointment isn’t until eight, so feel free to make yourself comfortable in the waiting area over there.” Aloe said, pointing to an area with reclining chairs, the type you find at theatres, only fancier. Sitting down on one of them, you unfurl the leg rest. The comfort, it was like something else entirely. You watched as Aloe walked over to her sister and looks as if she’s whispering something to her.
“Looks like Julia has a fuck date here.”
“Who, him?”
“Yeah, but he looks like he can hold his own. Maybe, maybe not.”
“Well, he’s going to be in for a wild ride.”
“Um-Hmm.”
Paying no mind, you sat back and allowed yourself some time to relax, relishing in the comfortability of your seat. For a while, you laid back and looked around at how well kept the place was. You surmised that the peaceful atmosphere contributes to the treatment, far from anything that would cause any unwanted tension. Your relaxation was interrupted by the ringing of a bell and the entry of someone familiar.
“Mr. Crunch,” Ms Harshwhinny greeted, clad in casual attire. “I must commend you on your punctuality.”
“Well, I’ve been waiting for about forty minutes, but it wasn’t a problem.” You replied.
“I can certainly tell you’ve had a chance to get comfortable before the therapy begins.” She then walks up to the counter and hands Lotus a bundle of money. “I’ll have the Ultimate Lustful Romance Special.”
“Sure thing.” Lotus replied as she put the money in the register, signaling Aloe to flip the door sign to ‘Closed’. At that point, apart from the twins who run it, you and Ms. Harshwhinny were the only living souls in the building, making you slightly nervous.
“Please, this way.” Aloe says as she escorts you to a changing room. “Now, strip down and put on that robe over there. It’s a full-body treatment.” You were at first hesitant with her suggestions. You didn’t mind being nude in front of women when it was appropriate. But being nude with your boss made you quake slightly. You were uncertain if word of what goes down here would spread and both your reputations would be destroyed, but then you realized that some of the money that Harshwhinny handed Lotus must’ve been hush money to ensure confidentiality. Being the head of the CSC, she has more than enough money to spare. After stripping down to nothing, you put the robe and walk out, being escorted by Aloe.
“Well, it feels kinda weird walking around with nothing under this robe,” you quipped.
“No need to worry about that,” Aloe replied. “For the treatment Julia paid for, nudity in front of the opposite sex is expected.”
“No doubt that she told you that she’s my boss.”
“She did, but we’ve sworn that we’d keep complete confidentiality about this matter.”
“Yeah, but it still feels sort of awkward.” You and Aloe reach a room where Ms. Harshwhinny is in a bath of mud and some sort of mask or her face with cucumber slices covering her eyes. You start to choke up over being in the same room as your boss, both of you naked.
“No need to be nervous, Mr. Crunch.” Harshwhinny said. “Only the four of us will have any knowledge of what happens here. Now, join me in the mud bath.” Still slightly hesitant, you slowly climbed into the bubbling vat of mud, resting near your boss. It felt weird at first but you began feel your muscles relax from the hot yet soothing mixture of spring water and volcanic ash. Lotus then began applying the same mask on your face, complete with the cucumber slices.
“What is the mud supposed to do?” You asked.
“Apart from doing wonders for your skin and circulation, it’s to help prep your muscles for the massage by loosening them, to make it feel more relaxing,” Harshwhinny explained.
“And the mask?”
“For cleansing purposes. And before you say anything, eating the cucumbers is not advisable.”
“No worries, I’m not much of a cucumber fan anyway.” You moaned. “Wow, this feels so good.”
“It’s good to know that you do.” Just as you were starting to get lost in the rapturious feeling, you feel a set of fingers gripping your right buttcheek. It startled you as Harshwhinny was the only other person in there with you and said hands were certainly not yours.
“Why would Ms. Harshwhinny do something like that?” You thought to yourself. “Now there’s definitely another reason why she brought me here. If it does end in sex, not that it’s a bad thing, I hope it doesn’t bite my reputation in the ass.”
“Okay, it’s been ten minutes.” Aloe sang as she and Lotus walked in. “Please climb out of the bath and step into the shower room here to rinse off the dirt. The massage is next.” Climbing out of the bath with Ms. Harshwhinny, the two of you walked into the shower room. The whole room was blanketed in a cloud of steam from the water coming from the showerheads. The curtains close and so do the doors. Once again, it’s just you and Ms. Harshwhinny. Here, you’ll finally be able to get some answers from her.
“Okay, Julia,” you started. “I know there’s another reason why you brought me here.”
“Well, I... thought you would do well having a nice massage therapy.” From the tone of her voice, you could tell her cover story was being torn down. You tried your best to not focus on your boss’s nude form. Her plump body, nice tits to ass ratio, and a well kept bush on her crotch, it felt so wrong to look at such a sight but it was hot at the same time.
“Well, I felt a hand grab at my ass earlier and it certainly wasn’t mine. You and me were the only ones in that bath. So, for both our sakes, don’t lie.” You braced yourself for what her reaction would be; being fired, getting your ass kicked, or both. To your surprise, she did neither, just a long sigh.
“Okay, very well.” She said, approaching you. “I suppose I should cut the theatrics here. I’m at that point in my life where I start to worry about my biological clock running out. I’m not sure how long I have unti- ah fuck it! I want you to put a baby in me!”
“What?!” You gasped, surprised but anticipated it.
“Yes, I want you to get me pregnant.” Harshwhinny circled you in a seductive manner, not characteristic of her usual demeanor. You just stood in place as she paced around you like a shark. “I’ve always wanted a child,but I’ve never been able to keep a long-lasting stable relationship because of my career. I got so close once, but my commitment to my career had been its undoing. I wanted a child to raise as my own, from my own womb.”
“Why not a sperm bank?”
“Sperm bank? HA! Would I honestly want any random man’s seed to fertilize my eggs?”
“But why me though?” Those words caused a stir in Harshwhinny. Her lust had overtaken her professionalism as you felt her surprisingly smooth hands move around your body, fondling your abs and even your lower region. It made you slightly shiver as you hadn’t had sex in a while.
“Well, I’ve taken a chance to study you since we’ve hired you. I have to say that you meet all my desired traits of physical fitness and intellect perfectly. You’re the type I want to impregnate me.”
“What about the potential bac-” Ms. Harshwhinny put a finger to your mouth, shushing you before the question could be finished.
“In case you were wondering, I have a high enough income that I won’t require you to pay child support. I’ll be fine raising a child on my own. As for word of what we’re about to do here, I’ve taken the steps to ensure no one else but the other two knows.” She still sensed a bit of hesitation within you. “However, I think we can come to an arrangement.”
“And what would that be?”
“As much as you try to hide it, I can still see that you desire a higher position with a better challenge and I do agree that your skills are being... underutilized, such a waste really. If you do this one small favor for me, I can bump you up to where a person of your mental caliber would be better suited… my personal assistant.”
Time seemed to freeze for a few moments as you were left astounded. Ms. Harshwhinny was willing to make you her personal assistant if you get her pregnant. You never saw it coming for all the time you’ve spent working for her. The implications seemed so wrong on an ethical level, but the thought of doing it with your boss, such a naughty act, turned you on and made your cock stand at attention. Harshwhinny grinned at the sight of your member, eager and wanting to be pleasured. You crave her and the reward she offered. There, you’ve made a decision and accepted her offer.
“Alright, I accept your offer, Ms Harshwhinny.”
“Ms. Harshwhinny?” She scoffed, pressing your body against you and wrapping her arms around your neck “I think we should do away with the formalities now, should we.”
“You didn’t even have to tell me.” You dove in for a deep and passionate kiss, grabbing handfuls of her juicy ass. All of that pent up testosterone over the last couple of years was finally let out as you moaned a beastly moan. You couldn’t help but enjoy the feeling having her flower against your shaft. For an older, uptight woman, her body looked and felt great.
“I think we should head for the massage tables, Calculus.” Harshwhinny said, breaking the kiss. “You’ll find it rather pleasing.”
“Anything about it I should know?”
“It’ll be a full body massage. So, they’ll be relaxing every muscle in your body, even your genitals.”
“Woah, so, they’ll be rubbing my cock and balls?”
“Yes, and don’t worry about ejaculating. It’s supposed to happen as a way to destress your mind and body.” She then walks over to the door and gestures you to her. “Now come on, we don’t want to keep them waiting, Calculus.” You walked with her to the massage room where Aloe and Lotus are standing next to two padded tables, big enough for a human to lay on.
“Please lie down on the tables here and we can begin the massage.” Both you and her did as instructed and took rest on the tables face down. Aloe would be the one to iron out the kinks in your muscles while Lotus would do the same for Harshwhinny. “For this treatment, we’ll be using a special vanilla-scented oil that is geared towards increasing arousal.”
“Hmmm, interesting.” You remarked as Aloe poured some of the pleasant smelling oil on your upper back and starts rubbing her semi-balled up hands along said region. With every motion, you felt your once tense muscles beginning to relax. It felt weird at first but the feeling of the soreness of your back leaving made it worthwhile. Plus, the heavenly scent of vanilla only served to calm your mind while also gearing your loins for some action. “Oh shit, this feels so good.”
“I’m glad you enjoy it.” Aloe giggled. “Is this your first massage?”
“Yyyyeeeessss,” you moaned back. “I’ve never considered- OH FUCK YES!- doing this before.” After she did your arms, Aloe sunk her oily hands further down your back, ironing out any knots before reaching your ass. If it were any other situation, other than a round with someone like the other cougars you scored with, you would’ve had some objections. If Ms. Harshwhinny’s moans were a sign, something like that was meant to be enjoyed. She then sunk lower and focused her efforts on your legs and thighs, starting from your feet. Her soft, slick hands moved further up your legs and eventually your thighs. As she grew closer to your package, you felt your cock beginning to harden.
“Okay, now please turn over so I can get the other side.” Like a rehearsed dance routine, you and Harshwhinny turned over onto your backs. Your cock immediately stood at attention, catching her by surprise. “Wow, the size of that thing.”
As she started work on your chest, you look to your left to see Ms Harshwhinny having her sizeable rack being worked on. Just seeing the size of those melons, you wanted nothing more than to just squish them in your palms as you nail her from behind. As you gazed on at such an arousing display, you failed to notice Aloe’s hands taking hold of your junk. The feeling made you snap your gaze back to her as she began applying light pressure to your shaft and balls. It wasn’t like the times you’ve had your cock handled in such a way, it was more gentle and it strangely felt better. As your balls tightened from the handjob, the corner of your eye caught a glimpse of Lotus brushing a spherical vibrator against Harshwhinny’s flower. Her moans, her lustful moans, you still couldn’t believe all that pent up lust was hidden within her but it still sounded erotic. However, like your boss, you too felt your release was about to arrive.
“It’s okay.” Aloe sang to you. “You may release when you want to.” She kept at it with her stroking and you did your best to hold on for as long as possible. It felt so good and you wanted it to feel even greater. But, try as you might, you couldn’t last forever as your cock throbbed, shooting streams of your hot seed into the air. Some of it landed on your chest while the rest landed on Aloe. All the while, you’ve heard Ms. Harshwhinny let out a shriek as her own orgasm exploded.
“How did you feel now?” Aloe asked, cleaning off your cum-frosted cock.
“Like… Like a new man,” you panted. Your mind was in a haze from the sudden release of your stress.
“It’s supposed to feel that way at first, but it’s par for the course of this treatment.” You managed to climb off the table and come face to face with Ms. Harshwhinny, her pussy was dripping with lovejuice.
“Feel better?” She asks you. “Heh, That’s alright, you needn't say anything. I can tell by your posture, as crooked as it is.”
“So, what’s next?”
“The steam bath.” Lotus spoke up. “Apart from relaxing muscles, it helps lower blood pressure and detoxifies the body. Follow us.” Following them to the steam room, You and Harshwhinny were given twenty minutes to enjoy the cleansing mist of hot water, powered by smoldering wood chips. Feeling overwhelmed by the steam at first, it eventually warmed on you. In fact, you found it very pleasing, feeling your skin being refreshed.
“I hope you’ve found the treatment to be exceptional, Calculus,” Ms Harshwhinny said.
“For it being my first time, I say it’s well worth while.”
“Hmmm, good to know.” She then scooched closer to you, putting a hand on your lap. She looks on as your member starts stiffening once more and observes your relaxed posture. “Please, rest your head on my lap.”
“Huh?” You muttered, mind still hazy.
“I insist.” Shrugging, you rest your head upon her soft, plump lap. You start to feel more relaxed as your head rested on her thighs… until a musky scent ran up your nostrils. Clearing your head, you found yourself facing her soaking wet petals, complete with a patch of pubic hair in the shape of a trophy.
“Hmmm, I guess I’m not the only one enjoying this,” you remarked as Harshwhinny grabs your length.
“And I guess you know what I want right now.” As if on cue, you dove your face towards her pussy lips, licking furiously as if it were your final act. Harshwhinny responded in kind and began stroking your pulsating spear, still slightly sticky from earlier. The carnal pleasure was like a drug, you craved more and more, like it was your first time all over again. Wanting to let Dr. MILFlove out of his cage once more, you surrendered and renewed your ministrations with the vigor of a beast. Her moans, like those from before, still surprised you as it was a stark departure from her neutral yet professional demeanor. Just as you were eating her out, Harshwhinny upped the pace with her strokes, reveling in the heat from your cock. Sadly, with that position, you were unable to do the classical tongue-in-pussy routine. She would’ve loved it but you had to press on and settle for her clit.
“Oh god, ohfuckyesthisisgood,” she gasped as pulses of pleasure wracked her body. “Fuck, I really needed this.”
“And I’m gonna give it to ya good.” You thought as you increase your licking speed, mixing it with some light nibbles in the nub. Judging by how fast her strokes were getting, she was getting close to orgasm… and so were you. You elected to both bite and lick her clitoral nub. If her moans were any signal, she was ready to cum. You’ve felt the all too familiar pressure as well as you try in vain to contain it any longer. Through a symphony of grunts and screams, You and Ms. Harshwhinny climaxed together. Ropes of your cum impacted the wall as streams of her ladycum soaked your face. It had a rather tangy flavor to it, like a sweet mixture of oranges, lemon, and grapefruit. Panting, gasping, and euphoria filling your minds, both of you laid in each others arms, kissing and exploring your bodies. You’ve never expected your boss, of all people, to have this sort of attraction towards you, if only for something you both desire apart from carnal pleasure. Then again, you’ve had your fair share of banging some of Canterlot’s resident cougars and she might’ve heard about you from someone… as you were accustomed to by now.
*RRIIIINNNGG RING*
Like splash of ice cold water, You and Harshwhinny were snapped from your stupor. Both of you walked out of the sauna with a big cloud of steam veiling your exodus. Being directed by Lotus, you were lead to the mineral bath, hot and smelling of some rather pleasant smelling aromatic. Strangely, the aroma seemed to arouse you like that one dinner with Ms. Chrysalis. You begin to suspect that the water also has been laced with a blend of aphrodisiacs.
“Now,” Harshwhinny said as you both climbed into the tub. “I do believe it’s time to get down to business… dirty business.” She spreads her legs, putting her pussy on display. Your cock twitches from just the sight of it. Your time was now and you swam to her side, scooping her in your arms and penetrating her honeypot, all in one move. You pushed further and further until your cock met the cervical entrance.
“OH, MY WORD!” Harshwhinny gasped, in shock and awe. “If I knew you were this… big, I would’ve done this a year ago!” You planted a short peck on her lips, making her blush.
“Well, let me give you what you’ve been missing out on.” You began pumping your hardened cock in and out of her snatch. The feeling, oh how you’ve missed it. It felt incredible and even more so since you were doing it with your boss. Your moans and hers filled the air with beautifully sounding symphony of sensual pleasure.
“Oh god yes! Fuck me! Fuck me like you want that promotion!” Losing all inhibitions, you held her tighter than before, bringing her in for a passionate kiss as you thrust your hips faster. She didn’t seem to mind at all. You didn’t think her to like it rough. More and more things about her continue to surprise you by the minute. You kept going at her, in and out, ever so fast until you felt something familiar. Knowing that it’s what she wanted, you summoned all of your strength and carried her over to the nearby bed, holding her in a spoons position.
“Why?” She asked.
“I want to make sure it all goes to plan.” You kiss her as you resumed your thrusts, not deterred by the hot water that would kill sperm. When your balls tightened further, you could take it no longer and shot ropes of your life giving seed into her womb, causing her an orgasm of her very own. Even as you were emptying your balls in her, you continued to thrust like you were mad. You just couldn’t get enough. It felt good for it being the first time in a long while that you’ve had sex. Eventually, the last bit of your load left your balls and you take a few to catch your breath. Looking down, you were shocked to find yourself still erect.
“Hmmm, looks like you’re not yet satisfied.” Harshwhinny remarks.
“Well, haven’t had any action in a while, not even a single wank.” You replied.
“Well, I guess that what my friend Abacus Cinch said about you is true.” You gave her another passionate kiss.
“So, how about a couple more times to be sure?” Nodding in agreement. You continued to pound away at her, cumming in her twice more until fatigue sets in for the both of you. You drifted off to slumber with your boss in your arms.
Your eyes open, vision still blurry from the nap. As your eyes began to focus a bit more, you could make out the figure of Ms. Harshwhinny in the outfit she arrived in.
“Ah, you’re awake.” She chuckled slightly. “For someone who likes to get it on, you sure do tire easily.”
“It’s been a couple years since I got any.” You groaned.
“Well, just so you know, I’ve been grading your performance. I have to say… an 8/10 should suffice. You have decent stamina, but you were somewhat rough around the edges. I guess, as you said, lack of sexual activity for sometime made you a bit rusty. All in all, I enjoyed the experience.”
“Hmmm, grading me? You remind me of some old teachers of mine.”
“How nostalgic,” she scoffed. “Anyways, I have to return to my home.”
“What?”
“Yes, I have to. But I have a question. How did you get here?”
“On foot,” you replied.
“Well, from what I can see, you look too exhausted to go walking around and the cabs usually don’t run around this time. So, why don’t you relax here for the night?”
“But-”
“It’s okay. My two acquaintances here will take good care of you.” She points to her right. You shift your view to meet Aloe and Lotus, all clad in bikinis. “They’ve agreed to help you have a comfortable night here. By tomorrow, you should feel as right as rain.” She then starts walking to the door, shaking her ass in a way that you knew was on purpose. “Enjoy your two weeks off. I’ll let you know if the test comes out positive. I may even request your services again. Farewell, Mr. Crunch.”
Like that, she was gone and you were left at the mercy of the two spa runners. They walked to either side of you and lifted you up as you felt too weak to walk.
Before you knew it, you found yourself in a bedroom on the second floor, sitting on a bed on your knees and still naked. Then, Aloe and Lotus walk in front of you, buck nude and seductively posing.
“We've seen how you've been treating Julia.” Lotus purred.
“And since then, we've been rather hungry for what you're packing.” Aloe chuckled as she straddles your lap and Lotus places her mouth at the tip of your cock. It wasn't the first time that you've done two fine women at once and it certainly wouldn't be the last.
“So, enjoy this.” Wrapping her arms around your neck, Aloe engages you in a rather heated open-mouth tongue kiss as her sister began bobbing her mouth up and down your the length of your shaft. The combination of both a kiss and a blowjob made the hairs on your back stand and tingle at the sensation. Your nerves were on fire from the sheer pleasure of their servicing. If you knew they were that good and offered something like that, you would’ve been a regular customer. You held on to Aloe’s sexy body tightly as you felt another climax on approach. Soon enough, you busted your load into Lotus’s mouth, shooting hot and sticky ropes of your cum down her throat. Still, she continued to suck on your spear, swallowing every last drop of your seed. As she removed her mouth, you fell down to the bed.
“Hmmm, salty and sweet.” Lotus giggled as she and her sister collapsed on either side of you.
“Mmmm-hmmm. Now, I want to know what it feels like inside my pussy.” Aloe purred as she unceremoniously impaled her pussy with your still throbbing erection. Though you were still in ecstasy, she motions Lotus to come over and plant her lips on yours. To you, thinking that they like to do things like this together, makes your sex drive spike. “Now, let’s conclude this treatment.”
Aloe bounces up and down your member like a pogo stick while Lotus forcefully invades your mouth with her tongue. They were incredibly passionate with their movements. It was like that with all of their experiences running the spa, they knew how to bring intimate pleasure to anyone, male or female. All you could say in your mind was…
“God damn, they’re good!”
Soon, with a few last good bounces, you came inside Aloe’s pussy, making her moan loudly from the heat of your seed coating her inner walls. As soon as she came to her senses, Aloe gets off your cock and switches places with her sister, trailing a strand of your seed from her stuffed cunt. Like an episode of deja vu, the same happens again. You couldn’t help but respect the fact that Aloe and Lotus, presumably twin sisters, would share anything between them, even a man’s cock.
Soon enough after another round of coitus and another snatch filled, both sisters took rest beside you, resting their heads on your chest as they rub their folds against your leg. You felt incredibly relaxed and at peace as the last bit of your accumulated stress has left your body.
“Sssoooo, has our guest enjoyed the treatment?” Aloe sang. You were too relaxed and tired to speak, you could only slowly nod in agreement with a moan.
“Oh, how cute.” Lotus giggled. “He’s too tired that he can’t say anything. Well, don’t you worry, you can spend the night with us.” They snuggled closer to you, sharing the body heat between the three of you as the both gave you a peck on your lips before drifting off to sleep. In your mind, it felt good to indulge in the pleasures of the flesh once more. However, something long dormant had awakened.
“After two long years, Dr. MILFlove has returned! To all the MILFs and cougars of Canterlot, bring it on!”
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
MILFlove's 2 Weeks off - Part 2: Inna Gadda Da MILF-a (Posey Shy (AKA: Fluttershy's Mom))
“I would like to start this camping trip by saying congratulations to my friend Ignacio and his engagement to Sunny Flare!”
You and your friends did a toast in celebration of Ignacio’s impending marriage. You, him, Sunny Flare, and Fluttershy all gathered around the campfire took drinks of beer. Cheers filled the evening air as the light from the fire danced around. Hearty chuckles were shared all around as reminiscing and an exchange of stories were had.
“Here's to you two.” Fluttershy remarked as she sipped her beer. She shuddered a bit at the taste but her shocked expression gave way to a smile… and a loud burp.
“Why thank you.” Sunny giggled. “I'll admit I was caught off guard when he bent the knee.”
“And after that, you nearly crushed my lungs with that hug.” Ignacio walked over to the grill, cradling armfuls of food. “Gotta admit, Fluttershy. You being friends with Gloriosa Daisy really has its perks.”
You stared at the food with a great sense of hunger. Steaks, burgers, veggies and tofu (in Fluttershy’s case), it all looked incredibly appetizing. Licking your lips, your stomach grumbled. The only thing you had before the trip was a bag of sweet granola that Fluttershy’s mother shared with you. Though it was filling, it didn't keep you that way for long.
“Umm, Calculus?” Fluttershy tapped you on the shoulder, grabbing your attention. “If it's no trouble for you, can you go find my mom and tell her dinner is an hour away?”
Being pointed in the right direction, you walked off into the woods with a nod. You took a few to appreciate mother nature in its purest form, undisturbed by civilization and unfettered by technology. It was like you tasted fresh air for the first time in a long time.
You found it odd that Fluttershy’s mom, Posey Shy, wanted to tag along. But, her being a lover of the great outdoors, she was adamant on going. From all the times you've hung out with Fluttershy, you got acquainted with her dear mom. Not as shy as her daughter, Posey had the kindness to match her natural beauty. Every aspect of her form was natural, even her busty chest. Oh, and that charming smile of hers was a sight to die for.
After roaming the the area for about five minutes, your eyes come across a clearing where, sitting in the middle of it, was Posey. She was in a meditation stance, likely as a method of clearing stress. The way her legs and arms were positioned looked majestic yet erotic. Again, like the many countless times, your shaft began to harden. As much as you wanted to, the risk of potentially scarring or pissing off Fluttershy drove away your desires to go at her mom, doggy style. She took a quick glance in your direction before a giggle broke the ambient silence.
“Pleasure seeing you, Calculus,” Posey sang. “How's my dear daughter doing?”
“Steadily becoming more extroverted,” you replied. “Umm, Dinner is about an hour away.”
“An hour away? I do believe we have time to relax. Come, sit with me.”
Taking her advice, you sat on the grass across from her. Admittedly, you enjoyed the calm of being away from the noise of merriment. However, the fact of being in close proximity to yet another MILF, one that is mother of your shy friend, made a certain thing between your legs awkwardly erect. But, you being the conqueror of cougars, you took it in stride, hoping Fluttershy doesn't see.
As you sat and endured the awkward silence, you were interrupted by the familiar rumbling. Putting a hand on your slim gut, you lamented not packing that bag of beef jerky before you left home and Posey was quick to notice. Sighing that her homemade granola wasn't as filling as she thought, her mind was reminded of two things: her lecherous desires and the things she has to make it happen. With a veiled smirk, she knew what to do.
You saw Posey digging through her knapsack and pull out a plastic bag containing something you couldn't identify. She leans over to you and holds one the contents of the bag in hand. It looked like some sort of cookie but it clearly wasn't. It looked like some charred round slice of orange with some sort of stem that some funky scent.
"Here," She said. "Take it."
"What is it?" You asked, suspicion grips you.
"Oh, It's just a little snack. Quite nutritious as well."
You looked at the object with uncertainty. You don't know what that thing could be. But with dinner about two hours away, your hunger overrode your sensibilities as you took the snack and put it in your mouth. As you chewed, the thing had a hint of a stale taste to it yet it was offset by some strangely asian seasoning. You enjoyed the flavor and the semi-crunchy texture.
"Wow, This is good," you thanked her. "Where did you get this?"
"My darling Flutter's friend Treehugger gave me these." She giggled. "It was from her personal stash."
As you swallowed the food, your head began to feel light as your senses dulled, almost as if you overexerted yourself during a workout. Soon, you began to hear things that had no visible source, seeing things that weren't really there. There, you realized what you ate wasn't a snack at all.
"What the fuck?" As your vision began to be more distorted, Posey knelt in front of you with an innocent smile. A wave of confusion washed over You as You began freaking out. "What the fuck was that?"
"Shrooms." Right off the bat, you knew what she was talking about. She drugged you with some hallucinogenic mushroom. Your first reaction was to get angry at being tricked into taking an illicit substance. As you were about to raise objections, Posey put a finger to your lips, silencing before you said even a whisper.
"Shhh, just relax and enjoy the experience." Just all of a sudden, as if you've let your phone on, a familiar tune began playing in your mind as Posey sashayed her hips seductively. As your surroundings turned into an undulating void of tie-dye colors, you were uncertain about many things but one...
You were in for one wild trip.
Rubbing your eyes in the hope that all the insanity would go away, you were in awe at the pure display of MILFy beauty before you. Posey stood there with her arms under her breasts. However, she wore a rather elegant dress like the ones worn by women in the times of Ancient Greece. Even more bizarre, feathery wings sprouted from her back, further magnifying her beauty to the levels of Aphrodite herself. Lord, your heart could barely stand it.
She sauntered over to you, taking a knee before she touched her lips with yours. With a boop to your nose, you felt as if the ground beneath you, or lack thereof, disappeared and you began falling down to a vast ocean. As you were about to make impact, you worried that you'll sink down to the bottom and drown. Fortunately for you, it wasn't the case as it felt like landing on a bed of feathers, the water barely getting past ¼ of your legs.
As you regained for bearings, a quick glance forward revealed the angelic MILF before you in her natural naked beauty. With a blink of your confused eyes, she stood a few inches away from you, making you slightly jump. Her arms and wings lunge forward to ensnare you in an embrace of skin and feathers. In any other situation where breasts and vulva made contact with your body, you only felt a slight shiver and jolts of sexual passion. But this time it felt different. Your cock began to quickly harden as tidal wave of ecstasy filled all of your nerves as if you were close to cumming, but you never blew your load.
Posey took your head in her hands as she gave you a most forceful kiss. Goes to show you that the term, “Like Mother, Like Daughter” isn’t always the case. The way she forces her tongue into your mouth was enough to drive you to grind your throbbing shaft against her cunt. Yours and her moans filled the air as you engaged in a tongue wrestling match that was fueled by the sheer pleasure from constantly ramming your member against the outside of her lower private area. It felt so good that you couldn’t help but grab two handfuls of her delicious ass.
Ash she broke the kiss, your surroundings began to flux and undulate into a tropical rainforest, as beautiful and tranquil as you’ve sometimes seen in documentaries. Posey then broke the lustful moment as she took several steps back. Reaching out to her, you felt your arms being constricted by some force. Looking around and to your shock, the vines lifted you slightly off the ground and opened your legs. Never once did you ever think of bondage. Yet, you were willing to try something new, even in some drug trip. Judging by the smirk on her face and the licking of her lips, you knew full well what Posey indends. Hell, anyone with several brain cells to rub together would know what a woman licking her lips wants when they’re confronted by a big throbbing cock.
She wasted absolutely no time in cupping and fondling your balls. Your already tense and achy loins felt even more so, especially when she began breathing on them. Without even a subtle hint, she licked your your shaft and deepthroated the whole thing. You swear that all the MILFs you encountered over the years had varying degrees of experience but like this time, there are some diamonds hidden for the trained eye (or cock for this case). Resuming to grope your nads, she kept giving you some rather amazing head as your package felt close to busting.
Yet you didn’t bust a nut. Somehow, strange forces in your hallucination prevented you from climaxing. Still, your groin felt full from the lack of a proper climax. It was as if a dam or an overfilled balloon was about to burst. If it was anything to go by, your impending orgasm would be remembered for years to come.
The vines released you and you took a few moments to catch your breath. Seeing Posey walk back a good distance, a recliner made of vines and various flowers of many colors, more consistent than the fluctuating sky above you. She sat upon the seat and spread her legs, revealing her sopping wet vagina to your very eyes.
“Come… and eat my pie out, you hungry stud.” Gesturing you over with her finger, you dashed to her and gripped both her legs with your hands. You started by lapping up the dripping fluids in her inner thighs. You knew she was enjoying the slow route from how she moaned and laughed. You never took Posey for the ticklish type.
Finally reaching her glistening flower, the strong musky smell of ladycum hit your nose like a backhand. The small nub of her clit winked in and out of its sheath. It was go time and you immediately dived in to her crotch, likcing her flower and occaisonally nibbling on her clit. Her screams and moans filled your ears and desires. You then surprised her by snaking your tongue in her caverns, wiggling it inside her inner walls. Out of unchained lust, she presses your head further into her crotch as her screams became more wild and loud. Anyone who is experienced knows that it’s the sign a woman was about to cum… and cum she did.
Juices exploded from her pussy, drenching your face in her lady cum. It had a flavor that tasted like sun ripened raspberries, tangy yet sweet. She continued to buck her hips as she rode out her orgasm, forcing you to swallow up those tangy fluids. Her grip loosened as she slid down from her seat.
“Wow, far out, Calculus.” You took the back of your hand and wiped the juices from your face. Then, the vines came back and made Posey get on her knees. Her arms were restrained to the ground, leaning her backwards and opening her legs. “You know what to do now, hun.”
Your cock was aching, testosterone was spiking, and horniness was ever so high. You crawled on your knees towards the older lady, mounting her and aligning your cock with her vaginal entrance. One thrust forward with your hips was more than enough to get you fucking her without any thought as your desires hijacked your mind. You wanted this, you desired the sweet release of your orgasm.
Grunting and grunting, moaning and moaning, you held on to her tightly as you humped and humped her with all your speed and might. As you did, you felt your climax draw near. But, you were certain that it was going to happen and you wanted to amplify the pleasure. Increasing your grip, you gave a few final thrusts before your ever sensitive cock began to writhe and quiver, it’s release imminent.
You began shooting the biggest loads of your life as a tidal wave of bliss floods your mind, making it go blank. You were not sure how long it lasted but it you knew it lasted minutes, minutes and minutes of a shrooms-fueled orgasmic high. As it ended, your vision grew dark as you fell backwards, exhausted and content.
“Mrs. Shy, are you sure he’s going to be alright?”
“Yes, shrooms don’t leave any permanent adverse effects. The strain was designed to make the effect a tad shorter but more vivid. I gotta say he satisfied me quite well.”
You began opening your eyes as Ignacio glanced over towards you.
“Oh hey, he’s coming to.” You looked up as Posey, Ignacio, and Sunny Flare gathered around you. “Man, you can’t keep your hands off a MILF for long, can you?”
“Nope.” You groaned to their laughter. You were amused but your thoughts drifted elsewhere. “Where’s Fluttershy?”
“She’s right there.” Sunny said, pointing to her right. Turning that direction, you saw Fluttershy standing there with a shocked horror expression on her face. It was then you realized that she caught you going balls deep in her mother as her eyes closed, fainting and falling to the ground. “Oh shit.”
“That’s alright,” Ignacio said as he and Sunny began carrying an unconscious Fluttershy. “We’ll take Flutters back to her tent. Can you take Calc back to his?”
Posey nodded as she scooped you in to her arms and carried you back. Your mind was still a fog of pleasure and tranquility. Looking down, Posey drew a smirk.
“Don’t worry about my Fluttershy.” She said. “I’m sure she’ll get over it. But, how good did it feel?”
“Far out, ma’am.”
“Was it worth it?”
“Fuck yeah it was.”
Author's Note
I promised and I delivered. I hope y'all enjoy this.
Here's a teaser for the next chapter (Gonna make a habit of this):
You woke up to the thunder's loud clap. The sky outside flashed brightly as the bolt of lightning streaked across the sky. Shaking your head, you noticed a mound underneath your sheets, between your legs no less. Feeling a chill run down your spine, you slowly lifted the sheet to a sight that nearly spooked you.
"Stellar Flare?"
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
MILFlove's 2 Weeks off - Part 3: Mother May I (Stellar Flare)
The lights go out and so does your AC. Going around your house, checking the appliances and circuit breakers, you confirmed the power went out. Just fucking great, just as ou were about to waste some hellspawn, lady luck rained on your parade. Checking outside, the same could be said for the neighborhood. Using the almighty power of cellular data, you found online that a substation catching fire was the cause.
“Fuck,” you whispered. “Hope I can spring for that generator.”
Just as you were about to grab your car keys, you heard a knock on your door. Opening it revealed a familiar face: Sunburst, an old college buddy of yours. After college, you thought it was the last you would hear of him but no. He moved into town a year back and since then, you’ve been having monthly gaming tournaments with Button Mash with some DnD thrown into the mix.
“Hey Calc,” he greeted. “You’ve heard about what happened?”
“Yeah,” You shot back. “And it looks like it’ll be a day or two until they can fix things. I was about to make a run up to the hardware store for a generator.”
“Sorry to burst your bubble, but that store is on the same grid as your place.”
“Really? Goddammit. I was just about to play Hellhunter Forever .”
“Well, my place has power. You can bunk there for the night if you want.”
You never entertained the thought of spending the night at a friend’s house. You always found it an awkward situation if it came down to it. But, desperate times call for desperate measures. Knowing that he too pre-ordered the game, your choice was clear as rain. Nodding your head, you agreed and left in his car to his house on the other side of town.
Sunburst’s place, from the outside, looked rather plain like the rest of the residences on his block with the exception of a couple Batman lawn ornaments and a Captain America shield on his door. Still, it looked like he kept his lawn nice and tidy.
“Calc,” He sighed. “I must warn you… I have a relative visiting me for the weekend.”
“Really? Why the long face? Is it your twin sister Sunset Shimm-”
“Errr… no.” Sunburst turned the doorknob. “It’s a little complicated.” The second the door opened, your ears were greeted by a sing-songy voice.
“Welcome back, my wittle Sunburst!” There, in his living room, sat a woman, more than twice the age of Sunburst. Her getup and hairdo gave off the look of one of those pin-up models from the 60s and 70s. It didn’t take putting two and two together to identify her as Stellar Flare, his mother.
“Hi… Mom.” Sunburst groaned in embarrassment.
“Aww, you shouldn’t have to be embarrassed about your dear mother.” Stellar Flare pinched his cheeks, much to his displeasure. Soon, her gaze turned towards you. “Oh, and I see you’ve brought a friend over to play. Who might you be, Mister?”
“Calculus, ma’am.” You cleared your throat. “I’m an old college friend of his.”
“Oh yeah, I remember him talking highly of you back then. Although, I half anticipated him bringing Starlight Glimmer over to announce they’re expecting.”
“MOOOOM!!!” Sunburst yelled in annoyed embarrassment. “Please, don’t talk about stuff like that when he’s here!”
“Oh come now, is it that much of a crime to voice my desire for grandchildren?”
“No, just not in the company of my friend!”
“Oh please, would you mind if I count the times that you brought Starlight-”
“Mom.”
“And heard the creaking of your bed from the hall-”
“Mom!
“You have to admit that the walls aren’t that soundproof as they should’ve been.”
“MOM!!!”
“It’s alright, broski,” you said, patting him on the back. “I’m no stranger to the intricacies of the ol’ horizontal hokey-pokey.”
Sunburst was left flabbergasted at the situation before him. Over the course of your friendship in college, he did mention some bits of him having some intimacy with Starlight Glimmer. Over time, you trusted him enough to talk about some of your ‘conquests’. With the first mention, he was left dumbfounded at first. But, he eventually changed as you explained how they all happened. Still, he was left somewhat puzzled.
“See, no need to be embarrassed. We’re all adults here.” As you sat down, You found Stellar Flare sitting next to you on the couch. She sat so close to you that she was a hair length away from having both your legs touch. The distance made you slightly uncomfortable but not to where it was visible. If there was one thing you’ve adapted your body to, it’s being able to hide your lust. “So, what brings you over to my son’s place?”
“The power went out in my area and I neglected to buy a generator,” you explained.
“Awww. no need to fret. We’ll both have some fun together tonight.”
“Well, I wasn’t about to change my definition of fun to slowly cooking like a roast in my house.”
“Good thing I had the sense to install centralized air.” Sunburst said as he reached for his phone. “I'm going to order some chinese. What do you want, Calc?”
“General Tso’s chicken and chow mein sounds good.”
“Alrighty then.”
After phoning in dinner, you, Sunburst, and Stellar Flare spent the better part of the next twenty minutes chatting and making the air alive with conversation. As ever, Stellar Flare was intent on telling some rather crazy stories of her son during his youth. You found those stories funny, much to his chagrin, especially the one where he got hyperactive after eating some particularly sugary candy at a mall one time and the commotion he started.
Eventually, dinner had arrived and it was still piping hot as if it came straight from the pan. Hunger took over as the three of you dug into your meals with little abandon. It was rather weird that you felt hungrier than usual as of late. After dinner was finished, you and Sunburst began playing his copy of Hellhunter Forever and it was ever so glorious. Slaying all manner of hellspawn was like a symphony apart from the fact that Ms. Flare occasionally dropped in to chat.
Stellar Flare, apart from a different getup, looked to be a typical run-of-the-mill cougar that you were used to, but there was something different about her like a different vibe she gives off. It was motherly, more so than the last ones but with a hint of playfulness. Yet, it all masked a woman with plenty of experience under her belt and the guile to match.
Soon enough, night had arrived. Though it was 9PM, you preferred getting to bed early. Your day took a bit of a nose dive but it was all inconsequential in hindsight. Taking one of the guestrooms, you found that the mattress was firm yet cozy. Lord, did it feel so good for your back. It was like sleeping on a cloud. No sooner than when a good half of an hour passed that the comfy mattress dragged you by your toes to slumberland. You slept like your soul went to the great beyond.
You had no clue to the amount of time that passed as your eyes slowly opened to the room shrouded in darkness. The bright light of the moon nearly blinded you as you adjusted your sight. Rubbing your eyes, you noticed a moving mass between your blankets, right between your legs. Your spine began to shiver as you ponder what it could be. Slowly, you lifted the blankets to behold…
… nothing, except Stellar… Flare… fondling… your package. Dafuq?
There she was, the mother of one of your college buds was copping a feel of your unit. You were frozen in place as only one question plagued you.
“How the fuck did she not wake me?!”
Just as you were about to open your mouth to say something, one of Ms. Flare’s hands reaches out and holds your lips shut, unable to make a sound.
“Hush now, my guest.” She cooed. “Just sit back and let mama take care of things. There’s no reason to be upset.” The way she handled your cock and balls felt like the silkiest of velvet stimulating every length of nerves in your crotch. Clearly, she was no slouch and she demonstrated her expertise by removing your boxers without waking you up. Fuck, she is good.
“Well Ms. Flare, I ain’t complaining.” You moaned with ecstacy. “Whatever you do, don’t stop.” With a chuckle and smirk, Stellar Flare stopped her ministrations and crossed her arms, much to your dismay.
“Well, I’ll keep going if you do one thing for me.” Is she really doing that, teasing you? You were used to women being up front and wanting to hump you without any delay. But never, ever, were you teased. Then again, it felt fresh to go at it with some cougar that was playing hard to get. It should be fun and challenging and a break from the norm.
“Alright, what are your demands?” you asked.
“I… would like you to call me… Mommy.” That last word rang in your ears. Is she seriously asking you to do some roleplay, incest roleplay no less?! “Well, Mommy’s waiting.”
And it looks like she wasn’t going to easily back down either. Though you’ve engaged in many sexual taboos, pretend incest was one thing you’ve never considered, even though you’ve gotten your jollies off to two sets of sisters doing it before. Still, like always, the more you thought about such an obscene and morally questionable act, the more it made your pecker tingle with excitement. The thought sounded wrong but erotic at the same time.
“Okay, M-M-Mommy.” You mumbled.
“Louder so I can hear it clearly.” She commanded.
“Okay, Mommy.”
“Better.” She resumes her ministrations on your package, now more sensitive and eager for pleasure. From just a slight touch of a fingertip, your balls quivered, causing you to grunt in erotic pain. “Awww, does it hurt when I touch you like that? Would you like mommy to kiss that boo-boo for you?”
Holy fuck is she charismatic. Her unique quality was starting to shine through. She has the body, nice for an average MILF. But, where she lacked in any specialization of any particular part of her anatomy, she makes up for it with heaping helping of charm. She must’ve driven her husband, where he was, crazy during their nights of passion.
With a “Yes, mommy” from you, her lips made contact with your nutsack, pelting it gingerly with the softest kisses imaginable. She eventually started including her tongue which led to her licking up and down your shaft. Soon, the blowjob began in full, smooth and sensual and leaving you nothing short of speechless. You wanted to grunt loudly but the risk of repeating what happened last week was enough to shut you up. You could only grunt in your mind as Stellar Flare helped you see heaven.
The feeling of her velvety tongue slithering around your knob was more than you could as your balls blasted the inside of her mouth with hot, life giving seed. Gasping and gyrating your hips, the wild ride of your orgasm reached its peak before it steadily landed for a soft touchdown. As you felt a sucking motion on your cock, you knew then and there that she swallowed your entire load. Impressive.
“There we go, the boo-boo is all better,” Stellar cooed as she took off her shirt to reveal her supple and firm chest balloons, leaking with milk. “Since mama made you feel better, how about you help me with something?”
“Like what?”
With a smirk most mischievous that was masked by a motherly aura, Stellar Flare sat on her knees as a musky scent pummeled your nose. Her wet and puffy snatch was dripping with arousal and waiting to be pleased. You were compelled ny instinct to sit up and prepare to dive into her honeypot…
...only for her to send you back onto the bed with a flick of a finger.
“Now now, it’s best to enjoy your dessert, young man.” Before you knew it, her winking vulva hovered above your face, slightly hairy and winking with excitement. There, she lowered herself on your face with her wet sex landing on your mouth. Facesitting, strange, new, but exciting to try. “Go ahead, dig in.”
Upon her command, you began lapping up her juices, on and around her flower. The occasional brushing of her clitoral nub produced some sharp loud gasps. You could tell that the poor MILF hadn’t seen any sort of pleasure in quite some time. As you pressed on your tongue assault with plenty of nibbles on her clit, Stellar Flare petted you gingerly on the head, howling into the night.
“Oh yes, OH FUCK! GIVE MOMMY WHAT SHE NEEDS! OH YEAH! FUCK! MMMMHHHNNNN!!!”
The moment you pushed your tongue in her vagina, time seemed to have froze for the motherly cougar. Then, her moans became gradually coarse and longer in duration. You thought that some MILFs were sex hungry women but Stellar Flare… she was starved of it like she was trapped on an island. Of course, from how quickly her pussy dripped, It didn’t take to long for her climax to speed across the finish line, soaking your face with her juices. You endeavored to lap up as much of it as you could but weren’t able to get it all. After her mind became lucid once more, she got off your face and laid beside you, panting and fanning her face.
“Oh yes, good boy. You did well.” She turned her back to you, giving her firm ass a jiggle. “Good boys like you should be rewarded. You must feel a little cold being in the nude. Come and I’ll give you… and that thing some warmth.”
Needing no introduction and with an excited erection, you scooched up behind her and slid your spear inside her cunt. Goddamn mother of mercy did her pussy feel so good. Holding her tight like a tree, you began thrusting in and out of her honeypot. Spooning a seasoned woman certainly brings back memories of the last time you did it, even acting out that fantasy with Cadence years ago. The feeling of such intimate skin to skin contact surely brings a warm and fuzzy feeling to your nads. The constant jabbing of her cervical entrance only made her vaginal walls tighten further around your cock. You know she was ready to burst and so were you.
With a few more mighty thrusts, your pole convulsed as hot milk spewed forth from your balls. The feeling was incredible, holding the most motherly MILF you knew in the spoons while ramming at her cunt. In the wild throes of yours and her passion, You surprised her with a deep kiss and quickly invading her mouth with your tongue. As the last of your seed trickled out of you knob, you slid on top of her and rested your head on her breasts.
“I have to say…” Stellar Flare said as she petted your head once more. “You did a good job, Calculus.”
“Oh, you don’t need to worry about that.”
“Why?”
“Funny story. While I was visiting him last year, he caught me pleasuring myself with a dildo. I guess the reason why he didn't complain was he didn't like the thought of me naked. Though, I bet even his headphones can only do so much against my moans. Oh god, I'm so loud.”
“Nah, it's alright. The sex was well worth it.” Your mind began to feel heavy as your eyelids began to shut. You were about to fall asleep when a thought occurred to you. “I hope I don't end up getting you pregnant.”
“I'm already on birth control. No need to worry.”
“Good to know.” With a yawn, you completely went back to sleep, satisfied and exhausted. Contrary to what she said, the “birth control” Stellar Flare said she was taking was the exact opposite.
“Sometimes, if your dear son is slow to give you grandchildren, time to take matters into your own hands. But I will admit, his friend was amazing. I’m certainly glad Elaina told me about him.”
Author's Note
Here's the chapter dedicated to MLP's newest an motherly MILF to date. I honestly had a lot of fun characterizing Stellar's personality and writing it in a way where it also encompasses lust. To be honest, I've been rather fond of Stellar Flare as of late. Anyways, I hope y'all enjoy this. There's more to come and more MILFs to be pleased.
Preview Time:
"Alright, Mrs. Velvet," You said. "I propose a challenge."
"What kind of challenge, young man?" Velvet asked back.
"A game of Rock Paper Scissors. Best two out of three. If you win, you can have the book and I won't complain. If I win, I get the book... and that sweet perky ass of yours."
Twilight Velvet pondered your words for a bit. She really wanted to read that book you were about to rent. But, the lack of satisfaction from her husband has been driving her crazy. With her pussy quivering in excitement going toe to toe with her desire for the book, She agreed to your challenge, knowing that it's a win-win situation for her.
"Alright, you have a deal."
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
MILFlove's 2 Weeks off - Part 4: Of Books and Babes (Twilight Velvet)
There are many things that are known about you. The first and foremost is that you’re a slightly muscular health nut. However, the lesser known thing about you is that you’re also a nerd, or an egghead by Rainbow Dash’s definition. On top of working out, you like to indulge in things like video games, DnD campaigns, and even books. During school, you loved reading a good book. It was like reading the description of a picture in motion, beautifully written as like how a painting was made. They were like the written form of the imagination.
It was a nice clear day in Canterlot as you walked over to the local library. Upon entry, your skin was greeted by the rush of cool air, courtesy of the building’s AC system. Standing at the checkout counter was an old yet familiar face: Moon Dancer. Like you, she was one of the bookish students at CPA. Hell, she was probably like that on the same level as Twilight Sparkle. For her, you were a regular visitor there.
“Oh hey, Calc,” she greeted. “How are things today?”
“Largely uneventful, but surviving.” You looked around at all the other visitors either reading books or using the computers for research purposes. You knew what you had to do there and that was to pick up a book that you’ve been dying to read lately. “Do you have “The Moon Is a Harsh Mistress” available?”
“One moment please.” Moon Dancer then turned her bespectacled self to her computer. She flipped through the catalogue of all the books they have on shelves. Her eyes darting and clicking persisted for a minute before she grew the ‘Ah ha, found it’ face, usually a good sign. After jotting down the location and ID code for the book on a card, Moon Dancer hands it off to you. You gotta admire her efficiency. “Here it is. It’ll be in the Science Fiction section on the second floor. Just use this as a reference and you’ll be good. Take care.”
Nodding, you walked up to the 2nd floor. It was filled with shelves upon shelves of books like the floor below. It wasn't any Library of Alexandria, but it is big for a local one in the midwest. They were like monolithic towers of knowledge and projections of the imagination.
You then arrived at the pinnacle of human imagination, the science fiction section. Following the note on the card, it didn't take you terribly long to find it. Sitting on the shelves was the prize you've sought, waiting to be read. You reached forward, ready to take your prize…
...until a dainty hand blocked yours. Looking up, you saw it was a woman and that she looked familiar. She also gave you a similar look.
“Oh my god, Calc?” she gasped. “It’s me, Twilight Velvet! You were part of my daughter’s math club.”
Twilight Velvet, that’s a name you remember. Mother of one of your friends, Twilight Sparkle, she looks so much like her daughter. If it weren’t for the different hair colors, she would’ve looked like an older clone of her daughter or vice versa. Unlike her daughter however, her MILFiness was well seasoned. Nothing too big nor anything too small. Perfectly balanced… as all things should be.
“Oh yeah, now I remember you, Mrs. Velvet,” you replied. “How are things for you nowadays?”
"Just thought I might come here for a good book. You?"
“Oh, just trying to get my writing career to take off. I’m just here looking for inspiration.”
You gave her the brief rundown of what you’ve been up to for the past few years. It started a friendly conversation between the two of you with some light laughter. Some friendly banter about school and current events had ensued. Velvet mentioned that she was working on a romance novel that she hoped would be a hit. As you were pulling the book into your arms, her grip on it tightened.
“Umm, I’ve actually been wanting to read this. Can I please have it?” Even though she asked, your desire to read what you’ve sought withered Your manners. You were there first and you would be damned if you were going to leave without the book.
“Sorry, but you have no clue how much I’ve been wanting to read this,” you stated as you pulled the book back, visibly annoying her.
“Well, I’ve been a fan of the author’s work long before you were born, young man!” The anger in her voice hadn’t reached levels of high passion but was still visible. It was clear that she wasn’t going to let you have it and she pulled it back to her.
“Well, I’ve read all his books except this one! I was here first!”
“Yeah, but ladies first!”
A brief session of wrestling control of the book ensued as you two exchanged brief invectives throughout. The battle was heated and it became clear that it would only end if either of your wills ran out. You had neither time nor patience to deal with it. Quickly, your mind came up with an idea for a quick resolution to the conflict. However, there existed the possibility that you could lose. Still, you saw two things before you that you crave: a book and a hot MILF ass to fuck.
"Alright, Mrs. Velvet," you said. "I propose a challenge."
"What kind of challenge, young man?" Velvet asked back.
"A game of Rock, Paper, Scissors. Best two out of three. If you win, you can have the book and I won't complain. If I win, I get the book... and that sweet perky ass of yours."
Twilight Velvet pondered your words for a bit. She really wanted to read that book you were about to rent, but the lack of satisfaction from her husband has been driving her crazy. With her pussy quivering in excitement going toe to toe with her desire for the book. She agreed to your challenge, knowing that it's a win-win situation for her.
"Alright, you have a deal."
“Excellent,” you huffed as you ball up a fist, ready for the challenge. “Let’s begin, shall we?”
With a count of three and the shaking of your fists, the first move was made. You drew scissors while she got paper, your first win. You scoffed in satisfaction of your first round won, but it was far from over. You had at least one more round to win before victory was yours. The next round began the same as before ,but you got paper that was beaten by her use of scissors. She giggled in smugness as she claimed her first victory.
“Okay now, It’s sudden death,” you state as your adrenaline hits an all time high. The anxiety is intoxicating and nearly made you break a sweat. “It ends here and now!”
“Let’s get it on!” There it goes, the final move to determine who walks away with the spoils of victory. You closed your eyes and mentally prayed for good luck. You opened them to see that she drew scissors and that you drew rock. It was an incredible victory for you as the look on her face spelled acceptance of her defeat.
“Well Mrs. Velvet,” you cheered. “It looks like I’ve won.” Taking the book in your bag, your gaze now turned toward your second prize. “Where shall we take this?”
“There’s a bathroom near the biographies section,” Velvet remarked. “No one would suspect us there.”
“Hmmm, feeling kinky aren’t we?” You were amused by her suggestion. The idea of doing it with her in a public place felt rather exciting. The risk of getting caught was there but it was less so than that camping trip you were on last week.
Following her to said bathroom, you looked around to see no prying eyes. Waiting for her to enter first, you follow and locked the door behind you. It was one of those small bathrooms made for only a single person to use but could fit multiple people. Once you set your bag down, Twilight Velvet suddenly pulled you in for a sloppy yet passionate kiss. The fervor she did it with was amusing. She eventually stopped for a moment to catch her breath.
“I presume that your husband left you wanting,” you breathed.
“Oh, you don’t know the half of it.” She dove in for another kiss, but that time with her body pressed firmly against yours. From the demeanor, you could tell that she was the romantic type. But then again, romanticism seemed to be the veil of lust. Twilight Velvet moaned into your mouth as her crotch made contact with yours, arousing your member and making it hard as granite. Such an amazing feeling compelled you to hold her tight and began dry humping her. Grinding and bumping your crotch against hers made the lustful side of you emerge. Now that you have the book, you have a sweet hot MILF to relieve yourself with.
“Okay,” Velvet breathed, breaking the hug and kiss. “I think you know the drill.” From the way that she was stroking your bulge, you knew very well what she aimed to do. Putting the toilet seat lid down, you sat down and undid your belt and pants zipper. Once your member sprung up with tremendous pride, her hands grip your cock and balls. Holy mother of god she was fast…
...and very, very hungry.
She slithered her tongue around the base of your shaft as her silky smooth hands worked their magic on your coin purse. Good lord, for the mother of an egghead and a veteran, she knew how to balance passion and smarts. Velvet somehow knew which nerves to hit and hit them sensually.
“Oh my fucking god!” You gasped as her tongue climbed up to your tip before she took it into her mouth. As she blew you, she still continued to fondle your sack. She was persistent in getting you to cum and you were going to, but on your own terms. All the sexual stamina you’ve built up over the years were going to come in handy as you want to prove how long you’ll last. With the sudden rush of pleasure up your spine, you grab her head and deepthroated her. You were at first worried about how she’ll be hurt by the maneuver, but her increased pace of the ball massage said otherwise.
Soon enough, you felt your nads tighten and your spear throb and convulse as you shot an entire load down her throat. From what you’ve felt, Velvet managed to swallow it all. How she managed it, you weren’t sure. Still, her experience was amusing to say the least. With an audible pop, she pushed away from your cock and wiped away the excess from her lips. From the look on her face, it was clear that she enjoyed it.
“I’m glad that you lasted longer than my husband,” Velvet said as she turned her perky rear end toward you. “I think it’s time for the grand finale.” She undid her skirt and pulled her panties down. Her cunt was sticky and wet with want and desire. It didn’t take a single pair of brain cells to figure out what it meant and what she wanted. “If you wouldn’t mind, I want anal. I don’t want to risk getting knocked up and having to explain it to my husband.”
It was surprising that she wanted it up the ass. From how her pussy was dripping, one would assume that she wanted it up there. But still, you were in no way opposed it as you took up position behind her, hotdogging her buns for a moment. With your hunger at a momentary high, you slowly pushed your still erect cock inside her ass. It was a tight fit but god damn did it feel so good. Her moans, her gasps, she was processing the sensation but was still legible.
“Go on! DO IT! I WANT TO WALK HOME WEAK LEGGED WHEN THIS IS DONE!” With the knowledge of the no noise leaving the room, You began thrusting in and out of her tight rear. With how tight it was, you feared that you were going to cum too early. Fortunately, you had the willpower to carry on for a long time. Slipping your hands down Velvet’s hairy crotch, you began fondling her vulva, taking care to sync the rhythm and vigor with your thrusts. She moaned and screamed in a way that seemed so out of character for a bookish MILF like herself. As it dragged on, the pace and volume of her noises increased, even so as you slipped two fingers inside her love tunnel. She loved it, she craved it, but most of all… she needed it.
As both your orgasms came close, you moved your other hand from her ass to under her sweater, copping a feel of her perky tits. She screamed louder as her inner walls clenched tighter around your fingers. Then, with a final long winded yelp of satisfaction, Your fingers became drenched in a tide of ladycum. Since she came first, you no longer felt the need to hold back and came into her ass, blocking any of your seed from her pussy with your hand. If any did, You could only hope she has pills to stop that. Riding your orgasm, your hips spasmed as you thrusted a final few times before coming down from it. Your bodies were sweaty and weak but all that didn’t hold back a post-coital kiss.
“Wow,” Velvet whispered in astonishment. “You certainly lasted longer than my husband. You know, Cheerilee wasn’t wrong about you at all.”
“Well, I aim to defy expectations,” you said as you got your respective undergarments back on and washed your hands. “This was rather good for a quickie.”
“Sometimes, a brief moment of passion is all I really need,” Twilight Velvet said as she opened the door. “Anyways, I’m having a dinner with my son’s family, so I have to go. Enjoy that book!”
“Oh, I will,” you shot back as your gaze turned to your bag. “As will I what we just did.”
Walking back down stairs to the main floor, you checked out the book while making great effort to hide what you did. Satisfied with obtaining not one but two prizes, you walked home with a smug look and satisfied stride. Along the way, the scent of your sweat caught your nose.
“Hmmm, there goes my cardio for the day.”
Author's Note
Well, here's one of the two chapters I've been working on for the past couple of weeks. Sorry for the delay, but good things come to those who wait..
...and this is a good thing.
Anyways, be sure to read the next chapter after this. It'll be one of the craziest things I've ever written for this series. No preview this time because I want no not spoil anything about that chapter. Thanks and have fun.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Spoiled Rotten (Spoiled Rich\Milk)
Who knew that you would get into all sorts of crazy situations after high school? Who also knew that you’ve struck it big on top of all that? Well, you’d have to chalk it up to that fateful day that when you had that lustful encounter with the dean of CPA. From there, it was a job at the CSC and a sensual night at a spa that bumped you up to being the assistant of your boss: Ms. Harshwhinny.
But, there was one stipulation to that arrangement.
As was agreed upon, your sexual night with Ms. Harshwhinny resulted in her getting pregnant, just as she desired. Over the next four and a half months since your return from a state mandated vacation, her belly grew bigger over time as the life within her developed. Though she was prone to mood swings and the occasional cravings, she kept them under control. But still, you saw that she was going to be a good mother… and a damn sexy one at that.
It was medium paced day at work, making your rounds and verifying data gathered by financial. The days were becoming more hectic, but you kept your cool through all that. Why were things becoming increasingly busy? Well, It’s because the Canterlot games were due to happen in the next two months. Around those times, the CSC’s efforts are kicked into high gear, ensuring that their efforts are always at 110%. Because of you being Ms. Harshwhinny’s assistant, you get some hard tasks on your hands, but it all provides your brain a worthwhile challenge and freedom from boredom. Everything was optimized and in order. As far as you were concerned, all was well.
*BUZZZZ* *BUZZZZ* *BUZZZZ*
Your phone buzzed and rang in your pocket. Answering it, you were greeted by a familiar voice.
“Hello, Mr. Crunch,” said Ms. Harshwhinny. “I trust that things are going well over in financial.” The tone of her voice sounded more casual to you than it was five months ago; almost into friendly territory.
“Yes, Ms. Harshwhinny,” you answered. “Apart from a few minor discrepancies, all the numbers seem to be in order.”
“That’s good to hear. Your talents are were they should be. Now, come to my office. There’s an assignment that I need your assistance with.”
“Alright, I’ll be there in a few.”
Hanging up, you wondered what she wanted help with. Could it be a personal matter, something job related, or something of a more lewd nature? Well, there was only one way to find out.
You arrived at the double doors to her office, so grand and fitting for a Opening them, you saw a casually relaxing Ms. Harshwhinny, five months pregnant and reading a book. As the doors closed, her attention was directed towards you.
“Ah, Mr. Crunch,” she warmly greeted you as she rubbed her belly. “so nice of you to join me.” For others, she would’ve been a lot more professional than she was. But for you and due to the fact that she’s carrying your child, she was more cordial. With a wave of her finger, you walked over to her, placing a hand on her warm and bulbous midsection. It was clear she had a sort of affection towards you, but in an arm’s length sort of way. So, the relationship was professional on the outside.
“So, how’s the baby?” you asked.
“It’s doing fine,” she replied. “I had an ultrasound on top of my checkup last saturday. They asked me if I wanted to know the sex of the baby but I told them that I wanted to be surprised.”
“Hmmm, didn’t know you were like that.” In response to your statement, Harshwhinny gave you a quick peck on the cheek. You blushed, but not for long.
“There’s a lot of things you don’t know about me, Mister.” Then, her face snapped back to her serious and professional expression. “Now please, take a seat.” Doing as you were told, you sat back on the couch, relaxed but alert. Clearing her throat, Ms. Harshwhinny prepared to speak. “You may recall that the Canterlot Games are due to take place in the next two months.”
“Yes, no wonder things are in a bit of a rush as of late.”
“Indeed. Now, we get our funding from not only the business we do, but private organizations, private entities, tourism, and the event itself. Most of the time, we end up with a surplus which we can devote to other functions related to the event. With you being my assistant, I’m putting you in charge of the overseeing of these factors.”
In your current position, you expected this eventuality. Due to how long you’ve been working on things too easy, this would be a welcome task. After all, idle hands are the devil’s playthings.
“Really? W-Well, I won’t disappoint you, ma’am,” you replied with a tinge of excitement.
“I know you won’t, considering that your *Ahem* ‘skillset’ would be fit for this assignment. One of our financial benefactors is Filthy Rich and his wife, Spoiled Milk. He owns a lot of businesses around town and in a few other nearby cities. When it comes to making decisions, it would be a mutual agreement between them… and that is where the problem lies.”
“What could be the problem? Ms. Harshwhinny let out a long annoyed sigh before explaining.
“As of late, their marriage has run into shall we say… ‘problems’. Judging by the last time her and I spoke casually, it’s that not only has her husband been increasingly busy as of late, he’s also been ‘unsatisfactory’ if I may use that term. As a result, the stress of the situation has rendered Spoiled unwilling to contribute to the funding, which leaves us slightly underfunded.” Judging by the tone in her voice, the situation annoyed her greatly. From what you could understand, It would mean that she would have to make changes to the budgetary baseline. Moreover, when she mentioned your ‘skillset’, you could already tell what she intends for you to do.
“So, what do you need for me to do?”
“Spoiled Milk is doing some chores around town this afternoon. You’ll be tasked with chauffeuring her around as she accomplishes her tasks. You’ll be advised to help her around and maybe take her to lunch on your dime. If she hasn’t calmed down by then, do what you do best at your discretion.”
‘Do what you do best at your discretion.’ basically meant she was giving you liberty to sway her attitude toward the funding, even if it meant giving her some carnal pleasure. Though it would seem to be not too difficult of a job to accomplish, you would only resort to sex as a nuclear option.
“Alright, I’ll do it” you agreed with a nod.
“Excellent,” she replied with a wry grin. “Now, for this plan, I’ll permit you to go home early to prepare yourself. Make sure your well cleaned and dressed in your best suit. Be sure pick her up at 3:30 PM, to use your new car and oh, watch out because she’s a bit quick to irritate.”
Quick to irritate? Well, that can complicate things. But then again, you’re a patient man. Getting home early would net you two hours to prepare, more than enough. Shaking her hand, you left for your car, a Jaguar F-Type. It was an expensive car, but Ms. Harshwhinny just makes things happen.
Arriving at home, you took a few minutes/hours to rest up before making yourself look like a million bucks. You showered, shaved, and anything to make yourself the most presentable since your interview. Once all that was done, you hopped in your jaguar and drove off to the address Harshwhinny gave you. It was an incredibly fancy mansion, one that stuck out like a sore thumb. It was almost made in a way to assert the owner’s superiority.
Giving the horn a few honks, a woman stepped out and boy was she a sight to see. Thick thighs, ample cleavage, a lovely dress and flowing magenta hair. However, the only blemish you saw was the sour look on her face. Aware of her irritable nature, you took a deep breath and braced yourself.
“Afternoon, Ma’am,” you greeted as she entered your car.
“You’re a minute late!” she said with a huff of self superiority. “Then again, I never expected Julia’s assistant to be so… young.”
“I actually get that quite a lot.”
“Indeed. I hope you’re smart enough to follow simple orders Now, I want to hit the nearby clothing store on 8th Street. I certainly hope you know where you’re going.”
“I do, know the town like it’s in the back of my head,” you said as you revved the engine. I’m not an idiot… bitch.
Following her instructions, you drove Spoiled Rich to her destination. It was a ritzy clothing store that only those with deep pockets could afford to go. For an hour, you and the rich MILF roamed around the store, seeing her try on shoes and clothing of varying types. When that was done, you walked out hefting six bags of the stuff she purchased.
“Hmmm, you’re not even breaking a sweat. I’ll give you that,” Spoiled said as you loaded the cargo. “So far, you’ve proven a reliable servant.” The last part she said was with a condescending tone. It infuriated you, but you had to stay your hand of anger and not screw up. Hopefully by the night’s end, you’ll walk away with her renewed commitment towards the funding. “Now, I’m a little peckish. Take me to Lorenzo’s Villa. I’m in dire need of some good chicken cacciatore.”
As you command, Mrs. Bitch.
Driving about ten minutes away, you reach the eatery she informed you of. You recognized it from your occasional walks or your trips to the smoothie bar. At first glance, it was a pricy place. Hell, you’ve looked at it’s menu online at it was quite expensive, but the reviews say the food was good. Even during those trips, the scent of its kitchen enticed your curiosity. But hey, her wish is her command. After getting seated, you both ordered your drinks and food. An awkward moment of silence lasted for minutes after before Spoiled broke the silence.
“So, Mr. Crunch,” she asked. “How did someone so young such as yourself became Julia’s assistant?”
“Well, I was junior level accountant for two years. She noted how my skills was being underutilized and decided to bump me up to her personal assistant.”
“Hmmm, I see. I would see that you’re not as dumb as your body makes you out to be.” That quip of hers infuriated you. At that point, you wanted nothing more than to just reach across the table and clock her. However, you didn’t want to get into untold fathoms of trouble. Thus, you decide to endure her swath of denigrating language.
“Well, I’ve found that a good body and mind go hand in hand.”
“Interesting. But, how did you become her assistant in such short amount time? Then again, her being the president of the CSC, she calls the shots.”
“Yes ma’am. Though, I do feel you know what this is about.”
“I know. I’m still pissed that my shriveled up sack of impotency of a husband is on yet another trip!” She blurted out with a slam of her fist. Her eyes spelled the irritation of a unsatisfied wife, a dangerous prospect. “What about me?! All he ever talks about is business. He had the nerve to ask about the games last week. So, I told him to stuff it and I’m not changing my mind until I say otherwise!”
“Sounds like your relationship with your husband is contentious.”
“You don’t know the half of it,” she replied as she took a sip. “I know Julia wants the funding. I’m open to reconsidering my stance but that’s a ways off. At the end of our time together, I may or may not so don’t be upset or surprised if I decline.”
Her anger and discontent was made clear in her tone. It was clear that it would take way more than just a few good gestures to crack the shell. You knew then and there that you’ll inevitably have to resort to the nuclear option. Though you’ll have to wait for the right time. Before you could further muse about the situation, your meals arrived.
After dinner was done, you drove her to another couple of places. Everywhere she went, you followed like a pack mule. For her, that’s all you were. Your strength was more than enough to keep up, but her usual string of insults towards you made your anger climb ever higher. Still, to avoid problems, you had to endure them to the same degree you endure pain in a workout.
After a trip to a jewelry, you drove her home. You followed Spoiled in, hefting all those bags of merchandise she purchased. You could barely see ahead of you but she was cautious enough to lead you around. After off-loading the cargo in her room, you both met in the living room. Your anger was still present after her choice of words.
“So, Mr. Crunch, you did good for someone of your... calibre,” Spoiled said with a hint of sarcasm.
“Well, I aim not to be a slouch in my work,” you shot back.
“And it certainly shows.”
“Thank you. Now, as for the situation about the funding…”
“I know you want to know about that. As of now, I see no reason for me to change my stance. I’m still stressed as it stands.” Spoiled got up from her seat with her voluptuous chest jiggling about. “Now, I’m going to go freshen up in my bathroom and skinny dip. Don’t come for me until I say so. If you’re going to help yourself to a drink, clean up or I’ll make you regret it.”
“If you say so,” you said as Spoiled walked away from your sight. “Bitch.” Feeling a little parched, you grabbed a tea from the fridge. As you took a sip, you mused how Filthy had the patience to put up with someone as insufferable as Spoiled. Though nice looking on the outside, inside was pure bitchasaurus rex. Sometimes, you just have to bless someone for their high degree of patience.
As you began to kick back on the couch, you heard a moan coming from one of the bathrooms. It wasn’t like a normal stressed moan. It was more guttural and driven. It kept on going and going, sometimes accompanied by a sharp yelp. You want to go to ensure she was alright but her wrath is what you feared the most. After a while, it eventually subsided into silence and her footsteps were heard getting more distant. As soon as you knew the coast was clear, you made your move.
Taking a peek inside, the bathroom was spotless with a fresh floral scent. It was like she wasn’t there at all. You scanned your eyes around until you found something at the corner of your eye. It was a light yellow object with a light earth brown base. Taking a whiff, two scents became apparent: one was musky while the other was of ginger. Putting two and two together, it became clear what she was doing.
“Heh, how naughty of her.”
Arriving at the pool house, you opened the door with a deft movement of your hand. Walking in, you saw her: Spoiled Rich, naked, swimming around with water running down her hair. Your presence didn’t go unnoticed however as the moment she saw you, she screamed and covered her mounds and lower lips.
“Mr. Crunch, what in the hell are you doing?!” she yelled.
“I could ask the same of you!” you shot back with a mischievous look on your face. “For a rich socialite, you do enjoy some rather profane activities.” She starts to growl and fume with rage, rage over being interrupted during her private time.
“That is none of your business, mister!” she screamed as she climbed out of the pool. “As soon as I can, I’ll file a suit against you. I’ll have every single penny you have!” You began to laugh at her threats of a lawsuit, even as you pulled out a piece of shaved ginger root. The sight caused Spoiled Rich to freeze for a moment. “What is that?”
“You tell me. I’m not the one that turned to pleasuring myself with roots after years of dissatisfaction.”
“How did you find out?”
“Well, you should’ve thrown that other root away.” She began grow more alarmed with her eyes darting back and forth before attempting to run. However, you anticipated it and pinned her against the wall. Your already throbbing erection presses up against her snatch, though restrained by your clothes. You’ve spent a good while hiding it from such a specimen of MILFy goodness. Now, you were going to make her repay those insults.
“Unhand me, right now!” She protests.
“Oh no,” you said as you began unbuckling your pants, kicking them away as well as your shoes. “We’re going to address this, now! I have a feeling our little ‘meeting’ could make you more receptive.” With the miracle of just one hand, you unbutton your shirt. Then and there, you were completely nude in front of a woman that is prepared to sue you at any minute, but you knew you couldn’t walk away empty handed or Julia would have your ass.
You turned her around, wrapping your arms around hers and taking her to the ground with you. Spoiled struggles as she tries to break free but your strength made it impossible. Try as she might, she couldn’t break away, even as you put the piece of ginger root up her cooch. She tensed up from the surprise burning effect of the root’s juices. Each and every movement of the ginger gave her more burning pleasure than ever and lessening her resistance. Still, you had to pacify her and you want to do it fast and be done with it.
Using your other hand, you fiddled around with her clitoral nub. In that moment, her will to resist had eroded completely. For the longest time, Spoiled never felt that good before and her husband was to blame. Now here you are, filling the void he left. It didn’t take her that long to reach her climax as she soon soaked your hand with streams of her essence. Her moans subsided and gave way to panting and exhaustion. It became clear that Spoiled liked it, right where you wanted her.
“My word,” she panted while sitting up. “Filthy never made me feel this good.”
“What can I say, I aim to please,” you replied.
“Indeed. I can certainly see why she chose you to be her right hand.”
“How did you...”
“Know? Julia told me.”
“Oh. Well, I’m glad you liked it.”
“Hmmm, indeed. Now, I suppose it’s only fair if I repaid you.” Before you could react, she grabs hold of your erection. It throbbed in her hand, sensitive to her touch. For a second, you felt as if you were about to blow your load too early. But hell no, you weren’t going to give her ammo to mock you. “Shouldn’t you be kissing me, sir?”
And kiss her you did. Mashing your lips with hers, the sudden arrival of your smooch caught her off guard, leaving you with a window to invade her mouth with your tongue. Shaking at first, Spoiled eventually warmed up to such an amazing kiss. She eventually placed one of your hands on one of her breasts. Each squeeze and fondling of the bulbous mound earned a moan from her and an increase in the frequency of her strokes. You gave it your all, buckling down to endure as long as you could, never leaving the kiss.
Try as you might, you couldn’t last forever. With a final throb, your cock erupted ropes upon ropes of your sticky, life giving seed. You didn’t know why your hips involuntarily thrusted as you came. One could chalk it up to reflex action in the midst of an orgasm. Either way, relief flooded over you as your dick goes limp, still dripping a tiny bit of cum.
“Hmmm, that’s quite a lot and you’re… still hard?!” Spoiled remarked upon seeing your still hard shaft. Just the sight of it made her nethers salivate with her musky nectar. . “I have an idea: Get in the pool and allow me to take the lead.”
Following along, you climbed the ladder down into the pool’s deep end, resting your arms on the ledge. From the other side, Spoiled swam over to you. It was strangely arousing to see a woman in her natural form swim around in water. The very sight of her breasts and hair soaked in water made your member tingle and throb. The second she got to you, her arms wrapped around your neck and the entrance of her honeypot was parked on the tip of your spear.
“Shall we?” Slowly, your member was engulfed by her vagina. For an older woman, Spoiled was pretty tight, another sign of an unsatisfactory husband. She bounces up and down on your pole, splashing water around in all directions. As it went on, her motions became more wild and unbound. Starved and crazed, she moaned and groaned. Suddenly, her inner walls clench and let out a loud wail as she came. However, you were nowhere close enough to cumming.
“Why… why didn’t you cum?!” she gasped.
“Well, I didn’t want to disappoint you,” you shot back. “I want you to enjoy this.”
“Quite the charmer.”
Taking a few moments of reprieve, she resumed her ministrations, bouncing harder than before. She clearly wanted to feel your hot seed inside her and she was going to get it, even if she has to endure multiple orgasms. Holding you tightly, she uses the power of her hips to do the job, letting her give you a very hungry kiss. She would orgasm several more times before you feel your cock about to explode. She was starting to slow down but you aided with some thrusts of your own, matching with her rhythm as best as you can.
Soon, your cock quivered and exploded once more with your essence. You thrusted a few more times for good measure, seeing Spoiled collapse a bit, exhausted yet satisfied. You carried her out of the pool and onto a bench, allowing her a few moments to get her bearings.
“Oh my word,” she wheezed. “You’ve done more for me than what my husband did in a while.”
“The pleasure is all mine,” you replied as you dried yourself off. “Also, I’m willing to excuse your choice of words.”
“Fair enough.” Then, a thought occurred to you. You’ve done it without a condom and it was likely she didn’t take any pills.
“Are you going to be alright if you get... knocked up from this?”
“Don’t worry about it, kid. If I do, I’ll just say it’s his.”
“You sure he’ll buy it?”
“Yes. If not, it’ll be all the reason more to spite him.”
“Fair enough.” You got your clothes back on. Though they were a bit damp, they looked fine for the most part. “So, about our arrangement?”
“Yes, you can tell Julia that I’ve changed my stance. Our little dance earlier actually made me feel much better.”
“Good to know.”
“Indeed. Now, It’s best if you leave now. My daughter will be home soon.” Before you could lay a hand on the door, Spoiled’s voice called forth once more. “Also, I might be needing your services again. Don’t worry, I’ll come to you.” Nodding, you walked away and into your car. As you drove off, you dialed up Ms. Harshwhinny.
“Hello, this is Ms. Harshwhinny.”
“Julia, how were things at the office today?”
“They’ve been good for the most part. So, how did negotiations go with Mrs. Rich?”
“Swimmingly. She changed her mind and it looks like funding will be back on track.”
“Splendid. I knew your oratory skills would be optimal for job.”
“Why thank you, ma’am.”
“Likewise. I’ll be expecting you in tip top form tomorrow.”
“You know me, I’m hardly ever a slouch. Heh. See you tomorrow.”
You hung up the call, focusing on the road ahead. Since you lived on the other side of Canterlot, it was a ways away to your house. As you hit the stretch of road near the forest, you saw a car and it’s driver standing next to it, a blue haired woman. She looked to be struggling with her phone, calling for a tow. The moment she saw your car, she waved you down.
“Mister, would you mind giving me some assistance, please?”
Author's Note
Whew, been quite a while since I'v written anything for this story. To be honest, it took me quite a while and my motivation to write this story started to falter a bit. I do apologize for keeping you waiting like this. Again, thank you for the reception you've given this story of smut and MILFery.
Here's a short teaser of Milky Way's chapter:
Once Milky was done with the breast pump, you were briefly able to see a sight of the nipple. Though you were slightly aroused, the fact that you've just met her made you fear those thoughts. You looked the other way, causing her concern.
"As I've said before, I'm used to receiving looks because of my 'things'." said Milky. "I'm not even the least bit offended."
"Well, it's that we've just met." You replied. You've heard a click and a ruffling of cloth. Turning around, you saw Milky Way, no top or shirt on, baring her breasts to you. They leaked a bit of milk out of the nipples as if welcoming you to taste some of the ichor within. You struggled to react but the sight of such a large pair of breasts made you indecisive.
"Now, do you want to feel them?"
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Magnificent Motherly Milky Mounds (Milky Way)
Exiting the car, You got a closer look at her ‘features’. Apart from her hair, she has charming green eyes and freckles, all of which made her cute. And judging by her accent, she hailed from overseas, the United Kingdom to be exact. But, there was one thing in particular about her that stood out to you. Her breasts were quite large, possibly around an F-Cup. The sweater she wore over it could barely contain her impressive bust. You were left wondering whether or not they were natural. But knowing that you just met whoever she was, you put those thoughts to the side.
“Bloody piece of shit phone!” she angrily blurted out as she put it in her pocket. “Damned thing’s battery always dies at the worst possible moment! Ugh!” Her gaze turns back towards your way with her anger almost immediately disappearing. “Mister, do you have a phone?”
“That I do,” you replied as you looked on at her car. From what you saw, a smoking engine meant that thing wasn’t going anywhere without repairs. “Want me to call a tow?”
“If you wouldn’t mind. Thank you kindly, sir.”
With a few swipes and button presses, you called up your local auto shop and explained the situation and where you were. They gave you an ETA of about ten minutes which was shorter than you expected. Hanging up, you turned to the woman.
“Well, the truck is ten minutes out, so we’ll be here for a while.”
Why thank you, good sir!” she said. Instead of a hug as you anticipated, she joyously shakes your hand, expressing her gratitude. “Oh, how rude of me, I forgot. My name is Milky Way. What might your name be?”
“Calculus Crunch, Ma’am.”
“Well Calculus, I suppose I’ll have to compensate you for the petrol money.”
“Nah, don’t worry about it. Money isn’t an issue for me.”
“I mean, if you want-”
“Like I said, I’m good on funds. Just don’t worry about it.”
After a while of back and forth conversation about how your respective days went, a light on the road grew closer. Knowing it was the tow truck, you waved it down and pointed to her car. Once her car was attached, you escorted Milky to yours as you followed the truck to the west side of town. Along the way, she told a bit about herself. She was indeed from the UK, Trottingham to be precise. She moved into the country about five years ago to get away from family members that drove her nuts. Luckily for her, she had an uncle that ran some sort of dairy store downtown, so she was able to make a living.
After following the truck to the garage, Milky went to pay for the repairs which totaled to about three-hundred dollars. Seeing as how she was stressed enough about her car breaking down, you footed the bill, much to her objections. Though in the end, she mellowed down about it and was thankful. Following the payment, you drove her home. You recognized the area as you live a good few minutes from where her place.
Expecting to drop her off and be done with it, she invites you in. It wasn’t the first time any attractive woman let you in their abode and certainly won’t be the last. Not wanting to be rude to a nice, you obliged. It was a nice place, simple yet cozy. You both sat on the couch, turning on the TV to a rather funny game show. Though you weren’t into stuff like that, you couldn’t help but laugh at the over the top humor.
“When I first came here to live, I expected that I wouldn’t be enthusiastic about the programming here.” She remarked as she giggled a bit. “But I’ll admit, the over-the-top nature of shows like this have grown on me.”
“Well, people have an acquired taste.” You replied. “People either like it or hate it.”
“True.” As you watched the display of pie fights and obstacle dodging, your eyes slowly drifted to the alluring mounds on her chest. The size, the sheer size of those melons made you tight in the pants. However, she wasn’t oblivious to your gawking. “Is something the matter, Calculus?”
“Oh cra- O-Oh, no, Milky,” you stammered but you could tell that she wasn’t fooled by your words. Knowing that she’ll probably think of you as a pervert, you spill the beans. “Well, I’ve been wondering-”
“About my things?” She interrupted. To your surprise, she didn’t seem to be bothered at all. “I’ve received quite a number of stares and questions about my breasts. It’s nothing new.”
“Really? I thought you’d be annoyed my staring them, but alright. Are they… natural?”
“Natural? Why yes, yes they are. My friends during my school years remarked how lucky I was to be “gifted” so to say with my mounds. But, it wasn’t without… drawbacks.”
“What would that be?”
“Close to ending my twelfth year in school, I started to… lactate spontaneously. I mean I wasn’t pregnant at the time and nor did I even have sex. After consulting with the doctors, the diagnosed me with Galactorrhea, excessive lactation. It was a side effect of my gift.”
“I’m sorry to hear about that,” You replied back with genuine concern. “How were you able to deal with it?”
“Well, I use a breast pump whenever I have an episode. Luckily, I was able to hammer down the frequency at which they occur. That’s why I sounded angry about my phone earlier.”
Just as you were about to acknowledge her reasoning, Milky’s eyes started to wince, moaning in pain as she started to rub her right breast. A wet spot soon developed on her sweater, causing her to mutter something about her favorite sweater being ruined.
“Calculus,” she moaned. “Can you… go into the kitchen and retrieve my breast pump?”
Nodding, you entered the kitchen, searching the cabinets and shelves for what she needed. Opening a cabinet near the fridge, you found a strange device with two plastic domes connected by rubber tubing. Knowing that was what you were looking for, you grabbed it and returned to Milky, who was still cradling her breast.
“Thank goodness,” she gasped as you handed the device to her. Just as she was about to reveal her bulbous mammaries, you blush and turned your head. “What’s wrong, love?”
“Well, it’s just that I thought you’d want some privacy.”
“Oh no, I’m quite alright. You needn’t be so prudish.” She placed one of the cups over her nipples and switched on the machine. The whirring and suction action was immediately followed by a sigh of relief that bordered on moaning. Though you didn’t see it, the mental imagery was enough to give you a stiffy. “You have no idea how much relief this gives me every day.”
“I could tell.”
Her moans went on for minutes as the pump sucked the liquid from her breasts, From how it sounded, you could only imagine how much discomfort her condition causes. Once Milky was done with the breast pump, you were briefly able to see a sight of the nipple. Though you were already aroused, the fact that you've just met her made you fear those thoughts. You looked the other way, causing her concern.
"As I've said before, I'm used to receiving looks because of my 'things'," said Milky. "I'm not even the least bit offended."
"Well, it's that we've just met," you replied. “I didn’t want you to think of me as a creep.” Suddenly, your head was covered by her sweater. You took a bit to remove it. Turning around, you saw Milky Way, no top or shirt on, baring her breasts to you. They leaked a bit of milk out of the nipples as if welcoming you to taste some of the ichor within. You struggled to react but the sight of such a large pair of breasts made you indecisive.
"Now, do you want to feel them?"
“Really? Is that what you want?
“Oh, come on,” Milky said as she scooched closer to you, making your face feel hotter. “You treated my condition with maturity despite how nervous you were.” She got closer and closer to the point the skin of her tits made contact with your arms. Now, she was giving those bedroom eyes but something was different about hers. Along with her facial features, they all gave of an aura of cuteness, too much for any mortal man like you to resist. “Besides, I can’t possibly let you helping me with my car go unrewarded.”
Forcefully, she grabs your wrists and places them on her tits, urging you to give them a squeeze. They felt like a squishy mix of soft and firm. To you, it felt like squeezing balloons filled with sweet pudding, pleasurable to the touch. You ran on autopilot as you planted a zealous kiss on her luscious lips as you began to lay on her. The fact that no objections from Milky were spoken was reason enough to let your inner horndog loose. Soon you laid upon her completely and began grinding your hips on hers. All the while, she began to moan lustfully at your movements as it made her nethers tingle with excitement.
“My word, you’re certainly no stranger to love, aren’t you?” She gasped as you let go of her breasts and fiddled with your belt, removing your pants and undergarments. She was nonetheless surprised by the size of your girth but her eyes told you she was familiar with such a thing. “If it’s no problem with you, I’d prefer not to do any oral. It’s just not my thing.”
“Not at all,” you replied as you threw off her shoes. “Sometimes, you gotta leave things out to shake it up.” Removing her jeans and panties revealed a decently sized bush that didn’t hide the beautiful sight of her flower. It dripped with immense arousal as did her tits. Looking at the delicious looking ichor seeping out, you licked your lips with hunger.
“I see you fancy a taste. Go ahead, satisfy your curiosity.”
Diving back onto her, you pulled her up, latching your mouth on her right nipple and an hand on the other. As you suckled the warm creamy goodness from her teat, your grinding restarted, brushing your rock hard cock against her hairy vulva. Even though you hear her moan pleasurably, you wanted her to scream, to let her inner slut out.
Using your free hand, you reached under her and stuck two fingers in her pussy without warning. She yelped at the feeling but warmed up to it. The inside felt slick to the touch as much as it felt snug. You worked your fingers to find her magic spot while not skipping a beat on the other matters. All those times spent with horny cougars have made you develop impressive multitasking skills. After a while, you found her g-spot and insert a third finger, much to her screaming pleasure. From how progressively snug her vagina was getting, she was close… and so were you.
Grinding with the speed of a rabbit in heat and suckling like you had a monstrous thirst, you eventually climaxed with a spray of your sticky white cum. Soon, it was followed by a spray of Milky’s essence soaking your hand. Pulling out your hand, you surveyed the damage. She was covered in your cum, both yours and hers, sweat, and breast milk. Her hair was also a disheveled mess from it’s perfectly curled form. She laid panting at your knees as she sat up.
“Bloody hell!” She cursed as she wiped the sweat from her brow. “I’ve never felt that much pleasure since my ex.”
“How long has that been?” You asked.
“God, I honestly can’t recall. Might’ve been a few years. Double dealing twat.” As she gathered her senses and was alert, she noticed your shaft at half-staff. Her pussy craved it but knew it wasn’t possible with you at half-chub. Knowing you were pleased with her gifts, she wasted no time in giving you a titjob then and there. Her perfect mounds felt like paradise made manifest. Though it was temporary as you became erect in short order, it was certainly something you’ll never forget.
“There, that should do the trick,” she said as she climbed back on the couch on all fours. Her ass and pussy were in plain view. The latter salivated for something fleshy to sate it’s hunger. “Come on, give me that big knob of yours.”
With a salute, you grabbed two handfuls of dat ass thrust your pelvis forward. You were amazed that you were able to slide it into her caverns without any visual guidance. Still, you had a job to do, one you enjoyed to do. You began your movements, thrusting your mighty spear in and out of her puffy wet sex. Grunting with every breath, you channeled your energy into pleasing this woman you just met. Indeed your efforts bore fruit as Milky’s speech was soon reduced to an incoherent mix of babbling, breaths, moans and gasps.
“OH GOODNESS YES!” She cried out as you got her on her knees, barely skipping a beat. “MY BREASTS! SQUEEZE THEM!”
You didn’t even need her request as you did. The softness of her chest pillows was more than enough to bring you back. You loved playing with those orbs in your hands and her moans told you the feeling was mutual. As long as she liked it, you were willing to do it for as long as she liked, even if it would kill you. You’d die happy that you were in the presence of such perfect boobs.
Like the finest of wines and brandy, it was not fated to last forever as you felt your groin trembling. You knew very well with your body meant by that but you weren’t going to stop for that. Oh no, you wanted to keep thrusting, even as you blew your load inside her. Still sensitive, your continued thrusts drove the nerves in her nethers in a frenzy. Followed by a long winded wail, the inevitable happened and your junk was basted by a rush of her juices. Once she came, you relented and collapsed with her on the couch.
“I-Incredible!” Milky wheezed as she slowly turned around. Though tired as you were, you gathered enough strength to rest your head on her breasts. “That was the first time in years I’ve had any... ‘action’ as you americans say.”
“It pays to be with someone that’s experienced,” You remarked as you buried your face in between her breasts. “It also pays to have an amazing gift.”
“Indeed. I suppose you’ll be staying the night?”
“Yeah, too tired to go- *yawn* anywhere.”
Truth be told, you were fine with staying the night with her. Just as you got done with another woman, another happened by chance. Sometimes, you wondered if luck was woven in your genes. But you knew part of that was due to you and your charisma. It causes you to give pause and look back on how you’ve come since your years in high school. Still, you couldn’t help but smile as your eyes shut, content and satisfied.
Author's Note
When I promised Milky Way, you'd bet your ass I would deliver. Anyways, another chapter bites the dust and Somnambula is next. Stay tuned.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Jewel of The Past (Somnambula)
“Ninety-eight, ninety-nine… one hundred!”
You wipe the sweat from your brow, climbing off the machine as you stretched your arms. Spending the morning working out to jumpstart your body made you sore for sure but it woke you up better than coffee. As you caught your breath, your stomach began rumbling, nagging at you for sustenance. It was a good time as any for a light breakfast of an egg white omelet.
As you gathered your fixings, you heard a few short raps on your door. Walking over, you opened it. To your surprise, it was Julia Harshwhinny, clad in her casual attire instead of her formal business wear. Strangely enough, she had a faint smile on her face as she rubbed her rotund midsection, calming the life within.
“Ms. Harshwhinny,” you greeted her.
“Mr. Crunch,” she replied. “How are you doing this morning?” She takes a look at you. Right away, she saw you clothes were damp, raising an eyebrow.
“Good. Good. Just got done with a work out. Please, come in and have a seat on the couch.” You escort her in, helping her on the couch. You couldn’t help but rub her stomach a bit, knowing that it’s your child that’s growing inside her. “Would you like something to drink? Coffee? Tea?”
“Just some water will do.” You did just that, getting her a glass of ice water in the kitchen. Sitting down across from her, you you kept staring at her figure being hidden by her purple sweater. Still, it wasn’t like her to make visits to her employees for casual affairs. You knew what she wanted with the games happening in less than two months. She had a job for you and used the weekend to relay some info. You had to hand it to her for being cautious and calculating. Even then, you’ve known her long enough to read her like a map.
“So, what’s the job?” you asked to which she snickered.
“Hmmm, how perceptive of you.” She giggled as she took a sip. “No wonder I value you in our… ‘relationship’. With what you did for Mrs. Rich, our budget for the games is back on track. Still, I see that a surplus represents a big boon for our endeavors. So, with the games, the Canterlot Museum of Ancient History maintains a partnership with us because of the tourism the event brings.”
“What would you like me to do?”
“It’s a simple matter really. Late noon tomorrow, I want you to oversee and sign things with the museum’s curator, Ms. Samaya North. Normally, this would be a job I usually do in person but an appointment with the doctors about my *ahem* condition leaves me unable to. With that in mind, I’ve let her know in advance that you’ll be going in my stead. You don’t need to do anything aside from a bit of talking and signing some documents with my authority. And no, you don’t need to get in her pants or anything. Just talk and sign. ”
“So, nothing else beyond that?”
“No, Mr. Crunch. She’s actually quite personable for someone in her position. I assure you that you’ll have no trouble in this assignment.”
Not that you needed any reassurance of success, what’ll happen between now and Monday was another thing. It should be a simple matter if all it involves is a bit of oratory skills and signing a few documents while being the CSG’s representative. Boring for sure, but work is work and it pays the bills.
“Ma’am, consider it done,” you replied as you helped her up from her seat.
“You know me,” Harshwhinny replied. Before you knew it, she gave you a quick peck on your lips with a sly smile on her face. “I expect results. Now, you don’t have to show up tomorrow but it’ll count for a full day of work. As always, get the job done and report to me after.”
“Yes ma’am.” You waved at her as she left your house, speeding off in her Jeep. Musing at how you were lucky to have such a great job and a softie for a boss, You thought of how things would’ve been different if you didn’t stay after school all those years ago. But it is what it is and you plan to enjoy every ounce of your fortune and success. Still, there was the matter of your hunger and demanded to be sated. As you were chopping the peppers, you did a quick glance at your clothed member, standing tall and proud.
“Crap, she always gets me all hot and bothered.”
The Next Day
It was five in the afternoon, the skies were a brilliant burnt orange and the winds were pleasantly cool. You made a took one last look at yourself in the mirror, examining your features. Everything was in place and not a single strand of hair went rogue. Putting on your suit, you dusted it off a bit and nod. Truth be told, you were never a fan of wearing suits, finding them to be stuffy. Still, you soldiered forth and took it in stride. Now was the time for work.
Driving towards the downtown area, your view was flanked by the towering buildings, reaching towards the sky. A little off in the distance, you saw your objective. It reminded you a bit of a greek temple, made with marble and pillars at its fore. You saw it many times while heading to work or while on lunch break. You’ve never been there before but there’s always a first time for everything. Though, it wouldn’t be the first time you’ve traveled through time. Entering the building, you were greeted by the lady at the front desk.
“Hello, welcome to the Canterlot Museum of Ancient History. How may I help you sir?”
“Hi there,” you said, straightening your bright red tie. “I’m here on behalf of the CSC to discuss business matters with Ms. Samaya North. Can you let her know I’m here?”
“Yes sir, I’ll let her know,” she said as she picked up phone. “Ms. North? Yes, there’s some person from the CSC wan- Yes. I understand. Alright. *Click* She’ll be with you shortly, sir. Go ahead and take a seat.”
For a few minutes, you twiddle your thumbs. This was the second time you’ve been handed a responsibility of such magnitude. Failure would mean your ass is grass. Then again, you weren’t the one to disappoint. Soon, you saw a woman in a black business suit approaching. Violet eyes behind a veil of glasses, neat dark arctic blue hair in a bun and an aura of experience followed her. You knew for sure she was the woman you were expecting. She then locked her eyes on you and approached.
“So, you’re Mr.-”
“Calculus Crunch, ma’am,” you finished as she shook hands with you. “Pleased to meet you, Ms. North.”
“Nice to meet you, too. I never expected Julia’s assistant to be so… young if you don’t mind me saying.”
“Don’t worry, I get that a lot.”
“Indeed. What happened to Ms. Peachbottom?”
“Well, she… ‘switched jobs’.”
“I understand. I’ve seen how stressed she was the last few times I’ve seen her.” You got up and turned toward the rest of the museum. “So, would you like a little tour while we discuss the details?”
“Sure,” you replied, following her further into the building. Inside were various display cases that held artifacts from various time periods. You wonder how the museum was able to obtain them but they were still a sight to behold. Weapons from civilizations either long gone or from the past of others and various other things like clothing, tools and texts were on display. So much stuff to take in but so little time for you. Eventually you came across a bust of a bearded man with the inscription “The Father of History”.
“Calculus, I would like to introduce you to Herodotus,” said Samaya. “an ancient historian. We have much to thank him for what we do.”
“Sounds like he was an incredible person,” you remarked as your gaze turned away from the display. “Though, my profession is with running numbers. I’m not well versed with history.”
“I suppose we all have our faults,” she remarked as turned around. “Well anyways, let’s finish the rest of the tour before we take care of business, shall we?”
Nodding, you followed her around for another ten minutes before you arrived at her office. Like the rest of the museum, it had the same sort of design. However, it had an egyptian-styled chair made with fine wood and gold with some jewels adorning it. It looked rather odd for a museum curator to have something like that in their office. Still, it was a nice looking chair.
“So, Mr. Crunch,” Said Samaya as she sat upon it. “I trust that everything during your visit is up to par.”
“Very much so,” you replied, taking a seat. “I can tell that this place will be quite busy when the games roll around. So much to see to entertain the mind.”
“Quite,” she replied as you exchanged sets of papers, browsing over the contents within. “Hmmm, these don’t look to have changed since last time. Then again, it’s just an annual confirmation thing.” For minutes, your eyes perused the mini-stack of papers handed to you, putting your signature where needed. It was nothing new for you as your former and current positions required it large quantities. At times, you’ve found comfort in the tedium of such a thing to let your mind rest from running numbers.
“Aaannd, finished,” you muttered as you exchanged folders, standing up and shaking her hand. “I have to say this meeting has been enjoyable and productive.”
“I’m certainly glad you’ve seen it that way,” Samaya said as she waved you off. “Well, I hope you have a pleasant rest of your day.”
“Thank you, ma’am.” You made your way to the door, putting a hand on the doorknob. But, it wouldn’t turn. You tried turning it a few more times to no avail. “Locked, what gives?” Little did you know, Samaya was right behind you with a an amused smirk drawn on her face. Within an instant, she gently turned you around and pinned you against the wall, pulling you to her face by your tie. From what her half-closed eyes spelled, you knew what she wanted. What was surprising was that you never suspected her to make a move of that nature. “Wh-What’s going on here?”
“Come on now, Mr. Crunch,” she moans as she presses herself against you. “I’ve been checking you out since our time here. Did you really think you would get away before we’ve had some… one-on-one time?” Licking her lips, she planted hers on yours in a way that felt forceful yet silky smooth. Clearly, she had experience but more so than the others before. The kiss soon broke, leaving a strand of saliva. “Mmmmm, what a nice example of a man you are, by this era’s standards.”
“Era?” you gasped. “What are you talking about?” Samaya took your hand in hers and led you to your chair, forcing you to sit down before having you remove your coat and shirt. Her eyes opened wide as she marveled at your physique, nicely toned pecs and all.
“My my, what an excellent body,” she mused as she reached into a drawer. “I honestly can’t quantify the many times I’ve engaged in moments of lust. But, it’s been millennia that I’ve been having those moments…” She pulls out two pairs of handcuffs, smiling lustfully at their sight. “And two centuries since my last.”
“Though I’m not opposed to some bondage, what did you mean by centuries and millennia? What is going on here?”
“Shhhhh,” she whispered as she cuffed your arms to the chair. Struggle as you would, you knew you weren’t going anywhere. “I suppose I should tell you the truth. But, let me get more comfortable first.”
Disappearing into her private bathroom, it felt like a fourth of an hour that Samaya’s been in there. As you wondered what she was up to, the door opens and out came Samaya, clad in some new garb and holding a cup of something. She wore a white silk bra that was held up by a lace around her neck, covering her D-Cup mounds. Her panties were also of the same make, covered by a see through skirt. Gone was her hairbun as it was now flowing, covered by a gold-headed white headdress. One could say that they would go blind from staring at such a fine display of beauty.
“Goddess...” You muttered to her to laughter.
“No,” she replied as she got closer. “but I’m a close second.” She danced and sashayed her hips. As she got closer, your spire began to rise tall and proud. Clearly she was amused by the sight and licked her lips in anticipation.
“Ms. North, what is this?”
“Oh yes,” Samaya said as she put the cup on the desk. “That is merely a pseudonym I use in this day and age. My real name… is Somnambula, former high priestess of Cyrus The Great.”
"How are you in your thirties if you claim to be thousands of years old?"
"I'm glad you've asked. As per my covenant with King Cyrus, I also became his chief explorer. During a trip to Egypt, I was a bit careless and fell into a hole. Waking up in some cave, I found myself in front of deposit of water which radiated some strange energy. Me being thirsty at the time, I took a handful and it rejuvenated my youth to my prime. As a result, I never grew older beyond 33 years of age. However, I knew the dangers of such a discovery and made sure that the water's existence was lost to history. From there, I made it my calling to preserve the history of the world and its nations."
At first you were in disbelief at her being thousands of years old and still look to be in her 30’s. Then again, you were accustomed to the stranger things of the universe like time traveling and being your friend’s father as a result. Even then, something in your gut tells you that she spoke truth.
“Well, let’s just say that I’m used to the strange and unusual,” you answered. “Quite honestly, I’m familiar with the past so to say.” She answered back with a smirk on her face.
“How so?”
“It’s a long story, and an embarrassing one.”
“If there is anything I’ve learned in my long life is to know when something is best left unasked.” She once again held the cup in her hands and held it in front of you. “Sometimes, it’s best to just enjoy life as is.” Your nose caught the scent of the liquid. It smelt vaguely of lavender and honey. It was pleasant yet you knew not what it was. “Here, drink. It’ll come in handy for what we’re about to do.”
“What is that stuff?” you asked with a shudder. “The last time I’ve ingested something strange, I hallucinated like mad.”
“I understand your tension but there’s no need to fret. This mixture enhances your sexual desire. That’s all it does.” Holding it to your lips, she tipped the cup as you opened your mouth. Like what it smelled, the liquid had the faint flavor of honey but passable enough for you to drink it all. The effects immediately became apparent as your loins grew hot and your member and balls ached yet you felt nowhere near close to cumming. Looking down, Somnambula swiftly undoes your belt and pulls down your lower garments. The look of surprise as she nearly got slapped by your cock made you chuckle internally but it was clear that she was impressed by its size.
“Dear Hathor,” she gasped in awe. “Your girth… impressive.” Her hand begins to caress your length. The skin to skin contact made it shiver and quiver, sending jolts of pleasure through your nervous system. Your reaction hasn’t evaded the attention of Somnambula. “Heh, your reaction is so priceless. It reminds me of the many men I’ve been with over the years like Herodotus. The look he gave me was utterly priceless.”
“Sounds like you have experience,” you replied with fascination. Though you’ve been with many women in your life, you’ve felt outclassed by the woman before you. For the first time, your experience pales in comparison. Somnambula then straddles your lap and began the most erotic dance you’ve seen. Brushing her clothed breasts against your face, sliding her hands all around her body and grinding her crotch on your pole, your loins felt more and more sensitive by the minute. It almost felt that your orgasm was due to arrive but it didn’t, only fueling your desire of the immortal woman dancing on you. As much as you wanted, you couldn’t touch her beautiful form as your wrists were chained to the chair. For now, all you could do is enjoy the show.
“Jesus, how are you this good?” you asked
“That would be the story of a thousand lifetimes,” quipped Somnambula as she got off your lap. Her arms snaked to her back as she danced her hips around. “Now, let me show you beauty that is the envy of women.” With an audible click, her entire dress comes undone. Now, you got a good view of ancient beauty unveiled by clothing. Her nethers clearly dripped with arousal, hungering for your meat. You were left speechless at the sight but unable to touch.
She knelt between your legs, breathing upon your quivering erection. It didn’t take many synapses to guess what her intentions were as she took your spear into her mouth. However, she sucked slowly yet sensually. Her inumerable years of experience shined brightly as she went about her work. It felt glorious and heavenly. As much as you wanted to cum, you couldn’t. You suspect it had something to do with the potion she made you drink. Still, the experience felt more incredible than you originally thought. You endured minutes of her sucking until she popped it out of her mouth with a confused look on her face.
“Hmmm, your stamina is higher than I expected,” Somnambula mused, stradling you once more, placing the tip of your cock at her wet entrance. “But, you will cum before I do.” Cupping your head in her hands, Somnambula lays another kiss on your lips, swiftly invading your mouth with her tongue. The desire to hold her naked form close was maddening but her body was pleasurable nonetheless. She exited the kiss, allowing you to breathe before she made her next move.
Somnambula impaled herself on your quivering cock, parting her lower lips. Strangely enough, she barely made any noise apart from a nearly silent moan. She was well familiar with carnal pleasure and today was the first time in years she’ll experience it again. Taking a moment to process the pleasure, she takes your chained hands in hers and began to ride you. She started in a slow and fluid motion, never skipping a beat. It was perfect, absolutely perfect. Every bounce she picked up her speed. Every rise in tempo was met with an equal increase of her moans and squeals. She was enjoying this more than you did. Nay, she craved it.
Then, you began to feel her inner walls clamp around your shaft as it began to convulse. You felt like letting go and blowing your load. However, Somnambula felt that you needed some extra stimulation. Bringing her mouth to the nape of your neck, Somnambula bit down and began sucking. Though you felt pain, it was short lived and replaced by rapturous pleasure, pulsing intensely throughout your nervous system.
That was it, the one thing that sent you over the edge. Your package quivered and writhed as your cock let forth an eruption of your cum. Somnambula felt the rush of heat as your seed filled her insides, further clamping down to ensure that you’re milked to your every ounce. With a loud yelp, Somnambula’s orgasm came with a vengeance, soaking your crotch and filling the ambient air with a musky scent. She rode out her orgasm until it began to die down, falling limp but still lucid. The moment she freed you from the cuffs let the beast within you free as you held her tight and kissed her passionately. It felt good to finally touch pure beauty.
“Calculus,” Somnambula moaned as she ran a hand across your cheek. “You were the first to pleasure me after all these centuries. I’m glad you’ve made me feel that... good.”
“And yeesh, you gave me a run for my money,” you shot back, rubbing her back and firm ass. For a woman with years of sexual experience that dwarfed yours, it was amazing, reminding you of losing your virginity to Dean Cadence. It felt like that all over again and you enjoyed every minute of the afterglow while caressing her body. But as your mind refocused, your eyes were directed towards the clock and it read 9 PM. “Holy shit, it’s 9!”
“The museum usually closes at 11.” Somnambula said as she got off you. “I think it’s best if you left now and we can avoid any risk of suspicion.”
You entered the bathroom with Somnambula, cleaning each other to erase any hint of your earlier deed. Sadly, as much as you wanted another round, she said it wasn’t a good idea. After a moment of washing yourself, you donned your suit once more with barely anything out of place.
“I suppose this concludes our *ahem* meeting,” Somnambula said, handing you your briefcase with the paperwork. “I may require your services again soon.”
“Well, it’ll have to be discreet, Somnambula.” The utterance of her real name earned you a quick but delightful kiss from her. With a wave, you bid your farewells and walked out of the museum, acting like nothing happened but intent on remembering the experience. As you drove away, hitting an empty intersection, you made a quick adjustment to your front mirror before the light turned green.
At the corner of your eye as you began to move, a truck darted toward you. You had not enough time before it made impact with your car and sending you crashing against a nearby wall. The shock of the impact was enough to render you unconscious with a good knock to the head, turning your vision black and rendering the world silent.
Author's Note
Well, I came and delivered. Here's a new chapter about an ancient beauty. As for what's going to happen with Calc, no need to worry. The next chapter will put you at ease. Stay tuned and enjoy.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Sensual Healing (Nurse Redheart)
Your eyes began to open, vision still blurry. As your awareness kicked in, you felt an ache all over your body. It felt like you’d been through a match with a championship boxer and had your ass royally handed to you. It hurt like hell, much more than you’re accustomed to in a workout. Soon your senses and motor faculties started back up but you were still unaware of where you were.
However, there were a few clues that caught your attention: you were lying on a bed, tubes stuck into your arms, a rhythmic beeping, a nice and clean room, and a blonde haired pregnant woman holding your hand as she stared off into space. You knew who she was and were amused she would be there for you. You moved your thumb over the back of her hand, grabbing her attention.
“Calculus?!” Ms. Harshwhinny gasped. She stuck her head out the wall of sheets. “Nurses, he’s awake!” She then turns to you with suppressed relief. “Thank goodness you’re alright.”
“Wh-What happened?” you moaned as you rubbed your head in pain.
“You were in an automobile accident. I don’t recall the details of the scene but your car is a wreck. Fortunately, your insurance will cover both automotive and medical. So, don’t have a heart attack over it, please?”
“How long have I been out?”
“A week.”
“Shit,” you groaned. Being out for a week probably would see you piled with a lot to do. It’s not a pain to be carrying a lot of work on your plate. You were more worried about how you were going to get things done in your current condition. Looking down, you saw your right leg in a cast. “Where am I?”
“St. Mary’s Mercy,” replied Harshwhinny. “They were going to send you to Canterlot General but I wanted you to have adequate care.”
“Heh. I’m touched you care so much for me,” you snarked. Try as you may, your laughter caused a jolt of pain that silenced you. A doctor with a set of brown hair then came in, holding a clipboard.
“Glad to see you’re alright, sir,” he said, clearing his throat. “I’m Dr. Horace, a senior orthopedic surgeon here at St. Mary’s. I have to say that we expected the worst when you were brought in after your… accident.”
“Thank you, doc.” You yawned. “How bad is it?”
“Well, It was nothing major nor permanent.” Horace said, flipping through his papers “You have a fractured leg, some bruised ribs, and a minor concussion. Judging by your talkative demeanor, it seems as though you’ve recovered from the latter.”
“Even then, I was running the numbers to see how high the bill is.”
“That’s good. No brain damage. But still, you need to spend two more weeks here to ensure you can rest at home with care. We still have quite a bit of work before you’re cleared for release.”
“Really? Dammit.”
“Calc, the doctors here are some of the best.” Harshwhinny said. “They’ll be the ones delivering my child when the time comes. As I said, you’re in good hands here.”
“Right.”
“Anyways Mr. Crunch, I have to get going. There’s a meeting I have to attend. I just came up here to make sure you were alright. I hope you get well soon.”
With a wave, she left the room, leaving only you and Dr. Horace. Not long after, a nurse came in. She had pink hair in a bun and wore a set of blue scrubs with a stethoscope around her neck. Even the aura she exhibits gave off a focused, cheerful, and caring vibe. And her smile, one can only hope to see a one that's as warm and nurturing as hers. On the I.D. badge around her neck gave you her name: Redheart. It was a fitting name for one dedicated to healing the sick and injured.
“Mr. Crunch, this is Nurse Redheart” Horace stated, “She’ll be taking care of you for the duration of your stay.”
“Yes, Dr. Horace,” Redheart sang. “I’ll make sure Mr. Crunch is as comfortable as possible.”
“Glad to hear it,” Horace said as he started for the door. “Now, I have another matter that requires my attention. Ms. Redheart will take care of you from here on out.”
“Yes, doctor.” With his departure, Redheart turned her gaze towards you with a frown on her face. “Oh, you poor thing. It’s amazing you’ve recovered from being so badly injured.”
“I… do appreciate your concern, ma’am,” you replied as you sat up. “How bad did I look when they wheeled me in?”
“My goodness, you were a mess,” she muttered as she fluffed your pillow. “Glass shards sticking in you, a bleeding head, and your face… yeesh, it looked painful. It was a miracle nothing else happened otherwise it would’ve been a very different story.”
“Well, color me lucky. Though, I wish I could say the same for my recovery. This is going to throw a wrench in my workout routine.”
“No need to worry about that. Sometimes, it doesn’t hurt to relax.” She then reaches for a small table grabbing a few small items from it. “But still, We’ll be putting you on daily calcium supplements along with your pain medication to speed up your recovery.” She hands you a cup of pills of various sizes and shapes. If there were any guesses, you knew they were going to taste horrible. Bottoms up and past the gums, you swallowed each as fast as you could, followed by a generous amount of water. Just the taste of the medication made your spine quiver and cringe.
“Jesus Christ!” You shuddered. But slowly yet surely, the effects of the painkillers took shape.
“I know,” remarked Redheart “But, you’ll be feeling better before you know it.”
“Hope so.” Then, your stomach began rattling its saber. It desires sustenance in the worst way possible. “But, I’ll say that I’m famished.”
“Don’t worry.” Redheart started towards the door “I’ll send for some food. Just relax and I’ll be right back. But after dinner, it’ll be time for your sponge bath.”
“Sponge bath? Christ, that’s going to be humiliating.” For most of your life, you carried yourself as a self-reliant person. Rarely did you ask anyone for help. But the thought of you, a grown man being washed by some admittedly cute looking nurse was embarrassing, to say the least. But there was nothing that could be done about it. You had to suck it up and swallow your pride because you’ll be spending the next couple weeks under medical care. You just had to hope the food is at least somewhat tolerable.
You finished chowing down on the last of the pizza that was given. Though the taste was subpar, it was still good. Pizza is pizza. Being unconscious for a week would work up an appetite of a ravenous beast. All in all, you were satisfied and less grumpy. Soon enough, Nurse Redheart walks in with a reserved smile on her face. Something tells you that you certainly won’t be growing tired of her smile.
“I hope you found the food to be filling,” she sang.
“I can’t complain,” you shot back. “It is what it is.”
“Well, it’s time for your sponge bath, sir. I’ll help you out.” You sat up, turning around and letting Redheart help you into your wheelchair. You were then wheeled into the bathroom, complete with a bath and everything. She starts running the water, checking to make sure it was relaxing hot “Here, I’ll help you out of your clothes.”
You raised your arms up, allowing her to take your gown off. She blushed as she looks on at your lean yet muscular form. But the moment she took off your lower garments, she sat in shock for a moment. Though you weren’t fully erect yet, you were still quite sizable while flaccid. Snapping herself out of her trance, she brought her focus back to the task at hand. She took a garbage bag and made sure your cast won’t get soaked.
“Okay, it’s bath time.” Redheart remarked as she helped you into the tub. The water felt hot yet relaxing to the touch, soothing your achy muscles and bones. You couldn’t help but let out a relaxed moan as you sat back. It was much needed and it felt like the pinnacle of nirvana. “Okay, I would like you to sit up so I could get those arms.”
And scrub those arms she did. She paid close attention and never let a single speck of dirt remain on your skin. She was soft yet thorough with her scrubbing. She later moved onto your other arm before reaching your back. Just the way she ran that sponge up and down felt like a much-needed massage. However, her actions had the side effect of hardening your quivering cock. You hope to god that she wouldn’t work her way down there.
“Okay, now for your front.” She said, running the soap and water soaked sponge over your chest. Every movement and circle soothed your muscles. The further down your chest she went, the more you got nervous. Like a great many things, the inevitable happened as the sponge made contact with the base of your shaft with the side of her hand touching the skin. For a moment, Redheart froze with embarrassment and the air was beset by dead silence.
“Oh, I’m terribly sorry,” she said as she turned away but never removing her hand. “Did I offend you?” Truth be told, you weren’t upset at all. You were a little embarrassed for sure. Your mind warned you to not to enjoy it out of the moral quandaries that’ll result. However your member, the very part of your biology that is associated with sensual desire, was calling the shots. Slowly and cautiously, Redheart started jerking your dick, going faster by the moment. Soon it got to the point where it sent water splashing about. Looking around, an all too familiar grin soon formed on her face.
Standing up, she removed the top of her scrubs and then the bottom. Your jaw dropped at her nice figure. She had a decent set of C-cup breasts and some nice hips with an ass to match. Soon her lacy bra and panties were gone and there was nothing keeping your eyes from her pure form in all its glory. Reaching behind, she undid her hair bun and let it flow freely.
“Goodness,” you gasped. “Where have you been all my life?”
“Life’s greatest question,” Redheart replied as she advanced towards you, fondling her breasts and nethers with her stride. “Well here’s another. Can I join you? No need to worry. I’m always careful with my patients.” Nodding enthusiastically, she climbs in, seating herself between your legs. Her eyes darted back and forth, examining your body with a lick of her lips. “Hmm, nice body? How hard have you been working out?”
“Pretty hard,” you said. “Though, I’m irked that I can’t for a few weeks.”
“All bodies need rest and that time has come for yours.” Redheart then leaned back and flanked your cock with her feet. “Now, allow me to take care of you.”
Her feet then gripped snuggly around your member, moving up and down its length. Your jaw went slack as her feet pleasured you. Never in your years of getting around did you ever think that a foot job would be enjoyable. Good lord did it feel so good. Still, you weren’t the one to be the sole receiver of pleasure. Thinking quick, you brought your free foot to her puffy pink slit and rubbed it furiously, brushing her clitoral nub. Moan after moan, gasp after gasp, a litany of obscenities escaped her mouth. As much as you like seeing her enjoy it, that was never enough for you. You wanted her to scream until the cows came home.
Without a single hint, you jammed your big toe inside her vagina. She gasped from the sudden entry as you wiggled it around inside her moist sex. After some time, you managed to find her g-spot as indicated by a sharp yelp. Even as you tackled her button, she responded in kind with added speed and pressure on your spear. Your balls tightened and her caverns closed around you as you both picked up the pace, driven by the surge of ecstasy coursing through your veins.
With a loud yelp to the heavens, she came but you didn’t feel it due to the water. Very shortly, you came too as you quickly aimed your cock at her tits. Splurt by splurt, ropes of your jizz coated her mounds. Just the thought of emptying your load on her breasts turned you on, making your orgasm all the more pleasurable. After a minute of riding your orgasm, the air fell quiet, save for the occasional splash of water.
“Christ, who never thought nurses were so kinky.” You breathed. With a blink of your eyes, Redheart was crawling on top of you with a look of hunger. Latching her lips onto yours, your tongues danced in a display of passion. Her wet and slender body pressed against yours as you held onto her juicy ass. She was so irresistible that you started to grind your still erect shaft against her groin. “Hmmm, still hard, aren’t ya?”
“God, you have such an amazing body.” You breathed. Redheart reached down and positioned the tip of your dick against her slit, rubbing it to increase your desire. You wanted it, you wanted her… bad. Lowering herself down, she let out a shuddered breath as she hilted herself on your spire. Resting her body on you once more, her hips bounced up and down, massaging your pole.
“Oh my,” Redheart gasped. “Your cock is huge. Where has it been all my life?!”
Your bodies ground against each other, aided by the soapy water that soaked you. Her ass was so soft and big that you couldn’t help but squeeze it like a bag of soft clay. With every squeeze, she’d let out a moan. You then decided to sync your groping to the rhythm of her bounces. Clearly, she was pleased as went faster and faster, lost in the haze of her lust. As her walls tightened around your cock, she snaked her arms behind your back, holding you tightly as if you were her lover.
“OH GOD, YES! PLEASE, GIVE ME YOUR CUM! PLEASE! PLEASE! OH YES! YEEESSSS!!!”
With one last bounce, you both came at the same time by cosmic coincidence. It was so intense that you held onto her for dear life. Shot after shot, you filled her to the brim, riding the afterglow as you engaged in a little post-coital cuddling.
“Wow, who never knew that I’d strike luck today.” Redheart moaned as she traced a finger along your chest. “Though unprofessional, it was simply impossible to resist.”
“Same here when I got assigned a cute looking nurse as my caretaker,” you whispered.
“You flirt.” As much as you wanted to stay as you were, Redheart still had a job to do. Draining the water, she gave you a quick scrub and rinse before getting you into some fresh garb. As you sat in your wheelchair, you were in awe as she cleaned of her ever so slender body. Seeing the water drip from her tits and down to her vulva made you want more then and there. Alas, the both of you were spent. After getting redressed in her work gear, she wheeled you back to your bed, helping you on it and making sure you were comfortable.
“So, Redheart,” you said, grabbing her attention. “Do you want another go tomorrow?” She looked down, blushing at your remark.
“You serious?” She breathed.
“As sure as the sunrise, ma’am.”
“Well, I think we can work something out. I have to admit, that was the best I’ve had in five years.”
“Is it now?”
“Indeed. Get some rest now. You still have some work on your legs tomorrow. Sleep tight.”
When the lights flickered off, you stared out at the night sky. Somehow, the lunar lights lulled you to sleep. All that you could think about in your dreams was nailing Redheart. You have two weeks to spend at the hospital. With her keeping you company, it won’t turn out so bad after all. You just wished you could walk.
Author's Note
Hello. I know that you all were wonder what I've been up to. I've been working on three chapters, back to back. They'll all be making landfall tonight, starting with this one. As always, I hope you enjoy this.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Comforting Food with a Healing touch (Cocoa Lavender(Guest OC))
To think you could shrug anything off and keep soldiering on is putting it lightly. Even after your accident, you found the resolve to work, albeit from home. The only drawback was that apart from being mainly cooped up in your house, your injury threw a wrench in your workout schedule. Thankfully you were able to manage it by doing sit-ups and arm strength training. You adapted and were willing to make do with what you have for now because it’s going to be another three weeks until you’re back in your prime.
As per your temporary lack of mobility, the hospital assigned you a helper starting today. Though it cut a bit into your prideful nature, you had to swallow it for the time being. Like always, you channel that emotion into your exercises, leaving you level headed for the day. After getting ready for the day, you sat down and watched some old movies to stave off the boredom until lunch time came.
Soon, you heard a knock at the door. Giving a shout to come in, the door opens and through it came someone that surprised you. What you could say about the young woman that walked in left you speechless. She had light lavender hair that was long and flowing, autumn orange eyes, and freckles. Most of all, she had a nice set of tits and ass for someone that you guessed to be eighteen. She was more than just simply sexy or cute, she was adorasexy.
“Hello, you must be Mr. Calculus Crunch,” she said with a noticeable aura of shyness. “My name is Cocoa Lavender. I’m a nurse in training. This is my first day on the job so let me know if there's anything I’ll miss.” You were at a loss for words. Not only was she incredibly beautiful, but her voice was also like a sweet melody. She looked upon you with a concerned expression. “I-Is there something wrong, sir?”
“N-No, Ms. Lavender,” you replied with a blush. “It’s that… I never expected the person they’ve sent to be so… cute.” She was taken aback by your remark but it wasn’t one of offense. If her blushing was any indicator, she took it as a compliment. For a moment, you thought you were going to get a slap in the face and a visit from the cops, but you internally breathed a sigh of relief anyways.
“A-Are you serious?!” she stammered.
“I’d never lie to a woman.”
“Oh wow. I uh, I can't believe someone actually thinks I'm cute.”
“I’m the one that views shyness as an endearing characteristic.”
All that you heard next was a nervous chuckle from her. It was evident that she was nervous about it being her first bit of work experience. For you to off the nose flirt with her would probably exacerbate things. But still, you saw she had potential to perform admirably in her duties. If it all involves helping you throughout the day, nothing will go wrong.
“Well, I thank you for the compliment,” she said “Since it’s lunchtime, I’ll make you whatever you want. It’s not an issue.”
“Thank you, Cocoa. There’s fixings and a recipe for stir-fry on the counter in the kitchen.”
“Okay, thank you.” As she walked by, you got a closer look at her booty. You’ve seen plenty of fine badonkadonks over the years but hers takes the cake. It’s the biggest you’ve seen so far but not obscenely big. It was… just absolutely perfect. Just the mere thought of sticking your turgid member between those buns was enough to give you a hell of a raging stiffy.
“Aw, fuck.” You cursed internally, focusing all your willpower to dispel your erection. “If her features are natural, she must’ve been blessed by Aphrodite herself. Not now, boner. Calm down!”
For now, you were able to get your member under control, avoiding an embarrassing situation. All those years of dancing with cougars paid off well. Turning on the TV, you flipped the channel to your favorite comedy show, The Whitest Kids U' Know. You swore that never will a show as that would be made. It was truly a one in a million deal. As you laughed up a storm, your nose was beset by the scent of garlic and ginger with a hint of citrus. Whatever she was doing to make your cheat day stir-fry, she was doing great. Never once did you detect a hint of something being burnt. Your mouth waters in anticipation of your meal.
“Okay, your lunch is ready, sir,” Cocoa chimed. “I’ll be bringing it out shortly.”
“Thank you, ma’am,” you replied. “Why don’t you grab yourself a plate of it as well?”
"Oh, uh, really?"
“Seeing as you’re my caretaker today, you’re also a guest here. I always treat my guests right. Now come, make yourself a plate and grab a seat here.”
She seemed nervous at first but soon accepted your generosity. Walking in with two plates of the delicious noodles, she took a seat next to you on the couch. The second she sat down, her breasts did a noticeable jiggle. Your nose nearly bled at the sight of it. Now it was going to be rather difficult to not get an erection.
“Gosh, I can’t believe someones being so welcoming on my first day. I’m pleasantly surprised,” Cocoa said as she dug into her meal. “This stuff is really good. Where did you get the recipe?”
“Ah, It belonged to my friend’s girlfriend who’s now his wife. It’s a favorite cheat day meal of mine,” you replied.
“Cheat day? You work out?”
“That I do. I even have a gym in my basement. It’s a great stress reliever. Though I can’t work on my legs right now, I mostly focus on my arms.”
“Well, you’re certainly keeping yourself in high spirits.”
“Moreso, I’m just thankful that I haven’t died. So, tell me a bit about yourself. Like for example, how you started working or what got you into nursing.”
"Well, I guess it all started when I was a kid. My dad is a chef, while my mother is a nurse, so I learned from both of them. Dad started teaching me how to cook and all that when I was 5, and Mom didn't get me on nursing stuff until I was 12, which is when I went through puberty. Now I finally get to put my skills to good work."
"Ah, so, this is your first day. Are you nervous?"
"A little bit, yeah. My mother is why I was assigned to you."
"So, she's your boss. I think I might've seen her last week. What did she look like?"
"Um. She basically kinda looks like an older version of me, but her eyes are blue."
"Yeah! Now I remember. She was a friend of Redheart, my nurse."
"Oh yeah. Redheart. She's like an aunt to me."
"She's also an incredible nurse."
As you ate, you continued to watch the funny shenanigans occurring on your TV. It was a treat for you and Cocoa seemed to be amused by it. Though she was shy, Cocoa was a delight to be around. Her timid nature accompanied by her luscious body made you wonder why nobody took her as a girlfriend. But hey, it’s their loss. Yet, you couldn’t keep your eyes off her. She was simply too sexy.
"I don't mean to make things awkward or anything, but uh, you, got a bit of a situation."
Not sure as to what she was referring to, you took a few glances around until you got your answer. Your erection had returned with a vengeance. To your horror, Cocoa was witness to it. Scrambling about, you took a pillow, hiding your shame from her view. But alas, it was already too late.
“Oh fuck oh shit oh fuck oh shit!” You internally panicked “Goddamnit all! Just don’t panic. Calm down and yo-”
"Um, is it okay if I touch it? Or would that be too weird?"
What? She wasn’t weirded out? Here you thought she was going to freak out and run. But here she is, asking you permission to touch your clothed junk. You had no idea as to whether you should be weirded out or anything. But at the end of the day, you were a slave to your carnal desires.
“Well uhhh… yes. I mean you can… if you want.” Cautiously, Cocoa nervously reached for your junk. The moment her hand made contact, your shaft started quivering, causing her to quickly retract her hand. “No no, it’s fine. You’re doing great. It’s just a natural reaction.”
“Oh, Okay,” stammered Cocoa. She resumed her exploration, fondling your clothed package. Her face blushed immensely but she soon got her bearings and became more confident in her movements. For a novice, she was doing rather good, but you could tell that it was her first time.
“H-How does that feel?”
“Very good.”
“Does it hurt being trapped in all that clothing?”
“Not exactly, but it does feel uncomfortable.”
“Would it help if I-I took your p-pants off?”
“Only if you want to. I’m fine with it.”
Cocoa got off the couch and situated herself between your legs. After fiddling with your belt, she was free to remove your lower garments, shorts and all. When your member sprang tall and proud, she blushed at its appearance.
"A-Are they always this big?" Cocoa muttered, visibly astounded by your member.
“It varies from person to person,” you replied, “It’s how you use it that matters.”
Her hand reaches out and wraps around your member. The warmth or her hand was most pleasing as it went up and down your length. It felt like a massage, so calming and mesmerizing. As she went on, her curiosity was sparked and wonder what it tasted like. With a flick of her tongue, she gave it a quick lick, retracting it and shuddering. To her, it tasted salty, and yet, she wanted more of it.
In a split second, she resumed licking it. With each lick, she became bolder in her movements. Soon she took your entire length in her mouth. You swore you saw heaven as your jaws went slack. Slowly and surely, she kept sucking on your cock. She was getting the hang of things and you were impressed. You ran your hand over the back of her head, letting her know she was doing a good job. The reward was her going faster and faster. Lord have mercy. You were almost about to cum before she popped your cock out of her mouth.
“Do you, want me to take my clothes off?” Cocoa shyly asked.
“Well, go ahead,” you answered. “I don’t think it’s fair of only one of us is nude.”
Standing up, Cocoa removed her coat and shirt, revealing a pink lacy bra underneath. Her pants followed suit to reveal a pair of panties of the same make and color. Reaching behind her, an audible click was heard before she let the article of clothing fall to the floor. Now, nothing was hiding her bountiful chest, E-cup sized if you had to guess. Not long after, her panties followed suit, revealing her dripping wet vulva with a sizeable pubic bush. She was clearly embarrassed but you found her rather beautiful.
"Is my body okay? And is it weird I don't shave down there?"
“Yes, your body’s more than okay. It’s your business whether or not you shave there. I find your body… beautiful.” Blushing at your compliment, she took a few steps towards you before straddling your lap, taking care to not put pressure on your cast. You cock writhed at such a young beauty as Cocoa. Her breasts were level to your face and your member stood in front of her groin. “I got a question. Are you a virgin?”
"Y-Yeah..." You reached out and traced your thumb on her chin.
“How about we do something about that, shall we?”
“But, can I go at my own pace?”
“As you wish.” Laying back, you watched as Cocoa positions her dripping pussy above your spear. Slowly lowering herself on it, your tip enters her vagina. More and more of your length makes an entry before being stopped by a wall, very much her hymen. Her eyes start to water with pain as it began to push past it before it finally breaks, hilting herself. Sensing her distress, you held her in an embrace rubbing her back while shushing her, reassuring her that she’ll be alright. After a few minutes, she calmed down and broke the hug. Looking down you noticed a small trickle of blood coming from her pussy. You smirked before returning your gaze back to her.
“You should be proud that you’re no longer a virgin,” you purred “Go ahead, Cocoa. You may begin.”
Starting off slow, Cocoa bounced up and down your member. She was incredibly tight and felt just right. More and more, she grew more confident with her movements, occasionally massaging her voluptuous mounds. Soon, her breathing evolved to moans, yelps, and then to screams. She was having a good time and so were you, but her bombastic booty still hypnotized you.
To her surprise, you grabbed handfuls of her ass, squeezing it in your hands like dough. She gasped and moaned at every squeeze. Stars above, for a shy girl, she was going wild. She kept going faster and faster, letting the feeling of lust drive her mind. More and more, you kept squeezing at her luscious ass. For someone her age, she certainly has it going on, being blessed with an incredible body and a charmingly cute personality to match.
"S-Something's gonna happen..." she gasped as her inner walls began to tighten. Within a split second and a scream that could shake the mountains, she let loose her orgasm with a gush of her ladycum. As her ministrations slowed, you were nearly about to cum as well. Out of desire of avoiding an accidental pregnancy and invoking the wrath of her mother, you used your strength to pick her up, placing her between your legs.
Gripping your member firmly, you began beating off furiously until you busted a nut. Ropes upon ropes of your seed decorated her tits. You kept shooting loads until your last ounce left your balls. After all that, the air fell silent with the exception of some silent breathing. Both you and her were spent yet felt alive… satisfied.
“W-wow,” breathed Cocoa. Looking down her chest, she saw splotches of your hot seed on her breasts. Out of curiosity, she takes a bit of it with a finger and tastes it. Her face scrunched up at first, but she eventually warmed up to the taste. “Hmmm, salty.”
“So, how did you like it, with it being your first time and all?” you asked.
"I actually kinda liked it," she said with increased confidence “It felt… incredible.”
“Well, it should for being your first time.” You looked down and saw that like hers, your body was covered with sweat. You certainly didn’t want to spend the day as a stinky sweaty mess. “How about we both get cleaned up?”
“Sounds good,” she replied as she helped you up.
You both arrive at the bathroom, drawing a tub of hot water. You spent a good twenty minutes bathing and scrubbing each other. As much as you both wanted another round, time and energy didn’t afford you that prospect. But still, the sex from earlier, though a bit awkward, was well worth feeling spent. Though she would be leaving in the afternoon, she’ll be back again tomorrow…
...and you can’t wait for that.
Author's Note
For those of you who are wondering, this isn't the planned OC chapter. I wrote this as a thank you/shout out to my friend Shimmerblade(Saber), using his OC as the subject for this chapter. I would also like to give him special thanks for helping me with his OC's dialogue and personality, writing her dialogue.
Here's his OC:
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Double the Pleasure, Double the Fun (Dean Cadence Revisited)
The liberating feeling after having been robbed of something and getting it back never felt so good. It seemed like only a week ago that after many weeks prior you got the use of your legs back with the additional help from physical therapy. For you, It seemed like a bad dream. But all in all, you didn't complain the entire time. It at least earned you some much-needed rest.
Seeing that the skies were clear and the temperature was mild, it was a perfect day to go out for a walk. As the breeze brushed against your skin, you let out a relaxed sigh. It was a welcoming feeling after being cooped up in a house for such a long time. As you walked, you pondered chilling out at the beach after a work week. With your income, you pondered the idea of buying some beachfront property.
As you neared the commercial part of town, your peripheral vision caught the familiar sight, a familiar sight with tri-colored hair. As her face came into view, you recognized who it was, Dean Cadence. She was still easy on the eyes, complete with that MILFy figure. She stood in her front lawn, watering her flowers while humming a pleasant tune. As you near her house, the sounds of your footsteps caught her ears. Turning around, her eyes widened as she dropped the hose, caught off guard by your presence.
“Calculus?” she gasped. “Oh my god! It’s so good to see you!” She rushed to you and wrapped you in a big embrace, planting your face between her breasts. Hugging her back, you blushed as she held you against her beautiful body. Slowly, you began to feel tight in your lower region as your erection prodded at her groin. Noticing this, Cadence broke the hug and dusted herself off. “Sorry about that, I got a little carried away.”
“No worries,” you reassured her. “I’m just surprised to run into you.”
“Same here. Please, come in. You must be thirsty.”
Accepting her offer, you walk in with her. Cozy yet not too complex, it was home for her and her family. Sitting on the couch, You look around and noticed a picture of Cadence with her husband Shining Armor, holding each other in an embrace. From the way they were dressed, you deduced that it was their wedding picture. However, Shining’s suit was remarkably different than a standard suit and tie. He wore a distinctive looking white cap with it as well. Looking at the picture next to it, he also wore the same wear. Your thoughts were soon interrupted by Cadence walking in with a pitcher and two glasses.
“I never knew Shining was in the Marines,” you remarked.
“Yeah,” she answered as she sat down. “Back in college, a friend of mine introduced me to him as we were getting our respective degrees. For someone who is headstrong, Shining was quite the sweetheart.”
“He was quite passionate in pushing the sports teams to succeed.” You muttered as you took a sip of water.
“When he said that he was applying for the marine corps, I was worried that he would get killed in action. Then he came back and he proposed to me right as he got off the plane. The whole terminal clapped for us.”
“For a couple with an open marriage, you manage to keep the romance between you two alive.”
As you took another gulp, Cadence leaned in closer, resting an arm around your shoulders. Being well familiar with her, you were used to the advances from women you knew. Her being so close to you remember that day in the showers at Crystal Prep. Being caught masturbating to the thought of her, you never expected that your fantasies would come true. The memory of doing the ol’ sixty-nine and spoons with her on the tiled floor made your cock gradually harden.
“So, I heard about that accident you had a while back from Celestia,” Cadence said. “I’m surprised you lived through it all.”
“Well, It was nothing major,” you replied. “I was more pissed that I lost a car and use of my legs for a while.” Looking down, you observed the sizable scar on your right leg. “But, I did get a nifty looking tattoo so to say.”
“Still the optimist I remembered you as when you were a student.”
Soon, Cadence leaned closer and closer to you, holding you tighter like the seductive minx she is. It seemed like months since you last saw her and much longer since you had a piece of her booty. Slowly, her finger traced your chest and abs before it came to rest at your hips. You gotta hand it to her for being so seductively subtle. It is always nice to see a woman who can be playful. In the case of Cadence, it was something she knew intimately.
“So, where is everybody?” you asked.
“My darling Flurry Heart is being babysat by my mother-in-law and Shining is with a friend of his. He’ll be home in an hour. Why?”
“No reason.”
Sliding a hand down her skirt, you started caressing her thighs. Being rewarded with a breathy moan, you dropped all subtlety as you went for her clothed vulva. Rub after rub, her panties became increasingly damp. She never bothered to stop you and make a verbal objection. Emboldened, you brush them aside and stuck two fingers up her hungry slit. You worked your magic as you endeavored to find her g-spot. With an “OH FUCK YES, CALC!”, you’ve hit your mark and knew what to do.
Adding pressure to your fingers, you diverted all attention to her g-spot. As you rubbed away at it, Cadence’s hips began to buck and gyrate with abandon. Panting and moaning, she was growing ever so close. Thinking fast, you decided to put the cherry on top with a wet and sloppy kiss. Eventually, your furious assault gave her quite a powerful orgasm, screaming into your mouth as she never broke the kiss. Pulling your essence soaked fingers out, you planted that hand on her left tit as you laid on top of her, breaking the kiss for some air.
“You’ve still got it, don’t you?” Cadence breathed.
“Well, only refined,” you snickered. I can’t begin to tell you of my exploits since our first meeting.”
“Well, prove it in bed.”
Rushing to her room where a bed fit for two resides, You grabbed Cadence by the waist and flopped onto the mattress. Furiously making out with your former dean, your hands caressed every inch of her beauty. Strands of her silky hair woven between your fingers, her bountiful chest against yours, your stiff erection prodding her clothed sex, it was good to be with Cadence for the first time in years. It was like having a sip of a drink you cherished ages ago for the first time in a long while. It felt familiar yet still invigorating as the first time.
“Oh god, yes!” She moaned as you gave her a generous squeeze on her nice ass. Like it as you do, her being clothed wasn’t enough for you. You want her to be hot and bothered to strip like the cougar she is. Sitting up, you removed your shirt in one fluid motion. The sight of your well-toned chest took her breath away so much that it made her fan her face. “Goodness, you’re still as fit when you were a student.”
“Well, a healthy body and mind go hand in hand,” you replied as you unbuckle your belt and kicked off your pants and underwear. Cadence sat there, staring at your cock for a good long moment. The sight of it made her remember that day during your senior year, barging in on you showing, shlicking herself and then having claimed your virginity soon after. Her nethers moistened with hunger, eager for your cock’s entrance. He craves your cock and you were gonna give it to her.
Lust driving her mad, Cadence started to quickly take her clothing off. Bit by bit, more of her tantalizing naked form were revealed. The moment her bra and panties were lost was when she pounced on you, assaulting your mouth with a flurry of tongue kisses while grinding on your dick. Her skin felt absolutely silky smooth, pleasurable to the touch which made squeezing her rump feel like squishing a bag of soft dough. Breaking the kiss, Cadence got up and positioned herself between your legs, licking her lips. You knew very well what was about to happen
Gripping your member tightly, she stoked it to ensure that it’s hard as rocks. It was like the highest levels of nirvana over how smooth her hands were. It felt like the softest of velvet. The inevitable tongue to cock contact made you groan with pleasure as she added a fondling of your balls to the display. You had to give it to her for going all out. She was just as incredible as your first time was. Taking the plunge, she took your spear in her mouth. You could’ve sworn that your eyes rolled to the back of your head. Cadence worked her magic with both her mouth and her soft mounds.
“Oh god, this is great. Ohhhhh yyyeeessssss…” You moaned as your balls tightened as Cadence smashed her breasts against your length as she blew you. You haven’t gotten the tit and blowjob combo in a long while and it was one hell of a treat. Soon though, your package could only endure so much as the inevitability of your orgasm dawned. As quickly as she could, Cadence swallowed rope after rope of your load. She made that quite clear as she sucked down on your cock, milking you for every ounce.
“Jesus tapdancing christ!” you gasped, sitting up and breathing heavily. “Certainly brings back some nice memories.”
“Did you regret masturbating to me in the shower?” Cadence slyly replied.
“Not. One.” Pushing her on her back, you brought her face to her puffy wet vulva. “Bit.” Licking your lips, you decided some teasing was in order. For making you feel good, it was time to do unto her as she did unto you. Licking the inside of her thighs, you went slow and sensual to make her scream your name to the heavens. Finally brushing your tongue on her labia, her cursing devolved into incomprehensible gibberish. Tangy, her cunt tasted good.
Readying up the curveball, you jammed your tongue right into her vagina. Cadence, squirmed, writhed, and thrashed around while holding onto the bed with all her might. You kept going at her insides as you teased her g-spot along with fingering her clit. Sitting up, she pressed your face in her crotch as you ate away at her with merciless abandon. She bucked her hips as you assaulted her snatch until a loud scream and an explosion of her ladycum drenched your face. After eating her out nonstop, you both caught your breaths for a few before you could think of your next plan.
“How many women did you bang after all this time?” Cadence breathed.
“More than you could shake a finger at.” You replied as you got on your knees. “Now, on your hands and knees.”
“Hmmm, you fancy doggy style, don’t you?”
“I always like to keep things fresh.”
Positioning yourself at her backside, you grabbed two handfuls of her ass and thrust into her honeypot. Surprisingly, she was still snug as she was back then, just as incredible. In and out, you pumped your cock in and out of her love tunnel. As you did, you gave her periodic smacks on her rump, causing her to yelp in pleasure. You then hilted yourself into her dripping wet pussy as you went in… deep and hard.
“Oh fuck yes, baby!” Cadence moaned as you pounded away at her. “Oh yeah, I’m gonna cum.”
“So am I!” You grunted as you gave 110% to your thrusts, cumming within minutes of her. Even as you came in her snatch, you kept on thrusting. The tightness of her pussy tells you that it was prepared to milk you of every drop and it will. After a few more thrusts, you slumped on top of her, panting and sweaty. The air was filled with the musky scent of sweat, cum, and sex. You both reveled in the afterglow as you laid in silence, oblivious to what was about to happen.
You heard the sound of the bedroom door opening. Turning your head, you saw a familiar face. Hair with differing shades of blue, you recognized him as Shining Armor, the swim team coach at CPA and Cadence’s husband. He wore a short-sleeved shirt that showed off a tattoo of the Marines insignia on his forearm. He took one good look at you before the realization sets in for him and you feared his reaction.
“Hey, I remember you.” He said as you remained in still. “You were on the swim team at CPA. Calculus was it?”
“Y-Y-Yeah?” you stammered as you assumed the worst. Was he going to use his USMC training to kick your ass ten standards to kingdom come? You drummed up a lot of scenarios in your head as to what’ll happen. But when his hands gripped the hem of his shirt, it became clear what his intentions were. “What the hell is going on?”
“Well, I’m a little disappointed in you two that you all didn’t wait until I came back.” With a fluid motion, he removed his shirt, revealing his marine-like physique which was on the same level as yours. “We could have some fun together.” Remembering that he and Cadence were in an open marriage, you nodded internally, shaking any and all awkward feelings you’ve had. The moment his member became visible to her, Cadence became filled with unbound excitement over the prospect of being fucked by two men at once.
“Yes! YES! NOW WE’RE TALKING!!!” Cadence screamed with orgasmic pleasure. “Come here, hubby! There’s plenty of room for three!”
Standing up, both yours and Shining’s members were gripped by the lust stricken MILF. Jerking you both off, Cadence brushed both tips on her sizable rack. Feeling your cock against her breasts felt absolutely sensational. You had to hand it to a woman that is skilled at multitasking. Jerking two men off at once is surely a daunting task yet she still manages to pull it off quite effectively.
Eventually, she gave your respective cocks a few more good jerks before being pelted by storm of cum. Ropes upon ropes of jizz blanketed her face as she opened her mouth to catch any splats that came it’s way. Taking a few breaths, you rebounded from your orgasm rather quickly. Looking at Shining Armor, he gave you an impressed look.
“I’ve gotta hand it to you, Calc,” he grunted as he wiped the sweat off his brow. “You’re quite good at this. The chicks would have a hard time keeping their hands off ya.”
“You don’t know the half of it, amigo,” you replied as Cadence got back on her hands and knees, giving her badonkadonk a good shake. “I think I know where this is going.”
“Indeed.” She purred. “I’ve always enjoyed the thought of being spitroasted. Calc, you get mouth while my husband pounds my pussy.”
“Fair enough,” you remarked as you positioned yourself in front of her face, inserting your cock in her mouth while Shining goes in through her front door. Once you both were in place, you and Shining gave each other a congratulatory high-five before getting to work. Cadence sucked you off with more fury than earlier while Shining Armor pounds away at his property. Though you couldn’t see her face, you already knew that she was thoroughly enjoying every second of it.
Bucking your hips, you too became lost in the rapture as you continued to service this woman with the aid of her husband. You thought to yourself how they managed to make their marriage work out when they allowed each other sexual liberties. Taking into consideration that it was a mutual agreement between them, you concluded that they had their methods of staying strong together. Still, you had the job of pleasing this woman and you weren’t gonna slouch on the job.
Receiving a tap on your lower leg, you took it as cue to halt, removing your cock from her mouth. As Shining followed suit, she motioned over to him and whispered something. It was too soft for you to hear. What could they be planning.? Whatever it was, it was sure to be exciting. Seeing them nod, Shining approached you.
“I have a plan. Follow my lead.” Walking back to Cadence, Shining briefly embraces her before taking her in his arms with her legs wrapping around his waist. At that point, you realized what was going to happen. Though you were a bit tired and winded, you were going to soldier forth with one last effort.
“Come now, Calc.” said Cadence. “My back door is open for you.”
Without a single word, you walked over and shoved your cock up her ass. She gasped from the sudden entry but was able to regain her composure as it was soon replaced by pleasure. In and out, you and Shining hammered each of her respective holes as the Dean of CPA was driven into a frenzy. Never did Cadence once think that she would take it both up her ass and pussy at the same time. At that point, all her mind could think about was dick and her craving for it.
You grunted and groaned as you picked up the pace, syncing your rhythm with Shining’s. As always, you were going to cum eventually and you were already sensitive from earlier. Giving it a final effort, you and Shining came in both of Cadence’s holes, filling her to the brim with loads of sticky white cum. Her tongue stuck out as floods of hot seed made her belly bulge a considerable bit. Riding out the rush of your releases, the three of you took a breather before bouncing back to lucidity.
“Oh my. Oh my. Oh my.” Cadence weakly said, laying between you and Shining. “I’ don’t know if I can walk.”
“Well, given enough time and you will,” you shot back. “I have to say, this was rather interesting.”
“I knew you’d like it,” scoffed Shining. “Now, there’s the matter of getting us and everything cleaned up.”
“Yeah,” Moaned Cadence as she got up. Though her stance was wobbly, she was stable. “All this sex has gotten me hungry. I can’t wait to go out to dinner with your mother tonight. Say Calc, would you like to join us tonight?
“What? Are you sure? I mean, should it be just a family thing?”
“Come now, you think we didn’t know about you fucking Ms. Velvet in the library a while back? She would be glad to see you.”
At first, the idea of having dinner with their family was an awkward idea. Being with just the mother on the other hand, it made you less resistant. Remembering the time of ravishing Twilight Velvet in the library’s bathroom made you smirk with joy. You liked the cute older nerd type in a woman. Nodding, you accepted their offer to the amusement of Cadence.
“So, who gets first dibs with the shower?” Shining asked as he cupped a fist in his hands. “Let’s decide with Rock Paper Scissors.”
“You’re on, marine!”
Following suit, you went through two rounds of the game before defeating Shining Armor. Gathering your clothes, you dashed into the bathroom and turned on the shower, washing away all traces of sex. As you got dressed, your stomach began to growl. Now you were glad you accepted their offer. You wonder what was on the menu.
Author's Note
Well, just got this out in time for Valentine's Day. I never wrote a threesome like that before but hey, first time for everything. To confirm, another OC character is next but the identity won't be revealed until it goes live. As always, I hope you enjoyed reading this. Stay tuned.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Golden Hearted Woman (Golden Brooch (OC))
“And in other news, the Canterlot Games are due to commence next month. Every year, this event brings in tons of tourists from across the nation and other parts of the world. This year, Ms. Julia Harshwhinny promises this event will set the bar for future events. With how she plans on making it possible remains to be seen but we are most certainly looking forward to it all. This has been Local 24 News and we’ll have more on this story later on tonight when we have an exclusive interview with her.”
Turning off the television, you stretched your arms and grabbed your keys. As you made your stride, you grinned a gleeful grin. Today was another cheat day, an opportunity to let loose and eat as much junk as you want. However, you also had a taste for the finer things in life. You craved Italian food this time around. Remembering the restaurant that you took Spoiled Rich to a while back, your mind was set on eating some carb-packed pasta goodness.
Driving in your replacement Jaguar, you drove to Cucina di Italia. You swore you could already smell the various sauces as you pulled up into the parking lot. All those seasonings and flavors in the air almost seemed like a finger that was gesturing you to come in. Dusting off your denim jacket, you walked in and were greeted by a waiter. Right off the bat, you were being led to a table. Taking a seat, out of all the patrons in your area, there was one that stood out to you.
She had set of scarlet-red hair, tied in a bun with a beaded necklace hanging graciously around her somewhat plump neck. Her lips had a shiny gloss of red and her eyes were a nice deep blue. She was chubby, but in all the right places and her rack was definitely no exception. However, she wore a sorrowful frown as she took a sip of her wine. What was she sad about? What was her story? Your thoughts were interrupted as the waiter came over.
“Hello, My name is Thunderlane and I’ll be your waiter this evening,” he greeted. “What would you like, sir?” Gripping the menu, you singled out the one thing that made your mouth water.
“I’ll have a Timballo please and with a sweetened peach-raspberry tea,” you answered.
“One Timballo with a peach bellini, excellent choice.” He replied as he wrote in his order pad. “Any soups or salads?”
“Chicken and Gnocchi soup, please.”
“One Gnocchi soup. Alright, your soup will be out in about a few minutes and your meal will be brought to you soon after.”
“Thank you, sir.”
As the waiter walked away, you saw the woman resting her head on her hand. Twirling around some pasta, she took a bite as she sighed, looking more down than ever. You’ve seen those eyes quite a few times before and they all spelled one thing: grief. She clearly lost someone near and dear to her. It was a sad sight to see someone in that condition. For how long she was dealing with that pain was a mystery to you. Soon, the waiter approached with a bowl of your soup. It smelled savory and delicious, making you eager to enjoy it. It was chow time and you plan to indulge.
Taking one last bite of your dinner, you were left satisfied. Though you were going to later experience a carb coma, it was worth it. All those flavors mixing together was like a festival, all exciting. After being handed your bill, you noticed the woman looking around. She appeared to be stressed as she shuffled around for something.
“Drat, I thought I brought my wallet with me,” she sighed as she dug through her purse, turning to the waitress approaching her. “Excuse me but I think I’ve let my wallet at home. Mind if I call my daughter to bring it here?”
“Certainly, ma’am,” she replied. As she turned around, you made a split second decision and waved her down. She looked like a nice woman that could use a break. Even though you don’t know what she was upset about, it never hurts to send a bit of good will towards others. “Can I help you, sir?”
“Yeah, can you put her stuff on my bill?” you asked.
“Are you sure?”
“Yes, I am.”
“Okay, I’ll send this up and I’ll be right back.”
With a nod, you hand her your card with the bill as she walked off. The woman gives you a most puzzled look. Picking up her purse, she walks over to you with a slight smile on her face. Now, one feature became apparent. Along with her busty chest, she also had a nice plump rear end. It jiggled with her stride yet she carried an aura of sweetness with her attitude. It was hard to believe that demeanor hid some sort of pain.
“Though it was unnecessary, I thank you,” she said as she took a seat. “What is a young man like you doing here?”
“It’s a cheat day for me,” you replied. “Even fitness nuts like me need to let loose once in a good while.”
“I see. But, why did you pay for my meal? I was a phone call away from getting my darling Silver Draw to help me.”
“I figured I’d take a worrying thing off your back. If I may ask, what is your name?”
“Golden Brooch; my name is Golden Brooch. Who might you be?”
“Calculus Crunch, ma’am.”
“Well Calculus, I would like to thank you for paying for my meal. Are you sure you’re alright with that?”
“I have enough income to spare, it’s all good.”
The waiter arrives, handing you your card and the receipt. Putting your signature down, you and Golden walked out. As you stepped on the street, you lost your footing and tripped. It didn’t hurt as you’d expect but it did create a tear in your jacket’s arm sleeve.
“Oh great,” you muttered. “Gonna cost me a bit at a dry cleaner. Shit.”
“What’s wrong, Calc?” Golden said as she inspected the rip. Notting and humming, she muttered something about needles, thread, and patchwork. “Ah, looks like something I can fix.”
“You’re a seamstress?” you asked back.
“Of course,” she answered with a smile. “By the looks of it, it would be cake for me to fix it. If you take me to my house, I’ll be able to fix it. My car is on the fritz and it’s in the shop.”
“Really? I mean… I have no problems paying for repairs.”
“Well, after you helped me back there, it’s only fitting that I’d help you.”
You were no stranger to receiving something in exchange for doing a favor. To you, that was the way the world works. Golden Brooch sounded like a sweet woman, one that wouldn’t hesitate to give you the coat off her back. All of that hid an underlying sadness. Still, she offered you a favor and you weren’t going to turn it down.
Driving Golden to her house as per her directions, the two of you made bits of small talk. The conversation that developed from it made you conclude that she was married at one point but something happened, something that she was reluctant to talk about. Pulling up to her house, you parked in her driveway.
The house had a cozy feel to it, complete with a vibrant garden in the center of the lawn. The inside was nice and orderly with a welcoming aura. Golden Brooch had some good taste and it certainly shows. Along with a TV, there was a piano and what looked like a sewing station, loaded with thread. The desk had various tools of the trade for a seamstress. It was like that not just a job for Golden, but also a hobby.
“Hmmm, that’s a lot of tools of the trade you have,” you remarked
“It pays to be prepared,” she chimed. “My mother taught me everything she knew. She even said I had a natural talent for it. When I was pregnant with my dear Silver Draw, I used my skills to make her a nice stuffed toy kitty. She never let it go since she was born.”
“How were you that good?”
“Oh, all there is to it is steady fingers and an eye for detail. You can go ahead and set your jacket on the desk there. I’ll get to work on it in a bit. You want anything to drink, like some tea?
“Yeah, tea is fine,” you said as you walked towards a hallway. “Where’s the bathroom?”
“Just all the way down that hall and to your left.”
“Thanks.”
Relieving yourself in the bathroom, you looked over your self in the mirror. You had a slight stubble on your chin along with your growing mustache. Nodding, it was clear the chin stubble had to go, but that was a story for another time. Walking out, you found your coat on the table, clear of the rip. However, Golden sat on the couch, holding a picture and audibly sniffling. Knowing she didn't want to talk about what bothered her, you silently got closer to get a better view of the photo.
In the picture was Golden Brooch with her hair in what looked to be braided. She looked tired and resting in a hospital bed while holding an infant wrapped in a blanket, definitely her daughter Silver Draw. You immediately deduced that it was taken right after she gave birth. Next to her was a man with dark brown hair that was slicked forward. Both people were smiling, tears of joy. Right away, you knew the man was her husband or used to be. Whatever happened to him could be anyone’s guess. Divorce or worse, the only way you were going to know was to ask.
“So, what happened to your husband?” you quietly asked, but loud enough for Golden to hear. She turned her head around, just enough to catch a glimpse of you. Knowing that you were watching her sorrowfully contemplating, she turned her gaze back to the picture and sighed.
“He worked in construction,” she sniffled with sadness in her tone. “When he was working on the statue of our city’s founder in the downtown area weeks after my daughter was born, a metal beam fell on him and crushed his lungs! When I got word that it happened, I rushed to the hospital as fast as I could but… but…” Taking a seat next to her, you put a hand on her shoulder and gave her a sympathetic look. “The doctors pronounced him as dead on arrival!”
Death, the ultimate finality, is a harsh concept. It was something you nearly had to deal with weeks ago. For Golden Brooch, losing her husband in a freak accident was a tragedy. It began to make you think on the concept of mortality, but you still had much of your youth ahead of you. Golden Brooch lost the man she gave her heart to and she still felt the sting years later. As she cried, it was as your heart linked with hers, feeling what she felt. Empathy was one hell of an emotion.
At first, you were planning to leave a bit after she fixed your jacket, but seeing her wracked with grief spurred something in you. It was the weekend and she had no one to spend it with as her daughter was out with friends. She needed a friend, a stranger that would show her compassion and you most certainly fit the bill.
Reaching forward, you pulled her into a hug. To your surprise, she offered no resistance. Rubbing her back, you gently rocked her as she returned the hug. Golden Brooch dug her head into your shoulder as she poured out her feelings. She felt relieved that some stranger showed her kindness after her tragedy. Even you could feel her heart beating powerfully through your body and her mounds being pressed against your chest. With your gesture, you made your intentions clear with no uncertain terms.
“Th-Thank you, Calculus,” she sniffled while locking her eyes on yours. Her mascara started to run down her cheeks. “This was… so kind of you.”
“Well, I thought you needed some company. I have no qualms about staying the night,” you shot back. “Besides, I have the weekend off from work.”
“Why would you sacrifice your weekend on the account of me?”
“I usually have a lot of free time by then.”
“All that free time yet barely anything to do with it.”
“Time is what I make of it. I do with it as I please. If you want to spend it with me, then I have no problems with it.”
Hearing those words from you brought a much needed calm to Golden Brooch. While she still laid in your arms, you didn’t mind it one bit. Admittedly, you found her rather beautiful, cute even, for a MILF. She was sweet enough to repair your jacket, all without asking for anything in return. For you, it was a nice way to spend the weekend.
For the next few hours, you and Golden Brooch spooned under some blankets on the couch while watching some old movies. Being the big spoon, you felt great warmth from holding her plump body close. Even as your lower region was growing stiff, she either wasn’t aware or didn’t care. Still, it was a nicely comfy way to end the day, holding a nice woman tight in some platonic way. It was like hugging the cuddliest of blankets or pillows.
Soon, the moon had risen and the night sky had come. Though awake, Golden Brooch was on the fast track to slumberland. With the power of your muscles, you carried her to her room. With the lack of available rooms, Golden Brooch permitted you to sleep with her in her bed. Though odd, there was little choice in the matter, not that you minded it at all. As you pulled the blankets over the two of you, she turned to face you with the oh-so-familiar bedroom eyes but with a healthy dash of sweetness to them.
“Calculus,” sighed Golden. “Though I haven’t said it yet, but thank you.” She scooches closer to you, wrapping her arms around her neck. Her being that close to you made your shaft throb about with excitement. Her embrace was tender and loving, a testament to her kind nature.
“Thanks aren’t really necessary,” you replied. “But I will admit this, it was a blast spending the night with you.” You wrapped your legs around hers and held her tighter against you. Her body was nice and cushiony, enjoyable. You had no problems with fat women, finding them cute in some way. After all, it was just more of them to love. “Also, I find you rather… cute.”
“Cute?” She was taken aback by your compliment. The only other person who called her cute with sincere and straight face was her husband. Hearing all that reminded her of the love the two shared back when he was still alive. Her heart pounded as you gave her a loving look. From paying for her meal out of the blue to keeping her company for the night, the same type of love from her past was rekindled within her.
With a relaxed sigh, Golden latched your lips to yours. Already lost in her warmth, you closed your eyes as you shared in the rapture with her. Good lord almighty, the fervor of her kisses was impressive. Long was she starved of the touch of a man and it certainly showed. Her hair smelled like a pleasant mix of cherries and mangoes. But you knew what she wanted, craved, and desired and you weren’t going to make her wait. Quickly, you put her on her back, never skipping a beat in your kiss. Being on top of her was even better. It allowed you to see more of her beauty.
“Do you think I’m fat?” she asked with a worried face.
“No, I think you’re beautiful the way you are,” you replied, resuming the kiss. Her face drew a relaxed smile, relieved that you find her attractive. A woman her weight and age would be a pass in some books but not you, certainly not you. She was perfect in her own right and nothing would change your mind. Soon however, you felt your lust creeping upon you and found yourself grinding against her pelvis. With each movement, she’d let out a laugh of joy. Golden enjoyed it and didn’t want you to let up, not that you were going to. Your erection soon became too stiff in your pants for comfort and Golden knew it.
“It must be getting uncomfortable down there,” she purred, marvelling at your bulge. Golden never saw a man’s girth that big since her late husband. “Here, get off me and I’ll take care of it.”
Nodding, you laid on your back as she got between your legs. Knowing this would lead to, you didn’t bat an eye. You knew the old song and dance of what was about to happen that it seemed to be a regular occurance. Undoing your belt, Golden Brooch removed your pants and undergarments. Nothing stopped your manhood from standing proudly. The look on her face when she saw it made you giggle internally. For her, it was a familiar sight, one that brought back memories from long ago.
“My goodness,” she gasped, still in awe at the size of your girth. “to think that big thing was being suffocated in your pants. It must’ve hurt. Here dear, want me to make it feel better?”
“If you wish.”
With those words, she started to gingerly stroke your length. Her hands felt so smooth, like the softest of silk. It felt like a massage, so good and so right. Golden enjoyed the warm feeling of your cock, but something inside her wanted more of it. With a smirk, she started to lick up and down your shaft. Soon her ministrations grew faster and more passionate. Her tongue was almost snake like, exotic and pleasing. Every pass of it made you give pause to the experience, so incredible. Golden enjoyed its taste and couldn’t get enough of it, so much that she took the entirety of it into her mouth. Good lord almighty from on high, that… was a blowjob.
“Oh my goodness! Golden! Please don’t stop!” you moaned as she continued her work, making sure every nerve ending of you spire wasn’t left out. She even showed your balls some attention as she massaged them delicately. Gripping the bed, you tried to contain your pleasure as it slowly ate away at you. You wanted to last long to please her, to show her what you were capable of. Fortunately, your stamina was high and well developed.
It couldn’t last forever, though. As passionate as she was, Golden Brooch was well determined to have a taste of your cum. Her sucking had gotten faster and faster until it nearly drove you mad. You were close and you wanted to hold out for a bit longer but not forever. When your orgasm erupted, you resisted the urge to buck your hips in pleasure. There was no way you were going to be rough with her.
“My my,” Golden said, wiping a few strands of your seed from her chin. “Salty, yet sweet. That was so much.”
“I hope that isn’t a problem, Golden,” You grunted.
“No, it’s quite alright.” Golden Brooch looked down and noticed a damp spot on her pants. All that pleasuring of your genitals made her feel moist in her nethers. Just looking at your body left her wanting and desiring the pleasures of the flesh. “Since I gave you some pleasure, how about you give me some?”
Sitting up, Golden Brooch removed her clothes, revealing a matching set of bra and a panties, sexy and alluring. That thought didn’t last long as those went soon after, revealing her beautifully naked body. Just the sight of it was enough for you to become hard once more, something that amused her. Her pussy flowed a trickle of juices, eager to be pleasure and wanting to be satisfied. She then laid on her back and spread her legs.
“Come on, give me some sugar, hon.” Climbing back on her, you gave her a quick peck to her lips before trailing some kisses. Down her neck and over her belly button, look out thighs, here you come. While you want to hear her beg, she was too sweet of a woman for that. With some soft pecks around her inner thighs, you brought your mouth to her pussy. Lapping up her tangy juices, you extended the same courtesy to her.
“Oh yes, dear! YES!” she screamed “You don’t know how long my pussy’s been without some love! OH YES!”
As sexy as her moans were, you focused on her cunt. Lick after lick, she lost herself further in pleasure. For a moment, all she saw was the ceiling. After having been without a man for so long, you couldn’t blame her reactions. You were going to give her the best orgasm she’ll have in a long time, even if it kills you. Not content with exploring her outside walls, you took it a step beyond and stuck your tongue right up her snatch.
She gasped in surprise at the sudden entry. The feeling of a tongue slithering around in her vagina was incredible to her. Never was she eaten out like that before. With your skills, you wiggled your tongue about, bringing her to orgasm in short order. Being that it was her first time in a long while, you never thought ill of it. You were more than glad to give her some much needed love. It made your heart quiver that such a sweet lady was left lonely for so long.
“Sweetie, that was…” Golden breathed. “...great!”
“Well,” you said as you wiped her juices from your face. “I’m always pleased with results.” You climbed on top of her once more, giving her your best half lidded eyes. Now comes the main course and it will be one she’ll remember. Before you started to slip it in her and your tip touched her entrance, Golden stopped you with her hand to your chest. You were puzzled as to what she meant until she moved an arm to her drawer. Reaching into her drawer, she pulls out a packaged condom.
“I’m not wild about getting pregnant right now, dear,” she said. “Plus, it’s one of those new ribbed ones.” Taking the rubber out of the package, you fitted it over your already erect cock, just the right size and never too tight. With that, the magic can now begin. Resuming your position, you slowly inserted yourself inside her to pleasured moans. The smile on her face… you never got of such a sight and never will.
“Oh yes, dear! Do it! Do it until I can’t walk!” In and out of her pussy you pumped your cock. She craned her neck back at the feeling of something new yet familiar. Golden was a sweet woman who deserved some love and wouldn’t be shy to show some back. She truly was something else in your books. Though grief wracked her for years, she seemed to retain her kind demeanor. But damn does she feel good.
Thinking for a bit, you shoved your face between her luscious tits without breaking rhythm. Blowing some raspberries, you proceeded to motorboat her. The sounds of her laughter ridden moans worked as your fuel. Golden was quite turned on by your move and her noises convinced you to do it more ferociously. Now your lust has gotten the better of you and you weren’t gonna hold back anything anymore.
Golden’s inner walls were getting tighter and tighter, a sign of her getting close to release. Feeling the same way, you put your hips into full throttle and pounded away at her vagina with all your might, hilting yourself. Tighter and tighter, her moist sex clamped around your shaft until the telltale shriek of pleasure signaled the explosion of her orgasm. Though close, you weren’t finished just yet. You gave a few dozen more pumps until you busted your nuts.
You worried that the condom would burst from the sheer volume of your load. Noting the brand she gave you, it wasn’t as high. Burnt out like a light bulb, you collapsed on top of her, managing just enough strength to remove the condom, dispose of it and pull the covers over the two of you. Laying on her was like resting on the fluffiest of clouds. You were never going to tire of holding such a magnificent specimen of beauty so close when tired.
“Calc, that was amazing, dear,” she breathed, brushing the back of your head. “You truly are a gentleman.”
“And you Golden… are a sweet woman,” you answered with a kiss. “And not to mention, cute.”
“How many times have you called me cute?”
“Dunno, lost count. But, I ain’t lying when I said it.” Shocked by your admission, Golden Brooch was yet again reminded of her late husband. When they first met, he regarded her as cute. More and more, she began to see more of him in you in a sense. With one last quick but passionate kiss, she bid you good night as she shut her eye with you following suit. Smiling, you rested comfortably on her, keeping her company and warm.
Your eyes opened as you noticed sunlight breaking through the windows. Still buck naked, you notice that Golden Brooch was gone. Where she went to opened up a number of guesses. You didn’t hear even the quietest of ambient sounds as a clue. But somehow, your clothes were nicely folded and clean while you weren’t. Still smelly with sweat and sex, you walked into the bathroom for a quick shower.
Turning on the hot water, the relaxing droplets rained down upon you immeasurably. It was like a light massage with a touch of soothing heat. As you scrubbed your arm with a soapy loofa, you failed to notice the shower curtains shift and a pair of arms wrap around your torso. It was only until locks of hair came into your view, smelling of cherries and mangoes.
“Hmmm, good morning, Calc,” Moaned Golden Brooch. “I trust you had a good night sleep in my arms?”
“Well, that was quite the slumber,” you replied as her hands neared your morning wood. “And sex in the morning, always a pleasant thing.”
“Since my pill should be working now, we can do it raw if you like, dear. But first, just relax and enjoy.”
Planting your hands on the shower walls, you braced yourself as Golden gave you a handjob. From that position, the feeling of her plump body and tits against your back made your member all the more sensitive. All of a sudden, you started having flashbacks to where Abacus Cinch did something similar. Despite being a bit terrified at the time, the experience was memorable. It was like a trip down memory lane, nostalgic.
Still sensitive from last night, your cock inevitably shot ropes of your life making seed at the wall. Splotches of thick white painted its surface as you groaned with pleasure. Combined with the feeling of Golden Brooch’s arms around your torso, it was the perfect feeling to wake up to. Turning around, you wrapped your arms around her, holding her tight and against the wall as you both shared a passionate kiss. Miracuously, you were still hard and the cure for that was her pussy, but you were eyeing something else.
“So dear, what other part of me do you like?” Thinking for a bit, you noticed she had a nice and round ass. If you had to guess, it would be soft yet pleasing. In your dreams, you dreamt of sticking your rod between her cheeks, hotdogging her as you fingered her folds. It was a wet dream so intense that it almost felt so real. So now, it seems fate has afforded you an opportunity to make your dreams a reality once again. Turning to face her, you spun her around as you laid on arm on her upper body and positioned another at her vulva.
“Your ass.” Firmly planting your cock between her buttcheeks, you set out to do recreate your dream. Her ass, like the rest of her, felt soft like a cloud with the firmness of a memory foam mattress. Having stuck an average of two fingers up pussies before, you felt the time was right and upped the ante. You stuck three fingers up her snatch, using your thumb to play around with her clit. With every moan from her, it pulsed with excitement. Ever before did she experience something so exciting. For you, the same can be said about her rear end. God, they felt so good against your pelvis.
“Hmm- *OH GOD YES* Yo-*oh* like my behind, do you?” She moaned ash your fingers continued their work.
“I craved it.” you grunted as you pleasured yourself. “Never got the chance to do it last night. All that fucking knocked the wind out of me.”
“Heh, such a vulgar mouth you have. But no matter, keep doing what you’re doing.” More and more, her lust-filled screams filled the air, so much that even the shower noise couldn’t mask it all. Golden was a screamer but screams are signs that you’re doing great. Since you and her were the only ones in the house, you let loose and succumbed to your inner beast and doubled your efforts, groaning coarsely as your cock pulsed between her luscious cheeks.
But soon, you couldn’t hold back any longer as you clenched your teeth and shot loads of your seed up her back. Likewise, Golden’s pussy quivered and trembled as it sprayed her nectar all over your hand. Managing enough strength you held a tired Golden Brooch up long enough for her to recover. It seemed that your efforts were super effective. After all, you had the gift of magic fingers. Like list time, her juices smelled musky yet arousing. Then again, you were still rock hard, ready for another round.
“My goodness, dear.” Golden breathed in astonishment. “How are you still hard as a rock?”
“Well, it just comes natural to me,” you replied which earned you a sly yet warm smirk from her. Now that she was properly aroused, she backed against the wall, spreading her lower lips open with her fingers.
“Go ahead, Calc. Do it.” Nodding, you slipped your dick into familiar territory. Oddly enough, it still felt lubricated enough from earlier. With each ministration, your body rubbed against her wet form. You’ve always had a thing for shower sex. Just the thought of holding a woman’s wet body tightly as you ravage her was a real turn on for you. But with Golden, it was a real treat. With an open tongue kiss, you picked up the pace, enjoying the experience of morning sex.
But you eventually had to nut at some point. The feeling of dumping loads of your seed inside her womb was heavenly. Knowing she was on the pill, you came inside her with gusto. Just being able to hug such a lovely woman was a nice feeling, making you feel tingly inside. As you reeled from the force of your orgasm, you looked at Golden as she smiled, content and peaceful.
“Hey Calc, I got a call that my car is done being repaired,” she whispered. “If it isn’t too much trouble, can you drive me to the shop?”
Nodding, you agreed to do Golden another favor. For making you feel so good, how could you deny her request? She scratched your back and it was only right that you repaid the favor. Golden Brooch was something special, a truly nice soul that was robbed of love, once upon a time. All in all, it was a treat to spend time with her, even if the circumstances amounted to chance. All is right and good.
Author's Note
Well, here's the secret MILF OC that I've been teasing for some time. This was a special chapter for me to do as I worked closely with an-tonio (the OC's creator) to make sure that she was faithfully portrayed. It was a blast working with him and he's been a real help with this chapter so he deserves a big cut of the praise for his help. Thank you an-tonio for allowing me to use Golden Brooch and thank you again for being of big help to me. :)
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
For some people, the thought of waiting months for anything was unfathomable. Degrees of patience can only go so far. Yet, any sort of effort always bears fruit at the end of a long road. For you and your boss Ms. Harshwhinny, it meant two things: getting the Canterlot Games set up and the end of her pregnancy. Harshwhinny wasn’t concerned about the games in the slightest. She knew everything she set to accomplish in that regard was in order, thanks in no small part to you. As for her pregnancy, you noticed her getting progressively worried about it as the clock ticked down to zero hour. She worried whether or not she would be a great mother or whether her child would grow strong and happy, but with all the private time you’ve spent with her, she seemed to calm down a bit. All in all, you were excited to see your efforts bear fruit.
You walked into the office, silent with the exception of a few murmurs about the events due to happen in the next couple hours. Everyone was excited and relieved that they could catch a break for the time being. Seeing their favorite athletes come into town and perform various physical feats and games brought them inspiration. You smiled and sighed as the workplace was calm for a change.
Opening the oh so familiar doors to her office, you were greeted by the sight of Ms. Harshwhinny, signing some papers. As she finished, she relaxed for while rubbing her rotund midsection with the warmest smile you’ve seen her wear. From the looks of it, she’s eager to see her child. It wasn’t until you closed the door that she noticed your presence, turning to you with the same look.
“So, Mr. Crunch,” she said. “All those months of preparation have led us to the culmination of our toil.” She got up from her seat, struggling to do so from her condition. She was eight months and three weeks along but she manages it through the sheer force of will. Waddling over, she shook your hand but soon pulled you into a hug. You took great care to not squash her belly or hurt it in any way. “And you sir… have been a great help to me.”
“Well, I set do what you said and as well as I could,” you replied. “I have to say… you’ve been a good boss.”
“Always with the flattery. So, no doubt you’re excited like some of the people in the office.”
“To be honest, I’ve never been one for sports. Maybe hockey. But yeah, it’s certainly exciting to see the games happen. Not wild about the traffic congestion though.” Harshwhinny lets out a slight snicker before resting a hand on your shoulder.
“If there’s one thing I can do without, it’s your sense of humor,” she deadpans before her smile comes back. “So, since I’ll be observing the events despite my *ahem* condition, you’ll be attending with me. You may leave anytime between now and twelve, but be there when I am.”
“Yes, Julia.” With a kiss to your cheek, she dismisses you. You sat in your office, playing Tetris like a slacker. It was one of those easy days and no one did anything. When the clock struck 10:30, you decided to go, hopping in your Jaguar and further into the city. Fortunately, the traffic didn’t get too bad. When you arrived at the stadium, you were treated like a VIP, odd yet empowering. Being the assistant of the boss has its perks and boy were they good.
You walked the halls of the stadium with some of the high-ranked employees following you. Everything was set and in place as they should and barely anything was out of place. The athletes and sports teams were all doing some warm ups as they prepare to push their bodies to the limit. Once the inspection was complete, all you had to do was wait for Harshwhinny to arrive and the events to begin.
It was 1PM and the games began in earnest. With a brief speech from Harshwhinny, the first event, pole vaulting, started. From the stands, you got a bird's eye view of people using momentum and gravity to hoist themselves into the air above a pole. It was a sight to behold and the mechanics, even more so. Once the medal winners were declared, the next event began: track running. Eight people were lined up and in a posture to work their lungs to extreme levels. It reminded you of the times you spent running the local college track for the sake of cardio. From the looks of things, they were going to get a weeks worth.
“Hmmm, my darling Spitfire has been pushing her body hard for this day,” said a feminine voice from behind. Turning around, a woman walked to your side. She had a darker set of hair than the one down there she called Spitfire. Nice hourglass figure and wearing jean shorts with a tank top, it was hard not to take a prolonged glance at her. “She never misses her mark, but there comes a time for her body to rest.”
“You always go to her events?” you asked.
“I always do. I was once like her, but the callings of motherhood told me to take it slow. But still, she idolized me.”
“You really are proud of your daughter, Ms.-”
“Stormy Flare, Mr-”
“Calculus Crunch, Ma’am,” you said as you shook her hand. Stormy had an oddly tight grip strength. It was amusing, making you wonder if he broke a poor man’s hand at one point with such strength. The aura she gave off was youthful, athletic, with notes of experience. Right off the bat, you knew her chest pillows were a solid DD-Cup with some decently toned muscles. Even in her age, Stormy treated her body right.
“Hmmm, with a name like that, you gotta have some impressive noodle in that skull of yours yet…” Stormy looked up and down your body with bewilderment. “...you have a nice body. How?”
“Well, I came to believe a healthy body and mind go hand in hand. Plus, my folks got me on various sports teams in high school, worried that I was going to delve into drugs.”
“I see. Nice.”
“You don’t have such a bad body yourself either, Stormy.” Though you didn’t see it as you looked down towards the track, Stormy blushed at your compliment. Those words of yours filled her with thoughts of lust. She imagined you naked, thirsting over your nicely toned body. As much as she wanted to tear off her clothes, mount you, and bounce on your knob in full view of hundreds, Stormy was a woman of patience. All she had to do was ask.
“That’s alright,” you said, snapping her out of her trance. “I’ve been stared at often by many women. It’s not a big deal.”
“How did you know?”
“I know that I’m attractive. I’ve caught many women giving me looks. I’m used to it. In fact, I don’t mind it.”
“Such confidence, that sort of thing can turn a woman on.”
“Really now?”
“It certainly has for me,” she whispered in your ear. Though it gave you goosebumps, you remained calm as a british royal guard. “Tell you what, I know of an unused gym in this place. “How about we head there and you can show me what you can do?”
Well well, another woman steps up to the plate… or rather, your dick. Athletic and spunky, it was certainly enough to give you one hell of a raging stiffy. Being one for sports, she certainly has attitude and an abundance of energy to spare. What she had planned for you was unknown, but you hoped you could keep up. You sorely hate to disappoint.
“Are you sure we won’t get caught? Are you absolutely sure?” You asked.
“I have enough tricks up my sleeves, so don’t you worry.” She then walked towards the exit for the rows, gesturing with her head for you to follow. Shrugging, you followed her down the halls and down a flight of stairs. To your relief, no one noticed the two of you. Whether it was luck or some other cosmic force remained to be seen. Eventually, you stopped at a door leading to a gym room. Inside, it reminded you of your setup at home. Weight stations, bikes, and ellipticals galore; it was like a candy store for you.
“Even my home gym pales in comparison to this,” you muttered as Stormy closed the door.
“I remembered working out here during the height of my career.” She snickered, walking in front of you and shaking her ass. “So many memories, but let’s focus on the present. Strip.”
“What?” You asked as your eyes shot wide open. “Now? Shouldn’t there be at least a bit of making out?”
“I’m not the one that likes waiting. Strip. Now.”
Nodding, you started to strip out of your Armani suit, from the coat and to your shoes until all you were wearing were your boxers. As always, you were aroused over something so kinky, getting half-naked in such a public place. A devious smirk drew on Stormy’s face, admiring your physique. Her nethers tingled with excitement and her mouth started to water with hunger. Noticing the bulge in your boxers, she wanted to see the whole thing.
“Now your boxers,” she commanded as she removed her shirt to reveal her red colored bra. “Come on, I wanna see how big you are.” You removed your boxers, letting your erection spring out of its prison. Stormy Flare was in awe at the size of your girth, but never paused removing her bra and panties. As she removed the latter, she briefly rubbed her hairy folds to heighten her arousal. Her lust climbed to unfathomable levels. But as much as she wanted to slob on your knob then and there, she had other plans. She wanted to test something out.
“Now, come to the bench press station.”
“For what?”
“I’ve heard of this study where a man did a bench press while a woman sat on his lap. According to what was said, his testosterone increased, giving more strength and will to lift. I wanna put that to the test.”
“If you say so, Stormy,” you said as you laid on the bench. To your surprise, Stormy set four 20lb weights on. The highest you benched was 140 and you sweated at the thought of it. But, you liked to push the envelope and improve. After the weights were set, Stormy straddled your lap with her vulva making contact with your cock, but not penetrating. As you brought the bar to your chest, you worried that you were going to tire easily. However, like a fire coursing through your veins, a surge of testosterone filled you with power and stamina. Gripping the bar, you began to lift as Stormy ground against your tool.
“Bench fifty, Calc,” moaned Stormy. “You’re doing great! Show me what you’re made of!” You knew then and there what she wanted to test you for: physical strength and sexual stamina. Not being a slouch in either department, you were up for the challenge. With each and every pass, your cock pulsed with pleasure, motivating you to keep lifting. Oh boy, you were going to be a bit sore after all that, but not close to cumming.
“48… 49… 50!” With a bit of struggle, you set the bar back on the holder. Panting a bit before sitting up, Stormy Flare gave you a smirk, indicative of impressed. “So, how was that?”
“Not bad, not bad,” she replied, climbing off your lap. “I see that the study was true after all. You performed quite admirably, but I wanna try something else.”
“Like what?”
“To the butterfly machine, egghead.”
You had such a machine at home, always doing a bit of it every workout day. It was one of the reasons you had such impressive pecs that bring the women running. Doing it would be a slight issue as you were a bit tired from moments ago. Still, you had plenty of stamina to spare and you weren’t gonna back down from this challenge. Stormy Flare wanted to know how long you’ll last and by god, you shall.
Sitting on the station, you gripped the handle bars as Stormy set the weights. To your surprise, it was the third highest setting, something you’ve done before. Finally, you were going to get something that won’t throw your achy arms further into pain. But what Stormy Flare wanted to do caught you a bit off guard.
“Hmmm, all that grinding my flower on your tool got me curious.” She muttered as she gripped your quaking member, stroking it rather quickly. “I wonder how it tastes. If you manage sixty reps before you cum, I’ll let you in my snatch. Deal?”
“Hell yes!” you groaned as her mouth slowly enveloped your cock. Starting the exercise, you slowly lifted, still winded from the benching, but the surge of testosterone gave you a much needed boost of strength. It was odd how such a thing would work in your favor as she sucked you off like it was the last thing she would ever do. Combined with earlier, you found the blowjob slowly bringing you to the edge and there was nothing you could do but finish before she finished you. If her moaning was any indication, she was clearly schlicking.
“51, 52, 53,” You felt yourself getting closer and closer. “54, 55, 56,” Your orgasm was imminent and you were nearly done. Bracing your arms, you prepared for one final effort. “57 58 59 60!” You were done, arms sore and sweaty. You cock quivered eagerly as it was nearly close. With a light tap to her head, Stormy disengaged and jerked you off furiously as your climax began. A barrage of your cum landed on her breasts, coating it in a sticky white. The feeling was much more intense than the last time and never did you think that a blowjob while working out would feel so invigorating. Yeah, science bitches.
“Good fucking god,” you wheezed, wiping some sweat from your brow. “Talk about putting me through a ringer.”
“Indeed,” Stormy moaned as she got up. “I have to say… you can withstand quite a bit.” She then heads to the adjacent shower room and turns on a shower head. The way she danced around, letting the water drip from her hair and down to her breasts was an erection inducing sight. Recovering and mustering enough strength, you joined her as she played with her breasts. Quickly taking her into your arms, you stuck the first kiss between the two of you. She had her fun being in charge and now it was your turn.
Lifting her up and supporting her legs, you penetrated her honeypot, still lubed up from her self pleasuring. She was a bit loose, but it didn’t subtract how good she felt inside. In and out, your turgid member made her moan almost as loud as a banshee, even making a face that nearly made you burst out laughing. She was completely lost, mind focusing purely on sex and nothing else. Lord only knows how long she’s been without any action or was left unsatisfied. Her being full of energy has made this latest round of sex for you a rather exciting adventure.
As mighty as you were known to be, you had to cum sooner or later. Neither of you cared who would cum first at that point; it felt too damned great. Just the rush of doing it in a place with a noticeable danger for getting caught was an adrenaline rush in and of itself. Soon, your vision turned white as the rush of your orgasm came at the speed of a train. Holding onto her with all your strength, you made sure that every drop of your seed filled her, even to the brim. Pulsing quivering, your spear continued to shoot every last bit of its load until your balls were empty and you left short of breath.
“Je-sus,” you gasped as you slowly came to your senses. Stormy Flare was left exhausted, leaning against a wall as she struggled to get her footing in order. Even as an exhausted mess, she was still hella hot.
“Though it’s a bit cliche, this was the best I had in years.” Stormy breathed as she recovered. “By the way, how was I?”
“Fucking incredible. But how are we going to clean up? Wouldn’t people eventually find out about this?”
“You needn’t worry about that. I have my ways… and a bit of hush money from my royalties. Now go, wash up and get out of here. Don’t worry about me, I’ll take care of things here.”
With a brief scrub down and getting back in your suit, you looked almost like what you did when you arrived. With the exception of a few damp spots here and there and slight exhaustion, others would hardly notice what transpired. Walking back to the arena, the soccer portion was in its third quarter with both teams tied. From what you could gather, it was an intense game. Walking back to Ms. Harshwhinny’s suite, you saw her cheering for her favorite team from Manehattan, a sight you rarely see and especially this passionate.
“Yeah, go Falcons! Wooooo!” She cheered as you walked in. Looking at you with blushed embarrassment, she chuckles before giving you a hug. “Sorry you had to see that. We all get passionate about sports.”
“No worries, it’s just that I rarely see you this excited,” you replied.
“Not everyone defaults automatically to one emotion.” You walked beside her and watched the game with her. Her eyes were fixed to the field as the players kicked the ball around. “It feels liberating to watch the fruits of your work, doesn’t it?”
“Yes, all that work and here we are, seeing the results before our eyes.”
“Yeah, and I have to say… Tha-” Her eyes darted back to the field, just in time to see her favorite team score a goal. Her eyes widened as a jubilous smile formed on her face. “YEAH, GO FAL-*Urgh!*” She staggers back, holding onto the railing while clutching her belly. Her face told you she was in a lot of pain. When you rushed over to see what was wrong, noticing a puddle of liquid beneath her gave you your answer. You felt that it would take too long for an ambulance to pick up a woman in labor. Allowing her to lean on your shoulder, you escorted her out of the suite.
“Out of the way! Move it! Move it! Woman in labor! One side!” You shouted repeatedly as you helped her through a small crowd and out of the stadium. Helping her into your car, you drove off and away from the area and towards the nearby hospital, all the while your heart was pounding immensely. You took care to avoid as traffic violations that you could as you took a fast route to the hospital. Once parked, you helped her out to which some nearby workers noticed and helped her in, cursing as she was wheeled off. Now, all you had to do was sign some paperwork, a staple of your occupation.
After all the paperwork was done and signed, you were directed to the room she was taken to. Unfortunately, you couldn’t come in while they were delivering the child. Sitting in the waiting room was a real drag, but your music library kept you for a time. During the wait, you were anxious, wondering what’ll go wrong. All those thoughts made your heart jump about as you feared the worst: either her losing her child or you losing your boss. Seconds became minutes and then hours as the clock ticked about before a nurse stepped in.
“Mr. Crunch?” She called you as you got up.
“How is she, nurse?” You asked before she gave a slight smile, gesturing you to follow her. Before entering the room, you drew a big breath and braced yourself. To your surprise, you were greeted by a most beautiful sight. Harshwhinny laid in her bed, cradling a bundle that sheltered her child. The exhausted and calm smile, combined with that motherly radiance, was a peaceful sight to behold. You walked over as she noticed your approach, sighing with relief.
“It’s a son, Calc,” she whispered, “I have a son.” You looked on at the infant as it slept peacefully in the bundle. He looked peaceful as she was in the arms of his mother. From what you saw, he had your eyes and you could guess that he would have the same color of hair his mother has.
“Would you like to hold him?” You were surprised when she offered you to hold her son. It made your heart skip a few good beats before you collected yourself enough to do so. As you held your son, he opened his eyes and reached out with his small hands as if he knew who you were. Some tears welled up as a flurry of emotions overwhelmed you. You were proud to be a father, even if you weren’t married to Harshwhinny.
“What is his name, Julia?” You asked.
“Julian,” she replied. “I named him after my grandfather Julian, who I considered as one of my mentors.” Julian had a nice ring to it and one that would hold high reverence to her. He was a lot like his mother, strong and filled with will. Though she had her doubts, being a mother came natural to Harshwhinny. Smiling, you returned the infant to her before she gave you a quick kiss to your cheek. “Thank you so much for this, Calculus.”
"You're welcome, Julia."
"You look tired. Go take a break. Don't worry about me, you've earned it."
After kissing her on the forehead, you excused yourself to go catch a breather. The last several hours had been exhausting but rewarding nonetheless. You figured that Harshwhinny should spend a moment alone with her newborn son. All the events of the past hours left you mentally and physically drained. Yet, it was all rewarding. God’s in his heaven, all’s right with the world.
*Buzzz* *Buzzz* *Buzzz*
Your phone went off and you pulled it out. To little surprise, it was your mother calling you. You always talked with your mother at least once a week. You answered the call, wondering what she wanted.
“Hello?” You answered to be greeted by muffled sniffles.
“Sweetie? Is that you? Thank goodness!” she said, barely containing her apparent sobbing. You wondered what was going on that caused her such distress.
“Mom, what’s going on? Where are you?”
“*Sniff* St. Mary’s Mercy. I-I need you here right now.”
“That’s where I’m actually at.”
“Wh-Why?”
“Long story short, my boss went into labor and I drove her here. Now, where are you?”
“A waiting room across from the first floor ER. *Sniff* Please get here, it’s best if I told you in person.”
“Don’t worry, Mom. I’m on my way.”
You hung up the phone, wondering what got her so upset. Was it one of her family members? Who knows. You weren’t going to get an answer standing around.
Taking an elevator down, you made your way down the halls of the first floor until you saw the waiting room. There you saw your mother, Rose Oak. Her hair, the same color as yours was kept in a bun and she wore that nice denim jacket you got her for Christmas last year. The moment she saw you, she rushed forward and wrapped you in a tight hug while crying in your shoulder.
“Calculus sweetie, thank goodness you’re here,” she sobbed.
“Don’t worry, Mom. I’m here.” You shushed to calm her down, to little effect. “What happened? Why are you so upset?” Wiping some tears and a bit of runny mascara from her face she sat down and explained.
“It’s your father, Calc. When he went for a nap this afternoon, he complained of bad chest pains *sniff*. When the paramedics rushed him here, I thought he was going to be okay until… Oh god no! Your… Your father is dead!”
You were instantly in disbelief. Denial set in as you struggled to comprehend what your mother just told you.
“M-Mom, are you serious?! Please tell me you’re serious!” She didn’t say anything. The only confirmation you got from her was a tear-filled face and an affirmative nod. Right away, it seemed as if the world around you had shattered into a million pieces before you. Your mind tried to stay calm as it could but alas it wasn’t any good. Corvus Glade, your father and mentor, had just died. Your eyes started to water as you walked back towards a wall, sinking to the ground before crying in your knees. It felt like your heart exploded into a red mist.
A nurse with long lavender hair and blue eyes noticed the scene and tried to comfort you but your mother stopped her, not wanting to disturb your grieving. Your father was one of your greatest friends, always pushing you to succeed. Though the two of you were sometimes at odds, things were nonetheless alright between the two of you. What stung you the most was that you never got the chance to say what you wanted to tell him. Now, you never will.
Author's Note
People asked for Stormy Flare, I deliver. With this in mind, I had the intention of revealing the names of Calc's parents at some point and figured this chapter was a perfect opportunity. So, I included a heartwarming moment and one heartbreaker to throw you one hell of a curveball. Anyways, there's more where that came from. Stay tuned.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Heart to Heart (Rouge Melody (OC))
*Beeeeeeeep*
“Hey Calc, This is Julia. I want to give you my condolences for your loss. I know what it is like to lose a father, so I can understand your pain. Take as much time as you need from work. Don’t worry about a thing. Just… give yourself some time to grieve. Hope you’ll feel better.”
*Beeeeeeeep*
“Calc, It’s Ignacio. I’m sorry that your father had passed. He was a cool hombre. I remembered him making all sorts of jokes whenever I came over. Anyways, I have some good news. Me and Sunny Flare are expecting. If it’s a boy, we’ll name him in honor of your father. See you at the funeral. Take care, amigo.”
*Beeeeeeeep*
If there were any day where you felt like lying in bed for the entire day, today was one of them. Ever since two weeks ago when you lost your father, you, your mother, and many other family members had been making preparations for his funeral. It was one thing to hear someone close to you died, but it was another seeing them buried. As much as it broke your heart, it was something that had to be done. It made you feel like utter crap.
Checking your suit, you let out a big sigh before you drove off to the funeral home. Though the sky was a clear blue, the atmosphere wasn’t pleasant. Out of all the times you’ve had disagreements, in your mind or vocally, you never held any long-lasting grudge against him. In fact, you thanked him for putting you on the path to success, making you the man you are with the exception of a few other things.
Walking inside, various family members, friends, and others were all conversing with the air carrying the somber tone. With the exception of a few aunts and uncles shaking your hand among other things, you kept to yourself for the most part. All you wanted to do is find the funeral room and pay your last respects. As you did, you were greeted by a familiar figure, lavender hair and all. There stood Cocoa Lavender along with an older woman that looks almost like her, possibly her mother. Immediately, she noticed you approach and rushed to hug you.
“Calc!” she said as you returned the hug. “It’s been a while. I’m so sorry about your dad. I’m sure he was a good man.”
“Nice to see you too, I guess,” you deadpanned, breaking from the hug. “Thank you for your kind words, Cocoa.” Then, the woman noticed the two of you talking and wandered over. She looked like a spitting image of Cocoa, almost as if she was a clone in some way.
“You must be Calculus. Hi, I’m Lavender Blossom,” she introduced herself. “I know you’re already familiar with my daughter.” You didn’t respond, still feeling down. Blossom took a good look before wrapping you in a hug, nearly burying your face in her ample chest. “I know you’re upset. We did everything we could for your father. I’m truly sorry.”
“It wasn’t your fault,” you muttered. “I know you tried and that’s all that matters. Thank you.” Breaking away, you walked into the room where many people, including your mother, Ignacio, and Sunny Flare were conversing. But most notably, in a casket, laid your late father, cold and lifeless. Walking next to your mother, you put a hand on the casket, sharing a silent moment of reflection with her. There were a lot of things you regret having left unsaid to him and now you’ll never get the chance again. That was the heartbreaker for you and it made you choke on your emotions. Turning around, you gave your mother a big hug before taking a seat near Ignacio.
“How are you holding up, amigo?” he asked with a somber tone.
“Trying to, at any rate” you sighed. “It just seems… unthinkable that a day like this would pass. With that heart condition that ran in his family, it was bound to happen.”
“Well, the thing about life is that people come and go. The same goes for loved ones. Eventually, we all must make that trip.”
“Yeah, I guess.” Sunny Flare approaches you with her hair in a bun. You rose up an gave her a hug which she returns. “I got your message this morning. I’m honored by your decisions. Thank you.”
“We felt that it would mean a lot to you.” Sunny Flare said. “I’m sorry for your loss.”
“Don’t be. It wasn’t your fault.”
Soon, the funeral director came in and everyone took their seats with your next to you. The ceremony was an emotional roller coaster for the lot of you, especially your mother. When she came to the podium to say her piece, it was impossible for her to hold back tears that you had to escort her back to her seat. When it came time for your turn, you had your own degree of struggling with breaking down, but you managed to hold yourself together and deliver your heartfelt spiel about your father before giving a final goodbye. When all was said and done, the hardest part began.
You walked beside your mother and many others as you carried the casket to its final destination: a dug out plot near a small hill. Once there, you and the congregation shared your final moment of silence as it was lowered into the ditch. The lower it got, the more you felt your heart sinking to your feet. So this was it, the final goodbye. You’ll never see your father again and he’ll now be buried six feet in the ground. The only thing you looked forward to was the after party where you could drink your pain away.
You sat there at the counter, senses dulled from sadness and alcohol. The world around you seemed like a bit of a haze as the effects of your drinks got to your body and mind. Your pain from earlier seemed dulled, but your reasoning had taken a hit. Never eating, you just sat there, not wanting talk or do anything with anyone. Numbing the pain was all that mattered and nothing else. Looking at the glass, you grew angry and didn’t want to deal with your emotions.
“Another,” you muttered as the bartender walked by with a worried expression.
“Sir, I think you’ve had enough,” he replied. You however, didn’t take too kindly to his advice. With the alcohol calling the shots, your mind swayed to irrationality. You dearly didn’t want to dwell on having to bury family and the thought of doing so filled you with rage. Grabbing the man by the collar of his shirt, you got in his face and snarled.
“Make me… another Manhattan… or I’ll knock your fucking teeth in.” Panicking, the bartender relented and nodded as you let go.
“Fine, one more!” he said as started making your drink. “After this, you’re cut off.”
“Whatever,” you muttered as he handed your drink and walked off. “douchebag.” As you slammed your fourth and final drink, you watched on as the congregation socialized with your mom as she tried to keep her composure. As much as you wanted to comfort her, you were a drunken mess and you had your own mental health do deal with. How you were going to cope with seeing your dad off to the halls of valhalla was your guess and you hadn’t the slightest clue.
“A man drink like that and he don’t eat, he is going to die.” Hearing the voice, you turned around until you saw the source. Tall, rugged, orange hair, and a scar across his lip, it was hard not to forget him as Leo Starblaze, a friend of your father’s that served with him in the gulf war. “I hate to say this to you when you’re like this, but you look like hammered shit.”
“No offence taken,” you scoffed. “I take i-*hiccup* it you're not doing too well either, right?”
“Nah,” he said, taking a seat next to you. “Though it wasn't literal, me and your old man were like brothers. After we both got back from Iraq, I was his best man at his wedding. It always sucks to say goodbye.”
“No shit. So, what do you want?”
“Well,” Leo said as he cleared his throat. “I’m looking at you and I see an all too familiar sight. This isn’t how one should cope with grief. My aunt was an alcoholic and that quickly ruined her life. I’m concerned about this slippery slope you’re about to go down.”
Though the alcohol dulled your senses, you could tell that Leo wasn’t pleased with your choice of words. He just lost a friend and to hear his son spitting on his name filled him with concerned anger. With much regret, he gave you a backhand across your face and grabbed you by the shoulders.
“Alright, I’ve heard enough!” he growled. “You just had to bury your dad and now you spit on his grave?! Shameful! Let me let you in on something. When your old man told me that your mom was pregnant with you, he made me your godfather, looking out for you when he’s not around! If your dad hadn’t been tough with you and pushed you to succeed, he wouldn’t be doing his job right! You have much to thank him for and the way you're going about this, you’re setting yourself on the path to losing it all! Are you hellbent on throwing your dad’s efforts down the drain?! If no, then get your fucking act together or you’ll be on the streets in short order!”
As much as you hate to admit it, Leo had a valid point. Much of your success was due to your father influencing your decisions. Though you wanted to pursue your aspirations, practicality had to take precedence. Realizing the weight of what you said, you hung your head in defeat, ashamed of what you said.
“Fuck,” you groaned. “I just... don’t know how to deal with this.”
“It’s okay, I’m not mad or anything.” Leo said, putting a hand on your shoulder. “I’m just concerned about you. If you need someone to talk to, I know of someone that would be more than willing to listen.”
“Who?”
“Rouge Melody. She was my son’s therapist when he went through the emotional hurdle of my divorce. Though she’s a family therapist, I’m sure she’ll have no problems with seeing you.”
“What good will seeing a shrink do?”
“You’ll never know, but she is great at what she does. If you’re afraid of her judging you on your thoughts, she won’t. Trust me.”
Pondering the advice for a moment, you had your doubts at first. Rarely do you express your emotions, even to a stranger. But now, you were in the position of not caring anymore. Maybe talking to this Rouge Melode lady would help. At this point, you were willing to do anything to find some semblance of solace.
“Alright, fine,” You groaned, feeling tired. “I’ll do it. What time?”
“She usually likes to do appointments at around noonish because her husband and daughter would be out and about.” Leo said. “Before I make the call, let’s get you home before you pass out. I’ll drive.”
“Fair enough.” Using his shoulders as support, the two of you got in your car and he drove you home. When you got there, you walked in, slammed a big jug of water and passed out on your bed. Though you were going to have a splitting headache in the morning, you hoped that the heart to heart with the therapist would help you find some closure.
You woke up, head throbbing with pain and eyes blinded by the solar light. Even with the immense amount of water you drank last night, you still felt hungover. As you struggled to get up, you picked up your phone and saw a text from Leo.
“Appointment is at 11AM. Hope you feel better soon.”
….and the clock read 10:15 AM. Upon realizing that, your brain did its best to kick into high gear, compelling you to do your daily morning readiness ritual. You put together your best day clothes, complete with a hoodie you got from a concert last year. Hopping into your Jag, you drove to the address he specified in another message, parking in its driveway. The house was made of bricks on the outside with a few small patches of flowers at the fore.
Walking to the front door, you gave a sigh, followed by a few short raps on the door. After a bit, the door was opened by a woman that was younger than you anticipated, definitely in her late 20’s. Her ruby-colored hair was styled nicely and hanged long towards the back. She had an incredibly welcoming smile and a pair of beautiful green eyes, very cute and beautiful. Though you would normally be flabbergasted at such a sight, your mind was still awash with gloom.
“Oh hey,” she said while shaking your hand. “You must be the one Leo spoke about over the phone. I’m Rogue Melody and it’s nice to meet you, Calculus.”
“Thanks,” you deadpanned, following her inside. The atmosphere of the living room was cozy and decorated with several plants, no doubt ones that calm the nerves. Taking your hoodie off, you sat on the couch, looking at your feet as you contemplate your emotions. “Sorry if I come off as short with you, ma’am.”
“Don’t you worry about it. As a psychologist, I have an understanding of emotions and I understand that you’re grieving. So please, lay down on the couch. Make yourself comfortable.”
Following her instructions, you took off your shoes and laid upon the sofa. To your surprise, it was cozy and felt good on your back. Your nerves began to relax as Rogue crossed her legs in her chair, letting you see a bit of her teal colored panties. As arousing of a sight it was, your mind was still in flux. You were unsure what or how to get it all out.
“Now Calculus,” she said as she grabbed her clipboard and pen. “Your godfather Leo said that you were having some issues with coming to terms with your father’s death. I just want to give you my utmost condolences for your loss.”
“I… do appreciate that, Rogue.”
“Okay. During his call, Leo mentioned that you, while under the influence of heavy amounts of alcohol, had some certain choice of words to describe him which included calling him a, pardon me: ‘fucking asshole’. Now, it’s natural to feel anger towards a family member over a perceived slight. I’m no stranger to it as my father-in-law Blaze Burn caused a rift with my brother-in-law Eternal Flames over getting married. So, I know what it feels like.”
“You don’t know half of it,” you said with a degree of venom. But to your surprise, she didn’t flinch, not even a word. “Though he made me who I am today, part of me hates him.”
“Well, what is the reason for your hatred?”
“It’s… hard to say.”
“Is it hard to say or do you not feel comfortable talking about it? I’m a family therapist and I know much about familial discord. You don’t need to wall yourself off in my presence. Now, what are the causes of your animosity?”
“I honestly don’t know.” Sensing your emotional barriers were showing some cracks, Rogue gingerly held your hands in hers. The warmth… your breath took pause over the feeling as your barriers weakened further. Even with your reluctance, she still was patient with you.
“Calculus, I know that losing a loved one is tragic, but, you don't need to keep your emotions pent up. It's okay to let them all out. I won't judge you in the slightest." She then reached to her side and handed you a small square pillow. “Let’s do this simple exercise. Pretend this pillow is your father.”
“What good will this do for me?” you asked.
“It’ll allow you a chance to vent your emotions, to let out what you left unsaid. Think of this as your chance for catharsis.”
Looking down the pillow in your grasp, you began to hear a familiar voice echoing through your head. Remembering its gruff tone, it was most certainly your father’s. Wondering if it was his spirit stalking you, the words he spoke were familiar to you nonetheless.
“Son, I know art was your passion, but you have to think about reality.”
“Goddamnit, you have to do better! Good grades are what’ll get you far in the world!
“Sorry, but the answer is still no!”
“Do better!”
“Son, words cannot express how proud I am of you.”
Snapping back to reality, you still held the pillow firmly in your grip. Your arms trembled the words echoed out. As your tears began to well up, you mind made up its mind and so did your heart. You felt no animosity towards him despite any and all contention. Upon that realization, your heart became wracked with guilt over all the things you said about him yesterday.
“Dad,” you squeaked out. “Th-There were times that I c-called you a hardass, asshole, and even worse. B-But, YOUWEREFUCKINGRIGHT! Thank you, I’m sorry!” Rogue, seeing you on the verge of tears, sat next to you and pulled you into a hug. Finally, your emotional barriers burst forth like a dam and you sobbed in her shoulder for a good while. She said nothing, apart from a shushing noise. As you did, your mind gave way to a feeling you needed since two weeks ago: relief.
“I know that leaving things unsaid tears one up inside,” she said. “As I said, you don’t need to emotionally hold yourself back here.” As your tear reserves dried, your mind became clear as the clouds faded away. Your breathing calmed as you broke from the hug. Rogue was right as you experienced catharsis, peace.
“Thanks, Ms. Melody.” You croaked. “Only later did I realize there was a reason for him being as such.”
“Well, your father wanted you to have a good life. Sometimes, your folks have to be tough to steer you in the right direction.”
“And he succeeded.” Taking a big gulp of some much-needed air, it felt like your troubles had left you. Freedom, freedom from your despair had come. Even as you looked upon her face, your heart still beat like a racehorse. Only now that your heart and mind was cleared did you acknowledge it.
“Is there something else on your mind?” Rogue asked. You looked down at your feet once more, still nervous to look at her. “Does it have something to do with me?”
“Well, actually, it does.” You admit, still flustered. “You look rather nice.” Rogue was at first, taken aback by your compliment but regained her composure with the blink of an eye.
“Why thank you, Calculus,” she replied.
“But, uhhhh, If you don’t mind, may I… give you a kiss?”
“A… kiss?” She ponders as her legs shift about. “Well, intimate contact is known to be a great stress reliever. I don’t see why not.” Slowly, Rogue cups your face with her hands as your hands latch onto her waist. For a moment, it seemed as if time held no meaning as your lips made contact in a display of affection. Steadily, your woes melted into nothingness as you broke away for some air. That was short-lived when she pulled you back for another with you hovering over her. She was an excellent kisser and a beautiful woman. To whoever has her for a wife is a lucky bastard for sure.
“Calculus,” Rogue breathly moaned. “I want you to take me!”
“Why?” You asked back. “Aren’t you married?”
“Yes.”
“Then why? Don’t you love your husband?”
“I do love him dearly. It’s just that we’ve been trying hard to give my darling Blitzwing a sibling, but we don’t know why it’s not working. You’re quite a virile looking man and I still can sense a bit of stress about you. How about this: I’ll relieve you of your stress if you give me a baby.”
Sometimes, you have to appreciate how forward some women can be. You remembered the time you got something in exchange for knocking your boss. Being down that road many times, you’ve begun to lose count of how many illegitimate children you’ve potentially sired. With this, you had a feeling that Rogue would have a cover story if anyone asks questions. Plus, she had a nice MILFy body for a woman in her late 20’s, the envy of many. Most of all, your mind needed release and Rogue would be the ticket.
“Okay, done deal,” you replied as you dove in for another kiss but grinding against her crotch as you did. Before your hand even reached her panties, it was stopped by the firm grip from her hand.
“How about we take this to the floor, Calculus.” She stated. “It would be easier to clean the carpet than a couch.”
“Fair enough.” Holding her tightly, you rolled down onto the floor, sheltering Rogue from the impact with your hand before resuming the kiss. Being above her netted you a nice view of her beauty. Slowly, her hands drifted to your crotch and cupped your throbbing erection delicately. Good lord almighty, she’s making you crave her caress that badly. Pulling away for some fresh air, she gently pushed you onto your back as she got on her knees and eying your clothed junk. Here comes the inevitable blowjob.
“I think I know where this is going,” you snarked as you unbuckled your jeans. “Been through the same old song and dance.”
“So, you have experience?” Rogue asked.
“Plenty, but it’s a long story.”
“I’ll bet.” Pulling down your jeans and undergarments displayed plenty of that experience before her eyes. The sight of your cock made her break a few droplets of sweat. Flexing it a bit was the last straw for her as lust blocked out her reason. She pulled off her sweater to reveal her nicely shaped tits, jiggling about like balloons. “So, like what you see?”
“Very much so.”
“Well, let me put them to good use.” Goodness gracious almighty, Rogue has some soft tits. Your eyes rolled to the back of your head as you struggled to contain yourself. They felt so soft and warm like bags of pudding. Feeling those chest pillows mash around your erection was priceless, felt so incredibly right. As much as you try, there was nothing within your reach to grab on to. For now, you were being taken for a ride and you have to endure it all.
“Good fucking god, Rogue!” you gasped as you felt your orgasm starting to build up about half-way. “You must really drive your husband crazy with this! OHGODYES!”
“That is sorely an understatement, sir.” She shot back as bits of precum start leaking out. “I can tell that your getting close, bit by bit. Feel free to hold back for as long as you would like, but I want your seed to cover my mounds.”
“Heh, I’ll be happy to oblige.” Biting your lip, you braced yourself as breasts went faster and faster. So much pleasure, pulsing through your nerves and back, it was almost unreal how good therapeutic sex would feel. You struggled to contain yourself as your cock grew ever more sensitive by the minute but it was inevitable. All you had to do was let go and let it flow. It quivered and pulsed as it sprayed Rogue’s ample chest with your thick white seed. You laid back, gasping and breathing as you rode out your orgasm, feeling as more of your stress left your being. You were in bliss if only for a moment.
“Holy shit!” You breathed as you sat up, taking off your shirt. “For solely a titjob, that was something.”
“It’s as if I have the magic touch,” she said wiggling her fingers. “But as much as you loved it…” She lifted her legs up and removed her skirt and soon her panties down to her ankles, revealing her salivating flower, hungry for attention and cock With a flick of her foot, it flew onto your face and filled your nose with the musky scent of her sex. Sweet, caring, yet kinky, Rogue was truly one in a million. “My pussy needs some love.”
Mouthwatering, heart-pounding, and cock quivering, the sight and scent of her moist folds was overwhelming to you. You wasted no time in diving towards her crotch and lapping away at her labia with your tongue. Occasionally, you teased her clit with a few passes while never licking it for long. For how good that titjob felt, you wanted her to beg for your meat. There, your brain hatched an idea, one that was based on familiar territory to you.
You stuck your tongue inside her, but only the tip. The way she writhed about and moaned told you it was working to great effect. Occasionally, your breathing on her clitoral nub sent pulses of ecstasy throughout her being. Just eating her out like this was enough to reinvigorate your spear back to fully erect. But you pulled away, much to her dismay. She gave you this puppy dog look that spelled ‘why’. Little does she know, you had her in the right spot for a proper fucking.
“Calc, I was so close,” she breathed. “Why did you stop?” Rogue’s mood changed from dissatisfaction to speechless as the tip of your shaft prodded her entrance. From your earlier display, she was sufficiently lubed up. Even as it felt slick to slide your shaft into her cave, It felt snug inside her. The look on her face as she felt the pulsating warmth of your cock deep inside her was amusing.
Giving her a quick peck on her lips, you began to thrust in and out of her slick hole. Her breasts bounced up and down in rhythm with your movements, hypnotic and erotic to see. For a MILF in her late 20’s, she sure looked and felt good. Skin to skin, lips to lips, your sweaty bodies bumped and ground against one another in a display of lust and carnal release. You’ve been miserable for the past several weeks since that fateful day and to say your spirits are no lifted would be putting it a bit lightly.
“NNNNGHHHHH! OH FUCK!” Rogue moaned loudly as her inner walls started to clamp around you. “ARE YOU CLOSE YET?!”
“Not quite!” you groaned back.
“GOD FUCKING L-OOOHHHHHHHH!” With her scream, her inner walls clenched around your scepter and a gush of her lust fluids erupted from her folds. Even as the pungent scent of sex and sweat hit your nose, you were not done just yet and you still had a bit more to give. You kept pumping and pumping in and out of her as she rode the remainder of her orgasm. Each and every time it made your nads sensitive and uncomfortable, but you wanted to hold out as long as you could for her. Sensing your fatigue, Rogue placed a hand on your cheek with a reassuring smile on her face.
“It’s okay.” She cooed. “You don’t have to hold on for so long for me. Go ahead, give me your cum. Give me a baby.” That was it, the straw that broke the camel’s back for you. Hilting yourself, your cock quivered and pumped loads of your life-giving seed into her fertile womb. The sheer volume of your load was enough to give her belly a slight yet noticeable pudge and leaving you winded, collapsing next to her. As you breathed, you’ve felt your aggravation leave you, but you still felt a bit wound up; nothing that you couldn’t manage.
“So, how did it feel pumping that load of yours inside me?’ Rogue purred as she gave your cheek a kiss.
“Liberating,” you quipped, sitting up. “It felt good but I still feel a bit uneasy. All in all, that felt great.”
“Well, since you still feel a bit under the weather, why don’t you take this day and have it be yours.”
“Well, I usually have a pretty open schedule. What would you suggest?”
“If it’s your thing, perhaps a day at the spa will put you in the right spot. I know of this great place in the downtown area called Canterlot Heavenly Spa. Though pricey, it’s worth the price.”
You recognized the name as soon as it left her lips. You’ve been there once before with Ms. Harshwhinny the day you knocked her up. Though you weren’t usually weren’t the one for a spa, your trip there certainly warmed you up to it. Plus, your night with the twins who ran that place certainly topped off the whole experience. It would be certainly nice to have fun with them again.
“Fair enough,” you said as you stood up. “But I can say that we can’t have these sorts of appointments due to… ethical reasons.”
“Good call.” Said Rogue. “Well, if you still need a therapist, I’ll give you a business card for my friend Dr. Cerebellum. She has an office uptown. Go on and get in the shower first. I’ll run a steam cleaner over the area a bit.”
Nodding, you grabbed your clothes and jumped into the shower, giving yourself a good scrub down. Another day, another MILF to add to your score. With your mind at ease for the time being, your mind felt much clearer than usual and at terms with your thoughts of your father. All in all, your were sound of mind and eager to meet up with the spa twins again. It seemed like a long time since you’ve shagged with them. You wondered how they were doing.
Author's Note
Well, with tragedy comes a need to cope with it, whether it be talking with someone... or other means. Sorry I was a bit late to get this chapter out and I hope you'll enjoy it. The OC in question is owned by my friend Israel Yabuki.
Also, I'm going to take a month long hiatus from this story to devote efforts to some of my other stories that I've not updated in a good while. But don't fret, I'm not abandoning this story in the slightest. Enjoy reading.
EDIT: Removed and changed the names of characters at the OCs owner's request.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Treat Yourself (Cloudy Quartz, Cookie Crumbles, and The Spa Twins)
The past few weeks had been rocky for you. You lost your father, buried him, and vented your feelings about him to some therapist you met just a few hours ago. Through all that, you were able to find some solace in her arms, understanding… and her incredibly beautiful body. At her suggestion, you decided that maybe a day at a spa would be a great destresser. The women who run Canterlot Heavenly Spa were amazing in their craft. It would be nice to see Aloe and Lotus once again.
Since it was nice out, it was worth taking a walk out to the nearby bank to withdraw some cash. After withdrawing a sizeable stack, you started to make your way towards the spa, cutting through a nearby park. As you strode across the green fields, your eyes caught the sight of something familiar. Two women, one was purple while the other was bright light orange. Respectively, their hairstyles of a ponytail and long and flowing curly hair. They were your old friends Twilight Sparkle and Sunset Shimmer, hanging with their respective boyfriends. You recognized the former from mathematics club.
“Calculus?” Twilight gasped the moment she saw you, dashing over to you and nearly knocking you to the ground with a hug, “Oh my gosh! It’s so good to see you.”
“Likewise.” You squeaked, “As much as I appreciate a good reunion, you’re kinda crushing my lungs.” Awkwardly, she lets go, blushing in embarrassment. “It’s great to see you and Sunset too after all these years.”
“Likewise, Calc,” Sunset chimed in, shaking your hand. “Hard to believe it’s been years since high school.”
“Same here, Sunny.” Then, the two boyfriends approach you as you shook their hands. The taller one had long straight red hair while the shorter one had bright orange. “You must be their boyfriends.”
“Yes, I’m Eternal Flames,” Eternal, the red haired man introduced himself, “Sunset’s main squeeze.”
“And I’m Heat Blitz, Twilight’s boyfriend.” He introduced himself, “Twilight spoke highly of you since her time at Crystal Prep.”
“Yeah, she has quite the focus there,” Sunset remarked. She reached to shake your hand but sensed a slightly stressed feeling. “Is something bothering you?” With a sigh, you prepared your answer.
“The last couple of weeks hadn’t been good to me, Sunset,” You answered. “My father died two weeks ago and I had to bury him yesterday.”
“Oh my, I’m sorry for your loss.” Twilight replied with a hug and Heat Blitz patting you on the back.
“He was.”
“Where were you heading to?” Heat Blitz asked.
“Well, my therapist recommended a day at the spa downtown.”
“Hmmm, never thought you one as enjoying a spa treatment.”
“Well Sunset, I thought the same way until my boss sent me there to start a mandatory two-week vacation.”
“Heh, always the hard worker. You remind me of myself from back then.” Twilight chuckled, “Anyways, we were on our way to somewhere for an early dinner. We won’t keep up more of your time. Take care!”
“Thanks! You too!” you answered back as the walked away, “Let’s catch up some more someday, huh?!” As you got back on your path, you remarked internally about how good it was to catch up with an old friend after so long. Then again, you’ve had plenty of run-ins of that sort. She really hasn’t changed much.
After an hour of walking, you’ve reached your destination. It looked to have barely changed if at all. Still, you eagerly awaited spending a day there in the hands of some of the finest (the only) masseuses you know. Walking into a nicely cooled room, you were greeted with the sight of Aloe and Lotus Blossom manning the front counter. The second their eyes locked onto you, their faces lit up like a christmas tree.
“Calculus!” Aloe sang as you approached the counter, “It’s been a while!”
“About nine months to be exact,” Lotus added, “I have to say you look to be quite stressed out right now.”
“Yeah, it’s not been good lately for me.”
“Yes, Julia talked to us last week. Our condolences for your loss.”
“Thanks.” Looking up at them, you’ve noticed that their bodies had changed a fair bit since last time. Their breasts are certainly bigger and they have a bit more bounce ao to say. It was like they’ve developed nice MILFy figures to accentuate their already smoking hot figures yet they appear to be MILFs. “Pardon me, ladies; But it looks as if your breasts have grown.”
“We have you to thank for that.” The twins said in unison, “After that fucking you gave us, it left us wanting. Only recently did we have a bit of breast enhancement surgery.”
Thank goodness. You sighed internally, No need to pay child support, then. You dug into your hoodie pocket and pulled out your sizeable stack of cash. “I would like the best and biggest treatment you’ve got… all day.”
Just as you’ve slapped the cash on the counter, two different sets of hands slapped two more stacks of cash on the counter. What followed was two pairs of sizeable tits pressing against your arms. Though you were used to it, you were caught off guard nonetheless. Darting your head from left to right, you recognized the women from a joint school event. One of them had gray hair in a bun with a pair of chained glasses while the other had a more stylized set of indigo hair. You knew them as the respective mothers of your friends Pinkie Pie and Rarity.
“Heh, never did I expect to see you both here, Cloudy Quartz and Cookie Crumbles,” You scoffed.
“Neither did we, Mr. Crunch,” Cloudy purred as she seductively rubbed your arms, “I have to say you certainly kept your physique from school. Not too shabby.”
“Most certainly.” Cookie replied with a kiss to your cheek, “It seems age hasn’t slowed you down one bit.”
“True. So, what are you ladies doing here?”
“Well, we should ask you the same thing, hon.”
“To make a long story short, it’s been a stressful past couple of weeks and I need to unwind.”
“Well,” Cookie Crumbles said, “how about we treat you for this session if you’re doing the all-day?” You’ve always known Cookie Crumbles for her generosity. Hell, you could even say that some of it rubbed off onto Rarity. Still, part of you had this pet peeve about others paying for your stuff. Yet, you wanted to relax.
“How about this, ladies.” You smirked, pushing your stack further up the counter, “Will this be enough to have the spa all to ourselves for today?” After a moment of staring at one another, Aloe and Lotus silently nodded as the latter locked the door and switched the sign to ‘Closed’. It was official and the time had come for some fun. “I guess that sealed it.”
“Quite,” Aloe said as she stashed the bundles in a safe, walking towards one of the changing rooms, “If you would, Please follow me, Mr. Crunch.” You did just that, all the while staring at her nicely shaped ass jiggle around. As much as you wanted to do a quickie with her in the room, you have some old acquaintances to entertain first. “Now, please remove all articles of clothing.”
“You didn’t even need to tell me that.” You thought as you kicked off your shoes and threw off your shirt. Once the undergarments came off, you were once again fully nude in front of Aloe, blushing at your still sizeable member at half mast. “Yeah, I still got it.”
“Woah,” Aloe gasped, “Evidentially, you still do.” She walked over to you and planted a quick but passionate peck on your lips. She still has it and her newly MILFy body made it better. “How’s that?” Through the power of that lustful kiss, your cock became fully erect.
‘Yeah, that’ll do.” You nodded as you followed her to the mud baths.
In the eight months since you were last there, the mud bath area changed quite a bit. It was a bit bigger and with a larger central bath, built for multiple people. Now, it was filled with a relaxing mixture you were familiar with. The other doors opened and the naked forms of Cloudy and Cookie. Where oh where do you start to describe these fine examples of MILFy beauty. Cloudy Quartz, though with D-cupped breasts, has that old-fashioned charm from a traditional woman with the slender body to match. Cookie Crumbles on the other hand… chubby in most of the right places, bubbly, with E-cupped breasts to match. Oh, lord have mercy.
“I think our daughters’ mutual friend is quite excited.” Cloudy chuckled as the two walked over to you.
“Yes, I never knew he was quite… gifted.” Cookie moaned as she traced a finger around your abs. “I see that Twilight Velvet wasn’t exaggerating.” Just before she could lean in for a kiss, The twins got in between you three.
“As much as we encourage kissing and lovemaking,” Lotus said, “It’s best we save that after the mud bath.”
“Fair enough.” The three of you said as you climbed into the mixture of water, volcanic ash, and many other minerals. Immediately, the heat from the mixture relaxed you to the bone. God, you sorely needed it. Hell, it made you consider getting a membership there. Just as you were getting settled, Cloudy and Cookie laid on either side of you, slipping their arms under your neck as they scooched closer to you.
“Now it’s time for the cleansing masks.” Aloe sang as she brought out the bowl with the purifying mixture. “Close your eyes as we apply them.”
"My daughter recommends getting a facial, but I think I'd prefer a cream pie.” Cookie Crumbles joked to much laughter as her face mask was being applied. Once yours was applied, you took that as a cue to relax in the arms of some fine chicks. Two sources of heat and the soft skin of some hot MILFs, you are in for one hell of a treat.
“Well, enjoy your bath. After that, wash up and we’ll get to the massages. We’ll come back in about ten minutes.”
Once the doors shut, the only sound in the room was from the two naked MILFs laying beside you. Nothing was going to catch them as they rubbed their hands all over your body. The sensual touch, like the softest of silk, was incredibly smooth. Whoever were the husbands of these fine women, you considered them lucky. It wasn’t long before you felt Cloudy’s hand grip the base of your cock. Her hand felt smooth and warm, perfection.
“Is this good for you, young man?” Cloudy moaned as she continually stroked your erection, “I’ve been eager to try you after Ms. Velvet talked about you.”
“Same here,” Cookie purred. She rubbed your abs as she kissed your lips. “Since we have the spa to ourselves for the day, nothing will get in the way of our little fun.”
“Well now, there’s plenty of Calc to go around.” You chuckled as the women start feeling you all over. Being no stranger to taking on two cougars at once, it seemed like a welcoming thing after the last two weeks. Your cock twitched with every stroke as both Cloudy and Cookie pelted you with kisses. Just before you were about to bust your nuts, the twins came back in, still naked and blushing at the scene.
“I hope you both enjoyed the bath,” Aloe sang.
“We did,” You moaned as you climbed out with both women in tow, “As always, it’s relaxing to the bone.”
“Glad you liked it,” Lotus shot back, “Now, get cleaned up in the showers. After that, the massage can begin.”
Walking into the showers, the soothing hot water washed away the mud off your body. Soon, you saw the women’s nude forms, clean and serene. Nothing stopped you from jumping onto Cloudy Quartz and furiously making out with her.
“Oh my word,” she gasped in between smooches, “you really are a starved boy aren’t you?”
“You don’t know the half of it.” Resuming the kiss, you ground your still throbbing erection against her wet slit. In the midst of your relentless humping, Cookie Crumbles pulled you away with great strength and proceeded render you the same service. Incredible, absolutely incredible, her body was soft and cuddly, odd yet pleasing. You couldn’t resist grabbing two handfuls of her luscious ass. With each squeeze, she moaned loudly, followed up by more kissing. Good fucking god almighty, amazing.
“Okay, you three.” Lotus came in, blushing at the sight before her, “T-Time for the massage treatment.”
You followed the twins to the tables. Unfortunately, there was only two of them compared to the three of you present. But, judging by the looks on their faces, you can guess they have a plan for that.
“Cloudy, Cookie, Please lie down on the tables.” Aloe said as they did what she said. She then turns to you, “Calculus, pick whoever you want to lay on.” Closing your eyes you hummed for good five seconds before opening them. Your finger pointed at the beautiful Cookie Crumbles who blushes at your choice.
“Will there be some penetration allowed?” You asked.
“Yes, the massage he have planned is designed to both amplify arousal and intensify orgasms.”
“Oh goodie,” Cookie Crumbles sang as she gestured for you to come over, “I guess I’m in for a treat, am I.” Walking over to her, you mount the table, position yourself between her legs. Lotus then comes over and spreads a vanilla-scented oil over your body and Cookie’s. Right away, your body began to heat up with lust and want but she wasn’t finished. Shortly after, she slathered some lube upon your cock, already priming it for action. You were excited, you were horny. But most of all, you were ready.
Eagerly, you slid your throbbing erection inside her wanting slit. Almost immediately, you both moaned pleasure and eroticism pulsed through your bodies. At Lotus’s request, you laid on top of wanting MILF, giving her a quick peck for good measure.
“Okay, for this massage, you’ll be making love to her as give you instructions. Got it?”
“Got it.”
“Then… proceed.”
Once Lotus’s fingers touched your back, the party began in earnest. You started thrusting slowly to keep the moment going as long as you can. A bit loose, her cunt still felt good nonetheless, slick and warm. Her moans and sighs commanded you to carry forth as you pound away at her. Good lord almighty, she was amazing.
“Ohhhhh fuuucck,” Cookie moaned as her inner walls snuggled around your member, sliding your oily body against hers. “This is… I can’t describe it! Oh yes!”
After Lotus tapped you on the shoulder, you took it as sign to get on your knees and start massaging Cookie’s plump front. You swore massaging her luscious body belt like squishing bags of pudding. A sharp yelp here and a breathy moan there, you kept going as she seemed to melt in your hands. Hell, you could do it all day and never tire of it.
“Okay, Mr. Crunch,” Lotus sang, “Time to switch places.”
Briefly removing yourself from within her, you laid on your back on the table. Soon after, Cookie straddled your lap and impaled herself on your spear. Now all you had to do is relax and enjoy the ride. She gradually picked up her pace with her bouncing as she rubbed your hands all over your body. Bit by bit, you’ve felt your muscles relax as your mind became filled with a fog of tranquility. You could tell that you were close to cumming, but you could do little to resist the urge.
With a grunt, you felt your mind going momentarily blank as you busted your nuts inside the wonderful MILFy pussy. Spurt after spurt, each rush of your hot seed sent Cookie Crumbles closer and closer to orgasm until, with a loud wail, she came. A flood of juices coated your crotch as you both rode out the rush of your orgasms until you were both left panting for air. As your mind became clear enough, you looked over at Aloe and Cloudy Quartz as the former just got done railing her with a strapon.
“Holy shit!” you breathed, “I’ve had erotic massages before but damn!”
“And you weren’t bad yourself, young man,” Cookie breathed back.
“You know us. We always try to improve upon our technique,” Lotus chimed in as she helped you off the table. Your legs were still wobbly from the experience and you could barely keep your balance, “Now it’s time for the sauna.”
With the help of Lotus, you walked into the sauna room just as Cloudy and Cookie were getting settled. She helped you lay on their laps with your head resting on Cloudy’s nice thighs. Steam’s up, doors shut, post massage relax time is now here. Turning to your side, your face looked upon the sight of Cloudy’s nicely shaven vulva, still glistening with her juices. Perfect positioning, opportunity once again found you.
Turning your head, you began lapping at Cloudy’s succulent cunt, surprising her with your moist tongue. Soon after, Cookie grabbed hold of your cock with a mighty grip, stroking it until it became erect in short order. With every lick, Cloudy’s breaths quickened and you dove in hard, with a bit of extra attention to her clit. Still a bit sensitive from her previous release, pleasure dictated her to press your face further into her crotch. Though your breathing was a bit impaired, the musky aroma of her juices drove you beyond bonkers. Judging from what you’re hearing, Cloudy was reaching her limit… and so were you.
For the coup de grace, you began nibbling softly on her clit. The sensation proved too much for her as your face became drenched with her tangy juices, accompanied by a loud scream. As if by reflex, you blew another load all over her busty chest. Having just filled her up, it made Cookie laugh with glee as her bust became frosted in a white thickness. Taking a taste of it with her fingers, she hummed with delight as the spa twins opened the door.
“Alright, I hope you’ve enjoyed the steam bath,” Aloe sang.
“Now, it’s time for the hot tub,” Lotus finished.
Following them to the hot tub, the moment your toes touched the water, your muscles felt a penetrating heat all the way through to the marrow. You just slid right into the relaxing heat as you shut your eyes, tranquil and blissful. However, it wasn’t long until you felt something straddling your waist. Opening your eyes, you saw a very horny Cloudy Quartz just before she gave you a quick peck on your lips with her quivering womanhood above your lance.
“Now,” Cloudy purred, “it’s my turn.”
Closing her eyes, she let gravity do its duty as she impales herself on your member. The warm fleshy hardness of your cock filled her with pleasure that makes a dildo pale in comparison. Her mind went wild as it was the first cock she had in half a year. Bouncing up and down, she went at it like she was mad in the head.
“Ohhh, fuck yes, Mr. Crunch!” Cloudy moaned as she kept on riding your length with complete abandon. Soon, Cookie Crumbles got in on the action by groping her friend’s breasts from behind, rubbing her naked body against her. Lord help your aroused spear as you watched the two naked MILFs make out while the other rides you. There was no way in hell that you were going to last very long, even though your stamina is the stuff of legends.
With a grunt and a moan, you bust your third nut inside the wanting cougar. The sticky rush of your cum drove her into an orgasmic frenzy as her nethers quivered and her juices exploded all over. Already, your hazy mind went further into the fog you laid back with your senses dulled. You could still see as Cloudy got off you and the twins coming into view. All they did was nod as they picked you up and carried you upstairs.
Once you got to that familiar room, they laid you upon the memory foam bed. Though you could still move, you didn’t want to as they all gathered around you. Cloudy and Cookie kneeling above your hands, Aloe straddling your lap and Lotus’ crotch hovering above your face, you just couldn’t believe it. You took two on at once. But four, that’s a whole new ballgame and another record for you.
“Heh, Jackpot! ” You laughed as the greatest of all holy fuckfests you know began. With three fingers each, you started fingering Cloudy and Cookie. Their moans, oh boy. Aloe starts riding your cock and Lotus sits on your face, forcing your mouth to start licking her cunt. All over the place you were going crazy over being fucked by four hot women at the same time. Though you you want to do it all day, you knew that you were on your last bit of steam. What better way to top it all off.
Lotus ground her wet puffy snatch against your mouth as you licked at it with the occasional nibble on her clit. Jumping up and down on your shaft, Aloe was having herself a good time. Six of your fingers all being drenched in ladyjuices, the nice women who treated you to a fantastic day were doing you a great service. The thrill, one can only hope to experience it once in their lifetime and you drew the lucky ticket.
Soon enough, with a symphony of wails, screams, grunts, and curses, your respective nether regions couldn’t withstand anymore and the orgasms exploded all at once. It was like a beautiful opera of lust with the scents of musk and sweat as the ambient air around you started to grow hotter. After riding the last bits of the rush of pleasure, Lotus dismounted your head and laid down on the bed along with the other three. Tired, sweaty, and unwilling to do anything, you all cuddled together into a big sweaty mess as you felt your eyelids grow heavy.
“My my,” Lotus moaned, “still have the magic touch, don’t you?”
“That he does, dear sister.” Aloe agreed as she gave you a kiss on the cheek, “It’s no wonder he got Julia likes him. His dick feels too damned good.”
“And you were both right,” Cloudy Quartz whispered as she rested on top of your body, “Now, it’s time for a warrior to rest.”
“Indeed,” Cookie Crumbles yawned as sleep claimed her. Soon after, you felt that same pull as your eyes shut as you felt the relaxing comfort of serenity. From one to four in just one day, sometimes you just had to chalk it up to your heritage that luck is on your side. But hey, your stress is gone and you feel better after yesterday. Way to go for sex being a great stress reliever.
Jackpot.
Author's Note
Well, it's been a long time coming but it finally came. My hiatus on this story has ended and I present you with a new chapter. Sorry if it may seem a bit rusty in some areas but I suppose that's the consequence of a month-long break.
Anywho, I hope you enjoy this and be on the lookout for the next chapter because it's going to have one hell of a surprise.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Unthinkable (Rose Oak (OC))
“So, when do you think you’ll be coming back?” Ms. Harshwhinny spoke over the phone.
“Next week, I guess,” you sighed, “If I still do come off as a bit down, I can manage. I’m past most of my grieving.”
“Well, I hope the best for your sake. Whenever you’re ready, just come to my office. You can take things easy of you want.”
“Thank you. I’ll see you on Monday.
“Take care, Calculus.”
“You too, Julia. Take care.”
Beep
You hung up the call, slumping back into your couch as you drew a heavy sigh. While over most of the emotional shock, there was still that bit of you processing the loss. You missed your father and were fresh off visiting his grave some time ago. Though much was left unsaid, you’ve set yourself to dwell on only the pleasant memories as a family. He would’ve wanted that.
Walking through your house, you came across a photo that caught your eye. It was of you, your father, Corvus Glade, and your, mother Rose Oak at your graduation ceremony from Crystal Prep with big smiles. Though it’d been years since then, you remembered that sense of pride your parents felt for you at that moment. Hell, you even remembered how goofy you looked with that smile. However, the sight of your mother made your heart sink.
Oh Mother, I can only imagine the pain you’re going through. You thought as you set the photo back, I wish I could comfort you.
Then, a thought dawned on you. After the funeral, you didn’t have much contact with your mother, allowing her some space. Part of you wondered how she was holding up if she was. The thought of your mother wallowing in perpetual despair was something you couldn’t stand. It sounded as good a time as ever to pay her a visit.
Grabbing your keys, you hopped in your Jag and drove off to the place you called home for a good chunk of your life. For you, it was stepping like stepping back through time, figuratively speaking. So many good memories, too little time to reminisce. Parking along the boulevard, you walked up to the front door, rapping on it a few times.
“I hope you’re alright, Mother.” You sighed as the door opened. Before you was your mother, looking down in the dumps with her hair disheveled. The moment she laid her eyes on you, nothing stopped her from wrapping you in the tightest hug you’ve had from her. All the while, she cried in your shoulders.
“Oh, my dear sweet boy!” Rose Oak cried, “It’s so good to see you!” You held the hug for a bit before breaking it. A bit of mascara ran down her eyes as wiped away her tears. Try as she might, she couldn’t bring herself to smile, even in your presence. “Why have you stopped by?”
“I just thought you needed some company after recent events. I’m returning to work after this weekend.”
“Well…” sniff, “come on in.”
Following your mother in, you noticed it still looked orderly and nice as she always kept it. If anything, it was more her trying to keep her mind off her husband’s death. Sitting down the couch, you noticed a stack of photos on a coffee table. One of them was of her and your father in a hospital room. She laid on a bed, holding a swaddled infant in her arms, undoubtedly you. They both looked happy and proud, holding you in their arms.
“I remembered when you were first born.” Rose sat next to you, “You were quite a hefty baby, but also so happy. You should’ve seen the look on your father’s face when he held you. That was the first time I’ve seen him cry.”
“Yeah,” you nodded, “he always was a closeted softie.” One question dwelled on your mind, on that you were curious about, “So, how did you and Dad meet?” For a moment, Rose Oak went silent as she held the picture in hand. Such a memory was one of the fondest she shared with Corvus Glade. It reminded her of happier times before she lost him.
“Oh. It all started while I was in college for my geology degree. When I went to have lunch one day, my credit card went on the fritz. But, along came your father, paying for my meal. All throughout lunch that day, we’ve been chatting and the rest was history from there. After he got back from Iraq during the war with the 75th, that’s when he got on one knee and asked the question.”
It was years ago that Rose Oak sat nervously in that terminal at the airport. After hearing the news that the Persian Gulf War had come to an end, she was elated that she’d be seeing her Corvus Glade once more. Shuffling her fingers around as the sun shone in her hair, she watched as families were reunited with their mothers, fathers, or children. Yet, she eagerly waited for her love, to feel his strong arms caress her body.
Her eyes fixed to the gateway, a figure emerged that froze her in place. Wearing a ranger BDU with shield insignia containing a red lightning bolt, three chevrons and a rocker, maroon hair, and beard with ocean blue skin, Rose knew who it was. Seeing him back stateside after a long time made her heart quake and pulse. All in all, it was a sight she waited and braced herself for.
“Rose!” Corvus gasped, dropping his duffel bag.
“My Corvus!” Darting to his side, Rose jumped into her lover’s embrace and planted a emotionally passionate kiss. Seeing her battle-weary lover once again eased the tension she felt in her heart for months. “I’ve missed you so much.”
“The thought of coming back to you kept me strong through all the violence.” The weary soldier breathed, “The entire time… I’ve kept that photo of you in my helmet to keep me going.”
“Th-thank you, my Corvus.”
Hugging Rose, Corvus had a thought on his mind. Throughout all the firefights, explosions, and high-stress situations, it was always there. He put the plan in motion about a week before he deployed to the front, hoping to save it for when he came back. Holding the woman he loves in his arms, relishing in the reunion, he felt now was a good time as ever.
“Rose, close your eyes. I’ve got something for you.”
Heeding her lover’s words, Rose closed her turquoise eyes; heart racing with anxiety. What could it be that Corvus wanted to show her? Was it a souvenir he obtained during the months spent in the middle east? To her, the possibilities were endless. With a light tap on her leg, she took it as a cue to open her eyes once more, but what she saw was something she wasn’t prepared for.
There, Corvus Glade stood on one knee with a small black box in his hands. In the box was a ring with a small heart-shaped diamond on top. Rose’s breath felt like it was knocked out of her for the briefest of moments as she held her hands to her mouth. Emotions flooded her heart and mind as tears began to well.
“Rose Oak, with my brothers in arms as my witnesses, will you… marry me?” Corvus asked with a voice most sincere. Rose, heart fluttering from those words, looking all around with excitement and joy.
“Yes! Yes! Yes! A million times yes!” Rose screamed enthusiastically as she dove in for another passion-fueled kiss. Roaring applause was had all throughout the terminal as both returning troops and civilians cheered on the couple. Hearing all that raised their spirits to exponential levels. Soon, they were to be husband and wife, eager to spend the rest of their lives in wedlock. For Corvus Glade, it was something he wanted the most in the world.
“It must’ve been a happy moment for you.”
“It was THE happiest moment of my life, surpassed only by bringing you into this world.”
“I can only imagine.” Just then, you felt a trembling in your stomach. You’ve not felt hungry in the slightest since you woke up. Now, it’s come out in full force, nagging at you like a dog. Knowing your mother’s current state, she wasn’t in the mood to cook or going out somewhere. “Gosh, I’m actually kind of hungry. Want me to fix up something for us?”
“A-Are you sure, son?” Rose sniffed. Sensing her unease, You gave her a brief hug before giving a reassuring look.
“Of course I am. I haven’t cooked for you in a long while. Besides, you could use something nice.”
With a silent nod of approval, you sauntered into the kitchen, looking for whatever you could find. Bacon, linguine, parmesan, eggs and milk, all the fixings for a pasta carbonara bake were present. Being in a close tie with your usual cheat day meal, it was always a nice change of pace. Since you didn’t cook anything big in quite a while, it seemed like a good time to de-rust your culinary skills.
Propping your knuckles, you went to work on creating art. Pasta boiling, bacon sizzling, alfredo sauce bubbling, sound and the smell filled the air as the magic unfolded. You swore that you could already taste it. Once both were done and some careful tempering of the eggs, the sauce, bacon, and pasta were mixed and put in a pan. All that was left was waiting ten or so minutes as you found yourself mired in thought.
Rose Oak cried as she cradled a framed photo of her and your father on their wedding day. Judging by the looks of it, she looked to be around four to five months pregnant with you. You had to admit she looked like an angel, beautiful and radiant. All in all, she looked happy with Corvus and you in the picture. To have part of that taken away from her was like her heart being torn to shreds, painful for both you and her.
With a set of beeps, the oven was finished baking the cheesy, savory goodness. Opening the oven, your nose was hit by a full blast of the aroma from your handiwork. As you began plating servings, knowing your mother’s state, you thought of a way to calm her down as precarious as it sounded. You snatched a bottle of red wine along with some accompanying glasses. Setting everything down on the coffee table, you poured your mother a glass.
“Here,” you softly spoke, “this should help.”
She took a cautionary sip before, to little surprise, guzzled the rest of the glass in one gulp. What did shock you was her taking the bottle and taking a big swig from it. Now you were wondering if you’ve made a big mistake adding alcohol into the equation.
“Woah, mom!” You said, snatching the bottle from her hands, “That should be enough for now.”
“I~ can hiccup handle myself, dearie!” Rose drunkenly said.
“Riiiight. At the very least, eat something.”
Sipping your own glass, you ate your creation. Savory and cheesy, it was comfort made manifest as it warmed you to the soul. Your mother seemed to enjoy it for the most part but seemed lost in both grief and liquor.
“Mom, how was it?” you asked.
“It was good, dearie,” she croaked, “You didn’t have to do it... but thank you.”
“I wanted to do something nice for you. It’s not a big deal.”
“But, I’m so glad you came here!” She started to cry again, “It’s just that…” Sniff, “since your father died, it’s been so lonely around here! I just miss the company of him and you… you’re not even around anymore, all grown up!”
Reaching over, you pulled your mother into a hug, rubbing her back as your shoulder became soaked in with tears. It’d been a while since you’ve hugged her at the funeral. Just hearing her cry broke your heart. As she gave you comfort in the past, it all comes full circle. If need be, you weren’t opposed to staying with her for another day or so.
However, things took a turn real quick as she pulled you into a deep kiss with a blink of an eye. It wasn’t a motherly kiss on a cheek, it was an on-the-lips affair that a lover would give. You couldn’t tell if it was the alcohol or desperation. Even under the influence of wine, you still knew it was wrong. Breaking from the kiss, you lightly pushed your mother away, much to her chagrin.
“Please! Love me! I beg you!” Rose cried.
“No, Mother!” You breathed, still in shock, “This is not right! We can’t do this!”
“But you remind me so much of him! Please, love me!”
Wanting to get away from a stressful situation, you retreated to the bathroom, all the while you could hear your mother crying. Breathing and mentally processing what happened, your mother’s desperation just got a whole lot worse than you thought. Having been alone for weeks with only the pictures of you and your father to keep her company took its toll on her. For once in your life, you felt truly lost.
"What am I going to fucking do?! Oh, Jesus Christ!" You cursed as you paced around the bathroom. “I wanna see my mom happy but this… god motherfucking damn it! FUUUUUUCCKKK!!!”
Slumping against the wall, you found yourself torn apart on what to do. She’s your mother, the person you’ve sworn to cherish and keep happy no matter what. Kissing you squarely on the lips sent your mind in a conflict. You’d do anything to make her happy in a time like this, but intimacy with her was something you hoped never to do. Just hearing her cry out yours and your father’s names tore your heart asunder.
After another minute of hearing her cry, something stirred within you. You wanted her to move on and be happy for her sake and yours. If it would only be just a one-time deal and being the end of it, what was there for you to lose? Just a bit of an in and out and there, done! With a bit of alcohol, it might dull your memory of it all. Swallowing your inhibitions, you walked back into the living room, sitting back on the couch to her surprise.
“S-Son?” Rose croaked. You turned her around with a serious look on your face.
"Mother, just this one time and ONLY this one time. After tonight, not a single whisper of this is to be heard. Got it?"
With an affirmative nod from her, you hastily grabbed the wine bottle and took a generous swig from it, evening the playing field. Though I'm doing this for her, I'd much rather not remember any of it. With the rush alcohol flooding your veins, inhibiting your senses, you were ready to begin.
Holding her close, you slowly planted your lips on her, taking it as slow as you could. Admittedly, as much as you hate to, her body felt good as did her lips. E-Cup breasts and a decently sized ass, it was hard not to marvel at her beauty. Prodding at her teeth, her mouth opened to allow your tongue entry. The ecstasy was overwhelming for her as you leaned on her, pinning her to the couch, rubbing your hands all over her body, but the thought of being watched through the windows snapped you away from the passion.
Carrying her bridal style into her room, you fell on her onto the bed, resuming the passionate make out session. Your friskiness got to you as you snaked an arm under her shirt and gripped one of her tits. It was hard to believe that you used to feed from them at one point. Staff hardening from the experience, the resulting lust drove you wild as you bagan to dry hump your mother, causing her nethers to salivate with want and desire. Breaking the kiss for some air, you looked your mother in her beautiful eyes.
“Son?” Rose gasped.
“Yes?” you breathed.
“Thank you so much for this. You’re making mommy very happy. But,” She began to rub the bulge that’s straining in your jeans. Every pass pulsed your spine with pleasure unending. “Your poor thing is so cramped up in there. How about we do away with the clothes?”
“S-Sure.”
Grabbing the hem of your shirt, you took off your shirt and kicked off your shoes. Once your pants and underwear came off, you were hit in the face by a pair of panties. Radiating off them was a distinct musky scent, one that you were more than familiar with. Removing them from your face, your cock quivered at the sight of your naked mother. For a woman her age, she still looked beautiful, fit, and downright sexy. A shaven bush and her hair long and flowing, it woke up something within you, something fiery and passionate.
“Goodness, y-your muscles and… your thing!” Rose said, commenting on your body and the size of your shaft, “To think that… good lord!”
“Taking care of my body got me this far, Mom. I’m keeping that momentum.”
Getting back on the bed and on your knees, you pulled your mother into a passionate, alcohol fueled kiss. The feeling of her beautifully naked body against yours felt so wrong yet so right at the same time. At this point, your dick and all that wine were calling the shots. Just the experience of grabbing your mother’s firm ass while rubbing your junk against her body awoke your inner horndog.
“There’s something I’d like to do.” Turning you around, Rose pushed you back against the pillows, crawling between your legs, licking her lips at the sight of your cock, “I wonder what my son’s cock tastes like.”
That slick and velvety tongue of hers, the feeling of it scraping up, down, and around your lance caused you to spasm like crazy. Taking into account that it was your mother had a strange effect that you couldn’t describe. If it was what your father experienced, then he was one lucky man to have picked her, even as she took the entirety of your length in he mouth.
“Oh, holy shit!” you gasped which was answered by a slap to the knee from her. She was no doubt unamused by your choice of words. Leave it to your mother to still mother… even as she is sucking you off. Though you were tempted, you couldn’t bring yourself to force the woman that created you to deepthroat your dick. You weren’t the one to do so unless they say so, being a gentleman and all.
Persistent as she was, she kicked her motions into high gear, determined to have a taste of your seed. Your balls tensed as she brought you closer and closer to the edge. With a loud groan, you did the unbelievable and came in your mother’s mouth. You went cross eyed for a moment as you emptied your nuts, giving plenty for her to swallow. Sweaty and panting from such intensity, you sat up as you lungs and heart calmed.
“M-Mom, that was...”
“Incredible?” Rose giggled, “I know. And I can tell that it wasn’t your first time either.”
“How’d you-”
“A mother has her ways. But enough of it.” She then lays on her back, head resting against the pillows. Opening her legs, she gave out a light moan as she rubbed her wet flower, moaning slightly, “Would you be a dear and come please Mommy? A son shouldn’t have all the fun to himself.”
There it was, the visage of the place that brought you into the world. Slick and wet with arousal, it beckoned for pleasure and love to extinguish its heat. The only person that could sate its hunger was you and your tongue. Bringing your mouth to her crotch, you gave her vulva a few gentle wisps of breath before you started licking around her inner thigh. Judging by her moans, your mother sorely needed it.
“Oh, god yes! That’s a good boy!” She hoarsely moaned, stroking your hair, “You’re doing Mommy proud. She’s very happy you’re doing this!”
Approaching her cunt, you paired you licks with a bit of breathing on her sensitive clit, sending her deeper into a frenzy. Nibbling and licking every part of her pussy, along with her clit, you made sure that every nook and cranny got some attention. The magic of your fingers went to work as you gently yet firmly massaged her crotch. Moan after moan, scream after scream, and every breath, your mother enjoyed every moment of it.
“YES! YES, MY SON! MAKE MOMMY CUM!!! OHHHHH!!!”
Intending to finish her off, you jammed your tongue in her moist cave, wiggling it all around to her pleasure as she bucked her hips wildly. Once her g-spot was touched, it was all over for her with a wail and scream. A tidal wave of her juices drenched your face as you expected and tangy too. The musky smell stank up the room along with that of sweat and the bed was becoming a disheveled mess.
“Goodness!” Rose Oak breathed as she caught her breath, “H-How many women did you do to be this experienced?”
“That is a long story, Mom,” you replied, wiping the excess from your face. Looking down at your work, her entrance looked sufficiently lubed, ready for your newly erect member. Now is the moment of truth, “Are you ready?”
“Yes, dearie. Please, give Mommy some love.”
Gulping and sweaty, you straddle your mom and positioned the tip of your spear at her entrance. Closing your eyes and with a thrust of your hips, you felt a slick wetness envelop the entirety of your length. Eyes open, you found yourself hilted inside of your mother, becoming one with her. Now life came full circle as you’re now back in the hole you came out of. Poetic, isn’t it?
“Wow, you’re so big, dearie,” Rose Oak whispered, “How does it feel being inside Mommy?”
“I-I~ Incredible!” you gasped as she pulls you down to her and steals a passionate kiss from you. As it went on, your drunken mind was able to gather one coherent thought. You loved your mother, especially like that. As unorthodox and taboo as it was, your heart beckoned for her, nay… desired her. “I love you, mom.”
“I... love you too, my son.” Rose tearfully replied as you started thrusting in and out of her. It was odd to be boning the very person that brought you into the world, but you didn’t care in the slightest. She felt good inside and not too tight either. God, your wine-addled mind was being driven further into madness as you ploughed away at her, no filter and no shame. Passion and pleasure was all that mattered.
“Oh yes! Aaannnhhh, fuck yes!” she moaned as you picked up the pace with your hips. Her inner walls, slick and velvety, were starting to tighten. It drove you to put in a little extra effort into your thrusts, ye, you weren’t even close to cumming just yet. You wanted to show your mom what you were made made of, to make her proud. “Dearie, I’m going to cum!”
“Not finished yet!” With a few good slams, prodding her cervical entrance, her walls clenched and she screamed as she was brought past her breaking point and came once again. You held her tight as she rode her orgasm, locking lips with hers as lust nearly turned you into a beast. Skin against skin, you humped her for a little longer as her orgasm died down and she was left a sweaty mess. But you weren’t done, far from it.
Using your strength, you got her on her hands and knees, putting her nicely shaped ass in full view. You dove back in and resumed your work, in and out of her still slick entrance. You thigh slapping against her buttcheeks, the feeling stirred something in your loins. Never did you once thought that you’d be having an affinity for your mother’s ass. Good lord in all his heaven, you’ve hit the jackpot.
At that point, your mother was reduced to nothing but screams and moans as unbearable lust floods her brain. Seeing your mother in such a state was a bit of a weird sight to be sure, but one that had an aura driving you to keep going until she came a third time. The rush of her orgasm eroded your dick’s endurance further as her vaginal walls gave it another bear hug. Exhausted, you collapsed onto the bed with your mother in your arms, still catching her breath.
“Son,” she wheezed, “why haven’t you came yet?”
“I honestly wanted to impress you,” you said, pulling her into a spoons position and planting a kiss on her neck. She responds in kind with another quick peck to your lips, “Giving you a good time here is all that matters to me.”
“Son, you don’t have to prove anything to me. Just doing this for me makes Mommy happy. You can cum whenever you like.”
Reaching down, you aimed your pecker at her slit and slid yourself in once more. Your cock was already sensitive at this point and you knew it would be the time you were going come. Being that spoons was your favorite position, such intimate contact with her made your heart race like never before. You weren’t going to merely fuck her. You were going to make love to her and, as drunk as you were, you loved her.
Thrusting with all your energy, you inhaled the scent of her hair, smelling of sun-ripened raspberries and blueberries. It made you spasm as you kept on railing her from behind, holding onto her naked body for dear life. Sweat running down your hair, your energy was burning as you kept going at her with all the remaining stamina in reserve. It was one of the best nights you’ve had for the past week.
Soon, the sensitive feeling in your dick made it clear in no uncertain terms that your orgasm was soon to arrive. You still had much love left to give and you were going to give it your all, and to your mom no less. It was an incredible thought that you were going to cum inside the very woman that gave you life.
“Yes! I can feel that you’re close! Cum for Mommy!”
With a mighty and hearty groan, your mind went completely blank as your cock quivered, squirmed, and writhed as it blew the entirety of your balls in her snatch. The heat and volume of your combined load was enough to send her over the edge for the fourth and final time. Feeling high on your orgasm, you held your mother close as you rode your orgasm into the afterglow. Tired and exhausted, the post-coital cuddling was strangely magical.
“Son,” Rose yawned, “that was so much you blew in me.” You kissed up her neck while inhaling the sweet scent from her hair, “You gave so much love to Mommy!”
“Anything for my mother,” you sighed as your eyelids grew heavy with exhaustion. Before sleep claimed, you craned her head and planted a gentle loving kiss on her lips, tongue and all. Sparks flew, hearts fluttered, the intimacy was high. Never did you once imagine yourself laying with your mother but… it was worth it.
“I love you, Mom.”
Your eyes shot wide open as you gasped with substantial shock, sweaty and alert. Looking around, you were in your own bedroom and it looked to be eight in the morning. Mind still awash with what you saw, you concluded that it was all just a dream. Thank god that it was as such and a potential nightmare was avoided.
Thank fucking christ that was a dream.
Your phone went off and your still booting up mind was scrambling to find it. Grabbing it, you saw that it was a call from your mother. What did she want?
“He-Hello?” you yawned.
"Calc, dear, did I catch you at a bad time?" Rose answered.
"No, Ma. I just got up actually."
"Thank goodness." Her voice carried a tinge of tension and worry.
"Is there something wrong?"
Whew "I honestly don't know any other way to say this, but... I'm pregnant."
"W-What?!" You were in shock. Your mother just announced to you that she’s having a baby, something you never saw coming.
"Yes, dearie. I just found out from a test this morning." Coming off from the shock, the idea of having a little brother or sister was an exciting prospect. You were happy for your mother.
"Whoa. C-Congratulations, mom! Did you and Dad... you know... do it before he passed?"
"Yeah, about that. We didn't."
"What?"
"Remember that night about two days after the funeral? You know, the one where we both got drunk?"
"A~ Are you saying that-"
"Yes, I’m certain that the baby is yours."
Joy and excitement being replaced by fear and confusion, the realization soon set in. The dream you just woke up from wasn’t just a dream, but a memory from two weeks ago. Fueled by emotion and alcohol, you did bang your mother and now the consequences come crashing down on you. You did your best to not panic over the phone, ye, your head still felt light over the revelation.
“ Okay, Mom. I'll come over later on and we can discuss things." You answered as calmly as you could.
"Okay, deary. I'll see you then. Love you."
"Love you too, mom" You hung up the call, still in shock. You knocked up your mother and just couldn’t wrap your mind around it. Feeling faint, your eyes closed as you collapsed back down to the bed. "Fuck."
Your eyes opened, revealing a dimly lit void. You were confused as to where you were or what any of it was. The only remarkable was a faint orange light off in the distance. Soon, you heard a chuckle, one that sounded familiar.
“Oh Calculus, did you think you could forget about me after so long?” The voice asked with a playfully mocking tone
“Who are you?” You asked back.
“Do you not remember me? I thought the sound of my voice would’ve given that away.” The orange light grew closer until it revealed it came from what looked to be a lit cigar. The person smoking it petrified you with shock. “Then maybe my looks would drive the point home.”
Standing there was some entity that looked exactly like you, down to the hair and physique. However, he was more sharply dressed with a fedora, giving off the look of a prohibition-era gangster. However, his stance was miles more confident than yours with an air of ego.
‘Y-You’re me!” you shakily gasped.
“Partially correct,” the entity replied, taking another puff from his cigar, “I’m actually part of you, the part that you’ve swept under the rug for so long. I came into being the moment you stuck your thing in that teacher, Cheerilee.” Upon hearing that familiar, you mind connected the dots and you determined the stranger’s identity.
“MILFlove.”
“The one and only,” he dryly replied, “I’ve been keeping tabs on you since your graduation. Even as you pushed me to the back, I’ve seen how you’ve had all those chicks ridin’ your sack. Have to say, I’m proud of you.”
“What do you want? Are you going to… you know…”
“Possess your body? God no! I’m not going to play you like a marionette, as amusing as the idea sounds,” MILFlove finished, “I’ve come to lay down a few things.”
“What would those be?”
“You banging your own mother was the catalyst that set me free. To be honest, I don’t want to go back in that fucking place. I mean, it’s cramped in there! Look, I know that you have some sort of apprehension, but I’m not going to be some sort of malevolent ghost or whatever.”
“So you just want some just want some breathing room?”
“Yes.” MILFlove took another puff from his cigar, pacing around you like a shark, “that’s what I want the most out of this. But, from here on in, think of me as your own personal coach.”
“Coach? Well, as long as you won’t get overly annoying, I’m fine with it. And you better not be-”
“Watching you all day? No, even I have standards. Well, It’s getting close to noon. I’ll got to get going.” He starts to fade away with another puff from his stogie, “Oh, don’t keep your mother waiting.”
Like that, he was gone. The aspect that you’ve kept aside has now broken free and won’t be going back anytime soon. But, if he’s as laid back as he carries himself as, it shouldn’t be much of an issue. But the thought of knocking up your mother still got to you. There was much to talk about.
“Fuck.”
Author's Note
Well now, after a few chapters of user speculation, I've finally done it. Honestly, it was more of a matter of 'when' I was going to write it than 'If'. With that, Dr. MILFlove, the character, has returned.
Also, a big shoutout to Shakespearicles and his story (Un)Planned Parenthood for giving me the inspiration for writing this. Also, Rocka Leone , this goes out to you as well.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Workout Routine (Windy Whistles Revisited)
What a shocking turn of events has it been for you. Even after being back at work for two weeks, your mind still felt boggled. Even though you thought that the power of alcohol would blot out any memory of you porking you mom, hoping it was a bad dream, it wasn’t the case. Not only did you have to come to terms with what you did, but you also had to deal with the fact that she’s now bearing your child.
On top of all that, that one persona you made during your early years of MILFbanging had broken free of his cage. Knowing that he won’t be locked back up anytime soon, you have no choice but to deal with it. If he was going to be living in your head, you hoped he won’t hijack you like a car. Sometimes, you’d wonder to yourself if you were about to go insane.
With the weekends arriving at last, you could take a big sigh of relief as you were free to vent your mind. Wanting to catch up on some cardio, you decided to take advantage of the nice sunny day and take a jog around CHS’s track. Apart from some slight fixes, it hasn’t changed a whole lot since last time. Ever since Soarin’ and Rainbow Dash got hitched, it’d been rather lonely for you.
“Heh, I remember this place,” MILFlove smirked as poofed out of thin air in a puff of smoke, flipping a coin, “All those years ago, that nice lady gave you a nice smack on your ass.”
“Okay!” you replied, jumping a bit, “One, give me more warning the next time when you’re going to pop up and Two, that was a long time ago.”
“Looks like your memory serves you well. Heh, even that accident didn’t do a dent on it.”
“I much rather not remember that day.” You give your legs a good stretch, “I missed out on much and I loathed being wheelchair-bound.”
“I know that. But hey, at least you got to bang your boss again… not to mention that hot nurse.”
“Yeah, Redheart was something.”
“Heh,” MILFlove took another puff of his cigar and stood up, “she took real good care of ya. I’ll leave you to your jogging. Keep yourself in motion. You’ll need it.” MILFlove fades away with a wave of his hand.
“Thank you, sensei,” You sarcastically quip as you positioned yourself at the start of the track, “He’s going to get on my last goddamn nerves.”
Getting into your stance, you breathed deep before getting into a sprint. You never felt your legs tiring much as you always seemed to be in motion. Such is the life of a fitness nut. But hey, a healthy body and mind go hand in hand. In fact, you liked being quick on your feet, indulging in the adrenaline rush of running. You wanted to go as fast as your legs allow.
As you were on your tenth lap, your eyes caught a glimpse of something that was a mix of cornflower blue and light scarlet. Being able to zip past you, you took it as a challenge. Picking up the pace, you increased your running speed to where you were able to catch up to her. To your surprise, it was none other than another old flame of yours, Windy Whistles. Her body, tits and ass and all, still in their prime. She has aged quite well and with grace. After your lap, you retreated back to the benches to catch your breath.
“Heh, I wonder if you planned on coming here knowing that I’d be there.” You snarked as Windy walked to your side.
“Is that any way to greet an old friend with benefits?” Windy teased as she knelt next to you, “It’s been years, Calc. How’re things going?”
“Between becoming my boss’s right hand, busy working for a decent living, nearly getting splattered in a crash, and burying my father… things have been good as far as I can see,” you answered.
“All business and not much time for fun? You must be feeling quite… stiff right now, hon.”
“Yeah. I came down here to work out all that stress and whatnot. It’s a shame that your daughter and Soarin’ don’t have time for this anymore.” Your dismay causes Windy to brush a hand along your legs. Such a touch from her, it’d been a long since you’ve felt it but good lord does it feel good. “You never lost your touch. Haven’t you, Windy?”
“That’s an understatement, Calc.” Windy moaned, looking at the sight of your rising erection pitching a tent in your pants, “Hmmm, looks like your tool is still excitable as I last remember it.”
“You know me, I’m no slouch, Windy.”
Not by a long shot, bucko! MILFlove laughed.
Hey, how about you shut up! You snapped back, Not a good time right now.
C’mon. She’s feelin’ ya up there.
How about letting me do her in my own time!
“Something wrong there?” Windy asked with concern.
“Oh, nothing,” you answered back, “Just a little exhausted from the running. I’ve been active, but not as much as of late.”
“And it looks like you’re about tapped out. Even fitness nuts like us must know our limits.” Slowly, Windy brought her face close to your ear. The feeling of her breath against your skin felt tantalizing, to say the least, “My hubby is out of town until next week. How about you come back to my place and we can catch up on… old times.”
“Really?”
“Come now. I’ve been eager to see you again after our last encounter.”
The way she sounded… it was flirting if you were familiar with it. Though sly, she wasn’t very subtle. Ever since that one time she smacked you on your ass all those years ago, you’ve come to fondly remember her spunky attitude and one day getting some more from her. Her short hair makes compliments her C-Cup breasts and fine ass, cute, sexy, and youthful for a milf. With a sigh, you ultimately decided to surrender to your instincts.
“Yeah, why the hell not,” you said as you gathered your stuff, “Looks like the sun is about to set a bit. You have something in mind for dinner?”
“That I do.” She sang as you followed her to her car. “I have a feeling you’ll like what I’m making. Chicken parm, the good stuff.”
“Hmmm, now you’re making me hungry.”
Getting in her car, she drove you down the familiar path toward her house. All the while, you kept glossing over her beautiful slim figure. Whether it was by your own compulsion or the other one in your head, it was all the same thoughts. Her perky C-Cup chest orbs, firm ass, slim and slightly muscular figure and her sexy calves, a woman like her must treat her body like a temple. Though such thoughts made you hard, you didn’t even bother to hide it. Windy was no stranger to your johnson in all its glory.
“Heh, I know you want that fine piece of woman there.” MILFlove snickered from the back seat, “I know it and so does she.”
“I wonder if I should’ve made putting a muzzle on you as one of the conditions.” You groaned back.
“What fun would that be? I’m already beginning to enjoy our little exchanges.”
“But you’re making me feel like some mental case.”
“You’ll be getting a lot of that from here on in.”
“Jesus Christ, fuck me running.”
Arriving at her house, apart from what looked to be extra but small space, it still looked the same as it did years ago, inside and outside. But for the inside, there was a set of double doors that led to the extra room. In it was what looked to be a hot tub and all the fixings that usually comes with one. Lord only knows how much sexy time did Windy Whistles spent in that soothing hot bath.
“Looks like you made some additions to your house, Windy,” You remarked as you sat down.
“The hot tub? Oh yeah, we had that set up a couple of months back,” Windy replied as she brought out the ingredients one by one, “Bow wanted something to do with the extra bit of back yard we had and we both agreed on a hot tub. I mean, why not splurge for once in a good while?”
“True. True. I bet you had tons of fun in there.”
“You wouldn’t believe how many times I’ve driven Bow wild in there. Oh, the look on his face when he busts a fat nut. Priceless.”
“Now, you’re getting me all excited.”
“Well, keep that tool in your pants why don’t ya. We’ll get to that soon enough.”
Kicking back on the couch, you breathed deeply as you began to relax. Yet, the imagery of Windy Whistles scrumptious ass bouncing around in your mind caused your cock to twitch about with excitement. As badly as you wanted to whip it out and start spanking your monkey, you were more civilized than that and knew restraint. It’ll have it’s hour soon.
As you were about to close your eyes, the familiar figure of MILFlove, clad in his usual attire, manifested on the adjacent chair. He smoked from his usual cigar while reading what looked to be a newspaper. It seemed that your alter ego tries every attempt to look and act like a douchebag.
“Dude, remember what I said about a little warning?” You internally groaned.
“As I’ve said, only you can see and hear me.” MILFlove nonchalantly remarked, taking another puff, “But that’s not why I’m here this time. I want to discuss the elephant in the room or rather… the sexy hot babe in the other room over there.” Pointing to his right as he folded the newspaper, you drifted your sight to Windy reading from the book as she has all the fixings for dinner out. The jiggle of her ass… maintaining your restraint was quickly becoming a chore.
“Seriously? Listen, I want to take things slow with her. I’m a little winded and-”
“And what? Amigo, listen, she’s obviously shaking her booty on purpose! She’s basically begging you to come over there and get busy with her!” His insistence starts to anger you.
“Listen, you little asshole! You’re already starting to get on my last nerves! Remember, you’re the guest and I’m the homeowner! Got it?!” Your declaration earned only a light snicker from him as he stands up from the seat. He nods as looks on at you.
“Well, you are right in that you’re the homeowner.” MILFlove raises a palm towards you, “But, you got it wrong when you called me a guest. Like it or not, I’m part of your psyche, an instinct of yours. I’m you and you’re me, as fucking cliche as that sounds.” His hand began to glow and as if compelled by some unseen force, you began to stand up. Any attempt to resist was useless. “Plus, I know you want to tap her again. I can see it in your eyes. Furthermore, I’ve been caged up for years and I want to feel a little pleasure damnit.”
“What are you doing?”
“Assuming direct control.”
“...”
“Oh, YOU LYING PIECE OF SHIT!!!”
As MILFlove disappeared, you were puppeteered into the kitchen, stepping softly to avoid alerting Windy. Getting closer and closer to her rear end admittedly made your cock grow even harder. Once close enough, you were compelled to wrap your arms around her midsection and wedge your clothed member between her buttcheeks. She gasped in surprise from the sudden touch and groping yet a moan of pleasure escaped her lips.
“Got a little impatient, didn’t ya, buddy?” She moaned as you slipped one hand under her shirt and bra and the other under her shorts and panties. If she wasn’t sweaty down there, you could definitely feel her getting wet over the sensation, “Ohlordyes! You haven’t lost your touch one bit.”
“Only refined it, Mrs. Whistles,” you purred as you held her tighter, “God damn it! I... can’t… MILFlove! Fuck you!
“Nah, I don’t swing that way. Come on, the only way I’ll let go of the reins is if you would just surrender to the moment.”
“Asshole!”
“Hey stud, how about we wash up before we have dinner? Give it to me, hot with sweat in the shower.” Windy moans as you were compelled to drag her to the bathroom.
Once there and the door was locked and shut, all bets were off. You wasted not a single ounce of time as you stripped yourself and her of every bit of clothing. Naked and in your natural forms, her bare beauty whittled down your will to resist. Looking at her, your mind became more blinded with lust.
“As I’ve said, if you want me to stop playin’ ya like a fiddle, just surrender willingly to your lust and I’ll set you loose like the horndog you are.”
Hearing your alter ego’s words, you realized there was no way out other than to let loose. In all honesty, there were times where you yearned to tango with Windy Whistles once again as she had that bit of energy that reminded you of yourself. Then and there, your dick made your decision for you.
“Heh, I knew you’d think with your dick at this point. Go on, go hog wild on her! Atta boy!”
Feeling the reins being lifted, you at that point where you didn’t care about your previous inner gripes. Her twat was salivating with arousal, begging for the warmth of your dick. Holding her tightly from behind, you slid your thing between her thighs and near her cunt, thrusting back and forth as if you were fucking her in the ass. Her firm thighs provided the right amount of friction to keep you enjoying it. Even her moans, the oh-so familiar audio cue, said as such.
“Oh yes! Oh, how I’ve missed this so much! OH YES! KEEP GOING, CHAMP!!! WHOOOOOO!!!” Windy cheered you on as she got close to her orgasm, “It’s been a while since my last go! Show me what you’ve got!”
“Oh damn, and you’re not even close!” MILFlove remarked, “I wonder how many orgasms she’ll have before you blow your load.”
“Shut… UP!” You yelled internally, “This is my bitch!”
As you went on with your motions, her body tensed up and the herald scream signaled the advent of her blissful release. Even as she rode out her orgasm, you didn’t yield one bit. Oh no, not only were you going to give this woman a proper fucking but you were going to silence the entity inside your head. His influence or not, you were going to fuck Windy Whistles to oblivion.
Turning her around, you gave her a brief but passionate kiss before taking her into the shower. Turning on the hot water, you lathered up a loofah and scrubbed her from tit to toe. In between scrubs, you snuck in a few licks of her snatch, tasting like a light citrus drink. She reveled in your touch as your soap-coated fingers glided across her skin, moaning as if she was going through a dry spell.
“Oh god yes! I missed being touched by your fingers!” Windy breathed, “But I missed your cock even more!” Leaning against the wall, Windy gave her ass a hypnotic jiggle, akin to a ‘come hither’ gesture, “Come on, bad boy! My snatch needs some lovin’!”
“Well now… looks like roun-”
“ Ahem! What did I say!”
“Alright, I’ll leave this to you, slick.”
Grabbing onto her hind quarters, you slid your eager rod between her puffy wet folds, still as snug as you remembered. Wet with arousal and shower water, it was easy to slide right in all nice like. In and out, in and out, you pounded away at her cunt as you pelvis smacked against her firm behind, driving you further into your primal lust. Windy, the athletic mother of one of your equally athletic friends, felt good in the sack and her moans are evidence of that.
“Oh yes, Oh please, play with my titties like you wanted to!”
You needed no further instruction as you began to slowly massage her orbs as you rammed away at her. Twiddling her erect nipples between your thumbs and fingers, you drove her further mad as she howled your name with abandon. Though not as big as you were used to, they fit just right in your hands. It felt good to feel her erect nipples brush against your palms as you massaged her supple titflesh.
“Oh god, Windy!” you groaned, “I missed fucking you so bad!” As you forced her further into the wall, you felt her inner walls beginning to tighten around your hardened cock. You knew what it meant and you too felt close, “Damn you’re tight! I’m about to bust a nut!”
“Go ahead, big boy! Empty your nuts in my hole! It’s a champion’s reward!”
Slamming her ass a few more times, your pelvis firmly rested against her cheeks as you pumped a fat load in her quivering snatch. The hot rush of your cum was enough to deal the finishing blow and send her over the edge. You hardly noticed or felt the rush if her lady juices soaking your crotch as the hot shower water sprinkled over your respective forms. But hey, at least it kept the whole thing less messy.
Following the refocusing of your mind after a good fucking, you cleaned both you and Windy off and dried her first. Seeing as how her husband isn’t due back for a while, she suggested the idea of eating dinner in the nude. Though unorthodox to you, you didn’t mind it one bit, a chance for you to bask in the nude without worry and your dong to have some freedom. If it’s to keep MILFlove from annoying you, not a blink came from you and you agreed.
Sitting in the living room again, it took all your willpower not to masturbate at the sight of Windy wearing nothing but an apron. Just seeing her ass jiggle about drove you insane. You wanted nothing more than to stroke it and bust a quick one yet you felt she has something in mind for later on. When she called you into the dining room, the table was set. Time now to sate your hungering stomach.
Thirty minutes after dinner, you relaxed on the couch with your member standing tall and proud in the wind. With Windy off doing something, the creeping sense of boredom washed over you. To stave it off, you subconsciously started stroking your hardened erection while thinking of the round of sex you had in the shower. Not wanting to blow your lid too early, you went slowly and smoothly, almost feeling the warmth of her body.
“Calc, Champ!” Windy’s voice called out, “I’m ready!”
Your dick eagerly twitching, you followed the sound of her singing into the hot tub room. The room had a relaxing interior with a tinge of east asian decor. To say the place gave off calming vibes would be selling it short. Be it Bow or Windy herself, they had the right idea and the good taste to boot. Speaking of which, a very naked Windy Whistles, sat in the tub, spread eagle.
“I can already tell that you like what you see.” Windy remarked as you entered the tub, “Tell me, were you stroking it as you waited?”
“I’m going to plead the fifth on that,” you giggled, “If I did, I’d be thinking of that ass of yours.”
“Heh, I know you’re fond of my firm behind and that isn’t a secret to me.” Windy seductively wanders over to your side and straddles your lap, “And I don’t see you squeezing it like you wanted to.”
“Heh, straight to the point, Windy. You remind me a bit of myself.” Your hands drifted to her asscheeks and gave them a squeeze, earning a breathy moan from her, “But I must say… you and Bow have some nice taste in decor.”
“Have we come to fuck or discuss home improvement?”
“A little of both.”
“A little of both?” MILFlove asked, “We all know you’re here fo-”
“SHUTTHEFUCKUP!” You mentally snapped back.
“Okay then. Go get her, Alpha.”
Snapping back to reality, you pulled Windy in for a kiss as your hands traveled all around her soaking wet body. But your hands inevitably decided to stick with her asscheeks like superglue, squeezing it like the softest of clay. Windy truly had the ass that is the envy of many women and you were inclined to agree. Bow Hothoof was truly one lucky bastard for shacking up with such a gorgeous woman.
“Enough with the damn foreplay, Calc!” Windy gasped as she broke the kiss, “I want that thing inside me... NOW!”
“I doubt you’d care if I busted inside you like last time.” You aligned the tip of your cock at the entrance of her caves, “But in the off chance I knock you up, are you going to hunt me down?”
“Will I- NO! I’d do nothing like that to a friend with benefits! If I do get pregnant, it’ll be easy to convince my hubby that it’s his. Now, let’s give the champion his reward.”
Arms resting on the side of the tub, you held your breath as Windy impales herself on your shaft with a slight splash. Like last time, the interior of her cunt felt familiar yet nicely snug. Any mortal man would cum the moment they entered such a cavern but not you. You were no ordinary man. You have the power of experience, charm, and superhuman stamina on your side. Pounding away at her pussy would be a warm up for you.
After getting her bearings, Windy Whistles began jumping up and down your shaft with progressively increasing speed. Sometimes you had to admire a woman’s combined desire and motivation when it comes to sex. Your cock is the stuff of legends and she is enjoying every single inch of its fleshy form. Already warmed up enough from the last round, you had enough conditioning to withstand her ministrations. Yet all the kicking back felt boring to you and her jiggling breasts kept tempting you.
At that point, you gave a mental ‘fuck it’ snd sat up and latched your mouth onto one of her nipples. She gasped the moment your lips made contact and held you in a tight embrace while brushing the back of your head. Though you weren’t able to get even a trickle of milk, the feeling of sucking on her nipple was good enough. Hell, Windy absolutely enjoyed the feeling of her nipples being stimulated.
“Oh my, a hungry champion you are!” Windy moaned as you kept suckling from her teet. Out of curiosity, you supplemented it with a light slap to her ass, netting a lustful yelp, “OH GOD YES! OH, PLEASE, SPANK ME HARDER!”
“You got it!”
With additional force, you brought your open palm down hard on her firm ass with a wet slapping noise. Finding the right amount of force that doesn’t cause much harm, you kept spanking Windy to her pleasure. She became more lost to lust with every slap. It made you wonder if that was one of her kinks and if she was into BDSM yet the thrill of the moment prevented you from going further with those thoughts. There was some fucking to be done.
“Can you feel it?!” Windy moaned, “Can you feel my pussy walls clamping down on your cock?! Oh, I’m so close! Please, blow that big load inside me!”
Feeling yourself getting to that familiar point, you gave 110% to your moves. Thrusting in tune to her bouncing, you grit your teeth as you felt your member quiver and balls grow tight before the inevitable came to pass. Your vision became tinted with white as your sticky load filled her pussy in a tide of passion. Never did you stop as you came and you came so much inside her that her stomach pudged a fair bit. Truly, you were the biggest of horn dogs.
“You’ve never slowed down one bit since we’ve last met.” Windy wheezed as she collapsed on top of you, “Hmmm, neither has your figure rusted out.”
“I always find the time to treat my body right,” you replied, rubbing an exhausted Windy’s back, “Besides, my anger is my drive.”
“That’s the way it should be. I have to say… you did me like a champ and I like that. No wonder why I consider you a friend with benefits.” She shifted around in your embrace as she traced a finger along your pecs, “Would you mind if we stay like this for ten more minutes?”
“You’ll hear no argument from me.”
“I can certainly tell.” MILFlove remarked as he lit of another stogie from the doorway, “The way you went at her… Damn, you’re an animal.”
“And what did I say about barging in while I’m having me time!” You snapped back, “Now I’m wishing there’s a way to put you back in your cage!”
“And what would be the fun in that? I love our little exchanges. It’s like a fucking comedy.”
“As it stands, you’re a huge pain in my ass. Furthermore, stop interrupting me while I’m banging some woman.”
“Fair enough. But I will say this. Good work on fucking her like a beast.”
“...”
“Asshole.”
Author's Note
Cue the apologies for such a long wait. But, you know how it is with me. Schoolwork, IRL BS, other projects, and general laziness I've been bogged down quite a bit. But, I'm able to bring this chapter out this week before BronyCon (I won't be going so you'll not see me there.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
“Rise and shine, you MILF huntin’ maniac.” MILFlove said in a strangely calm voice as you slowly woke up, “Today’s weather is a mild 60 degrees with minimal clouds with a slight chance of afternoon showers and some nice voluptuous women to be bedded.”
“Come on, man,” you groaned as you stretch your back. “Not while I’m in wake up mode.”
“Now there, I’m just trying to get you psyched up today.” As you entered the kitchen for some morning brew, MILFlove appeared in a puff of smoke in the living room, sitting and reading a newspaper. “You have quite a lot on your plate today.”
“The story of my life,” you shot back with much snark, “I’m always busy. What else is new?”
“Well, you have that birthday party for your friend, Derpy. She’s quite the cross-eyed cutie. Heh.”
You had to admit that despite being cross-eyed, Derpy was rather cute for a woman like her. Along with the rest of your cadre of friends, she seemed to be the happiest around and that smile… pure cuteness. Yet she’s off-limits to you as she got married and had a kid of her own recently. Being a good friend, you try to not dwell on thoughts of you going to town on her but the elephant in the room is making it difficult.
“Even if I wanted to,” you took a sip of your brew, “I just can’t bring myself to think of that. She’s married to Sandalwood and I respect her too much to think of her that way.”
“Well, that didn’t stop you before, now did it?” MILFlove then put his paper down and laughed. “I mean, you went at Spoiled Rich and many others like a mad man. Good on ya!”
“That was completely different!” You snapped back, “I had to do that for a reason!”
“Yeah, keep telling yourself that. Not only did you bang your therapist, but you also fucked your mother. Face it, you’re a horndog that can’t keep it in your pants for long.”
Hearing him mention your mother nearly made your skin go pale white. You were still trying to get the memories of your deed out of your mind, but they still kept on coming without any signs of stopping.
Setting your mug on the table, you slumped against the wall as an immense wave of guilt washed over you. In the past, you rarely had any contact with your parents. After losing your father, it made you feel worse as all those days of neglect started to add up, making you feel worse knowing that your mother is now alone and pregnant with your child. Both of those things were of your own doing and it made you lower than dirt inside.
“Eh, Calc, you okay?” Looking into your regret-filled eyes, MILFlove knew what was on your mind. “Still gripping over that?” He didn’t get an answer apart from an affirmative nod from you. “Listen, I know that got you spooked a fair bit,. but it’s no use brooding over that. I know that I’m the last one you’d like to hear advice from, but the best you can do is own up to your mistakes.”
Hearing those words from your mental specter, it was the first time he really gave you any sound advice. For the last week, you’ve been mulling over what to do in regards to your mother. One of which is to have her move in with you, taking in the fact that you have more than enough space for her and her personal belongings. Though it would take a while, it all depended on what your mother thought about it. Pulling out your phone, you dialed in your mother and awaited her answer.
“Hello?” Rose Oak answered with a yawn.
“M-Mom, hey,” you answered. “I’m sorry that I woke you up.”
“You didn’t, dearie. I got up an hour ago.”
“Oh, thank god. Listen, mom, there’s something that’s been on my mind and… I just want you to hear me out.”
“I’m always willing to hear you out, my son. What do you want to say?” With your heart pounding and emotions peaking, you prepared to give a heartfelt speech.
“Mom, ever since I moved out on my own, I’ve… I’ve been neglecting you and dad quite a bit and I’ve rarely contacted you both. Ever since Dad died, I should’ve been there when you needed me but I wasn’t there and… I got you pregnant and I put an even greater burden on you! Mom, I’m so sorry. I’ve been a terrible son. I want to make it up to you in some way.” For a few moments, all was silent before your mom gathered her thoughts.
“Dearie, you have nothing to be sorry about.” She answered in a reassuring tone. “I understand that you’re an adult. You’re perfectly capable of being on your own and you don’t need me to hold your hand every step of the way. Your father and I prepared you for the event that when neither of us are around, you’ll be ready to tackle life on your own. I understand that you worry about me but you shouldn’t. I’m stronger than you think.”
“That doesn’t excuse me for not only neglecting you, but also knocking you up. I want to make sure that you don‘t live alone. That’s why I’m going to make arrangements to have you move in with me.”
“What?” Your mother gasped, “A-Are you sure?! I can do just fine living by myself! You don’t have t-”
“Mom, in your current condition, I can’t have you living alone all miserable and whatnot. I want you to be happy and that is what I want to do for you. Please, I hate to see you all alone.” You waited for a good minute as silence once again filled the air. Thoughts of your mother’s well being filled your mind as you you worry about every possible outcome. Not only did you worry for her but also for her unborn child.
“Son, I’m touched that you think the world of me. If there was one thing I’m familiar with you is that it’s hard to change your mind once you’ve made it up. If it’ll make you happy... I’ll accept your offer.”
“Wh-Really?” you stuttered back.
“Yes, my son.” Rose replied, “If me being happy means that much to you, I’ll move in with you. You’re not a bad son. I’ve loved you since the moment I brought you into this world and nothing will change that for me. The fact that you care that much about me is a sign that you’re a good son. Thank you for your concern about me.”
“Y-You’re welcome, mom,” you replied, breathing a sigh of relief. “Now, I have Derpy’s birthday party to go to today. When I get back, we can iron out all the details about it over dinner. I’ll pay.”
“Very sweet of you. Okay, I’ll leave you to your day and I’ll talk to you later. Love you, dearie.”
“Love you too, Ma,” you said as you hang up the call, breathing another sigh of relief. “Thank goodness. I hope I did the right thing.”
“I guess,” MILFlove said as you looked up at him. “On the bright side, you have that smoking hot mother of yours on deck at all times. Her hormones are gonna make her quite hungry if you know what I mean.”
“DUDE!” You snapped back, “Bad timing! I just spilled my guts out to my mom for the millionth time, trying to get her here where it’s comfortable and safe! You can at least let me have a tender moment with her.”
“I know, but you have to admit; she’s quite a looker and a fine woman.”
“As much as I hate to make such remarks about her, you’re right.” You stood up, taking another sip of your morning brew. “My dad was lucky to have picked her.”
“Yep. May he rest in peace.”
“You know, that’s the first sincere thing I’ve ever heard you say.”
“Really now?”
Your thoughts were distracted by the ringing of your phone. Unlocking it, it was Derpy herself that was calling you. What could she want?
“Hello?” You answered.
“Calculus!” Derpy replied with her familiar cheerful tone, “Hey, how are you?”
“Just waking up, but I’m mobile.” You stretched your back with a familiar yawn, “How’re things for you this morning?”
“Oh, just getting things decorated for the party later on.” You heard a sigh in her voice, knowing something is on her mind. “If you’re free, there’s something I need your help with.”
“Oh, uh, anything for you, Derpy,” you replied, “What do you need?”
“Well, I originally wanted Pinkie to help me with the decorations, but she’s off with Applejack baking some sort of cake and my hubby and daughter are with my parents doing something I have no clue about. I want to get things set up here but I’m short on hands here and I can use your help. Are you free?”
“Well, of course I’ll help,” you replied with a stretch and yawn, “The one annoying thing about the weekend is not knowing what to do with that time. What time will you need me there by?”
“Between now and three would be fine. It should be more than enough time for us to get the job done.”
“Done deal,” you said with a smile, “Let me get ready for the day and I’ll head on over.”
“Thanks. See you then!”
Hanging up the phone, you did another round of stretching all of your limbs and back. If the job was going to involve heavy lifting, you had to be well ready for what may come your way. The last thing you wanted was a thrown-out back that would make walking feel awkward.
“So, now we have a newly made MILF for ya, huh?” MILFlove huffed with amusement.
“For both our sakes, you’d do well to keep those thoughts at bay,” you shot back. “I’d much rather avoid any drama with my inner circle.” MILFlove then smirked before he got down to your level.
“But, what if SHE makes the first move?” He asked with a sly smirk. “What then, Mr. Restraint?”
“Well theeeeen… let me worry about it IF that time comes.” You stood up. “Right now, I have to get ready for the party. Couldn’t believe that she chose fancy dress-up for the theme.”
“I mean, that’s what happens when she gets the idea of literally writing down a bunch of themes to draw out of a hat.”
“Hey, gotta have fun with it once in a blue moon.”
After performing your morning readiness ritual, you comb your hair as neatly as you could. Checking it for any tears and stray hairs, you put on your nice black suit with a bright red tie, looking as sharp as a fresh razor. Taking a few more moments to admire yourself, you hopped into your Jaguar and sped off to Derpy’s place. Though more orderly than her parent’s house, it still had a bit of the same charm she was known for: a bit chaotic, but charming chaos nonetheless.
Pulling up to the boulevard, you walked up to the door and gave it a few knocks. Soon after, you were greeted by the familiar blonde figure with the bubbly smile to match. It didn’t take long for her to nearly squeeze the air out of you with a big hug. It was only with a tap on her shoulder that she relented.
“Heh, still as energetic as ever I see.” You smirked.
“It’s always so good to see you, Calc,” Derpy cheerfully said.
“The pleasure is all mine. Now, let’s see what needs to be done.”
Following her in, nothing special caught your eye in her living room, save for a small palm tree in the corner, but glancing around a second time, you saw a picture of her and Sandalwood with their daughter. Taking much after her mother, the amount of cuteness in her seemed almost unheard of. You remembered being there for the birth of Dinky and the joy her mother felt was heartwarming. Sometimes, you longed to settle down with just one good woman to love.
“Oh hey,” Derpy said as she grabbed the picture, “I remembered a tough guy like you getting all teary eyed when you first held her.”
“I do apologize for that. That much cuteness is… I honestly couldn’t describe it.”
“Awww, big toughie getting all teary eyed.” Derpy pinches your cheek, causing you to blush, “Just like a peanut butter candy, hard on the outside yet soft on the inside.”
“Yeesh, you sure know how to tease, Derpy.”
“I do that with Sandalwood on the daily.” Derpy giggled as she walked into the kitchen. “But that’s for another time. We do have a job to do.”
“What would that be?”
“We have two areas to prepare: backyard and in here. I want to make sure that everything is ready before the party starts. So, I figured that we’ll cover a lot of ground if we…”
“Split up and each of us take one area?” you finished. “Actually, that sounds like a good game plan. I’ll take the inside while you take care of the outside.”
“Done deal, Calc!” Derpy sang, putting a fist on the palm of her hand, “Before we really get started, let’s officiate our play the way football players do.”
“Odd but… what the hell. I’m in.” You snickered as you get in the same stance as Derpy, staring her dead in the eyes. Oddly enough, you were feeling hyped, energetic, and motivated to get the job done. Bouncing your fist in your hands, you prepared to shout.
“One!”
“Two!”
“BREAK!”
With that, Derpy dashed outside as you both got to work on your assigned stations. Doing a quick sweep around, you tidied up the house a bit before you got to working your magic on the decor. Anywhere you can see the potential for balloons, streamers, and anything to be spruced up, you got to it. It was like your canvas to do as you please and you reveled in getting everything set up.
As you entered the kitchen, you were able to get a good view at a youthful motherly beauty. For sure, her cuteness was legendary but since becoming a MILF, lord have mercy on your ever stiffening cock. All of her features were magnified: calves, breasts, her smile, and naughty bits, motherhood did a lot of good things for her body and the grace she carried with her only made it more alluring. Even as you subconsciously began to stroke your bulge, you never took your eyes off her.
Yet, like the forbidden fruit of Eden, it was all out of your reach and to do so would bring untold wrath upon you. Not that you were afraid of getting your ass kicked, it was the ostracization that spooked you but the latter had happened once before. Thus, any fantasy you’ve had about railing the beautiful Eve-like figure would have to remain that, a figment of your heart’s desire. Perhaps in another life, she would’ve been in your reach.
“Heh, didn’t know you like to get all biblical there.” MILFlove remarked as you continued to stroke your bulge. “But, I do agree with you.”
“On what?” You asked back.
“She is a genuine gem, a true forbidden fruit. To think if you were in the same school as she was, you definitely would’ve hooked up with her, but the only way you’re going to be able to tap her is if she makes the first move.”
“I know,” you sighed in acknowledgement, stopping your stimulation. “But I want to avoid getting bitched at left and right.”
“I know, but if she makes the first mo-”
“Then you let me deal with that!” You snapped back. You then noticed that Derpy got done with her work and turned back toward the back entrance, “Okay, this is where you exit stage left.” Hearing nothing back from your other half, you kept your silence as Derpy entered the kitchen, wrapping you in another hug. “You were always quite the affectionate one.”
“Just happy seeing an old friend, that’s all.” Derpy looked around and smiled at the sight of your handiwork. “Oh wow, you did a nice job here!”
“Well, all I needed was the materials and it wasn’t hard for me to get to work.”
“Hmm, you always think like an office worker.”
“That I am and do. But hey, it puts food on the table.”
“That it does and I’m fortunate that I can rely on you.” With her last few words of that sentence, you’ve felt something slap you on your rear end. It made you jump slightly in place from the sudden contact. You didn’t see it, but you knew who did it with her arms wrapped around you. “Though we came from different schools, I’m glad we became friends.”
“Yeeeaahh.” You cautiously agreed, still in shock from the ass slapping. A mix of emotions and thoughts slammed the walls of your brain like a tidal wave, especially after your earlier musings and stimulation. Why would she do that to you when she has a family of her very own? Nothing about what she did made sense. You needed time to think… and a quick piss break. “As much as I like to ponder on our friendship, mind if I go use the bathroom real quick?”
With a nod from her, you dashed to the bathroom and shut the door, taking care of business before you got a good look at your face. Barring admiring your good looks, what happened earlier took precedence in your thoughts. You may have been friends with her, but the way she slapped your ass and stared at you as she did it went beyond being merely friends. No, it was of lust.
“What the hell, Derpy?” You think to yourself as you splashed some water on your face and dried it, “I thought you were married but… seriously, what the hell?!”
As you had your eyes closed, you didn’t notice something until it was too late. Soon, you felt a pair of soft arms wrap around your midsection with one rubbing your abs and the other… going under your tighty-whities and caressing your package. As much as you wanted spasm about in shock, something prevented you from doing so. Whether or not it was the hands or the pair of soft MILFy mounds against your back, the world may never know.
“Before you go any further,” you breathed, “why, Derpy?”
“Why what?” Derpy mischievously purred.
“I mean… you’re married, have a daughter, and you’re now jacking me off. What gives?” Your protests, like many before, were met with soft laughter.
“If I may let you in on something? Though me and Sandalwood paint ourselves as a perfect married couple, we’re swingers.”
“Fuckin’ hell,” you sighed with astonishment, “I guess the whole ‘Free Love’ concept really caught on.”
“Tell that to my sister-in-law, Tree Hugger.”
“Only talked to her a few times, but she seems pretty chill.” As you eventually surrendered to her caress, the matter of your suit came to mind. “Okay, I’ll bite, but can we move it to the bedroom? I have an idea and I don’t want to get my suit caked in sweat.”
Pulling her hands out of your pants, you turned around to face her incredibly cute face. Horniness spiking and the beast’s chain hacked off, you held her gorgeous body close to you as you carried her to her bedroom while assaulting her with a storm of kisses. Holding her smokingly adorasexy form close was a dream come true since those dreams you’ve had of her. Yet a slap to the face would do you no good. It was a reality and a good one as well.
Entering the room, you kicked the door closed and pinned your cute friend against the wall, kissing her while you ground your crotch against hers. Within minutes, your shaft was hardened and you were primed and ready for action. Tossing her onto the bed, you stood across from Derpy, giving her a full view of you. A look of determined lust grew on your face, leaving her moist and wanting.
“W-What are you going to do?” Derpy sheepishly asked.
“This.”
With a snap of your fingers, you started a dance, spinning around while gyrating your pelvis with your erection yearning to be free. Arching your back, you let your suit coat slide off to your hands as you gripped it. Twirling it seductively around, you tossed it to one corner of the room, followed by your tie. Soon after, your shirts went flying and Derpy started to finger her clothed wet folds to your toned chest and abs. She was hungering for you in the worst of ways.
“Looks like the lovely woman likes what she sees,” you purred as you removed your belt and added it to your dance before it’s rendered the same service as your other clothing items. “Good. I want you to hunger for me.” Grabbing the belt line of your pants, you pulled it down far enough for gravity to do the rest and your shoes and socks followed soon after. All that was left was the tent that was your underwear. Even then, that went away and your unclothed cock sprang tall and free, greatly increasing Derpy’s hunger.
“Oh wow,” Derpy gasped with astonishment. “that’s so…”
“Big? Yeah, I know,” you moaned as you got closer and closer to her, “As much as I love that pretty dress of yours, I hate to see it ruined. If you will, Derpy, I want to see your naked body.”
With a smile so sweet and cute from her, Derpy stood up and removed kicked off her shoes and removed her panties, kicking them to your face. They were wet with the scent of arousal from her pleasuring herself over the sight of your stripping. Surges and pulses of erotic pleasure coursed through your nervous system. It was intoxicating, purely intoxicating. As your mind recentered, you laid eyes upon a sight you only occasionally saw in your dreams. Derpy may look cute but seeing her naked, displaying her MILFy from for you to see… adorasexy.
“Damn.” It was all you could whisper before Derpy got on her knees in front of you, intensely staring down your cock. With a firm grip and a few strong strokes, a drip of pre developed. Then you felt the wet and warmth of her tongue glide back and forth along the length of your shaft. You are no stranger to the good old fashioned blowjob as you’ve had it many times before but receiving one from the cutest woman you knew; it took a lot of willpower to not bust a nut immediately.
As she took it all into her mouth, her tongue wiggled around like a snake, causing your eyes to roll to the back of your head. Your legs started to buckle but you stood strong and proud against her onslaught like the warrior you are. Yet, she had a trick up her sleeve and said trick was her rack. Two cushiony chest pillows flanking your member with their warmth as she continued to suck you off like it’s going out of style. Sometimes, you often wondered if your dick had supernatural properties you were lucky enough to be blessed with.
“Sweet jesus,” you groaned as you felt your climax approaching like a freight train. “How are you this good? Oh fuck!”
She never answered, only increasing her pace to deliver the finishing blow. In the midst of your climax as you filled her gullet with your cum, your legs began to wobble about and you fell to the ground as your last shot went flying to her face. As you lay on your back, your mind and vision briefly went blank for a few short moments before you were face to face with Derpy’s dripping wet snatch.
“You know what’s coming, big boy!” Derpy said, giving you no time to breathe before she rested her crotch on your face, “I know you want this and don’t even try to hide it.”
She was right. As your tongue made contact with her folds, she let out a crazed yelp like a howl. What she wanted to do, it was new and alien to you. Yet, it made you hard nonetheless. Grabbing two handfuls of dem hips, you dove in and began eating her out like you haven't eaten in days. Drips upon drips of her arousal only served to drive you mad and want to go further to pleasure your friend. After a moment of thought, you decided that oldies are goldies.
After flicking her clit, you surprised her with your tongue’s entry into her moist sex cave. Her muscular reflexes kicked in as you snaked it up to her g-spot. Due to her pleasuring herself moments ago, it didn’t take long for her to reach her climax. Face still full of her crotch, the rush of her arousal made it even more difficult for you to breathe. Furiously tapping her ass cheeks, she got the signal to disengage, allowing you some much needed air. Sweat and heavy breathing permeated the air around you both as your minds rebooted.
“Okay, that was something new… and exciting.” You breathed as you sat up, “Facesitting huh? It can grow on me.”
“My hubby likes it whenever I do that.” Derpy breathed as you picked her up and placed her on the bed, “Hold on a sec.” Derpy fished through a nearby drawer and pulled out a wrapped condom, “Even though I’m letting you fuck me, I only want my hubby to out a bun in my oven.”
“Fair enough.” You nodded as you took out the rubber and put it on your hard cock, “Better safe than sorry, as they always say.”
With a nod of approval, you straddled the blonde cutie, intertwining her fingers with yours. The look on her face as your member prodded her entrance, both sexy yet heartwarming. Truly, her smile was a treasure to those who cherish it. Even as you penetrated her honeypot, you never ceased to appreciate it in all its glory. At that point, you gave in to your desires and planted another big sloppy kiss, driven by your heightened sex drive.
Breaking it for some much needed air, thrusting slowly at first, you took the time to appreciate the feeling of her cunt. Slick, wet, warm, and fairly tight, Sandalwood chose wisely with Derpy. With every thrust, you went just a little bit faster and harder, much to her delighted moans and screams. Even if she didn’t, the feeling of her pussy was your drive. You wanted to feel more of it, enjoy it, and savor it like it was the last.
“Good lord, Derpy!” You groaned as you continued to pound away at her, “You have such a good pussy! How are you this good?!”
“I try not to be!” She squeaked as your tip hit her g-spot, “I guess it all comes natural to me! Sandalwood always likes it when I drive him mad like this!”
“If there were any goddesses, you’d definitely fit the bill!” Seeing her breasts jiggle around, you grabbed them, squeezing that ever so lovely titflesh between your fingers, “Damn, your breasts feel like pudding!”
“Well, keep on touching them then!” She moaned as you rolled her nipples between your index and thumb to her delight, “OH YES! OH, KEEP GOING! YOU’RE GOING TO MAKE ME CUM!!!”
“You and me both!”
Feeling the familiar feeling in your loins, you realized the reality of the situation that the experience wouldn’t last forever. As good as her vagina felt, it brought you closer and closer to busting a fat nut. It was going to be a big one from how you’ve felt your balls tightening but there was one upside to it. The orgasm will be one hell of a ride.
Doubling down and some last good slams into her cunt, your shaft quivered as it emptied your balls into the condom. Even then, you never stopped thrusting; too good it felt. Though your sticky white life seed didn’t flood her caverns, the heat they emitted through the rubber was enough to finish her off and make her scream into the air like an orgasmic banshee. After all was silent and calm, you crash onto the bed right next to Derpy as sweat and sex soaked your respective bodies. Neither of you spoke or moved for the next several minutes.
“Calc,” Derpy breathed, “you’ve fucked the wind out of me.”
“Yeah?” You said as you sat up, “Well, you’re breathtaking. You really have it going on there. Lotta energy in you.”
“If only you were part of those wild nights me and Sandalwood have. I swear... I give him the best orgasms.”
“Hmmm, maybe I might join you both next time. I’ll have to say it’ll be a hell of a sexual symphony.” For a few seconds, Derpy said not a word or moved before she facepalmed in annoyance.
“Oh, muffins!” Derpy groaned, “I just remembered! My father was asking me about his music book the other day and I remember it being in one of the boxes in the storage space!”
“Want me to go get it?” You said, anticipating.
“If you wouldn’t mind. And also, don’t worry, I’ll get things cleaned up by the time you get back. Just, go grab a quick shower and head over to the storage lot. I’ll give you the key.”
“Okay. Shouldn’t be too hard to find it, I suppose.”
Grabbing a quick shower, scrubbing yourself from head to toe, you donned your suit yet again before doing some last minute grooming. Taking a ten minute drive down to the storage depot, it took a bit of persuasion to get the guard to let you through to go on your merry way. Remembering the bin number, you were able to find it rather quickly. You remembered all the contents of the bin from all those months ago. Memory is a powerful thing.
“Okay, let there be light.” You flipped the switch and nothing happens, not even a flicker, “Okay, bulb’s out. Plan B.” You pulled out your phone and turned on its flashlight as you scanned the room for the box and came across one labeled ‘Books & Misc’. “A-ha, found ya.” Digging around, you hoped that whatever your fingers were touching was the book but the box was big and you had to dig deep.
“Oh, I got you, ya little bast-Ahh~!” As you pulled, your grip slipped and you went tumbling back and into some locker like object. For some reason, the doors began to close as you shake your head to refocus. Then it hit you. The familiar interior, the rumbling of the box, you began to remember what it was and knew where it would now lead to…
...one wild ride.
“Oh, motherfu-”
Author's Note
Like all things, they take time and I hope that this was worth it. Working on multiple projects alongside this one is daunting for sure but I shall endure the rigors. Now, we have some more time traveling shenanigans but...
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Barnhouse Hoedown (Granny Smith)
Author's Note
Again, sorry for the long wait for this chapter. To explain some things, a combination of laziness, IRL shit, and other projects, have sidelined this a bit (Also, I was at a con earlier this month). On another note, due to creative differences, Alticron has stepped down from editing this story but will still be credited as an editor for his work up to this point. NineTailBeastBall is the new editor for this story.
Still, I feel like some parts of this chapter will draw some backlash for the way it was written and the direction it took. But, they will be addressed in the next chapter and I hope they'll put everypony here at ease. If you feel apalled by the direction taken, I do sincerely apologize. But, It is my hope that you'll enjoy this chapter in some way.
Happy Reading. :)
Barnhouse Hoedown (Granny Smith)
Like a drink in a cocktail shaker full of ice, you were shaken around in the time machine as it traveled through the time stream. The temporal turbulence reminded you of an event when you were 12. It was quite unfortunate, as during a fair, you got on the rollercoaster and ended up puking your guts out as you went around the final loop. Though an accident, you got a few less than pleasant looks from the other riders. Anyway, that’s a story for another time. More importantly, you were starting to get worried as to where the time machine was going to take you.
After what seemed like an hour, the machine stopped shaking and opened, allowing you to leap out onto the grassy, leaf-covered ground. You wasted no time in emptying the contents of your stomach onto the ground. You felt disoriented and your vision was getting blurry, so you decided to kick back against a nearby tree to collect yourself. Panting and gasping for air, a queasy feeling lingered in your being as you were once again thrust many years into the past.
“Well, looks like you couldn’t keep yourself from time traveling, Sam Beckett, ” MILFlove snarked as you were able to get your bearings back. “You got shaken more than a martini, like how the Brits like ‘em. ” As much as you want to slap your spectral other half in his face, you had little energy to do so. “Hmm, it looks like your suit didn’t get dinged up at all. ”
“That’s the least of my concerns.” Shaking your head, you got up so you could stretch your back, “It wasn’t the first time I got stuck with this bullshit.” Turning toward the time machine, you peeked inside to look at the chronometer, which indicated the date to see how far you’ve traveled. To your shock, you’ve gone bout forty-eight years back to the past, placing you in 1974, “Fuck me running, I’m in the damned seventies! Great, I’m going to be seeing a lot of potheads roaming the streets, the occasional protestors and other bullshit.”
“Won’t that be the first time you’ve taken you’ve taken drugs, bucko? ”
“Okay...” you sighed, “One, I had no idea what Posey shared with me was shrooms and I don’t like drugs, period. Two, I’ve paid attention to history class enough to conclude that the seventies were a fucked up and chaotic time no matter how you look at it.” You took another glance up and down your suit, “Well, at least I won’t stick out like a sore thumb, provided if I ditch the tie.”
“Yeah, right on the nose there, ” MILFlove said as your stomach began to rumble, “I doubt it’s been that long since breakfast. I swear, you eat so much yet still manage to look like a, dare I say it... one hot motherfucker. ”
You rolled your eyes. “Blame my naturally high metabolism.” You dusted yourself off as you started to walk off, hoping to find some shred of civilization or a corner diner. Either way, hunger was putting you in a bit of a bad mood. Looking around, you noticed a few of the trees further down your path had plenty of apples growing from them. As a perceptive man, you deduced that you were somewhere near an apple orchard, “Okay, now I have at least one issue on my mind. I’ve already used ‘Verdant Range’ as my alias once.”
You heard MILFlove chuckle dryly. “I’m no expert in how ever the fuck time functions, but I have a good idea that using the same alias is never a good idea. How about the name of that character from that book you like reading. ”
“Azure Glide?” you mused, “I suppose that can work.” Looking around, you found a stone that was quite sharp. Getting desperate because of your hunger, you took the stone and approached one of the apple trees. You tore a section of bark from it and carved ‘A.G.’ into it, a mark for you to find the time machine. “That takes care of that. Okay, let’s get going. I want some grub and a place to nap while the machine charges up.”
“Lead the way, boss. ”
Walking further into the forest, you saw more and more trees growing the familiarly sweet red fruit. Everywhere you looked, there was a nice, shiny apple hanging and practically begging to be picked. With your mouth salivated and stomach growling, your hunger soon got the better of you as you look a rock and threw it at a nearby bunch, knocking one of the treasures loose. Picking it up, you brushed it off with one of your sleeves, licking your lips.
“Come to papa...” you whispered, about to take a bite.
“WHAT DO YA THINK Y’ALL ARE DOIN?!”
Startled, you dropped the apple and slowly turned around to see a rather angry woman with a shovel in hand. You were in a bit of a daze, as despite her angry expression, she was rather beautiful. Bright orange eyes, short pale yellow hair held by a red hair band, an incredibly voluptuous figure with an incredibly sexy western accent. You were split between being captivated by her beauty and fear of an impending ass kicking.
“Uhhh... hello?” you managed to croak out.
“Ah said... WHAT DO YA THINK Y’ALL ARE DOIN’?!” The volume of your voice made a surge of fear pulse through your being. Gripping the shovel in her hand, she bounced it in her other hand as she bore her teeth, “Didn’t yer mama ever tell ya dat it’s wrong ta go aroun’ stealin’ apples?!”
“L-Listen, ma’am, I-I’m sincerely sorry...” you stuttered as you slowly backed away. “I-In my defense, I had no idea that these apples belonged to you.”
“Well, ya should’ve thought ‘bout dat before ya went around pillagin’ mah orchard!” The woman wasn’t going to be swayed by your words. Her temper grew too hot for reason to be effective. Seeing her grow closer to you, the aggression she gave off made you panic and you took off running. “Git back ‘ere! Ah’m gonna woop yer sorry behind beyond repair, ya no good thievin’ yokel!”
Suffice it to say, running from the livid woman was torture, given that you were still hungry. Though as you kept your distance, you couldn’t help thinking that she seemed familiar. Thinking of her southern accent and her appearance, you could’ve sworn that you’ve seen her around somewhere. Before you could put some more thought into it, the crazy woman had caught up to you and tackled you to the ground. You struggled for a bit before managing to break free and run with all the adrenaline you could muster.
Entering the main farm area, you saw a bright-red barnhouse and ducked inside, locking the door behind you. Still hearing her curse and scream with a level of fury that was unknown to you, you looked around for an escape route. Wanting to catch your breath, you slumped against a nearby post, still panicking internally.
“Oh, fuck me!” you gasped between breaths, “I got thrust forty-eight years into the past, I’m hungry, and now I have some psychotic, overly possessive owner of some apple orchard trying to kill me with a shovel!”
“Life is like that, my friend, ” MILFlove cooly said. “Sometimes, luck likes givin’ ya the finger but you’ll just have to roll with the punches. ” His last remark pissed you off a fair bit.
“Roll with the punches? ARE YOU FUCKING KIDDING ME?!” you snapped. “THERE’S SOME CRAZY FUCKING WOMAN OUT THERE TRYING TO KILL ME WITH A SHOVEL!”
“And Ah’m gonna do worse if ya don’t come out right now!” she screamed, making it clear she could hear you from the other side.
“Oh god no!” you screamed as you looked around but found no open windows, broken or not. You were trapped and your only way of escape is back where you came from with a shovel to the face waiting for you, “Damn it, why did I decide to go to that party?! FUUUUCK!!!”
Groaning in frustration, you knocked the back of your head against the post. One, two three, you vented your anger at the situation you’re in. No way out, you feared being either beaten up or worse... killed by a crazy, yet attractive woman. The fire she carried in her soul was unlike what you’ve seen before. You almost found yourself admiring such traits, but fear still gripped your heart.
Sighing, you resigned yourself to your impending fate. Before you could look up, a blunt metal force fell right on top of your head with great force. It was enough to get your brain shaking and send you to the ground, losing conscious. The last thing you saw before your vision faded, was a horseshoe-like shape.
In due time, your vision had slowly come back to you. Unfortunately, once you were wide awake again, you found yourself bound tightly in ropes. Struggle as you might, you were unable to more or run. The woman hovered over you with an irritated expression and stare that looked as it can pierce through souls. If there’s any good that came how she was looking at you, it’s that she’s calmed down at least a little and was no longer trying to whack you with a shovel.
“Well now,” the woman snarled, “y’all have a lot of nerve ta go ‘round stealin’ other fellers apples like dat.” Though you got a good look at her before, she still looked every bit as gorgeous, and her western drawl only amplified that beauty. “HEY! Mah eyes are up ‘ere!” she yelled, noticing you were looking at her bust.
“W-well...” you stuttered in a scaroused state, “I already told you I didn’t know those apples belonged to you, honest.” You struggled a bit in your bonds, but you weren’t able to get loose. Frankly, you hated being restricted. Your efforts to get free were made even more pointless due to the fact that you were still weak from hunger. When you finally stopped struggling, your empty stomach demanded food once more with a loud growl.
The woman’s eyes became more sympathetic when she heard your tummy, causing you to let your guard down. “Sounds y’all are real hungry dere.” Stepping outside for a moment, she ironically came back with a couple of red apples.
“‘Ere, eat ya little nuisance.”
“With what? I’m tied,” you snapped. It’s only natural for one to feel cranky when they’re hungry. Pulling out a knife, she cut the ropes binding your arms. Nervously taking the apples from her hands, you tore into it, tasting the sweet, fruity nourishment. Once that apple was nothing more than just its core, you dug into another one, but taking your time to enjoy it. “Who are you anyway?”
“Y’all are jokin’, right?” she answered your question with a question. All you did was stare back at her, making it clear you were being serious. “Unless y’all been livin’ under a rock, ya should know Ah’m da ownah of one o’ da mos’ prestigious farms in da land. Name’s Granny Smith Apple, remember dat.”
The name was faint in your memory, but thanks to that blow to the head, you still couldn’t grasp the last time you heard it. It made your head hurt trying to recollect that memory so you decided not to dwell on that for the time being. The matter of whether or not she was going to mess your face up still lingered in your mind. She sounded sincere when she gave you food but much was ambiguous.
“Right… Well, again, I do apologize for my *ahem* rude intrusion.” You reached your open hand out, “My name... is Azure Glide, Granny Smith Apple. I was just walking around for a bit while visiting family but I might’ve stumbled across here by mistake.” To your surprise, she reached out and met your hand, shaking it with a warm smile. It had a strange effect on you as your tension slowly started to melt away since she had a surprisingly soft touch.
“As lon’ as yer willin’ to give some honesty, Ah won’t have to whack ya with mah spade,” Granny Smith mused warmly, “If dere was one thin’ Ah was raised on, it’s good ol’ fashioned honesty. Ah can usually tell if someone’s tellin’ the truth and it doesn’t seem like y’all are lyin’...”
Shifting around, you took care to not dirty up your suit. Once you were comfortable, you were able to enjoy a good view of the lovely woman before you. Apart from her figure and smile, her bust and rear end caught your attention. If you had to guess, her cup size is a straight-up F-cup. “‘Ey, what are y’all starin’ at? Ah already told ya mah eyes are up ‘ere.”
“Uhhh, sorry...” you stammered, looking away with a blush, “I’m honestly quite surprised at how good you look...” You blushed deeper as you realized the scope of what you’ve said. Finally noticing the ring on her hand, it became clear to you that she was married. You, an unwilling time traveler, were hitting on some married woman whose husband could very well kick your ass if given the chance. “Oh crap. Please... just ignore whatever I said there.” Just as you were beginning to panic, a warm smile crept upon her face.
“Don’t ya fret yerself none,” Granny Smith assured, taking a seat next to you, “Ah get compliments like dat all da time. Seriously though, do ya honestly have eyes fer a married lady?” she asked, trying to tease you. However, brushing it off as a joke due to finding humor in her voice, all you did was nod nervously and chuckle at her remark.
“Ya know... Ah owe ya an apology fer da rough treatment earliah... Now dat Ah got a good look at ya, ya seem like a nice boy.” Her tone was every bit as genuine as you remembered from your friends during your father’s funeral. “Looks like da only thing dat hurt ya was dat horseshoe dere. Ah told mah husband dat puttin’ stuff like dat was dangerous. Gonna have ta talk ta him ‘bout dat when he gets back.”
“Gets back?” you asked.
“Mah dear Concord Grape is out at da town’s market fair,” she replied. “He always goes dere every year ta sell some of our harvest. It’s a great way ta bring business ta our here acre.” Granny Smith suddenly became depressed. “Ah wish Ah could go with him, but he insists dat someone has ta stay behind ta make sure da chores are done.”
You struggled to keep your eyes locked on the beautiful woman’s face, as it was so tempting to look down at her amazing cleavage for the third time. As your eyes drifted to her rack, she noticed right away and actually started to giggle.
“Maybe ya aren’t such a nice youngin’ after all, Azure...” She grew closer and closer to you, making you break out into a bit of a nervous sweat. “Don’t get meh wron’ now, dearie. Ah love mah husband, but since he’s been actin’ strange lately and always seems so busy, Ah can’t help gettin’ a bit lonely...” She then wore a smile that you were familiar with for many years. It was a sign that she was fixing to have herself a little piece of you.
“Well... there’s no denying you’re pretty, but you’re married and I don’t want to get between you and your husband.” You protested, “It’s just not right.”
“Well, that didn’t stop you before, bucko, ” MILFlove cracked.
“Not helping, asshole! ” you internally shot back, “As I’ve said MANY times, they were all different! ”
“Yeah, well, tell that to Derpy, horndog. ”
“DUDE! ” Your internal debate with your unfiltered other half made you oblivious to what Granny Smith was up to. She brushed one of her soft hands up and down one of your legs. Your internal temperature steadily rose at the sensation but your earlier protests still remained. How could she, a presumably married woman, would ever want to feel you up in such a way? For just a moment, you forgot about the other married women you’ve messed around with.
“Granny Smith, what are you doing?!” you demanded, and were met with a mischievous smile.
“Tryin’ ta find out if y’all are a well-behaved child or not.” The tone of her voice, while sweet as honey, was smooth and sensual as velvet. Entranced by her voice, you did nothing to stop her as she came up to press her lips against yours. You could taste the sweet flavor of the apples she spends many hours harvesting and growing.
While melting into the kiss, you felt your pants tightening and your clothed member made contact with her crotch. There are times that you were amazed that you can get an erection so quickly when the time calls for it. However, it wasn’t an appropriate time as Granny Smith was committing infidelity. You were torn between wanting to enjoy it and not wanting to be a homewrecker. Your mind can be a confusing pot of conflicting thoughts at times.
“Are ya still objectin’?” Granny Smith asked, well aware that your cock was poking her nethers. You knew there was no point in denying it, especially to a lady who values honesty. Remembering that, you decided to surrender to that one instinct and pull her in for a makeout session more intense than the last. Feeling her huge breasts against your chest, you hands glide across her back and sizeable rear. She moaned in the tongue to tongue kiss as you gave her asscheeks a good squeeze, “Looks like ya ain’t such a good boy aftah all.”
“I’m behaved when I want to be,” you chuckled. “May I?” you asked, as you held your hand inches away from one of her breasts. Right away, you could feel her hardened nipples poking through the fabric. It was interesting that a farmer would forsake wearing a bra, but you were sure she had her reasons. Regardless, her breasts felt like pudding, as if they could melt in the palm of your hands. You could only imagine resting your head on something so soft.
“Crazy as it sounds, mah husband nevah pays attention ta dese apples.” Granny Smith started to unbutton her shirt, “But since y’all seem ta like em, how’s about ya get a good taste?” She slipped off her shirt in one fluid motion, revealing the prize trapped beneath the fabric. You’ve seen many pairs of breasts before, but these looked amazing and appeared to be natural, nothing telling of any artificial enlargement.
“I’d be honored,” you said, kissing her cheek. But looking at your suit, which already a bit of dirt is on it, you wanted to spare it from any further damage. “As much as I am eager to get down and dirty with you, can I at least take my suit off first? I got it cleaned yesterday.”
Reaching for her knife, Granny cut the remainder of your bonds, allowing you to wiggle around and strip. Starting with your top, you took your suit off, bit by bit, and you were soon completely naked.
“Like what you see?”
“Like” ain’t da right word,” she smiled and began to massage your shaft. “Y’all don’t take as much time as mah husband ta get hard. Fer dat mattah, y’all are much biggah dan he is...”
“I’m quite flattered by that.” You groaned as she continued to stimulate you, “For a handjob, this is something-” You were silenced as she kissed you again, but continued stroking your cock.
“Honey, jus’ be quiet fer a second...” Granny Smith licked her lips, breathing lustfully on your cock, “Ah jus’ want ya ta enjoy dis.” Nodding, you watched as she got onto her knees and licked her lips a second time. It was obvious what was coming, and you decided to encourage the lovely farm woman by putting your hand on her head.
Without any more hesitation, Granny took your cock into her mouth and immediately sucked you at a quick pace. She went faster and harder in the hopes that proving her talent would get you to cum, but your stamina is godlike, built over the years of constant fucking.
If Granny Smith wanted to prove her sexual skills, you didn’t see why you shouldn’t do the same. With your hand still on her head, you pushed all the way in, making her deepthroat your manhood. She didn’t seem to mind the harsh treatment, even though she choked a little.
“Is it too much for you to handle?” you asked, pulling out for a moment so she could answer.
“A little...” Granny Smith replied with a look that silently begged you to put your cock back into her mouth. “It’s sweet dat ya care fer meh, but Ah ain’t made of glass, dearie. Y’all are free ta be as rough as ya like.”
With her blessings, you deep-throated her once more, adding more gusto to your thrusting. You could feel in your loins that you were about half-way to busting a nut, but with a mischievous smile, Granny Smith planned the finishing blow. She knew from your expression that you were reaching your climax, and decided to make it harder by pressing her huge breasts around your cock before she squished them in a massaging motion.
“Up ‘til now, Ah nevah got ta do dis since Ah told ya Concord don’t pay attention ta these gals,” she said winking at you.
“They... They’re a work of art!” You groaned as a jolt of pleasure shot up your spine. You couldn’t resist the urge to thrust as if reflex demanded it. Each thrust caused Granny Smith’s melons to jiggle like water balloons, and you couldn’t take your eyes off them. You actually started to drool a little, which ended up acting as a lubricant when some of your saliva fell between her breasts.
“Y’all are obviously still hungry,” Granny Smith said with a smirk before she let go of your dick and turned around to shake her rear at you. “But Ah think y’all should feed meh dis time! Ah’ve been workin’ so hard today, and Ah think a nice roll in da hay should make meh as good as new!”
You smirked as you got down on your knees and positioned your tip in front of her wet flower. The heat radiating from her folds was enough to make your cock quiver with excitement but Granny Smith had other plans. She got on her hands and knees and gave her plump rear end a good wiggle. You didn’t need to rub two brain cells to know what she wants.
“Doggy style, eh? I have to say that your ass is the stuff of legends.” To prove your point, you gave her a nice smack on her bubbly butt, watching how it jiggled from the impact. You were hypnotized by the ripples from the impact and decided to spank her again. “It’s beyond me why your husband ignores such a sexy wife like you.”
“Y’all don’t know da half of it...” she groaned, giving her ass another playful jiggle, “But enough ‘bout him! Since Ah’m flattered how much ya love mah behind, Ah’ll give ya all da right ta over come ‘ere and claim it!”
You leaned down so you were laying on Granny’s back and gave her some quick and powerful thrusts. “S-Seriously... if I could have you as my girlfriend, I’d take as much time as possible to worship this gifted body of yours!” you shouted, grabbing both of her breasts which had been bouncing out of control.
“D-Den... take meh ta c-church, Azure!” On her words, you thrusted in and out of her, taking your time to find a good rhythm. Looking into her eyes as your fun led to a new position where you were holding her against the wall, you smiled and kissed her passionately. You were so wrapped up in your intimacy, you failed to hear the barn door open. You only stopped thrusting when you saw Granny Smith staring at something... or someone.
“G-Granny Smith Apple?! WHAT THE FUCK!” A man, around the same age as Granny Smith, with bluish-purple skin and mint green hair, clad in various denim-based clothes, stood in the door with a shocked and enraged expression. It was clear that this was Concord Grape and as scared as you were of having been caught, you couldn’t help continuing your thrusts.
“Aw, clam up! Y-Y’all shoulda seen dis comin’!” Granny Smith groaned as she glared at her husband, “Ah work dis place ta da bone and ya hardly show meh any gratitude! In fact, if Ah didn’t know any bettah, Ah’d say y’all been doin’ more dan jus’ shoppin’ today!” Concord just so happened to have a faint lipstick mark on his cheek, but you could still see it.
You suddenly felt a whole lot less guilty about fucking another married woman. It always made your heart harden when a woman gets betrayed in such a way. You kissed Granny Smith on the cheek in case she was in need of some comfort before looking at her husband again.
“G-Granny Smith... I-I can... I can explain...” he stuttered, having obviously been found out.
“Save yer breath!” Granny Smith snapped in saddened anger, “Da answer’s prettah damned obvious ta meh! Y’all never loved meh as much as ya vowed on dat damned altar! One look at dat lipstick on yer cheek is all da proof Ah need dat ya betrayed mah heart by foolin’ with other broads-AH!” You had cut her off for a moment by giving her an especially hard thrust.
“Looks like Granny’s gonna need a new lover, ” you heard MILFlove internally speak to you.
“Dude, shut up and let me handle things here! ” you shot back, shutting out your other, more spectral half. “Believe me sir, I actually felt guilty helping your wife start an affair, but I feel a whole lot better now that I know she married such a double dealing asshole like yourself.” Your remark caught Concord off guard, filling his mind with a torrential mixture of anger and sadness.
“Y’all are really makin’ it hard ta decide if ya really are a sweet boy or not,” Granny giggled and suddenly lifted herself off your dick. “Anyway Concord...” she said approaching her husband, “...Ah figure it’s ‘bout time fer ya ta pack up and leave.”
Naturally, Concord Grape was confused. “E-Excuse me?” he tried asking before getting a nice slap to the face. He recoiled at the force of the impact, caressing the bright red mark left on his cheek.
“Dis farm, Sweet Apple Acres, was started by mah ancestors and Ah’m jus’ anothah in da long line of its caretakahs!” Granny Smith snarled, “Yer name is certainly not on da lease! So, git yer stuff and carry yer sorry behind on outta ‘ere, NOW!”
The next thing she did to add insult to injury and make their separation official, was take off her wedding ring and throw it at the defeated man’s face. It didn’t mean anything to her anymore, she didn’t even see it worthy of wasting her time trying to sell. It was nothing more than a reminder of a mistake she made, one her heart sorely regretted.
You thought Concord would leave on his own since there was no point in continuing this conversation, but to your amusement, Granny actually pulled his arm painfully behind his back and escorted him back to the house to pack. You got a good view of her wonderful bouncing rear as she walked away. Witnessing her strength, you were certainly glad you’re no longer on the receiving end of her wrath.
You’d probably never know how different things would have been if you hadn’t changed reality here, but you seemed to have done a good thing. Granny may or may not have learned of Concord’s disloyalty on her own. Either way, he was just about done packing his things. She still wore the betrayed look on her face as she knew that all the promises of love were nothing more than lies. Fortunately, you were confident you could cheer her up.
You got another good hint of who the beautiful woman you’ve fallen in love with was when she prepared some nice apple pie as a quick snack before you went back for some more fun. The last time you had pie this good, was when you were at a barbecue with Applejack. Now that you thought about it, the name of the place and the look of the woman did ring bells. But out of fear of wanting to avoid another crisis, you shook your head to try and relax.
“Ya like it, don’t ya? Such a tasty snack is what ya deserve fer lookin’ aftah meh.” You blushed as she wrapped her arms around your neck.
“Well, it’s really nothing big, Granny Smith,” you modestly answered, looking around. “Where are my clothes?”
“Ah put ‘em in da wash. It’ll take ‘em about an hour ta clean and anotha ta dry...” Taking a close look at her face, you noticed a few tears leaving her eye. You knew that she was heartbroken over the revelation of her husband’s infidelity. Betrayal is never an easy feeling to handle, especially from one who was in love, “At least someone appreciates mah work... Dat double-crossin’ husband of mine rarely even complimented me!”
“Come here,” you said softly, holding your arms out wide open for a hug as Granny Smith broke down crying. You never got used to the sight of a woman like her sobbing over a broken heart, much like your own mother. She was a beautiful, honest, and kind-hearted woman that didn’t deserve to have her emotions dashed across the ground behind her back. You couldn’t help but hold her tighter to comfort her, feeling her powerful heartbeat.
Sweeping her up in your arms, you carry her up the stairs like a bride, all the while staring at her beautiful face. It was so heartwarming to see her smile again after the day she’s had. Making it to the second floor, you looked around and saw an open door on your right.
“I’m grateful that you cleaned my clothes, but...” you set her onto the bed with an impish smile, “...we won’t be needing them tonight.” It just so happened that Granny Smith still hadn’t put her own clothes back on.
“Ah coulda told ya dat,” she said, giggling as you began kissing her neck. The giggles turned into moans as you gave her breasts some attention, first squeezing them, and then pulling her nipples. “C-Come on now, honey... Go ahead an’ gimme da good stuff already!”
“After what you put up with today, I suppose there’s no reason to hold back.” You kissed her forehead with a nice smile. “You’d best prepare yourself for some proper loving,” you warned and scooted up in order to align your cock with Granny’s dripping slit. Just like before, the heat and moisture radiating from her entrance made your cock throb with anticipation.
“W-We may have jus’ met today, b-but... Ah really hope y’all don’ have ta leave so early... AH!” As you got to work thrusting into her like a jackhammer, Granny lovingly reached up to trace her hands down your neck and chest.
“Y-Yeah... Oh... your pussy feels so~ GOOD!” you moaned as you decided to go even faster.
“A-Ah’m... glad y-ya like it... b-better dan dat ungrateful ex of m-mine...!” Granny Smith moaned as you continued to plow away at her cunt. Slick, hot, pulsating, and tight, it truly made you wonder why Concord Grape would throw away something so good for the sake of a quick, yet cheap high of pleasure, “Y-Y’all are w-way biggah... dan h-he was... and m-more carin’ as well...!”
“Empathy is a truly powerful thing, Granny!” Seeing her breasts bounce and jiggle around was hypnotic. However, her smile, sweet as the apples she grows in her orchard, caused something in your heart to stir, a certain sense of longing. Here you are, giving carnal pleasure to a woman you only just met some time ago... and you felt yourself falling for her. She was much too nice of a lady to just have a one night stand with. Human emotions are a chaotic thing.
Leaning down, you caressed both sides of Granny Smith’s face and repeatedly kissed her. “D-Don’t worry... I plan to stay a-and keep you company for quite a-” Before you could finish your sentence, the gears in your brain were finally making some progress and you pieced everything together. A woman named Granny Smith. Sweet Apple Acres. Best apples in the land.
“How’s that for a laugh? ” you heard MILFlove snicker. “You’re fucking the woman who is destined to become Applejack’s grandmother! ”
“E-Everythin’ alright, honey? Ya s-started slowin’ down...”
As big of a realization as it was to discover who you were messing with, you couldn’t deny you’ve developed feelings for Granny Smith. Ergo, you decided it was time to come clean. You confessed on how you lied about your name being Azure Glide, but things started to sound crazier when you added that you had traveled here from the future. All the while, you had a look of guilt for having deceived the farmer up until now.
“Do... Do you believe me?” you asked, hoping she wouldn’t slap you and make you leave. To your relief, she instead cupped your cheek with a small smile.
“Of course Ah do. Ta be honest, when ya said yer name was Azure, Ah kinda had mah doubts. But lookin’ at da guilt in yer eyes, Ah know fer sure ya ain’t lyin’ ta meh dis time.” Seeing you tear up slightly, she knew you still had unease in your heart, and she tried comforting you by pulling your head down to lie on her bosom.
“Even so, dat was quite a shock. Ah mean, a youngin’ comin’ from a different time,” Granny said, combing your head. “Den again, Ah guess Ah should be thankful ya came and changed history. Concord mighta gotten away with his shenanigans if ya hadn’t showed up in mah life!”
“You know that sooner or later, I’ll have to go back to my own time. Until then, we should keep the time machine safe,” you said, sniffing a little.
“A-Aftah we git done makin’ love, w-we can swing dat ting over t-ta da barn. No one will mess wit it. Now chin up, ya have all da time in da world...” Granny Smith cupped your face in her hands, “Ah know yer feelin’ down, but don’t worry. Ah know ya love meh and it’s not wild fer meh ta say dat Ah feel da same way.”
“I know, Granny Smith...” you sighed, “It’s just that you just got betrayed like that and you’re a sweet woman and all. But I’ll eventually have to go back and leave you alone!” Still sensing your apprehension, Granny Smith planted her soft lips against yours, invading your mouth with her tongue. It felt more than a simple kiss that’s born from just simple lust. It was caring, calm, and sweet like an apple, and you didn’t want to leave it. It felt too good as it had more emotion behind it.
“Is dat what’s eatin’ ya?” Granny Smith cooed, “Calculus, if dere’s one ting dat Ah’m known fer besides honesty, it’s bein’ strong. Ah know ya have ta go back ta yer own time. Don’t ya fret none, Ah promise dat Ah’ll remember always ya and keep yer secret safe.” Her words were filled with sincerity, despite having just met her moments ago. Like her future granddaughter, she was a lady of her word.
“Granny Smith...” You dove down for another kiss, planting your body squarely against hers. Holding her hands tightly in yours, you felt another connection form between the two of you. A big part of you loves her as if she’s the perfect woman for you, the one you’ve longed for. “I’ll definitely be staying to watch our child grow a bit...”
“Jus’ as l-long as ya go back ta da exact time dat ya left...” she replied, fighting back a moan as you picked up the pace of your thrusts. “F-Finally gettin’ r-rough again, are w-we...? AH!” You had grabbed one of her beautiful breasts again, roughly moving it in circles to give Granny more pleasure. They felt like sacks of warm pudding, easily malleable to your touch. For a second, you actually thought they were going to melt in your hands.
“E-Even after I go home... I-I’ll see if I can’t c-come back for a visit...!” you grunted and started to pull your lover’s nipple.
“J-Jus’ make sure... ya d-don’ travel ta a t-time where... Ah’m too old fer dis k-kind fun!” Part of it was meant to be a joke, so you let out a chuckle.
“D-Don’t worry about that... I know w-when to play things smart...” You started to plow Granny even faster, and she remained helpless and moaning as you held her down. Not wanting to stay in the same position all night, you turned her onto her side before scooting up behind her and putting your cock back into her pussy. This position was better to you, as it allowed you to hold her in an intimate and loving way.
“Y-Ya really like... m-mah body... don’t y-ya?” Granny teased, feeling you exploit the spooning position to once again grope her proud bust. You also remained close enough to plant some more kisses on her ticklish neck.
“I’m not j-just interested in your body...! Even if we just met today... I’ve come to g-genuinely care for you...!” Your voice was rising because you struggled to control the familiar pressure that was building up in your groin. “H-Hey Granny... I’m g-going to cum!”
“G-Go ahead...! Give me dat cream of yers! Ah want it all!” she demanded. “Don’ stop ‘til Ah’m full!”
“O-Okay... you asked f-for it!” With no reason to restrain yourself any longer, you let out the loudest groan of the night and finally unleashed your load inside Granny Smith. She stuck her tongue out as she felt your warm seed travel to her womb. The amount was incredible, even by your standards.
You reached over and rubbed Granny’s stomach, knowing she would inevitably get pregnant. “Ah have to admit, ya sure did a good job at givin’ meh some proper lovin’...” Granny Smith moaned with satisfaction, before giggling since your massage on her belly was starting to tickle. “No mattah how long ya end up stayin’, Ah know y’all will be a wondahful fathah...”
“I know, Granny Smith... I know...” you moaned back. “Listen, I just thought of a plan and it just might work. You see-” You couldn’t say another word, as Granny cut you off by moving on top of you and pressed her lips against yours.
“Save yer plans fer latah, honey...” Granny said with a tired smile. “Talkin’ ‘bout such things right now will jus’ ruin dis ‘ere nice moment...” Nodding slowly, you allowed the beautiful farmer to lay onto your chest, barely able to keep herself awake.
“Ah love ya...” she whispered.
“I love you too...” you whispered back before closing your eyes.
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Clearing The Head (Lavender Blossom (OC))
December 9th, 1975
- 1 year, 9 months later
“Good morning, ladies and gentlemen. This is Journal Print, here delivering you all the news this morning and midday to the fine people of Monroe County, Michigan. This morning, the temperature is a biting twenty degrees with a strong chance for flurries with a resulting two to three inches of snow. Exercise caution when out on the road and bundle up ‘cause the winter is only going to get colder. On another note, the president and his cabinet are still assessing the effects of five months ago after our withdraw from and subsequent end to the War in Vietnam. But, that’ll be the subject of this afternoon’s story. I’m Journal Print with Channel 7 News and we’ll be back shortly after a quick break.”
You sat on the couch next to Granny Smith, having your turn with cradling the son who became yours after you changed history—Bright Mac. Today just happened to be the giggling toddler’s first birthday and even if he was still a little to know what the word means, it didn’t mean you couldn’t bake something tasty during the celebration. It warmed your heart to see him dive face-first into the apple cake, as it showed he inherited his mother’s affinity for apples.
“Greedy little fella, ain’t he?” Granny chuckled, wiping Bright Mac’s face once he was done eating.
“Guess it can’t be helped. You told me big appetites have been in the Apple Family for generations,” you said, joining in the laughter. “Bright Mac here just proved he’ll be continuing that tradition.”
Honoring your promise to Granny Smith, you continued to watch over the child’s growth while at the same time, remembering exactly when it was that you left the present. With some difficulty, Granny Smith had moved the time machine into the barn like she said she would and it’s been kept hidden there for the last five years. To avoid problems for when you got back home, you were careful to keep your identity a secret in public.
You stepped into the barn wearing the same suit as you did when you arrived, and removed the big sheet that covered the time machine. Both Granny Smith and Bright Mac stood behind you, confident you wouldn’t leave without saying goodbye.
“Pa, is it time fer ya ta go?” your son sadly asked. You bent down to pat him on the head with a reassuring smile.
“I’m afraid so, big guy.” You gave him a kiss on his forehead. “But turn that frown upside down. I’ll be keeping that time machine close when I get back home. I’ll be back before you know it.”
“But pa, what about Christmas?”
“Don’t worry, sport. I promise I’ll be back for that. Tell you what. I’ll treat you and your mom to a nice dinner when I get back.” Scooping him up in your arms, you hugged your son. Not a tear fell from your eyes as you knew it wasn’t the end and your plan was clear as crystal. Yet, a lingering hint of sadness remained. You turned to face Granny Smith as the snow fell around you.
“Granny Smith, I hardly knew anything about the Apple family lineage, but I felt as though I messed it up somehow when I came here. But, no matter what, if I manage to fix things I’ll make sure you’ll have your happy ending.” Having said that, you got a nice kiss from the farmer, who knew she could trust you to keep your word.
“Ah don’t know da future, Calculus.” Granny Smith softly said, “But, whatever you have in mind, Ah know it’ll work.” Reaching into her coat, Granny Smith pulled out a locket and opened it. In it, was a picture of you, her, and Bright Mac at one years old. “If y’all are gonna stay in yer time, at least have somethin’ ta remember meh an’ Bright Mac by.” Putting it in your pocket, you gave her another hug.
“I’ll be back, I promise.” Exiting the hug, you knelt down to your son’s level and placed a hand on his shoulder. “Son, don’t cry. Daddy’s going to be gone just for a few hours. And when I come back, I’ll have a surprise that’ll make mommy happy.”
“Really?”
“Yes.”
Saying your final goodbyes, you turned to the time machine and stepped in. With a sigh, you put in the date that you remembered like it was in the back of your head. All those years of staying behind didn’t dull your memory of that one bit. It was just half an hour of traveling through the timestream but you noticed something odd about it.
When you came out of the machine back to your time, you’d thought you’ll remain the same age as when you left 1979. However, for some reason, the machine reverted you back to the age as when you left. You were left in slight shock over how it was possible, but you got over it since you realized this would eliminate suspicions as to what happened. Remembering the songbook Derpy’s father wanted, you picked it up and headed back to your Jaguar. Before you turned the key, you got a text from Derpy.
“Calc, due to something that came up with my parents, the party will be delayed by a couple of hours. ”
Way for providence to hand you some breathing space for your plan. You breathed another sigh of relief as you were handed an opportunity. Remembering a past friendship, you decided to make a call to a friend of yours, Sunset Shimmer. You asked her to meet you near Canterlot High. Hearing the tales of her homeland of Equestria, where magic exists, you figured there was some magic that can clone you. That was the easy part but the hard part was explaining it to her.
Sunset was in a bit of shock over your reasoning for requesting her aid and telling every bit of the story. However, after some pleading, she understood where you were coming from and respect your decision to set things right. Exiting the car, she escorted you through the mirror in the school’s statue to Equestria, her home.
You came out the other end into the residence of her friend Twilight’s home in a town called “Ponyville”. To your surprise, you were a pony like her, horn and all. Taking some time to get used to your change in the environment, you both came up with a plan. Sunset told you about a small pool in the Everfree Forest that can make a clone of yourself which you can bring back. Knowing she came from here and after the friendship games incident, you had very little doubt in her claims.
Much like its counterpart back home, the Everfree Forest had a strangely unnerving vibe to it as if were haunted. Fortunately, you didn’t get spooked so easily, but even so, you kept your guard up as you felt a creeping fear in the air. Sunset, knowing the lay of the land, guided you through the area without any trouble, with the exception of narrowly avoiding a hungry manticore.
Reaching the mirror pool, you took a deep breath as you felt the energy radiating from its waters. In a way, it was almost as if the pool was actually a living being. Upon Sunset’s instructions, you put one hoof in the pool and stared in awe at your reflection. You were still surprised that you were something other than human, but those thoughts were soon swept away by the presence of another pony.
At first, you didn’t know what to say as you were face-to-face with your clone. It was a weird experience to stare at a living, breathing, mirror image of yourself, voice and memories and all. But, you felt that there’ll be a risk of you being recognized by Applejack if you send him back. Differing with Sunset, she gave you a wink as she walked over to the clone. After all, she was the princess’s former protege and was capable of a lot of powerful magic spells.
“I think I can handle this,” she said, propping her hooves, “Let’s see if I remember this old trick Celestia taught me.” With a bright flash of her horn, she changed the appearance of your clone while leaving his voice and facial structure intact. You watched as his coat changed to a light blue color, and while his mane only grew a little longer, it became a grass green.
You hoped being a clone meant he would share your memory. “So... are we on the same page?” Humming, you clapped your hooves, grabbing your clone’s attention. “Okay, now, do you remember anything between 1974 and 1979?” It didn’t take long at all to get an answer.
“Of course I remember,” your clone responded to your delight. “Since we share a memory as clones, everything is still fresh in my mind. I couldn’t possibly forget our poor little Bright Mac’s face when we had to leave, nor could I deny how betrayed Granny Smith was with Concord Grape’s affair. Do I need to go on?”
It was a rhetorical question, as you were perfectly satisfied with your clone’s memory. Even so, you couldn’t have him using your real name if he was going to go back to the past to be a family with Granny Smith. “Okay, good. Now, you’re going to be using the name Azure Glide when you go back. Don’t worry, she’ll know what you’re talking about.” You turned to Sunset and nodded, “Hey, do you have a ring?” Sunset hummed to herself as she rubbed her temples for a bit.
“You know, I do actually have one in my purse back in your car.” Sunset said, “It was a thing I got from a friend that I had a falling out with. I’ve been looking for an excuse to get rid of that thing, but why now?” Winking at Sunset, she got the gist of your intent, “Ah, I get it.”
With that being said, the three of you made your way out of the mirror pool cave and sealed it off again. Heading back to Twilight’s castle, you took one last look around before you stepped through the portal with Sunset and your clone. When you got back, you were still in awe that you had set foot... or hoof, into another world. As much as you wanted to revel in such an experience, you had a timeline to fix and a clone who needed to be stuffed in a time box.
The moment you got home, you still had an hour to spare before the party began. Between bedding a woman in the past, fathering a child with her, and going to lengths to fix things, it had been a busy day for you. Knowing that Applejack was going to be there with some pastries, she’d be bringing her grandmother with her. The thought of confronting the one you changed history by getting involved with, was going to be heavy.
“So is it ready?” Azure Glide asked, snapping you out of your thoughts. You had paused from activating the time machine for what would be the last time. You and your clone have already agreed that he would destroy it once he had returned to Sweet Apple Acres.
“You got the ring?” you asked, wanting to be absolutely sure that things would go as you planned. From his seat inside the time machine, Azure Glide held up the small, but beautiful jewelry that he was going to make Granny Smith’s day with.
All that was left was to type in the date into the machine’s keyboard. Azure Glide slowly waved goodbye as the machine began to shake and you sighed as it vanished with a bright flash.
Almost immediately, your head was overloaded with years and years of memories of your clone living on Sweet Apple Acres. Some of the most prominent memories included: proposing to Granny Smith, attending Bright Mac’s wedding, and the day your son decided to set out on his own. It was a beautiful bunch of memories, but the strain of so many of them flashing before your eyes, caused you to fall to the ground, shocked and panting.
One such memory however, wasn’t very nice to look at. Being a clone didn’t do anything to stop Azure Glide from aging, and you saw that after being a devoted husband and father for many years, he died peacefully in his sleep 2 years before today. It felt surreal and unsettling to see what could’ve been your own death or rather. You nearly wanted to faint at such a thing.
“Holy shit!” You gasped, wiping the sweat from your brow, “What the- oh my GOD!” You were confused as to how such a thing were possible, yet it happened. You and your clone shared a memory, but ironically, you didn’t share a life.
As much as this was to process you remembered today’s plan when your phone began ringing. Looking at it, you saw Derpy was the one calling you and naturally you weren’t just going to ignore it.
“Hello?” you answered.
“Hey Calc,” Derpy responded, “The party is due to begin in an hour. If you can come in and give me, AJ, and her grandmother a hand, that would be great. I’ll see you when you get here. See ya.”
“See you then,” you said, keeping your composure as you hang up the call. This was going to be so awkward, but it couldn’t be helped.
After several minutes of driving, you pulled up to Derpy’s place and even from the outside, you could see everyone was having a good time. Things looked to still need prep work to some extent but looked to be set well enough. But knowing her, Derpy is a closet perfectionist when it comes to events with family and friends. Still, things were lively enough that those in attendance were having a blast.
“Hey, dere ya are, sugahcube!” You turned to see two familiar and pleasant faces. True to what Derpy had called you for, Applejack was attending the party and brought the woman whose life you changed for the better, Granny Smith. As weird as it was to meet her here, when Applejack gave you a hug, you looked up at the elderly woman with a small smile as she recognized you right away.
“Ya look prettah sharp in dat suit dere,” Applejack commented after pulling out of the hug. “It’s mighty generous of ya ta take time ta give Granny an’ Ah a helpin’ hand.”
“Y’all are such a sweet boy,” Granny Smith said, using a very familiar choice of words as she patted your cheek. You could only manage to nod slowly as you stared into the elder’s eyes. There was so much to discuss, but you couldn’t do it around Applejack, who knew nothing of your relationship with her grandmother.
Returning your attention on what Derpy had called you here for, you worked on moving all the delicious apple treats to their intended places. It took no more than a few minutes to get the treats ready to eat. Yet, your heart and mind were both in overdrive as you started to feel a bit lightheaded over seeing a lover after so long.
“Everythin’ alright, sugahcube?” AJ asked.
“Just feeling a little under the weather today,” you answered, and to your relief she bought your excuses, since it wasn’t exactly a lie. “Hey AJ, mind if I go use the bathroom?”
You took Applejack’s nodding as approval to excuse yourself to the bathroom to collect yourself. Splashing some water onto your face, you got a good look at yourself in the mirror. Even though you knew you’d meet Granny Smith during the party, you still hadn’t prepared yourself for what to say. Especially after five years of living with her and witnessing an entire lifetime flash before your eyes, your mind was washed up in a storm.
“Shit! Why did the party have to be today?” you gasped to yourself. “I’m so not ready for something THIS awkward...”
Unfortunately, this was a bad time to be thinking only about yourself. Applejack was out there waiting for you to return and help her, and you had no right to stand her up. Taking another moment to get your head straight, you dry your face up and got back to the party, keeping as straight a face as you can muster.
“Bettah, sugahcube?” AJ asked.
“Enough that I can continue helping,” you answered.
Trying not to make a lot of eye contact with your lover from the past, you resumed helping by setting the tables. Anything to keep your mind distracted from those memories helped, no matter how big or small it was. Though, you knew that sooner or later, you wouldn’t be able to resist having a good conversation with Granny Smith.
The party would start in 15 minutes, give or take, but you saw many old friends amongst those who decided to arrive early. There’s no way you couldn’t recognize Celestia and Luna, as well Sunny Flare and her husband, Ignacio. The latter two were expecting their first child, evident by the bulge in Sunny’s stomach. You sighed happily at the sight of another future mother.
“You seem well, Calculus,” Luna greeted, as she pulled you into a hug. “We’ve missed you.”
“Heh, I missed you too, Luna,” you responded before pulling out of her embrace so you could move on to hugging her sister. “And you, Celestia. How could I ever forget about you? Even though I didn’t go to your school, you were cool in my books.” You took a good look at her breasts and noticed they got a little bigger than they usually were the last time with a subtle damp spot where the nipples are. Not wanting to be rude, you brushed your suspicions aside for the time being. “You two look nice.”
Celestia’s cheeks heated up a little before she laughed softly. “Why thank you, Calculus. Luna and I do try to keep our figures up to spec in our age.”
You wanted to continue smiling, but that last sentence encouraged you to think about Granny Smith for the umpteenth time today. While you were busy feeling awkward, more of Derpy’s party guests have made their way outside. Obviously, they were lured by the delicious smell of the barbecue. Lots of old friends from CHS and CPA arrived: Jet Set, Upper Crust, Wallflower Blush, Twilight Sparkle, Fluttershy, and many others you remembered had gathered to celebrate Derpy’s birthday. It made you smile to see so many old faces once again.
“Thanks for coming, everybody,” Derpy spoke up, holding a cup of cold punch. “Words cannot express how happy I am to see you all here on my birthday. In my life, I was very fortunate enough to not only become a mother, but also to be surrounded by the most amazing friends that I’ll cherish. Though there’ll come a point that we may drift apart, the memories will never disappear. Now, let’s celebrate this day as one of friendship.”
The moment Derpy was done with her little speech, some music started playing, as if making the start of the party official. The birthday girl of course, got the first piece of cake, but Pinkie Pie rushed in for her share afterward. Applejack was bobbing for apples. Rainbow Dash was playing darts with Twilight, and Big Mac was playing Cornhole with his wife Sugar Belle and Derpy. All of them were playing around while Granny Smith was sitting on a chair smiling at all the merriment that was occurring. You could only smile as she sat peacefully in her chair. The moment she caught you looking at her, she gave you a wink.
Eventually, like all good things, the party soon came to an end as the sun began to set on the town. All that has happened today was making your head spin, so instead of going home, you decided to drive on down to the bar for a drink or two. By the time you arrive, you decided you would need more than just a few to calm your mind after the chain of events. Something really strong would suit your needs.
“Fuck me running...” you sighed as you reached the barstools, the heart of the bar and the thick of the action. When you got your seat, the bartender, Barley Pop, took a good look at you. “Hey Barley, what’s happenin’?” He grimaced as he finished cleaning a mug with a rag. He could tell you had a bad day. He saw many faces like yours since gaining control of the bar from his late father.
“I’m betting you’ve had a shitty day, Calc,” Barley remarked as he grabbed a mug, “I’ve seen faces like yours so many times that I can spot them from a mile away. What’ll be?”
“A bottle of the strongest lager you’ve got,” you muttered as you slapped a wad onto the counter. He was shocked by the amount of cash before him that he crooked an eyebrow many times. “I need a lot of them. It’s one of those days.”
“Like what?” Barley answered back, “Did a girl leave you, huh? Did you get fired?” He only either got a nod or a no from you as he saw the grim look on your face, like one who had been through one hell of an emotional rollercoaster. Of course, you weren’t going to tell him about your relationship with Granny Smith and your adventure traveling to the past. He wouldn’t have believed you anyway. “Today was THAT bad?”
“Yep,” you said flatly, “It’s a long story and I really don’t wanna talk about it.” After hearing the tone in your voice, Barley didn’t push you any further. Just as he handed you the bottle, a woman walked in that you remembered from weeks before. Seeing her at the hospital when your father died and again at his funeral, there was no mistaking Lavender Blossom, the woman whose daughter looked almost exactly like her. Since you were in a daze, you didn’t really acknowledge her presence as you took your first sip. Yet, she still recognized and sat next to you.
“Hmmm, didn’t think we’d be bumping into each other again in a place like this, darling.” She then noticed how much you were drinking. “Is... Is everything alright?”
“I’m having one of those days, Lavender,” you replied, taking a hearty swig, “It’s... a little too complicated to talk about.” Slamming the rest of your bottle, you gasped and shivered as you felt the rush of alcohol pulsing through your system. Even while inebriated, you still were able to smile at her tantalizing form. With perfect breasts to ass ratio, she looked to be the envy of many of the patrons. “So, how’s your daughter, Cocoa?”
Lavender hummed with a happy sigh. “She got married a few months ago to her girlfriend, Violet. Last I heard, they managed to get a place in Manehattan, and they’re apparently going to try for a kid through a sperm donation next year.” She smiled with a hint of a tear developing in her eye. My darling is growing up so fast. I do miss having her around the house.” Reaching a hand to her, you patted her back as you nodded with the same face you wore.
“I feel ya, Lavender.” You muttered, “I feel ya.” Looking to the bartender and knowing that Lavender didn’t drink alcohol, gestured him over. “Barley, she’ll have a Roy Rogers on the rocks, please.” Winking in response, Barley got a mug, cola, grenadine, and mixed it slightly, making said drink for the lucky lady. Motioning for another scotch ale, Barley hands you another bottle which you started chugging, “Forgive me if this sounds rude, but what’re you doing here, Lavender?”
“Oh, well, after another stressful day of dealing with some rather rude patients, I decided I needed a place to blow off some steam and this bar sounds like the right deal.” As Lavender explained, her drink arrived and Barley handed it off to her, “Oh, nice. Thank you!” She took a sip, delighting at the taste of cola and grenadine syrup; A perfect non-alcoholic cocktail to help the stressed woman unwind after a long day, “Yeah, that hit the spot. What’s going on with you?”
You opened your mouth to speak before the door opened again rather loudly. Glancing over, you saw another patron who appeared to have the same build as you, but he also carried an aura of rudeness with his stride. Slowly, he approached your area with a smug look on his face. Though you tried not paying attention, at the corner of your eye, you could tell he was eyeing Lavender with a look of hunger. “Hey hey, lookie at you, cutie. Why are you hanging with this lanky loser?”
“Excuse me?” you asked, standing up to look him in the eye. “That was incredibly rude, jackass.” Your words slurred with your speech, “One, You don’t talk to my friend here. Two, I’m far from lanky and I bet I can take you on in a fight if I were in the mood. Third, do you always like treating women li-”
Before you knew it, you were forced to move your head to avoid getting hit square in the face. But, seeing that, the patron gave you a swift but forceful backhand. Yet, you were stunned for only a few seconds and you processed the strength of the blow. “Did that teach you some respect, bitch?” Taking a moment to breathe, you felt some pent up anger bubble to the surface but you didn’t want to make a scene, especially not in front of an old friend.
Getting up, you motioned for another bottle of beer and took a few seconds to slam it, all the while keeping silent. Taking another breath, you mentally and physically psyched yourself before turning around, gripping the bottle. With a swift motion, you smashed the bottle over the patron’s head, sending him to the floor, out like a light. You knelt down to check him and he was still alive to your relief. Unfortunately, that did attract a few glancing eyes, Barley included. You knew then that you had to leave.
“Okay...” you mumbled as you hastily fished through your pockets, pulling out around a hundred bucks, “I suppose this covers the damages, Barley. I guess… me and Lavender will be leaving now.” With a nod from him, you escorted Lavender to your car but you realized that in your drunken state, driving was a no go, “Crap, I just now realized that I can’t drive. Hey Lavender, is it alright if you could drive?”
“Of course, dear...” she replied, still a bit shocked by what just happened. Even though you were drunk, you didn’t have a problem getting into the car.
“Okay, who was that asshole?” you asked, looking out the window.
“One of the most prideful douchebags I’ve ever had the misfortune of meeting,” Lavender answered. “His name’s Blizzard Rush. We attended high school together, and I remember that he got kicked off my school’s swim team for... sexual harassment. It would seem he hadn’t learned his lesson.”
“I just hope I don’t get charged for getting into a fight with him,” you sighed. “I wouldn’t be surprised if I end up getting banned from the bar.”
“Eh, if anything, you acted in self-defense.” Lavender explained without using her surprisingly vulgar mouth. “Barley saw the whole thing and I think he won’t bust you. Even though I could’ve handled it myself, I thank you, Calc.”
“You’re very welcome, Lavender,” you answered back, slurring your words “Why don’t we schlep over to my place? I have about another week before I my mother moves in.” Lavender gives you a puzzled look and you explained with your cover story, “Before my... father died, he managed to get my mother pregnant. I’m having her move in so I can keep her company and tend to her when needed.”
“D’awwww, what a sweet son you are to her,” Lavender complimented as you felt relief that she bought your cover story. “Now, come on. We’ll continue our time together somewhere more... comfortable.” The last part was said with in unmistakable tone.
“In other words, she wants you to take her to bed, ” you heard Milflove laugh in your head.
“Dude, not cool... ” You tried to think, but all that alcohol in your system jumbled your mind up a fair bit. “Let me handle things and have you not yak at me for fuck’s sake. ”
Getting into the car, Lavender was courteous enough to buckle you up before she did it to herself. Throughout the car ride, you couldn’t help but drift your gaze at her impressive F-cup rack. There would’ve been a point where you’d snap out of it and look the other way. However, with your drunken mind and Lavender’s veiled flirting from earlier, you didn’t put more thought into it.
Pulling into the driveway, you waited until she unbuckled you and helped you inside. Walking in, you internally remarked at how nicely you’ve kept your house. Your mother certainly didn’t raise a barn animal for a son. Sitting down on the couch, still clad in your slightly blood stained suit, your groaned at the thought of having to pay a sum at a dry cleaner to fix the mess.
“Hey Lavender...” you slurred, “...I gotta say that this is mighty kind of you. You remind me an awful lot like your daughter. I guess the apple doesn’t fall far from the tree at all.” You took a closer look at her features after catching a brief moment of sobriety, “But, there is one major difference.”
“What would that be, dear?” she asked. You had the answer and the alcohol gave you the courage to speak your mind with ZERO filter.
“Well...” you breathed, “...your ass.” She stood slightly surprised, mouth agape, for a moment, “I have to say that your caring personality is matched only by how nicely shaped your body is. Perfect tits and ass, I wonder why your husband isn’t around. What gives?” An awkward silence soon filled the air, and you feared you might have gotten carried away. But, though with a sour look on her face, she seemed willing to explain.
“That bastard cheated on me with a friend of mine.” She said with a noticeable growl, “I thought I could trust them but they’ve been doing it behind my back for years! What! Was I not good enough for him?! DAMN HIM AND THAT WHORE!” She banged her fist on the arm of the couch, but soon cooled down. “S-Sorry, it’s not something I’m too keen on talking about. I only bring it up if someone asks. The only good thing that low life gave me was my daughter.”
“Oh, uhhhh... I’m so sorry, Lavender...” You sighed, as you had another sober moment allowing you to think clearly. Your apology had its rewards, as the next thing you know, the woman’s soft lips were touching your own. Your spine surged like a power line as she straddled you without any prompt, but you didn’t mind. Following your primal instinct, you began feeling her back and deliciously plump behind. Her ass, while firm, was soft enough to squeeze in your hands. Every squeeze caused her to moan loud enough that you could tell it has been years since she got some action.
“Looks... like my daughter was right about you...” Lavender purred, showing her maternal side by cupping your face with adoration. She kept her hand on you, even as you started blushing. “Awww, you look so flustered yet… so virile. It had been a while since I was treated like a woman and I can say that you’re a fine example of a man.” To little surprise for you, she slid a hand down to your crotch, fondling your already stiff cock and balls. “And we both know that you’re already primed and ready to go. You’re such a naughty boy.”
“Well... I can’t help it with a fine woman like you on my lap.” You groaned as she gave your gonads a good squeeze. It both hurt and felt pleasurable at the same time. “As much as I find what you did to be hot, please handle the package with care.” You saw her smile as she got between your legs, sniffing up and down your crotch.
“You best prepare yourself sweetheart, because if we’re going through with this... I intend to be the dominant one.” You weren’t sure how to respond to that, and said nothing as Lavender tasted your cock.
“Oooh! Bet you didn’t see that one coming, ” Milflove laughed. “You probably thought she’d submit to you and play the erotic game by your rules. ”
“Honestly, I don’t mind it.” You shot back, “If she’s as horny as her daughter is, I’m… all for it.” Hearing your belt unbuckling, you looked down to see that Lavender had already unzipped your pants and pulled down your briefs, marveling at the size of your eleven-inch cock. Each puff of hot breath against the skin of your member made you shudder with pleasure. “Okay, you’d better give me your best shot.”
She looked like she wanted to reprimand you for giving her orders when she specifically said she wanted to be in charge, but she was more focused on giving your manhood some attention. With no hesitation, she took you all the way into her mouth so that your tip was poking the back of her throat, and managed not to choke as she held you there.
“Oh, holy shit!” you croaked, feeling as if your eyes rolled to the back of your head, “I wonder if she was preparing for this! FOR THIS! FUUUUUCCCK!!!” You groaned as you tried to grip her head, but it Lavender saw it coming and pinned your arms to the couch. Now, you were completely at her mercy... and you were just fine with that.
Even though you enjoyed exaggerating to yourself that your legendary stamina was something that could rival the gods, you couldn’t hold on forever. When Lavender gave you a mighty suck, it was enough to send you over the edge and make your cock quiver with its release. With rush of your orgasm hitting you like a ton of bricks, the border of your vision was changed to a frosty white. However, you didn’t close your eyes, as the sight of the fine woman sucking you off in such an aggressive manner, was too hot to ignore.
“So... you got anything you’d like to say?” she asked, wiping her mouth with eyes fueled with pride. It was only after she got every last drop out of your balls, that she started speaking again. You were too deep in the afterglow to answer her. Lavender had left you a heaving, sweaty mess, reminding you of the many cardio workouts you’ve done in the past. “Hmmm... I’ll take your silence as a ‘no’. However, you shouldn’t be the only one to get pleasure and you will return the favor, one way or another...”
Still sitting in silence while riding your orgasm, Lavender sought to leaving you even messier than before. Before you knew it, her flower, hot and moist, dripping with arousal, was only a few centimeters away from your face. You were finally about to say something before the lustful woman dropped on top of you, forcing you to keep quiet and use your mouth for something she deemed more... productive.
“Now, you know the drill so... GET TO IT!” With baser instincts taking over your mind, you decided to find out what Lavender tasted like. Sweet yet tangy, like a Sex On The Beach cocktail; it was an intoxicating taste that made you crave for more. Lavender did nothing to stop you as you went for more of her tasty nectar, and released some adorable moans as you lapped away at her sex. Yet, being dominant, she wanted to assert it.
While moaning, she began grinding her hips against your face, taking in every bit of pleasure you provided her. It felt like she was smothering you with her pussy but you were left with just enough air in your lungs. The moans from Lavender only served to further motivate you to please her. Even the added bit of her running your hands across your head had the effect of driving your arousal to new heights. But, if she wants it, you were going to go above to impress her.
While in the midst of her ecstasy, Lavender was completely oblivious to your plans as you licked away at her. Then without giving her any sort of warning or clue, you jammed your tongue inside her wet love tunnel. Shocked but not quite knocked off her knees, Lavender’s drive only intensified as her grinding got heavier and faster, holding your head against her crotch while moaning like she was insane.
With another wild moan that sounded like a wailing spirit, Lavender's nethers quivered with her orgasm, drenching your face in her tangy juices, a byproduct of her contained arousal. Even then, her ever lustful moans was enough to give you a throbbing boner as if the sound had some sort of mystical properties. She did eventually dismount your face to give you some much needed air.
“I wouldn’t get all comfortable if I were you sweetheart...” she warned once again enforcing her dominance, “...because even though my cunt has been pleased for the first time in years...” To your amusement, she mounted your crotch, lining the tip of your spear with her slit, “...I still crave some cock. And since I know for a fact that you want me, we can call it a win-win, dear.”
“Just do what you will...” you groaned before a question came to your mind. “I hate to ask but… won’t you get pregnant from this?” Your question earned you a light-hearted chuckle from Lavender. “W-What?”
“Oh, my dear...” she purred, giving your cock a few sensual strokes, “...I’ve had my tubes tied a long time ago. So, you don’t need to worry about putting a bun in my oven.” Her hands moved from your cock to your abs, stroking your muscles, “Just relax and let momma take care of you...” With a moan and a slick sound, Lavender impaled herself on your cock. Her warm insides, welcoming and pleasurable, felt like heaven. You couldn’t hold back a guttural groan.
“Oh yes, this feels amazing! This is the best cock I’ve ever had!” she cried.
“Rejoice my man! She just revealed you feel better inside her than her douchebag ex did! ” Milflove cheered. It annoyed you that your alter-ego didn’t know when to take a day off.
“Just shut up and let me fuck her!” you mentally snapped back. While he did stop talking, you could still hear him chuckling. Just before you could chew him out further, you felt Lavender’s velvety hands rest upon your abs just as she started bouncing up and down your cock. She started out slow, making sure to explore every bit of your length. Judging by her moans, she was loving it for sure. “Holy... shit! Your bastard of an ex-husband is missing out!”
“P-Please, he’s nothing compared to you!” she moaned as she picked up her speed, driving both you and her into a lust-filled haze. “B-But... I’m w-wondering if you’re a good... kisser.”
“What do you-” Before you knew it, she reminded you of the conditions of playing the game however she saw fit, by grabbing you by the arms and wrapping hers around your back and head. The look on her face and the licking of her lips, you knew what was coming. Tightening the embrace, she latched her lips on yours, invading your mouth with her tongue. YOu couldn’t talk at all as she had you right where she wanted you, bouncing on your knob and sucking face with you.
“You know...” Lavender breathed, briefly retreating from the kiss, “...I’ll allow you to grope my butt. D-Don’t think I-I didn’t... notice you l-looking at it... G-Go on and claim your prize... You’ve d-done a great j-job at... pleasing m-mama here...” You couldn’t resist when she was persuading you like this, and you grabbed two handfuls of her bubble-butt. Each squeeze netted you a breathy moan from her. Taking the rhythm of her bouncing into account, you timed your squeezing to sync with her ministrations.
“Oh yes! You’re being such a good boy! OH FUCK!” she shouted, no longer stuttering. You were almost convinced that she was insane, as along with her tone, her expression had completely changed. She was now sticking her tongue out, tempting you to make out with her, and her eyes were rolled to the back of her head.
“Imagine if her daughter was here to hear this! ” Milflove cracked yet again. You didn’t waste any time or energy dignifying what he said with a response, and just focused on having your fun with Lavender. Her cunt felt too good to focus on anything else. Just as you were about to give into the temptation to kiss her again, she acted before you did and grabbed the back of your head. With your tongues wrestling with all the passion you could muster, you soon found yourself getting closer to your release... and so was Lavender.
“Are you getting close sweetheart?! Remember, it’s safe to shoot it inside me! I’M STILL IN CHARGE HERE, AND I DEMAND YOU TO FIRE AWAY!” Being held tight against her, you tried to hold on for a bit longer before it became too much for you. Biting your lip, you shot loads and loads of your cum into her snatch. The power of your orgasm was so immense, that your fingers gripped her plump ass in order to keep yourself together. That and the heat of your seed was enough to send both of you over the edge.
“Oh... my... god...” Lavender sighed, bringing her chin down to rest on your shoulder before you both fell back onto the couch. Even though you were both spent, Lavender was more out of it than you were, as it was the first proper fucking she got in ages. She looked to be satisfied as she rested on your body. Taking it as a sign that her dominance has been calmed but not completely quenched, you chuckled and allowed her to do as she pleased.
“I’ll say it... again... You’re much... better than my... ungrateful... husband ever was...” she panted. She then let out a tired giggle as you brought your hand up to stroke her hair. “Not too mention... you’re more... affectionate.”
“Well, I’d treat any lady right.” You stole a kiss from her with an added smirk, “You, Lavender, are no exception.” Gliding your hands over the skin of her back, Lavender snaked her arms behind your neck, stealing a kiss from you, “I was just glad to have spent time with you to get over a shitty day I’ve had today.”
“And you’ve been such a good boy pleasing a woman like me.” Lavender snuggled into you, draping a blanket over your sweaty bodies, “Even a dominant woman like me knows when to reward such good treatment. How about I keep you company for the night and we can grab some lunch tomorrow. How does that sound?”
“I guess that sounds like a plan.” You yawned as you lay your head back, exhausted yet satisfied, “If it isn’t much trouble, can you help me set up the guest room down the hall tomorrow as well? I need to get it ready for when my mom moves in.”
“For you... done deal. But for now, let’s get some rest.”
With a big yawn, you surrender yourself to the lulls of slumberland with the fine specimen of a woman in your arms. Despite the temporal fuckery you got yourself into, you were confident that you wouldn’t have to deal with it for a long time. Your intimacy with Lavender seemed to distract your mind from that thought. All you wanted to think about, was getting your mother in a position of comfortable living... and spending time with the beautiful lady in your arms.
Author's Note
Well, another chapter released... more porn with story to the masses, lol. I hope you like this chapter because the next will be guaranteed to surprise you all for sure. I'm keeping my lips sealed about what it will be but... I think you'll love it.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Beaches and Babes (Mane Allgood, Lofty, Holiday)
Waking up in a cold sweat after another dreaming of one of the many memories you shared with your clone, your eyes darted around as you took a deep breath. Still remembering a day and a half, you were in the living room having fun times with one of your father’s nurses. That single thought was enough to give you a raging stiffy, but you were a man with standards. Ergo, you wanted to get ready for the day and see what life had in store.
You went through your usual morning readiness ritual, starting with a good shower, followed by a quick shave. A quick look in the mirror was enough to give you another flash of your clone’s memory. From Bright Mac’s wedding, the many rounds of sex Azure Glide and Granny Smith had, to his death, it was a beautiful life, but still a lot to experience in just a few short moments.
You got out of the bathroom so you could move on by preparing breakfast. Putting an egg, bagel, and bacon on the griddle, you took the time to make a fresh pot of coffee. Before taking a sip, however, you reminisced back to when you saw baby Bright Mac’s smiling face for the first time. It was those kinds of memories that made it impossible for you to regret going back in time.
Just as you finished building your breakfast, you heard a short set of knocks on the door, pulling your attention. With all the friends and lovers that you had, you could only imagine who would stop at your front door this early, besides the mailman of course. Looking through the peephole, you got your answer.
Standing there, looking nervous, was Granny Smith herself, dressed like she just got ready for the day. Remembering the look she gave you at Derpy’s birthday party, you knew it would only be a matter of time before she sought you out. With a sigh, you decided not to be rude by pretending you weren’t home and unlocked the door.
“Hey, Granny Smith,” you sighed, trying to keep a straight face. You were nervous, barely able to hold yourself together, “H-how are you doing today?”
“Ah’m doin’ good, Calc,” she sweetly answered. “Mind if Ah come in?”
“Sure, I guess it’s okay...” With a nod, you helped her in and closed the door behind her. Knowing she might be a little uncomfortable from standing, you helped seat her on one of your chairs. Sitting down across from her, an awkward silence filled the air for a time before Granny Smith spoke up.
“Listen dear, when Ah saw how shaky y’all were bein’ aftah seein’ meh at da party, Ah knew time was catchin’ up ta ya...” Granny put a reassuring hand on your shoulder, hoping to make this conversation less awkward. “Yesterday was da day ya sent yer clone back in time, ain’t it?”
“Yeah...” you admitted, slowly accepting that this embarrassing moment was bound to happen eventually. Even so, you didn’t find it so easy to look Granny in the eye, and preferred to stare at the ceiling instead. “I also made sure to destroy the time machine after Azure Glide was sent back to take my place. However, since we share a mind, years and years of memories came piling up on me.”
“...Please look at meh Calculus...” Hard as it was, you did what your lover from the past asked of you. “Ah’m not as young as Ah used ta be, but Ah haven’t forgotten da promise Ah made da day ya showed up on da farm. Even aftah Azure died, Ah haven’t told a single soul dat ya changed mah life by messin’ ‘round with time.”
“I know...” you groaned as you rubbed your temples, but then something funny came to mind. “No one would’ve believed you anyway, right?” The mood had finally begun to lighten up as you both let out a small laugh.
“Nah, dey wouldn’t,” Granny Smith replied as she reeled from her laughter. Still, she noticed you were a bit reserved even after the ice was broken between the two of you. In it, she sensed a bit of guilt over what transpired years ago, but that guilt was easily forgotten as she remembered all the good times she had with the clone you created for her sake.
“No doubt ya already know dis, but Azure definitely knew how ta treat a gal right,” she sighed. It was now her turn to look at the ceiling, since she felt that her husband was watching you from above. “Oh, how Ah loved him...”
“I’m just glad that you got a happy ending from the whole thing.” You sighed as you looked down at the floor with a frown, “I mean, will I ever find that for me? I’ve been with many women before over the course of my life. Will I ever find that one for me, the one that I can finally settle down with?” Granny Smith sat there, deep in thought for a moment. She got a good look at your face and soon wore one of her own.
“And ya treated each of em well, Ah assume,” she concluded, getting a nod which she knew for a fact was an honest response. “If y’all want mah advice, love ain’t somethin’ that ya can prepare fer. Ya just have ta be calm and patient. It’s like fishin’, good things come ta dose who wait. Y’all know it when ya see it, trust me. Aftah all, Ah found it when y’all came inta da pichah.”
You blushed a little, but at the same time, you smiled at Granny Smith’s little spiel. You were once again reminded that as the grandmother of Applejack, she very well was the one who imparted her honest nature onto her. As such, Granny’s words had not even the smallest hint of a lie in them. One day, you’ll find your heart’s desire through the chaotic mess of bedding the town’s local cougar population. It’s all just a matter of time.
“Well...” you sighed, “...you got me there, Granny Smith.” “You got up and stretched your back and muscles before hearing MILFlove’s voice.
‘Embarrassed that she knows about your antics, lover boy? ’ he snarked, ‘Well, I know you are. It’s just fun to see you mentally squirm about. ’
‘Wow, ’ you sarcastically shot back, ‘The fact that you’re a real asshole just proves that you really are a demon from hell. ’
‘I know. I always got on my co-workers’ nerves. Also, if you want to know who the bigger asshole is in the nine circles, look no further than Lucifer. ’
‘For fuck’s sake! ’ you shot back as you looked across the room at Granny Smith, smiling cheerfully. You smiled back to hide any signs of the argument occurring in your head. Knowing that Granny Smith probably had places to go and things to do, you offered to escort her to her car, which she accepts. She smiled the whole way, remembering how much of a gentleman you were to her years ago.
“Calc,” Granny Smith said with a smile on her face, “Ah knew yer othah self was happy with meh. Ah wish ya luck in finding yer own soulmate.” She followed it up with a tight hug that you swore nearly crushed your lungs but was no less sweet. “Ah guess we’ll be seeing each other soon. Take care.”
You didn’t just let the elderly woman walk out by herself. Instead, you acted as a gentleman and led her out the door and back to her car. You waved her off as she drove away, and you were left a mentally exhausted mess. Between your temporal predicament and the demonic entity anchored to you, you weren’t going to catch a break anytime soon.
After giving it a lot of thought, and the occasional forehead to the wall, you decided that some time to yourself was in order. Since you’ve already been to the spa a few times, you decided you wanted to try something different. Checking the weather, it was going to be a nice sunny day, a perfect day to catch some sun. So, you packed up and made plans for the nearby beach, hoping the sounds of the waves could do wonders in putting your mind at ease.
Changing into a shirt, which you intentionally left unbuttoned, revealing the t-shirt you wore underneath along with some sandals, you hopped into your car and took off. When you arrived, your nose was immediately hit with the scent of the ocean water, every bit as atmospheric to the senses. Remembering you had a small bungalow after saving up enough money, you offloaded your stuff before settling on camping on a chair under the shade of an umbrella.
“Shit, I needed this...” you muttered as you cracked open a beer and took a sip, “Just the lake, some beer, and fresh air... Oh, how the simplest things in life do wonders...”
Even though so many people were out in the water, you had no intention of getting wet. Yet, a figure rose from the water, someone who you remembered from your senior year. Sporting tan skin, cream yellow and white hair, and a bountiful rack, her mere appearance was enough to give you a boner. You recognized her as Scootaloo’s mother, Mane Allgood. You remembered seeing her attending a joint school event with Canterlot High along with her husband, his sister and the latter’s wife.
It just so happened that all three women were here having a good time. Holiday was a bit on the chubby side, but it was thanks to that that her breasts caught your eye. You didn’t mind the fact that Holiday had some weight on her, as it meshed well with her natural beauty. Lofty’s figure was almost the exact opposite. With some wrinkles under her eyes, the woman bore a skinny figure, but with an amazing ass to rival the olympian gods.
“God... damn...!” you gasped as Lofty was the first to climb out of the water. Though she was a lesbian, that mattered little as her jiggling ass didn’t do a thing to calm your erection. On the contrary, it only served to make it worse. You could only hope she didn’t notice you, as it was an embarrassing reality that just about every mature lady you strike a pleasant conversation with, eventually gets the desire to sleep with you, regardless if she’s married or not.
‘Target sighted, eh Boss? ’ MILFlove cackled, having found another opportunity to humiliate you in a mental conversation.
‘Fuck... you! ’you replied while groaning internally. ‘Don’t make me get an exorcist or something. ’
‘Well, I hate to break it to you, but that ain’t going to do shit. The only way you’ll be free of me is if you find the one you love—The one snatch you’d like to pound for all eternity. ’
‘You really are a demon... ’ you snarled. Even though you and MILFlove were prone to argue, you were ironically grateful, as the argument allowed you to take your mind off of the women in the water, which settled your erection a little.
“Well, well, what a pleasant surprise!” Next thing you know, Lofty’s arms were wrapped around you in a warm hug. Out of the three women you had your eyes on, Lofty was the most fond of you as she saw you as one to count on when they needed a job done. “I didn’t know you’d be here today. Funny how the world is nowadays, hmmm?” As she hugged you, she felt your stiffy poking her thigh, “Hmmm, I didn’t know I made you so hard. You naughty child.”
“Lofty dear, what’s going-” Holiday stopped mid-sentence as she too easily recognized who her wife was hugging. Unlike Lofty, she hadn’t noticed your erection. “Well, I recognize you, youngin’. You’ve mowed our lawns a few years back. Calculus, was it? It’s mighty fine to see you here and doing well.”
You silently hoped Lofty wouldn’t sell you out, but such hopes were quickly crushed. “I just discovered that the dear is getting aroused from our mature bodies, Holiday,” she purred as she giggled at your embarrassment and pinched your cheek as you blushed.
‘Forget what I said, you’re THEIR target, Boss, ’ Milflove teased. ‘They’re hungry for the thing between your legs. ’
“Come now Lofty, leave the poor boy alone,” Holiday scolded, putting a hand on her wife’s shoulder. “You’re making him uncomfortable and this is the first time we’ve seen him in years.” Having said that, she then decided it was her turn to give you a reunion hug. By some chance, her bountiful chest, an F-Cup by your guess, was against your head when she hugged you. Though unintentional, it did make your blush... and erection even worse. Holiday couldn’t even pretend to ignore what was poking her.
‘Thank goodness their niece Scootaloo isn’t around, ’ you thought. ‘It would be awkward for her to see all this. Not to mention she might spread the word to all of her friends. ’ Speaking of which, you looked to make sure no one was watching you and luckily, the coast was clear.
“Are you... really THAT happy to see us?” Holiday asked carefully, trying not to make this any more unbearable.
“Would it be weird if I spoke the truth?” you asked before nodding shyly, “...Yes.” You decided to just admit it, as you never were really that good at lying. Fearing a potential slap to the face, you closed your eyes. However, a familiar voice made them open wide as they met the view of Mane Allgood. Though beautiful from afar, she was even better up close. Lord help your beating heart. “Say, I remember you. You were part of Crystal Prep’s Swim Team from that one school barbecue.”
“Yeah, that was years ago...” you stuttered, trying not to lose yourself from the woman’s beauty. “And you’re Scootaloo’s mother, correct?”
“Why yes. Mane Allgood is the name, Calculus Crunch.” The last part didn’t surprise you as much as it should. She probably already remembered your name from so long ago. It was a rare sight to see Scootaloo’s mother in town, as she was a world renowned explorer along with her husband, Snap Shutter. Having read her blog posts and watched a few of her videos, the places she explored were captivating to say the least.
“Don’t take this the wrong way, but why are you here?” you asked. Thankfully, Mane didn’t take it as an insult.
“Well, after a year of traveling the globe, Snap Shutter and I decided to take a few months break here,” she explained, “Though we love what we do, the exhaustion and homesickness does bite at us every now and then. Plus, my dear Scootaloo is getting married in a few months and what kind of mother would I be if I missed it?”
You guess you shouldn’t be too surprised that Scootaloo was preparing to get hitched, as it wasn’t like she was still in school. She should still be about 25 by now, and was ready to decide the next step in her life. You saw Mane was getting teary-eyed just thinking about it.
“I realize this must be an emotional moment for you...” you softly remarked, “From what my friend Thunderlane mentioned, his brother Rumble was more nervous than ever before when he took the knee.” You remembered Rumble from your days of LAN parties where Thunderlane would bring him along to play games and then some.
“I’m just... I’m just glad my daughter found someone she loves...” Mane sniffled, wiping her tears away. “The mess I’m in right now, doesn’t compare to how much I’m going to tear up when I walk her down the aisle. And what about you sweetie? Any lucky girls got your attention?”
“Funny you ask that...” Lofty said with her tone dripping with mischief. You bit your lip, knowing what was coming. You had thought you’d be able to have a relaxing time and avoid getting either aroused or humiliated... you thought wrong. “We’ve seemed to catch this naughty child’s attention...”
“Just what do you mean by...” A single finger pointing down your pants answered Mane Allgood’s question, but Holiday spoke before she could. “Ever the dirty mind of a young man. But, as much as we'd like to see what you're packing, doing so out here isn’t appropriate.” The plump, but beautiful woman looked around to try and find a safer area. "How about we take this inside your little place over there?"
You followed their eyes and saw your bungalow behind you. “Uhh... sure.” You got no prior warning before you were dragged inside your bungalow by Lofty. You had to admire her strength. She could possibly snap off your arm like a twig if she wanted.
Closing the door behind you all, Holiday locked the door and opened the curtains slightly to check for onlookers. To her relief, there were none. “Well, thank goodness for no peepers.” She then turned to you as Lofty pushed you onto the couch and sat right next to you. “Now we have you all to ourselves.”
Lofty pulled your shorts down, being much more hasty than her wife, and rubbed your cock. “I told myself I was done with men long ago, but I simply MUST make an exception for one this healthy...” she muttered, admiring your tool as she stroked it with her soft hands. “Come on Holiday, the sweet boy needs your attention too.”
Though Holiday wasn’t as horny as Lofty, she was still horny, nonetheless. But, in her excitement, she was slow and methodical, reminding you a bit of Twilight Velvet. You do admire this level of slow intimacy as there was much more build up and more time to enjoy it.
“Okay, I’m starting to like this...” you moaned as Holiday traced her hands around your clothed abs. Taking time to show how impressed she was with how muscular you were, she continued to trace her hands upwards until she was standing and looking you in the eye. Even though it would probably make Lofty jealous, she couldn’t stop herself from kissing you. Holding her close as you make out with her, you couldn’t resist dry humping her as you did, as well as fantasizing bikini so you could get your wish. about her naked form. Your fantasies started taking control and you undid the plump woman’s bikini. “What a huggable body.”
“Oh, you silly boy,” Holiday giggled, “Why waste time with words when there’s so much more we could be doing?” Getting up briefly, she let gravity undress her, revealing her beautifully plump naked form... and her clearly soaking pussy with a small bush to match. “Even though I prefer women, I have to admire your youthful handsome body” She continued to move her hands around your muscles, worshipping every inch of them. “My my, you’ve taken care of yourself quite a bit.”
You could no longer just sit still when Holiday’s huge breasts were bouncing right in front of you. You wanted them, to feel them, to squeeze, lick and suck. Sitting up, you grabbed her massive chest orbs and began squeezing them like water balloons. It was no use denying that you were addicted to older women.
“Oh, that’s no fair Calculus! What about me?” Lofty pouted, joining you both on the couch. Due to the attention you were giving Holiday, you didn’t even notice that her wife had stripped out of her bikini as well. You once again examined her body like you did back on the beach and saw that while her face was wrinkled, there was no sag or wrinkles anywhere on her breasts. Lofty was most likely jealous that her bosom wasn’t as big as Holiday’s, but her ass made up for that. Together, Lofty and Holiday were like a MILFy Yin and Yang. “I know I don’t have the chest of my dear wife, but she loves my big behind.”
You shifted positions, temporarily letting go of Holiday so she could make herself comfortable sitting on one of your legs while Lofty sat on the other. Each woman kissed your cheek, making you blush. Even so, you kept up the good work by wrapping one arm around Holiday’s back in order to claim one of her huge breasts again. You used the other arm to take care of Lofty, moving down to caress her butt and even inserted a finger into her pussy.
“Oh, goodness! How naughty of you, youngin’,” Lofty gasped as you fingered the inside of her pussy, “Going straight for my womanhood and not even taking time to butter me up? But, I do admire you for being experienced.”
“You have NO idea,” you shot back as you used your thumb to please her clit. The contact of your skin against her nub was all it took for her to go wild with pleasure, but you were a man that loved to savor every moment of your sexual encounters and opted to tease it. Just the look on her face was enough to make you smirk a devilish grin. Every breath she took progressively got more frequent.
“So, how do you lovely ladies like the treatment?” you asked. Hearing you compliment them and call them beautiful in spite of being middle-aged, made the lesbian couple blush.
“You flatterer...” Holiday whispered before she gasped from you squeezing her breast and playing around with her sensitive nipples, “An experienced man that’s well mannered, quite a rarity if you ask me. Lots of women could do well with more of your type. Makes me wonder if you found one to call your own.”
“Not yet but I’m still searching,” you replied as you began to sync your movements on the lesbians. “I mean, I do want one I can call my special someone, but...”
“Say no more sweetheart,” Lofty cut you off obviously feeling guilty for starting such a personal conversation. “You’ll find that someone eventually.”
“Now that that uncomfortable topic has been dropped...” Holiday pulled your hand off of her breast and got off of your knee in order to sit on the floor. “Don’t you even think about resisting, child, I know what’s going on in that mischievous mind of yours...” To show what she was referring to, Holiday engulfed your erection in between her plump breasts.
Your voice and breath hitched from the contact, trying hard not to surrender to the pleasure then and there. You wanted to enjoy it for as long as you can endure. With a deep breath and an exhale, you sat back and enjoyed the ride, regardless of how long it would last. Holiday’s soft mounds were like a memory foam pillow, warm to the touch.
“Admit it sweetie, these are the things you think about,” Lofty whispered into your ear, rubbing your arm with her own bosom. With trembling hands you reached over to grab onto one, not minding that there was an obvious difference from the breasts currently pleasuring your manhood.
“Lofty, instead of being lazy and making fun of the boy, why don’t you help me out down here?” Holiday suggested with a smirk. Though she rolled her eyes at the hypocrisy, Lofty nonetheless decided her wife’s idea could be fun and once again forced you to let go of her breast.
“Don’t worry, you’ll get the chance again sweetheart,” she assured and as unexpected as it was, she gave you a loving kiss right on target with your lips.
Your mind went blank for ten seconds straight before it could comprehend getting blown by one woman with her tits and being kissed by another. Your spine quivered and quaked from the sheer sensation of two women at once, something you were no stranger to but enjoyed nonetheless. It was... simply magical. Still, you endured and enjoyed it.
Sadly, Lofty remembered her instructions and pulled away from your lips so she could join Holiday on the floor. It didn’t take you two brain cells to figure out what she was going to do as you felt her breasts join Holiday’s in pleasuring your cock. Then, with a plop, your meat left Holiday’s mouth and Lofty’s mouth took over.
The entire time, Mane Allgood had been standing in the corner, not yet having the confidence to join the fun since it would be like cheating on her husband. She was however, feeling aroused from the show and had taken off her bikini in order to finger herself. The only reason you didn’t know was that she had her bikini in her mouth to muffle her moans. When you finally noticed, your cock shook with excitement at the sight.
Lofty caught your eye and turned to Mane with a quizzical expression. “What are you doing over there Allgood? Come join the fun!” she encouraged. This earned her a glare from her wife, who seemed to understand Mane’s reasons for keeping her distance.
“Leave the girl alone, Lofty,” Holiday scolded. “Surely you can understand how much pressure it would put to do such a thing without my brother’s consent. Let her come into that on her own.”
“I agree...” you grunted, holding back a jolt of pleasure, “I try hard to be an empathetic man.. She can come over whenever... she feels up to it...” Mane gave you a small smile, but didn’t come any closer. You gave her a nod as she let out a yelp when she presumably hit her g-spot. It was cute and sensual, the right combination for a sexy sound. You ignored it however and focused on fighting off your impending release. The soft pairs of breasts were making it a very difficult task.
“Come now, Calculus. Just take a deep breath and give in like a good boy,” Holiday cooed as she and Lofty rubbed their breasts against you even faster.
“Indeed. A nice coating of a young man’s seed should be better than any kind of sunscreen they’re using out there,” Lofty giggled. “You’ve already proved how long you can last. Now do as your elders here say and blow your load all over us.”
After another minute of holding back, you and your cock simply couldn’t take it anymore. It wasn’t exactly pleasant being treated like a child, but the lesbian couple’s seductive tones did the trick in bringing you closer to your climax. For the next half a minute, all you saw was white as the rush of your orgasm came with the full force of a tsunami. Lofty and Holiday both closed their eyes, but left their mouths wide open as you granted their wish and sprayed their faces.
“Good lord, so much in one load?!” Lofty gasped. “You truly are a healthy one, Calculus.”
“But we’re obviously not done yet, now are we?” Holiday asked and without anyone’s permission, she climbed onto your lap. Both you and Lofty were shocked at how she was rushing for the good stuff, though, the latter was more annoyed than surprised since we didn’t decide whose turn it was.
“Excuse me, but who said you could try the stud out first?” she pouted. Rather than answer, Holiday just grabbed onto your rock solid shaft and forced the tip into her pussy. While not a virgin, the plump lady’s walls were extremely tight since her lesbian lifestyle has kept them from being used for so long.
“I want to know how good your cock will feel inside my cunt...”
Gripping your half-flaccid member, she began stroking it. Even with the rush of your orgasm, you could still feel her soft hands reinvigorating your member as she slowly descended. Shaking from how tight she was, you reached to squeeze her bubbly ass to her delight. She was still in ecstasy from your entry and the groping of her behind only added fuel to the flames of her lust.
“H-Holiday... you’re clenching... me pretty hard...” you groaned, looking at her crotch. “And I can tell... you already came...” You slowly turned over to Lofty and since you had a good heart, you sympathized for her for being left out of the fun. Though one hand continued playing with Holiday’s rear, you held your other one out to encourage Lofty to sit next to you. “I-I’d hate to... l-leave you dry, Lofty...”
The mature woman caught your drift and cheered right back up as she climbed back on the couch. Slipping a hand under her, you gave Lofty no warning before you began brushing her wet cunt with three fingers. She gasped and shuddered from the touch, blissfully unaware of what was about to happen. When those three fingers went in, she seized up and her face was of pure shock from the new feeling.
“See...? I can take care of... b-both of you at once...” you chuckled. You then used your head to motion Lofty to come closer so you could have another session of kissing. She did so without pulling off of your fingers, and her velvet soft lips and ability caught you off guard once again. Fortunately, this time you were able to overcome the shock and as you continued fingering and kissing Lofty at the same time, you decided to see just how bouncy Holiday’s rear was by delivering a good smack.
“Oooohh!” Holiday moaned, briefly stopping her bouncing, “W-What are y-you thinking y-young man...? S-Smacking the lady who’s t-trying to... please you...?” You sensed playfulness in her voice, so you took the liberty to slap her again. “Oh my! Such bad manners!”
Just when you thought things couldn’t get any better, you felt a warm tongue sliding along your nutsack. Looking down, you found to your shock that a completely naked Mane Allgood had finally given into the temptation and was giving your balls a good licking. She then took one into her mouth and began sucking, leading you to groan as you heated up your kissing with Lofty by pushing your tongue against hers.
“This will be on my guilty conscience later, but seeing you tend to the needs of my sister-in-law and her wife at the same time, I have all the proof I need of just how big of a heart you have,” Mane said, letting go of your balls so she too could take a seat on the couch. By now, you had pulled away from Lofty’s lips so you could regain your breath and turn to get a good look at your new prize.
“Oh, my god...!” you gasped with shocked bliss. “I... this is unreal, yet so right at the same time...”
“Well, while you two are lost in the moment I’m going to go ahead and take my turn,” Lofty announced as she got off the couch to stand in front of you. “Move aside, Holiday. We can’t have you hogging the stud for the whole ride, you greedy woman.”
“Oh c-come now, d-dear... Let me enjoy m-myself a little... l-longer...!” Holiday said as she made no attempt to dismount your spear, but you wanted to abide Lofty. With your strength, you grabbed Holiday by her hips to lift her from your cock and placed her on the spot that Lofty had previously occupied.
“Don’t get me wrong, I’m having the time of my life, but your wife should have a shot,” you said, giving the chubby woman’s rear another slap. “I’ve never been one who approves of greed, and I assure you there’s plenty of Calculus to go around.”
Holiday didn’t attempt to argue any further and just watched quietly as Lofty took her place on your manhood. As you slowly inched into her pussy, you quickly found out that Lofty was as tight as her wife. Be that as it may, it wasn’t anything you couldn’t work with.
Things continued to rotate from there, as you were soon fingering Holiday while Mane Allgood was treated to your lips. You thought Lofty had skills, but the moment Mane decided to let go and have some fun, she made the older woman look like a novice. It was as fierce as a raging fire and a hurricane all vying for dominance yet, at the same time, was gently sensual. It was like perfection in its purest form.
She might just be the best kisser of these three MILFs, but remained generous and pulled away so you could turn to kiss Holiday. Getting excited at the naughtiness of you kissing her wife in front of her, Lofty grabbed onto your shoulders and betrayed her aging hips by picking up speed. She was lost in a spell of pure lust, moaning and howling your name into the air. The dramatic sounds only stopped after Mane’s unoccupied lips became too much for her to bear, and she decided to take Lofty’s.
“How naughty this is...” Holiday moaned as the two of you took a small break so you could watch what was happening.
“I don’t know, it works for me,” you shrugged while chuckling. “But this... it’s magic... Oh yes!” Lofty was really getting into it now, purposely tightening her walls around your member as she bounced on your lap. It was clear she was going wild for your famous cock, savoring every last inch of it in her sex and hoping you she would be the first to receive your load.
“S-Shoot it in me, dearie...! It’s fine... I had my tubes tied years ago...!” she urged, throwing her arms around your neck in a warm hug to show how appreciative she was of you being so good to her. With neither Mane nor Holiday doing anything to stop you, you returned the embrace by wrapping around the mature woman’s back before you bust a fat nut in her snatch. The borders of your sight grew a frosty white as you shot several bursts of your cum in Lofty. She too was enthralled by the pleasure as she screamed and howled like mad.
“Oh, and I’m the greedy one,” Holiday snarked, yelping again as you slapped her again. “Dear, all that talk is just you projecting. But, why don’t we let your sister-in-law have a crack at him.”
“Fair enough...” Lofty moaned as she dismounted you. Drips of your seed leaked out of her snatch. For some reason, you were still as hard as a rock. You were a mix of weirded out and amused. “Mane, go on. It’s your turn and I can tell how bad you want it.”
The beautiful woman’s shy demeanor was coming back as she looked at your impressive manhood. You waited patiently and quietly as she slowly moved onto your lap and placed her soft and gentle hands on your shoulders. Grabbing your shaft, she lined it up to her slit and let gravity take care of the rest. She gasped but was quick to recover. You could tell that she has quite a bit of experience.
“Hmmm, not lacking in skill at all,” you said. “I guess you and your husband had some fun when travelling the world.”
“Not to mention, I'm incredibly horny." she purred, gripping your shoulders no longer bearing a timid tone. “Now, I may be an old lady, but I’m still more than capable of giving you the same wild treatment I give my dear husband.”
Tightening her grip, Mane started slow and sensual, pivoting her hips as if she were dancing. Already, your cock quivered from the joy and excitement of being inside an athletic cougar. It reminded you of your time with Windy Whistles—Same energy, but with slightly more style.
“Ready sweetie? I think a nice boy like yourself deserves a fun and wild ride for being so good to all three of us,” she announced, rapidly kissing all over your face. Blushing, you were forced to endure it as her grip didn’t get any looser. The fact that she was hanging onto you as if wrangling a ferocious beast proved just how much she embraced the life of adventure.
“Treat her nicely and I’ll let you have another go with me,” Lofty purred, sitting next to you and obviously not sated.
“And you still haven’t filled my own beaver, so you’d better hurry up,” Holiday added.
“Going to be plenty occupied here, ladies...” You grunted as Mane began to ride you like a ravenous beast. “Y-You both did... a pretty good job... Always a chance for more... later on...”
“K-Keep your eyes on me, baby...!” Mane demanded while stuttering. “After t-today.. ah... who knows w-when we’ll have the... chance t-to do this again...?”
You didn’t respond to the woman’s distress with words. Seeing how none of that might ease her, you locked lips and invaded her mouth with your tongue. Gently, you caressed all around her beautiful body to ease her tension. She seemed to be melting into you and her worries were fizzling away.
“Don’t focus on the future...” you whispered before playfully slapping her rear, “...just pay attention to what’s happening right now. I thought you were a WILD gal, was I mistaken?”
“Right...” Mane said as she took a deep breath. As she stared into your eyes with a look of extreme hunger, you had no idea what you’ve just awakened. “Thankyou for the encouragement. Now I’ll show you what a wild gal can do... Buckle up, young man!”
Taking your arms and pressing them to your sides, Mane purred as she wrapped her arms around your form. Her sheer strength prevented your arms from moving around. Caught in a cougar’s embrace with no easy way to break free, all you could do was sit idly and let the woman ride you till the moonrise.
Holiday meanwhile wanted your attention as well, and you felt her grab your arm and guide it to her moist pussy. Lofty grabbed your other arm and brought it up to her breast, encouraging you to get another feel.
‘Three for the price of one? Are you feeling lucky today or what?! ’ Milflove chimed in with a laugh. Unfortunately for him, you ignored him and focused on giving Mane a good time. ‘Ah okay. I’ll leave you to this. Didn’t save me some.’
‘Fair enough, ’ You mentally replied, ‘This is my time and you can just watch.’ You shifted your focus back to the cougars crawling all over you. Face full of tits, hands and lap full of succulent pussy, few could only dream of such an opportunity.
Living up to her reputation as a wild woman, Mane, with no warning, got up and forced you to the ground. Hovering over you, she licked her lips like a lion hungering for its prey. You couldn’t move and were at the mercy of one of the hungriest MILFs you’ve seen so far. Beautiful and wild, you had to respect her husband for choosing wisely. Lucky bastard.
“Sorry, my sisters.” Mane purred as she aligned your cock to her slit, “I want this young man all to myself. You both had your run.”
You had to stop the woman right there as you detected greed in her voice. “Hey Mane,” You groaned as she impaled herself on your cock once more, “If you’re going to be going this, shouldn’t your sisters also join in? How greedy of you.”
“I want you all to myself!” she growled. “I love the feeling of your cock so much!”
“Now, now,” you spoke up to prevent another argument. “If you refuse to share, I won’t please you anymore. I told you three already that I won’t tend to a lady who only thinks about herself.”
Before you knew it, your cock hit past it’s capacity and shook as it unleashed its life giving seed into Mane’s womb. With the knowledge that her tubes were tied, you were able to enjoy it tons more. On instinct, you thrust your hips without even thinking about it. Your hands remained where they were, with your right hand squeezing Lofty’s breast tightly, while the left hand thrusted into Holiday’s pussy almost as fast as your manhood.
“Fuck me...” you wheezed as drops of sweat dripped from you. “If sex was a sport... I’d be a motherfucking champion...”
“I-I can... vouch for that sweetie...” Mane whispered as she dismounted you and gestured for Holiday to take her place. “Okay, step-sis... It’s your turn now...”
As Mane crawled to your now vacant hand, Holiday swiftly dropped all of her weight on your manhood, making you grit your teeth. With that huge, plump rear of hers bouncing on top of you, you just had to to take your hand off of Lofty’s breast so you could smack her wife’s ass again. Rather than moan like last time, Holiday immediately giggled.
“That... is a nice snatch, ma’am...” You groaned as she began to bounce up and down your pole. Feeling that you were about to climax again, you gestured Holiday to come down and give you a kiss. Lowing her body down onto you, she didn’t kiss a beat as she began to passionately make out with you. The feeling of her tongue in your mouth was enough to send you over the edge.
The magnitude of your orgasm was something worthwhile. Lofty had forced your hand off of Holiday’s rear and back on her breast, while Mane continued to enjoy your fingers. Having two women exploiting your hands while another humping your cock was as hot as it sounded, and definitely an experience worthy of memory.
You moved away from Holiday’s mouth with a string of saliva keeping you linked. “B-Brace yourself...!” you warned before doing something most unusual by biting her ear. If you had to come up with an excuse, Mane’s wild nature was starting to influence you into acting like one of the many hungry predators she’s encountered on her journeys.
Even after your life-giving seed erupted from your pecker, filling the mature woman to the brim, the trio refused to let the fun stop. You lost track of how many times you filled each of the beautiful MILFs, but since you didn’t have to worry about impregnating them, you held nothing back as you continued having your way with them throughout the night.
Author's Note
Sorry for the wait. Between school and this damn quarantine, been quite stressful. Anyway, here's another chapter. Hope you'll enjoy it. :)
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
Chance Encounter(Dean Cadence)
It was another day Crystal Prep and another day of staying after school for a swim team meeting. You got pressured into joining by your overbearing parents to help you be more outgoing. But, you knew the true reason they made that move for you. They were afraid that you’ll get hooked on doing hardcore drugs, barring the fact that you’ve never had nor will entertain such thoughts. But, you being you, you rolled with the punches to see where it would take you. As you spent more time with the team, your physique started to improve and you lost quite a lot of extra fat. Over time, the girls at Crystal Prep took notice of you, sometimes gawking at your build. You weren’t incredibly muscular but handsome enough to where you could have a good chance with the ladies.
As you and the swim team wrapped up the day’s practice for the upcoming games, you sat at the bleachers while you saw the rest of your teammates leave. Ignacio, one of your friends on the team walked over to you with a quizzed look on his face.
“Yo Calculus, why are you staying behind?” Ignacio asked “Everyone else is leaving.”
“I’m just catching my breath.” You said with an exhausted look.
“Well, hurry up if you don’t wanna get locked in and Dean Cadence is going to do her door locking rounds soon.”
“Ok, I’m going to be taking a shower here though. I much rather not have my car smell like a dirty gym sock.”
“Well ok, but be quick about it. If Cadence catches you here this late, both she and Cinch will tan your hide.”
“Don’t worry about that. I can deal with them.”
After your friend walked out the doors, you breathed a sigh of relief. Your last statement, however, was a half-truth. While you didn’t fear their anger, their impending call to your parents made you quake. If there was one group of people you didn’t want to anger, it was your parents and they can get rather angry if you stepped out of line. However, Ignacio’s mentioning of Cadence eliminated your worries to an extent.
As you stripped naked and hopped into the shower, your thoughts drifted to that of one of the women of Crystal Prep you had the hots for: Dean Cadence. While young, compared to the other staff members, her commanding position is betrayed by her sheer beauty. Cute face, gorgeous eyes, stylish hair, perfect figure and luscious hips make her the subject of a lot of your fantasies. Sadly, she got married to Shining Armor a few years ago and they recently had a kid. While your chances with her are nil, erotic thoughts about her still danced in your dreams. Even just a mere mental image of her in work clothes is enough to make your dick stand at attention.
As you thought more and more about Cadence, you felt a certain area of your crotch tightening up. You looked down and noticed that your shaft became rock hard from just a thought alone.
“Aw fuck,” you muttered. “Might as well then.” Contemplating a solution, you decide that since the flowing water was going to keep you clean as you whack off, there wasn’t anything keeping you from a quick masturbation session. Double checking for anyone nearby, you waste no time in grabbing your dick with a single hand.
“Here goes nothing.”
Slowly, you stroke your dick as images of the ever-so-sexy Cadence invade your conscious, images of her naked, busty form. Fantasies of you and her doing the spoons position only furthered your arousal as you quickened the pace of your strokes. You eventually found yourself lost in your own pleasure and the hot streams of water only served to magnify the effect. Little did you know, the moment was soon about to turn awkward in a big way.
In the midst of your self stimulation, you failed to notice the soft sounds of footsteps on approach. It was truly amazing how a showerhead could be a pseudo sound muffling device from its squeaking noise. At one point, you swore that you’ve heard a voice sounding off but you weren’t sure what it was. Then, at the corner of your eye, you saw a pink hand grab the shower curtains.
“Hey, whoever’s in here, what are you doing here at this time? It’s supposed to be clo-”
Just then, the shower curtains were pulled aside by the subject of your masturbation session. Dean Cadence just stood there as you held your erect shaft in your hand, staring at you in shocked embarrassment.
“Well… this sure is awkward.” You said in your mind. Awkward doesn’t even come close to describing what the situation felt like. There you were, in the showers, making eye contact with the school’s dean with your dick in your hand. Your instinct badly wanted you to freak out like a jumpy person watching Stephen King’s IT late at night. Your rational side, however, dictated that you’re to stay calm. Still gripping your pride, you worked up the courage to break the awkward silence.
“Ummmm… Can I help you, Mrs. Cadence?”
Her face registered all levels of embarrassment as her face blushed a deep red color. With her hands covering her mouth, all you could see was her eyes and they seemed to paint her mood quite well.
“I-I-I-uhhhhh… So sorry to bother you, s-student.” As quickly as she spoke her words, she dashed away from the sight of you showering. For the next minute, your mind processed a wide range of scenarios that would happen next. Would she just run off and the next run in be awkward? Would she call the police and the both of you face serious charges? Expulsion? Each mental visualization of different possibilities only served to heighten your already rapid heart rate. All you wanted to do was to try to de-escalate the already precarious situation.
Wrapping the towel around your waist, you walked out of the shower and began searching for the spooked Cadence. You eventually found her sitting on one of the benches near another row of lockers. You heard what could be quiet gasps as you approached her from behind, curious as to what she’s up to.
“Hey, Mrs. Cadence?” You called to her with no response. “I-I would like to apologize for what you saw me doing back there.”
…
“I could explain what you witnessed me doing.”
…
“Mrs. Cadence, are you ok?”
“I’m… I’m fine, student. What were you doing here past closing?”
“Bathing after swim team practice. I don’t like my car smelling like a gym bag.” You knew that she thinks you weren’t telling the complete story. She saw you beating your meat in the showers and she probably knew you were. But, she didn’t know that she was the one you jacked off to.
“Well, you should know better than to stay on campus after closing.” She said, standing up with her back still turned to you. “You are in some deep trouble for that. W-We *gasp* ssshall discuss this *gasp* next week with Ms. Cinch.”
You paid no attention to her words. All you could focus on was the fact that she was gasping with every other word she uttered. With careful observation, you noticed that her arms appeared to be centered towards the front of her waist and only her right arm was making slight movements. You began to put two and two together: her gasps, hands presumably centered towards her crotch, and only one of her arms were moving. You had a good idea of what she was doing but you needed visual proof to confirm it.
“Ok, what are you doing, Mrs. Cadence?” Your words appeared to have made her jump in surprise, like a reaction towards something she was hiding about to be discovered.
“N-N-nothing! Never mind! Mind your own business, student!” You didn’t buy it. She was clearly up to something and you knew it. Walking closer to her, you quickly grabbed her right arm. She struggled to break free of your grip but your inquisitive attitude only made you all the more determined. As you finally grabbed hold of her wrist, to much of her objections, you saw a coating of moisture on her fingers. You took a quick whiff and found the liquid to be musky and… oddly arousing. Snapping back to reality, your earlier suspicions have now been confirmed.
“Mrs. Cadence, ” You gasped in shock. “Y-Y-You were schlicking, weren’t you?!” You knew it, you fucking knew it! Though, you did see it coming after she caught you in mid-masturbation. She was aroused by the size of your member, but, she was a married woman. Why did she suddenly run off just to fingerbang herself to you being buck nude? Why didn’t she immediately close the curtains or never opening them to begin with? At that point, you had a lot of questions and no answers to them. Still gripping her wrist, you start to pull her closer, causing her to try to get away.
“Let go now! I’m warning you, student! You’re on the thinnest of ice here!” She screamed as you started pulling her back towards you.
“No! We’re going to talk about this! I’m not letting you go until I get an explanation!”
“You’re not the one to talk! I saw you with your… thing in your hand!”
“Well, then why were you staring at me for that long when you shouldn’t have opened the curtains?”
As she pulled away again, you responded in kind. However, it was the spark that had finally set off the powder keg the situation was. Her high heel shoes weren’t slip resistant and she slipped and fell on top of you, knocking you to the floor like a wooden domino. With a loud thud, you winced at the pain of your hand being bashed between the tile floor and your hard skull. The good thing was that your head didn’t suffer anything other than a minor bump.
However, Dean Cadence laid on top of you, her beautiful mounds squeezing against your chest and her lips locked with yours. Immediately after you both opened your eyes, Cadence had hastily broke the kiss in embarrassment, not that you didn’t mind the accidental gesture. The atmosphere felt incredibly weird and erotic at the same as your now unveiled member tightly pressed against Cadence’s clothed nether lips. A tingling sensation ran down your spine as you tried to process the situation, looking into her blank stare.
Without warning, Cadence suddenly resumes the accidental kiss. It felt different that time, like it had a deeper meaning and purpose behind it, similar to how a lover would give one. Becoming more relaxed from the sensation, you closed your eyes and allowed yourself to become lost in the kiss, resting your hands on the back of her head and her nicely firm yet soft rump. As the kiss went on, your shaft got harder and harder, causing Mrs. Cadence to let out a soft moan breaking the kiss.
“Mrs. Cadence, why?” You asked in slight shock, still reeling from the earlier experience.
“Just seeing sight of you like that made me wet. I never expected you to be that… gifted.” She replied, referring to your dick. Admittedly, you felt flattered that one of the hottest women in school complimented your lower anatomy. Still, part of you felt that it felt wrong because she is a married woman and the potential fallout would be painful.
“But, you’re a married woman, to Shining Armor no less!” Holding your face in her hands and caressing it with her thumbs, Cadence gave you those half-lidded ‘bedroom’ eyes.
“No need to worry about it.”
“What?!” You gasped in surprise.
“Me and him are in an open marriage. He said that it’s fine for the both of us to have sex with whoever we want as long as it doesn’t result in pregnancy.”
“Hmmm, that sounds… reasonable.”
“Oh, it is, Mr…”
“Calculus.” As you gave your name to her, Cadence stood up and put her hands on her damp coat. You anticipated what she was going to do next but not how arousing it’ll be. The sensation ate away at your mental fortitude, making your anxiety grow stronger. You badly wanted to strip her naked and spoon her. But, you decide to go along with what she has planned for you.
“Ok Calculus, I have a couple of questions before I go any further: How old are you and are you a senior?”
“Yes, I’m 18 and graduating this year.” You softly said.
“Who were you jerking to in the shower?” Damn, she got you there with the question you were ashamed of answering truthfully. But then again, due to the predicament you’re in, it didn’t really matter. It was more of those scenarios of admitting to a crush that you love her deeply. With one big gulp, you swallowed your pride and decided to tell the truth.
“Y-Y-Y-You, Mrs. Cadence.” With your admission, Cadence gave a rather mischievous smirk as you closed your eyes and braced for the worst. However, after several seconds, you opened your eyes to a sight that you’ll never forget.
Cadence stood before you, completely nude. Her D-cup breasts jiggle as she swayed her rack, side to side. There were no signs of a bush near her nether region, a truly wonderful sight of the Dean. There, Cadence gave you a smile that could only be known as the bedroom smirk.
“Okay Calculus,” Cadence started. “ I'll make you a deal. Get me to cum first and I'll let whatever fantasy you have about me come true.” She said it, she was going to make your dreams. You were going to spoon her but you have to fight for that pleasure.
Without warning, Cadence straddled your face with her puffy pink vulva level to your mouth. It was dripping wet with the same fluid you found on her hands. Like before, the scent was musky and arousing.
“Just the sight of your package is making me wet down there.” Cadence moaned as she brought her mouth close to your shaft. The subtle breaths from her sent shivers of ecstasy through your spine as she brought her mouth closer and closer to your pride. “Please, don't disappoint me.”
As you brought your mouth closer to her pussy, you felt a wet and squishy sensation snaking around your rod as Cadence gives it a lick. The spine-tingling sensation of sensual pleasure was only magnified by her taking your the length of your dick into her mouth, bobbing her head up and down. To say that it felt good would be underselling how it felt. It felt like getting blown by a goddess. In that moment, you remarked in your head that Coach Shining Armor was truly lucky for getting a wonderful woman like Cadence. Getting those thoughts out of your head, you divert your focus to licking her vagina.
Once your tongue made contact, you heard what sounded like muffled moans from her as your tongue began its assault upon her nether lips. From how wet she’s becoming from your licks, she was enjoying this as much as you were. Despite the smell being musky, the wetness tasted like the perfect ratio of salty and sweet. You were determined to taste more of it. YOU were determined to make her orgasm first.
While you were licking her lower lips, your tongue brushed over a small nub that made her quiver. Pulling your tongue away for a brief moment, you realized you hit her clitoris, her achilles heel. With her muffled moans fueling your drive, you continued to ravage her clit with your tongue, flicking it, brushing it, and even rubbing it between your teeth. With each maneuver, you felt Cadence quiver and writhe with pure bliss. Little did you know, she was planning her endgame. In the midst of her pleasuring your knob, she landed a firm but soft grip on your balls, massaging them as she continued to suck on your shaft. The sensation was powerful, briefly stopping your assault. You were, in no way, going to let her get away with it. Thinking hard and fast, you devised of a plan to rock her world. In a heartbeat, you jammed her tongue in her moist love tunnel.
*Gasp* “OH… MY GOODNESS!” Cadence gasped as she was overwhelmed by the feeling of your tongue in her pussy, momentarily removing her mouth from your penis. With that, you had a brief moment of respite but you were sure she was going to recover from the surprise pretty soon. You wasted no time in resuming your tongue’s intrusion into her vulva. She was still recovering but you planned on keeping the momentum and then some. You used two fingers to scout around for her clit and rubbed it between them. She let out long and loud gasps and cries of pleasure as you ravaged her on two fronts.
It wasn’t long before she let out one final scream of orgasmic bliss as she came, drenching your face in her ladycum. You felt her inner walls grip tightly around your tongue as her orgasm went on. You held her lower lips to your face as she continued to become lost in her release, taking in more of her sweet ladycum. After a minute of intense pleasure, her orgasm died down, rolling off of you and on to her back, panting in slight exhaustion.
“That… was amazing, student.” Cadence panted as she sat against the lockers with you. “You should know that I’m a woman of my word. You made me cum first so I’ll be willing to make your fantasy come true. What is it you want to do?” It didn’t take long for you think on that end. Your earlier masturbation session made you think of a most sensual fantasy about her. Wasting not a second more, you blurted out your answer.
“I’ve always wanted to spoon with you, Mrs. Cadence!” Your words were met with a loving smile from her and a peck on your lips. As she stared you in the eyes, she held your chin with her index finger.
“Please, just call me Cadence. You deserve that privilege.” With those words, she turned her back towards you and laid on her side, lifting a leg up. “Now come, take your prize. You also don’t need to worry about getting me pregnant; I’m on the pill.” Gulping at the realization that this was the moment you’ll lose your virginity, you wasted no time in getting behind her and wrapping one arm around her midsection and guiding your shaft to her vulva with the other. Once you felt that feeling of her wet lower lips on your tip, you took the guiding hand and held her raised leg with it, pushing your lap howitzer into her vagina. It was an all new feeling to you. You were finally having sex with the woman of your dreams, the dean of CPA no less. Her love tunnel was gripping your member tightly as its warm and wet feeling sent new levels of pleasure throughout your nerves.
“So, how do you like it?” Cadence moaned with a sultry tone.
“I-I-It feels… magnificent.” You stuttered back, still in shock.
“Congratulations, consider yourself a virgin no more.” Catching you by surprise, she plants another kiss on your lips. However, it was fueled by pure lust than the earlier ons from just the spur of the moment, it was pure unbridled passion. Fueled by lust and confidence, you began to thrust in and out of her pussy, earning muffled moans from her as she kept the kiss with you.
“Calculus, please! Harder! Faster! Deeper!” Oh that naughty Dean of yours, talking dirty to you only added fuel to the fire that was your passion. Obliging her request, you redoubled your efforts and did what she begged of you. As your dick reached further and further into her love canal, you were stopped by a fleshy wall. From your time in biology, it didn't take you any thought to figure out that you reached the entrance of her cervix. Each and every time your tip rammed against it, Cadence would let out an excited Yelp as her inner walls gripped tightly around your member, as her climax was near and yours was soon to follow.
“C-Calculus,” Cadence with a pleasured stutter. “ I'm… about to cum!” It also didn't take that long for you to reach that level of buildup in your loins.
“Me too!” You grunted as you upped the tempo of your thrusts. “Let's cum together!” Letting go of her leg, you wrap your other arm around her chest as you held her tightly against you. With a few more hard thrusts, your dick quivered and throbbed as you released your seed into her womb. Spurt after spurt, your seed filled her insides as her walls tighten around your member with her own orgasm, milking you for every drop you had in your loins. As both of your respective orgasms died down, you held Cadence against you, not pulling out yet as you brush her face with yours while engaging in post coital cuddling.
“That was wonderful.” Cadence said as she got up from the floor, breaking the spooning embrace. “How did you last that long?”
“Dunno, I guess it was from training my stamina while on the swim team.” You replied with a shrug, getting up as well and reaching for your spare clothes.
“For your first time, you did good.” Cadence complemented. “With that level of stamina, you can have a line of ladies wanting to do you.” Truth be told, you were approached by quite a few of the girls in the school, sometimes with them doing the flirting whistle sound. But, your busy and structured schedule prevented you from reciprocating those advances.
“Well, I tend to go with the flow when in that regard. If it happens, it happens.” After you got your spare clothes on, you noticed Cadence putting her still slightly damp attire on as well. “Anyways, I have to get going. My parents like to freak whenever I'm out for a long time.”
“Don't worry about me, Calculus.” Cadence giggled as she put her coat back on. “I still have part of my rounds to do. I'll see you next week. Take care!”
“You too, Cadence.”
As you traveled towards your house in your Camaro, you reflected on what happened earlier: you lost your virginity and you realized you fantasy with the woman you had the hots for. You considered it to be not only the best day of the week but also of your high school career. You drive on down the road in satisfaction as you feel proud of yourself.
Little did you know… you lit the match in the metaphorical room of gasoline and the flames are about to burn you.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
MILFlove's 2 Weeks off - Part 1: Payback (Principal Abacus Cinch Revisited)
It was a bright and cloudless morning and the sun was beaming its light upon your face. You reveled in the calm as you began your two weeks vacation. Initially reluctant, you accepted it as your mind and body needed some relaxation. Since it was mid morning, it was the perfect time for a walk. It was a good way to start your morning, but hunger began to make itself known well into your exercise. Preferring something light and something with caffeine, you walked into a nearby coffee shop. It was atmospheric and somewhat pricey, but your income didn’t make you worry.
“One medium iced green tea and an egg & cheese bagel, please.”
“Okay, that’ll be $7.34.”
As you grabbed your breakfast and took your seat, scanning through the newspaper in front of you. You didn’t find any story that caught your interest except for one about the new community center being opened next week. As you flipped through the pages, your ears caught the sound of someone taking a seat.
“Was it two years or four? I wonder how long it’s been, Mr. Crunch.”
Lowering the paper, you were greeted by a familiar face. Sitting in front of you was Principal Cinch. You were a bit surprised to see her since high school, in a coffee shop of all places. You remembered her dragging you into her office and doing the horizontal hokey-pokey, all of that due to you banging Cadence. Still, you were amazed by how word spreads like fire.
“Woah,” You said. “I never expected to see you here. How are things going for you, Cinch?” As you examined her more, you could tell that she looked like she barely aged a day. Aside from that, you noticed that she didn’t have her glasses, which struck you as odd. “Did something happen to your glasses?”
“Oh, I actually had laser eye surgery last year.” She responds. “It feels so liberating to finally see without having to worry about them.”
It was odd at first to see her eyes not behind any kind of lens. However, those beautiful fuschia eyes look absolutely captivating to look at. She still has the look of a woman gifted with experience.
“I can tell. So what brings you out here?”
“Well, Cadence and her husband are helping me do some renovations to my house today. I actually was on my to the home improvement store.”
“Alright. Would you like some help with that? I'm on some ‘state-mandated’ time off.”
“Well, only if you want to.” She said with a smirk.
“Eh, I'm just looking for something to do.”
After a few more moments of chatting and shooting the breeze, you went with Cinch to House Like New, a home improvement store that opened several months ago. She mentioned to you that she was redoing her back patio and that it would require a bit of extensive work. You walked down the aisles with her, grabbing lumber of varying sizes and purposes while grabbing paint and other stuff.
All the while you were helping with her errand, you could've sworn she was giving some sway to her hips, making her nice badonkadonk jiggle slightly. Looking at such a strangely hypnotic sight, words from years ago echoed through your mind:
“Well now, run along. And remember, we might run into each other again.”
It took you a few to process the situation and its inevitable conclusion. Still, you couldn’t believe that she’s presumably keeping her word after all that time. There in the aisle, it all came back to you how she caught you by surprise and copped a feel of your junk, all because you screwed Dean Cadence. Knowing her, she probably would try to do the same thing again. For now, you decided to play her game but on your own terms.
After you helped her gather all the materials she needed, you took a ride with Cinch to her house, making standard small talk along the way. She asked you how life was going for you and all that stuff. She seemed amused by your answers, noting how hard she worked to get to where she is. But there, you noticed a subtle seductive twang in her voice. It was as if she was metaphorically shaking her ass at you. As much as you want to mount her the second you enter house, you knew that she would be expecting something like that. You had your own plans and won’t be giving her any hints.
After about ten minutes of driving, the two of you arrived at her house which was rather big for an average fix around town. It had a rustic yet modern theme to it. You had to admit she has good taste. As soon as the vehicle parked, the front doors opened from which another familiar sight came out. You recognized as one of the girls you were friends with at CPA: Sunny Flare. Your head buzzed with a swarm of questions and a desire for answers.
“Ms. Cinch,” you asked. “What on earth is Sunny Flare doing here?” With your question came a small chuckle from your former principal, making you cock a brow.
“Well Mr. Crunch, she happens to be my daughter.” You were taken slightly aback by the revelation. In all the years you hung out with Sunny Flare, rarely did you ever suspect her of being the principal's daughter. There were a couple reasons you thought of as to why they've never acknowledged their relationship at school, but the reasonable conclusion is the avoidance of perceived favoritism.
“Calculus,” Sunny said, noticing you. “What are you doing here?”
“Well, it's a bit of a long story,” you replied. She took a bit to examine your confused expression with an amused smirk.
“Hmph, I bet you're surprised that Cinch is my mom.”
“Well, I sorta suspected it since, well, you do look a bit like her.”
“Well, like mother, like daughter as the saying goes,” She remarked as she motioned to her car. “Anyways, I hate to cut this conversation short but I have to get going. Ignacio is taking me out on a special date. See ya later, Calculus!”
As she sped off, you looked back on the times you, her, and Ignacio hung out after Crystal Prep. Though as awkward it was to see the two getting all lovey-dovey in front of you, you had to respect the amount of affection they shared. In fact, last week while you and Ignacio were having some bro time, he flat out told you he was going to propose to Sunny one day. Today might be that day.
“Every now and then, I have to take a moment to process how my dear Sunny growing up so fast.” Cinch started offloading her SUV. “Can you please handle the lumber for me?”
You nodded and hauled the lumber to the back patio. From your perspective, it looked rather nice with a few areas need for improvement. The amount of supplies you helped her procure told you that she wanted a complete redesign. After setting the lumber down, you walk into the living room where Cinch was waiting for you.
“I do appreciate the help, Mr. Crunch.” Cinch smiles. “I guess this would be the part where you leave, no?”
“No, I was actually looking for stuff to keep my mind busy.” You remarked. “I was originally going to watch bad movies at home until you surprised me.”
“Why thank you, Mr. Crunch.” She said, walking towards a hall. “Since Cadence won’t be here until around 1-ish, I’m going to go take a shower. Feel free to make yourself at home and grab something to drink if you want.”
As she walked away, you kicked back on the couch, cozy as the room it resides in. As soon as you heard the shower turn on, the heralds of lust returned bearing the most lecherous of thoughts.
You visualized your former principal standing naked in the shower, scrubbing herself down as her hands move all around her body. The very thought of seeing soap flowing from her perky yet sizable chest then down to her hips and flower and her long flowing hair dripping down onto and between her buns was enough to make you fully erect.
Wanting to satisfy that itch, you reached down into your jeans and began stroking your cock. The visualization of her bathing was further enhanced by the sound of her singing voice, smooth and sensual as velvet and seductive as the sirens of myth.
Then, a thought dawned on you as the word ‘seductive’ crossed your mind. You, in a vulnerable position on her couch while jacking off, would be an easy target for her if she snuck up on you. Knowing how she did it the first time around, you felt that it was time for some payback and you were gonna give it to her good.
You stripped naked and quietly approached the bathroom with your erection standing still and proud. Peeking through the keyhole and the semi-transparent shower curtain, you saw Cinch bathing herself. She had on hand on a soapy scrubber and another focused entirely on her crotch. It didn’t even take you two synapses to figure that she was pleasuring her cunt. Another thing you noticed was her hair was long and wet, nearly touching her sweet ass. All that before you made you subconsciously stroke away at your pecker. To see such MILF material before you was almost maddening to the eyes.
Having enough of just the visual, You did your best to sneak into the room. You worried that she might’ve noticed you approaching but you saw nothing to that claim. Seeing an opening in the curtains, you slipped into the shower to see pure mature beauty before you. Her hair, her figure, it was intoxicating. Being slow and silent, you wrapped your arms around her midsection and took hold of her hand with the scrubber. Cinch shook with surprise at first but eventually welcomed it.
“Hmmm, so you finally got the message.” She said as you began groping her tits and beaver to which she moaned. “I wonder when you first got the hint.”
“Well, I would have to say back at the store where you clearly shook that ass of yours.” Mentioning said part of her anatomy, you took that as cue to wedge the length of your cock between her asscheeks. You were still amazed at how good her ass felt. As Cinch moaned, you began grinding your erect cock against her ass, holding her tightly as you began kissing up her neck before meeting her lips with yours. She turned around to embrace you, squishing her D-cup breasts against your chest.
“My word,” Cinch gasped. “You have some nice pecs. It looks like you’ve never lost your build since you were my student.” As she resumed the kiss, you felt her embrace getting tighter. If it were any situation, you would have welcomed it. However, you knew what she intends and you were going to get some payback.
Without warning, you turned Cinch around with one swift movement and resumed your original position. The look on her face at the surprise turn of events was one of shock and arousal. You connected your lips with hers, dominating her tongue with yours with passion and determination. You didn’t let up, not one single bit, even as you began groping her tits and pussy. Though you couldn’t hear it, you could feel her moan.
The second you slid two fingers into her wet vagina, her head jerked back, breaking the kiss with some gasps for air. Now you could hear her lustful moans and they were as sensual as you last remembered them. Soon though, you found yourself grunting as your balls began to tighten as they prepare to unleash the timeless tide of cum.
You strengthen your embrace as your cock throbbed and pulsed as it opened the floodgates for your seed to shoot freely. Even as you came, you couldn’t stop grinding against the luscious ass of your ex-principal as both her ass and your crotch were covered in your thick white cum. Even your hand got drenched with her juices as her climax exploded. The volume and magnitude of her orgasm suggested that she was holding back since you last saw her. Letting your orgasms die down, you lessened you grip on Cinch, content that she’s exhausted, right where you want her.
“Jesus… fucking… christ!” Cinch panted. “How the living hell did you find the energy for that?” You found amusement in her using such vulgar language. To you, Cinch comes off as one of those people that never usually swear. However, from her lack of resistance, underneath all that commanding and intimidating aura is a woman with a rather unusual submissive streak.
“Well,” you said, aligning your cock with her glistening vulva. “Since you caught me off guard all those years ago, I think I should repay the favor.” You slammed your cock so deep inside her that it hit her cervical entrance. The sensation of the sudden impact caused Cinch to shudder and moan as her legs felt weak from such sudden pleasure. She was in the spider’s web… and you were the spider. “Interesting. Didn’t know some prim and proper woman like yourself could be a glutton for submission.”
“T-Touché, Mr. C-C-Crunch.” You brought your mouth close to her ear, your nose bellowing air that sent shivers down her neck.
“It’s Dr. MILFlove now.” You whispered as you began the assault upon her pussy, pumping and pumping your member in and out of her sex. With each thrust, you can feel her inner walls progressively constricting around your spear like a snake. As it grew tighter, the more effort you had to expend, but the pleasure heightened as well.
As you were giving Cinch the banging of a lifetime, she was able to swivel her her head enough to plant a kiss on your lips. With that, it was the catalyst to put you on the fast track to cum. But you weren’t done yet, far from it. You were going to make her your bitch like she nearly made you hers.
With several more good slams against her cervical entrance, your cock throbbed and pulsed with excitement as it expelled another load from your balls, flooding her womb with your seed. You continued to hump and hump her as you came inside her until the load was gone. Looking at her, you found that you load has caused her stomach to bloat slightly. By appearance, it looked like she was two months pregnant.
“Ohhhhh yeeeeaaaahhhh!” Cinch moaned, legs still weak but able to stand. “You’ve certainly improved since last time. How many women did you have, Dr. MILFlove?”
“More than I can count.” You nonchalantly replied as your cock slipped out of her pussy, still just as hard. You had the energy and it looked she was half-way exhausted. You weren’t finished and you were going to fuck her until she can’t walk. “So, I’m no slouch... ma’am.”
With those words, you align the tip of you spear to her anus and thrust forward with all your might. She screamed, gasped and moaned as her ass was invaded by your cock. As Cinch began to process the sensation, pain was soon replaced by a sense of pleasure. Never in all her time of having sex did she once consider anal, but she started to enjoy it.
“Oh god, DO IT!” Cinch groaned in a hoarse tone. “FUCK MY ASS AND MAKE ME YOUR BITCH!”
That was it, any and all restraints were gone. Nothing stopped as you started pounding her in the ass with the fervor of a tiger. Goddamn, her ass felt tight yet pleasurable, like the other times you tapped those holes. In the cacophony of her moans, screams, swears, and yelps, you sped up your ministrations to ensure you held up your promise.
The longer you thrusted, the more your grunts became pronounced. You were close to unleashing yet another load but you wanted to make the pleasure last longer. Using the sheer force of your will, you mustered up your reserve stamina and doubled your efforts as you balls tightened once more.
With one final thrust, your balls emptied themselves once more in a tide of hot white goo. You let out a primal roar as the last of your sexual stamina was ran dry, pulling yourself out of her ass as collapsed to the bathtub floor, dragging the exhausted Cinch with you. As much as you wanted to make small talk and do the occasional post-coital relaxation, you gaze drifted towards the clock in the room.
“Oh shit.” You muttered, snapping Cinch out of her daze. “It’s 10 til 1! We need to hurry up and get ready!”
With a nod, Cinch got up with your support and began cleaning each other spotless. Not a single hint of musk and sex emanated from your bodies. After all that, you got your respective clothes back on and relaxed in the living room, almost as if what happened earlier never did. However, the memory was still fresh in your mind and you savored every moment of it.
It was 1:22 pm and you and Cinch were relaxing in the living room watching the news while you drank some iced peach tea. The quiet calm was interrupted a pair of loud raps on the door that heralded the entrance of Shining Armor. Shining took a quick glance at you as if he remembered you from when he was coach of the swim team.
“Hey, I remember you,.” He said. “You were on CPA’s swim team. What brings you here?”
“Well, I’m mandatory vacation and was looking for something to occupy my time.” You explained. “It’s nice to meet you again, coach.”
As the two of you shook hands, the corner of your vision noticed the approach of Cadence, still as beautiful and radiant as ever. The moment your gazes locked, she gave you a subtle sly smile, like she was remembering what you and her did all those years ago.
“Nice to see you, Calculus.”
Author's Note
I would like to start this off by saying I'm sorry for not releasing the next chapter for this (for better or worse) fine and wonderful series. I would write a paragraph but I won't because I don't want to bore any of you peeps. But the tl;dr of my explanation is work, school, writing ideas for new stories and other IRL shit that would be too much to list.
However, over the course of my semi-stealth hiatus, I've managed to come up with a few more creative ideas for some future chapters. In fact, I would like to share a sample of the next chapter starring Posey Shy,
You saw Posey digging through her knapsack and pull out a plastic bag containing something you couldn't identify. She leans over to you and holds one the contents of the bag in hand. It looked like some sort of cookie but it clearly wasn't. It looked like some charred round slice of orange with some sort of stem that some funky scent.
"Here," She said. "Take it."
"What is it?" You asked, suspicion grips you.
"Oh, It's just a little snack. Quite nutritious as well."
You looked at the object with uncertainty. You don't know what that thing could be. But with dinner about two hours away, your hunger overrode your sensibilities as you took the snack and put it in your mouth. As you chewed, the thing had a hint of a stale taste to it yet it was offset by some strangely asian seasoning. You enjoyed the flavor and the semi-crunchy texture.
"Wow, This is good." You thanked. "Where did you get this?"
"My darling Flutter's friend Treehugger gave me these." She giggled. "It was from her personal stash."
As you swallowed the food, your head began to feel light as your senses dulled, almost as if you overexerted yourself during a workout. Soon, you began to hear things that had no visible source, seeing things that weren't really there. There, you realized what you ate wasn't a snack at all.
"What the fuck?" As your vision began to be more distorted, Posey knelt in front of you with an innocent smile. A wave of confusion washed over You as You began freaking out. "What the fuck was that?"
"Shrooms." Right off the bat, you knew what she was talking about. She drugged you with some hallucinogenic mushroom. Your first reaction was to get angry at being tricked into taking an illicit substance. As you were about to raise objections, Posey put a finger to your lips, silencing before you said even a whisper.
"Shhh, just relax and enjoy the experience." Just all of a sudden, as if you've let your phone on, a familiar tune began playing in your mind as Posey sashayed her hips seductively. As your surroundings turned into an undulating void of tie-dye colors, you were uncertain about many things but one...
You were in for one wild trip.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
MILFlove's 2 Weeks off - Part 5: Southern Comfort (Pear Butter)
MILFlove's 2 Weeks off - Part 5: Southern Comfort (Pear Butter)
You woke up, head still reeling from slumber. You took a few moments to stretch your back and scratch your morning wood a bit. Doing your usual morning routine of shower and shave, you were ready to conquer the day with confidence-fueled machismo.
As you were brewing the usual morning java, your phone buzzed on the table. Opening it, you saw that a text message was sent from “Julia. H ”. In it was a picture of her fingers holding a pregnancy test. The test read positive and the message read:
See you tomorrow, assistant.
“Same here, Ms. Harshwhinny,” you muttered as you set your phone down to read the newspaper that was dropped at your doorstep earlier. Apart from some of the funny comics that are usually included, nothing in the bundle really caught your eye with the exception of a bit talking about the impending arrival of the Canterlot Games. With your recent promotion to Ms. Harshwhinny’s assistant, you know that she’ll use your ‘skills’ in some form or another. But hey, you usually like to keep yourself busy. “Idle hands are the devil’s playthings.”
Just before you were about to take another sip of your morning wake up juice, your phone goes off . Picking it up, you saw who was calling you. Applejack was one of your friends from CHS that you always admired for her character. Honest and hardworking, she was the most dependable gal you want to have your back when the need calls for it. Answering your phone, your ears were greeted by her trademark thick country accent.
“Hey Calc,” She greeted. “It’s been a while since we’ve talked. How’ve things been for ya?” You always like how warmly she usually greeted you and others. She still sounded like the most down to earth girl you knew. To think that you would’ve hooked up with her after high school if you weren’t the cougar magnet you are.
“They’ve been good,” you replied. “Been so busy at work that I was given time off two weeks ago.”
“Heh, Ah figured that your focus wasn’t lost since school.”
“Not one bit.” Readily, your instincts told you that she didn’t call for the sake of idle conversation. As much as she tried to be subtle, you and even those who knew her could read her like a map. It was clear that she wanted something.
“So, what is it that you need help with?” With that, you heard her charmful chuckle as she gets to business.
“Ahright, our friend Derpy is wanting to clean her parent’s house before they come home tomorrow night. She asked me for help and Ah figured that bringing you along would help things.”
Derpy, Derpy, oh how you remember that girl. You saw her quite a bit when you were hanging out with Applejack and her friends. Goofy with a heart of gold, she was always a delight to have around. However, one of her eyes seemed to be crooked. Could that have been from lazy eye syndrome or an injury, the world may never know. All that mattered was that she was nice to have around.
“Well, things have been boring around here as of late. Sure, why not. After this, Sugarcube Corner on me.”
“Why that’s might nice of ya, Bucky.”
“Right, I’ll be over there in a few minutes.”
“Ahright, see you there.”
Hanging up the call, you did a round of preparatory stretches, wanting your limbs to be ready for the inevitable lifting of heavy objects and general cleaning. Not like your body wasn’t capable of withstanding intense physical labor, the last thing you wanted when carrying a heavy box is a cramp in any of your limbs. Even after a couple days of resting from intense workouts, you were eager to feel active again.
You arrived at Derpy’s folk’s house, about a ten minute drive. Like quite a few houses you passed by, it was big for one deep in the residential area. With a touch of old and new flair, it was a beautifully chaotic combination with its own unique charm. As you pulled into the driveway, you saw Derpy and Applejack sitting on the porch. Noticing you, they wore gleeful smiles. As always, Derpy’s smile was as cute and bubbly as ever.
“Calculus? Oh my god!” Derpy exclaims as she hug tackled you. “It looks like you’ve barely aged! What’s your secret?”
“Other than lots of working out, nothing special.” You got up and dusted yourself off with a slight chuckle following. “It’s good to see you too, Derpy.” You looked towards Applejack who was recovering from a hearty laughter from the brief spectacle.
“Nice of ya to be here. I knew I could count on ya, Bucky.” You and the two girls walked into the house. Like the exterior, the inside was an interesting mixture of both old and new styles, beautiful. You can indeed see that the house could use a fair bit of cleaning. Dust, a few scattered cobwebs here and there, and some clutter that seemed out of place, you can see why it would take the three of you tackle this job.
“Okay Calc, here’s the plan. Me and Derpy will tackle the upstairs area where the thick of it is. You can take care this floor and then you can move onto the basement. Derpy has a truck coming in and she wants to take some of the clutter to her folk’s storage space in the city.”
Looking around, it looked like there wasn’t that much to do on this floor. But, you can guess that the basement is where you would be needed the most. As of late, you’ve been lifting more in your workouts so it shouldn’t be terribly difficult at all. With a nod and a verbal agreement, you split from the girls and got started cleaning the first floor. You first made sure that any and dishes weren’t in the sink and cleaned if they were. After that, Your efforts began in earnest.
You dusted, vacuumed, swept and mod the various areas of the first floor. Because the bedrooms were on the 2nd floor, you didn’t have to worry about any of it. As for the bathrooms, you made sure they were as polished as a pair of boots and smelling fresh and clean. It took you a little more than an hour to get the job done. Now, time to make use of your muscles.
You climbed down to the basement. Most of what was down there was either in boxes or veiled with tarps. It looked as if Derpy’s family wanted to use the basement for something. A leisure room, a second living room, the purpose is a mystery. However, one object caught your attention.
It looked like a box with a bunch of lightbulbs and coils adorning its top. In the of the construct was a door, big enough for a human to fit through. It was like one of those time machines that would typically be seen in school plays.
“Heh, didn’t know her father was a set designer.” You mumbled to yourself as you entered the object. Inside, it was mostly blank with the exception of a panel with various buttons and dials. At a glance, it looked to be where you would input what time period you wish to visit. On a whim, You input your exact birthdate as a joke. “Here goes nothing.”
Pushing the biggest red button, you chuckle to yourself as the box made noises and shined brightly. But as smoke gathered and the box rumbled, You knew then and there that something was amiss. All of a sudden, a portal of blinding light pulls you into an undulating void of blue and light yellow. You were in too much shock and terror to acknowledge or process what was happening. Then, a bright light grew bigger and brighter as if it were actively approaching you until it enveloped your form.
Coming to, your eyes open to reveal you’re still inside the machine or whatever it was. Stepping out, You beheld trees and an early noon sky. Wandering around aimlessly, you found a small dirt road with a discarded newspaper nearby. To your astonishment and shock, the paper’s date revealed that the machine worked and you were indeed thrust back in time.
“Holy fuck, Holy fuck!” you whispered as your heart began to race from the revelation. As much as you want to go back, the machine’s computer said that you had to wait four hours to travel back. As you processed your quandary, you remembered from watching enough sci-fi that messing around in the past was a good way of fucking things up, right down to using your real name. Pondering for a brief moment, you elected to use an alias that you’ve just made up: Iron Wingheart.
You wandered around in the hopes of reaching a nearby town, frequently marking your path back. But, with a snap of a twig, you realized that you failed to watch your footing on a ledge. The last thing you saw before you lost conscious, hitting the ground was a particular tree with your alias’s initials.
Your head was buzzing pain as you slowly opened your eyes. As your vision slowly became more clear, you were able to make out your current environment: couch, some old styled living room, a taxidermy deer head over a fireplace… and an angelic feminine humming of a familiar tune.
Turning your head but wincing from the soreness, you found the source of the melody. It was a woman with bright orange curly hair. From what you could gather, her beauty was indeed matched by her honey-sweet voice. Her face then came into view… and it jaw-droppingly cute. It could make hearts skip a few good beats.
“Hey, take it easy,” she said in an alluring southern accent. “You suffered a helluva fall there. It’s a miracle I found you while I was hikin’.” With her support, you were able to sit up. Though you were sure that you could walk around, you knew it was better to take it easy.
“I appreciate your… *ERGGH, Dang it* … help, Ms. ”
“Pear Butter, pleased to meet you…” As your still intact memories spurred their gears, the one concerning your pseudonym immediately came to mind. Not sure of who she really was, you kept to your story.
“Iron Wingheart, ma’am,” you replied. Pear Butter then set down a tray of tea on the table in front of you. A pleasantly calming aroma of apples and cinnamon sucker punches your nose. Taking a sip, it became apparent that the scent didn’t lie. Impressed by the taste, you took another sip.
“Wow, this is pretty good. Who taught you to make this?”
“Oh, my mother-in-law taught me that.” Pear giggled as she took a seat close to you. “Though things were shaky at first, we got along quite well thanks to my hubby.”
Her scent, it smelled something like apples. Pears, maybe? Regardless, it was pleasant and welcoming, warm as the arrival of spring. Her close proximity to you allows for a better view of her features. Jumping Jesus, the only word you could describe her with is… adorasexy. From what her body spelled out, she was clearly a MILF with all the trademarks: a nicely shaped ass, bountiful bust, and a nice hourglass figure with a dash of confidence and cuteness. What’s more, she has freckles on her cheeks and a flower braided in her locks. Lord help your beating heart in the presence of such an adroasexy woman.
“Is there something bothering you?” Pear said, breaking your inner contemplation. You admit that she is a nice woman but you didn’t want scare her your real thoughts. With your restoring strength, you concentrated efforts on keeping your boner flaccid, feigning a headache from your injury.
“*Ergh* No, nothing is. Just my head sorta wandering, but I’m fine,” you explained. Thankfully, from what you could tell from her smile, she bought it.
“Alrighty, Iron.” Pear chimed as she got up. “I’m gonna go make some grub. Feel free to walk around if you feel you can.”
She disappeared into the kitchen, leaving you free to explore the living room with your legs still feeling a bit wobbly. It had the look and feel of a nicer variant of an old country home, simple yet cozy. The windows showed what looked to be some sort of orchard. What it grew, you didn’t know. Turning your attention back to the inside, a framed photo caught your attention. It was Pear Butter, a man with blond skin and red hair that looked to be her age and presumably her husband, and a young boy.
From a glance, he was obviously Pear Butter’s son and looked much like his father with his skin and hair colors switched with the latter a darker shade. However, you couldn’t help but shake the feeling that you’ve seen him before. It was a big case of deja vu as you’ve sworn you saw that someone before but possibly older?
“I bet you’re wonderin’ about that picture there.” Shifting your head, you saw Pear Butter entering the room with a tray of sweet-smelling baked goods. “Me and my husband took that with our son when we went on a fishing trip. The look on my son’s face when he caught his first was priceless. Wished my camera was working that time.”
“Hmmm, and that looks like a happy moment there,” you quipped to Pear’s delight.
“You bet your noggin it is. Here, have something. You have to be famished.”
You looked upon the tray. Good lord does it all look scrumptious and smelling of sweet sweet apples. You chow down on what looks like a turnover and the taste was absolutely magnificent yet strangely familiar.
“So, how is it?” Pear inquired.
“Delicious. Out of all the turnovers I’ve had, this beats them all.” With an excited squeal, Pear Butter wraps you in a sudden embrace. As much as you liked the hug, the awkward feeling of her breasts against your chest made you not like it as much, fearing your erection coming. “By the way, where is your family?”
“Oh, my son is out sleeping over at a friends house while my husband is out of town for something concerning the farm. He’ll be back in two weeks.” You notice her last bit was said with a sigh which concerned you. If your experience was anything to go by, such a sigh was the calling card of loneliness. On one hand, you were concerned, on the other, you wanted to avoid an awkward situation. But like always, your concerned self won over.
“Is there something the matter? You sound upset.” You ask with genuine concern.
“Oh, it’s nothing.” You could tell it wasn’t the truth. People who are lonely usually tend to hide the fact they are or what causes it.
“Come on, I’ve seen that face and tone quite a bit. I can tell that you miss your husband.” With a sigh and a hanging head, Pear butter had relented and elected to spill her emotions to you, a complete stranger that she only met hours ago.
“It that sometimes when my husband is on these long trips, I sorely miss his company. He’s so loving and caring that being without him for a time makes my heart hurt.” That was it. With her admittance, she buries her face in your shoulder, wrapping her arms around your torso. It was there that you’ve discarded your previous mantra and embraced her with empathy. At that point, you no longer cared about your hard-on developing. Her embrace felt nice and warm and so did her nice chest orbs. “It’s not everyday that I get visitors.”
“I’m sorry for your loneliness.” You replied. “I would like to thank you for the hospitality. Is there anything that I can help with?”
Without no hint or verbal warning, Pear Butter dove into your face with a kiss, even managing to force her tongue in your mouth. You didn’t know what to think or do except play along until she stopped. Still, You couldn’t help but admit that she was an amazing kisser, passionate and loving. She then stopped to catch her breaths, still blushing with bedroom eyes.
“Pear Butter, Y-You’re married! Why?” You were genuinely at a loss for the first time having sex. From her tone, Pear Butter genuinely loved her husband. Yet, she was making sexual advances on you. It made sense if the MILFs you’ve scored were either divorced, unsatisfied, or in open marriages. But Pear Butter was different. Her feelings and words were truthful, like someone you knew.
“Iron,” She started, pushing some hair away from her eyes. “You seem like a nice feller. I know you think the same way. I DO love mah husband… but being without him hurts. Whenever my son is home, I can withstand it all. But with both them gone, it’s another story.”
“Sounds like a strong relationship,” you muttered. “But even if I agree to this, wouldn’t your husband find out? I don’t wish to get you in trou-” Pear Butter then held a finger to your lips. To you, the gesture was… strangely sensual.
“No need to worry about it.” She cooed in a southern tone. “To tell ya a little something, me and mah husband are having a bit of trouble tryin’ to have another. I’ll tell him it’s his if you do get me pregnant. So just enjoy this.”
With you lounging back on the couch, Pear Butter straddles your lap, nearly touching your package with her clothed snatch. Gripping the bottom rim of her sweater, she pulls it up, revealing her busty breasts being supported by a lacy bra.
“Like what you see?” You nod your head in agreement and open your mouth but was silenced by a shush from her. “It’s okay, you don’t need to say anything. You couldn’t hide your erection from my eyes.” That was it, all restraints were off, especially when she starts rubbing your throbbing cock in your jeans. “How about you set that thing free. I promise I’ll make it worth your while.”
Not giving a single fuck anymore and surrendering to your desires, you fiddled with your belt and kicked off your shoes, allowing you to pull your jeans and undies off. The length of your member sprang up and caught Pear Butter by surprise but didn’t make a noise apart from a silent ‘wow’. The heat of sexual arousal got to you and compelled you to remove your shirt as well. Pear Butter wasn’t far behind as she removed her bra to reveal her bountiful E-Cup tits.
The bedroom eyes, she gave you those all too familiar eyes. Seeing them countless times, you know at that moment that she was horny… and you could even smell it as the scent from her aroused pussy made itself known. She plopped those magnificently soft orbs on your lap and sandwiched them around your cock. Rubbing and rubbing, squishing and squashing, it was an amazing titjob. Over the years, you’ve built up some impressive stamina but it wasn’t limitless.
“Holy mother of god, this is awesome!” You groaned in pleasure. She then locked eyes with you, never breaking her rhythm.
“Oh, I can do better that that, slick.” Indeed she did do better as she began tracing her warm tongue up and down your shaft. Coupled with the massage from her breasts, it made your spine quake from lust. After a few more licks, she straight up takes her length in your mouth. Your jaw goes slack and you somehow broke a sweat as she garnishes her ministrations with fondling your sack.
“Oh fuck, oh shit, oh fuck, oh shit!” You gasped as you felt the tidal wave that is your orgasm approach with haste. You channeled all your will to make it last as long as you could. But alas, the inevitable still came to pass. You held her head tightly on your cock as you shot ropes and ropes of your load. Then, you felt a sucking motion which drained your load quicker. You knew right away what she did: she swallowed.
“Holy shit!” You laid back on the couch, catching your breath. Pear Butter wiped away the excess of your cum from her lips with a rather cute giggle. Wiping the sweat from your brow, you look towards Pear Butter who was now completely nude. The sight of her vulva with a nicely trimmed bush was enough to reinvigorate your spear.
“Well, I would like to thank you kindly for lasting so long,” Pear said as she laid upon the couch. Spreading her legs open, her pussy was revealed to be soaking with arousal. The scent of apples, cinnamon… and pears hit you. It was a strange combination but pleasing nonetheless. “If you would like, please have a taste of my pie.”
Barely a hint of subtlety was in her voice. You knew full well what Pear Butter wanted and dove in, licking her pussy with great fervor. Her moans and gasps made for a beautiful song of lust and eroticism. It served only to fuel your drive to please this lonely woman. As you took rapid nibbles at her clitoral nub, Pear Butter wraps her legs around your head. She enjoyed what you are doing but you want to give her something that she’ll enjoy even more.
With her pubes slightly tickling your nose, you quickly jammed your tongue in her cunt. Her loud scream was sign enough that she liked it and she wanted you to continue. You wiggled and snaked your tongue in her moist inner walls as they grew tighter and tighter around it. That and her hips gyrating around told you that it wasn’t long before she came. You wanted her to feel good, even when she inevitably orgasms. With a loud scream of your alias, a tidal wave of ladycum soaks your face. Squirming and screaming, Pear Butter rode her orgasm for a full minute before she calmed down, gasping for air like a fish out of water.
“Oh my stars and garters!” She gasped. “That reminds me of how my husband does it! Thank you so very kindly for this!”
“Glad you enjoyed it,” you replied.
“I do appreciate it. However, I want more.” Seeing her rub her pussy told you one thing: she beckons for you to fuck her, then and there, raw. “Please, fuck me!” You were hesitant at first to fulfill her wish but you remembered what she said at the start of this whole thing. If what she said was true, you didn’t have anything to worry about. She was one hot MILF and you were going to fuck her, even if you just traveled back in time.
Hovering over her, you look into her eyes, full of longing and desire. She wanted this and so did you. You slid your member inside her still wet vagina. The collective moans from you and Pear Butter seemed almost in sync as you both processed the feeling of being united so intimately. With wingding eyes and a loving smile, you and Pear Butter shared a passionate kiss, losing yourselves in the throes of intimacy.
Tongue against tongue, you held your bodies close in an embrace as you began thrusting in and out of her moist pussy. From the way she held herself close to you, it was clear that she craved it from being without her husband. One might call it clingy but others would call it devotion. From that picture, it was clear that their marital bond was incredibly strong. Sadly, it would often make loneliness troublesome. You were going to give her attention, even if it involved fucking her.
“Oh god yes! YES! I NEEDED THIS!” Pear Butter screamed as you continued your thrusts, not skipping your rhythm even once. As much as you want to spend an eternity banging her, good things couldn’t last forever. Her inner walls tightened around your cock her moans and screams became more rapid and hoarse. Her climax was near while yours wasn’t too far behind.
With one loud, unrestrained, and lustful scream, Pear Butter’s orgasm exploded around your crotch. Even as yours exploded, you continued to thrust, again and again and again. Not only did you want to please her, but you wanted to enjoy it as well. It felt so good, so blissful, and amazing. It was among the best orgasms you’ve had in a long time. Taking a few to catch your respective breaths, you both shared another passionate kiss, though short as it was.
“That was… amazing.” Pear Butter moaned, snaking her arms around your neck. “I feel much better now. Thank you.”
“My pleasure and yours.” You purred as you moved your hands through her hair. Just as you were about to lean in for another kiss, You heard the phone ring, slightly startling you. As much as you didn’t like it, you let Pear Butter go so she could answer it.
“Hello? What? Uh oh. No, don’t worry about it, dearie. We’ll go out for dinner tonight and maybe we can catch a movie. Don’t worry, I’ll be there in about ten minutes. See you then, my son. Mama loves you.” She then turns to you with a slightly disappointed look on her face. “Sorry about that, but my son’s friend got into trouble with his parents and his sleepover is cancelled. So, I have to go pick him up.”
“So our time has been cut short then,” you said with a sigh. “Mind if I go grab a quick shower before I go?”
“Sure.”
After taking a shower and making sure that every trace of your lecherous deed was gone. Both you and Pear Butter were back in your respective clothes, standing outside the farmhouse.
“Well, I guess this is goodbye then.” Pear Butter sighed as she briefly hugged you. “Will I see you again?”
“Well, I don’t know. I’m just visiting relatives from out of state. Don’t worry, I can find my way back to my place.”
“Heh, Ah know a guy fella like you can handle things. Well, goodbye Iron and don’t be a stranger.”
“Don’t worry, I won’t.”
As much as you appreciated her company, there was a good chance that you wouldn’t cross paths with her again. Pear Butter was an amazing woman in her own right but It was best to leave her with her family. Who knows, maybe you would see her again but for now, you had to get home. The time machine must be done charging by now.
After wandering around for about a good half an hour, you came across a familiar-looking tree. Upon closer inspection, it beared the letters ‘V.R.’, the initials of your alias. You knew then which direction you had to head in, helped by the trail you’ve laid earlier. Before long, you found the time machine, undisturbed and buzzing with power. Hopping inside, you configured the panel to take you back to the exact day and time you remembered you were from. Now, all you had to do was endure traveling through the timestream once more.
“Is he alright, AJ?”
“Well, his eyes are openin’ and he’s breathin’. He’ll be ahright. He’s tough as a work horse.”
“I hope so. I honestly never thought that thing would actually work.”
“That time machine thingamajig?”
“Yeah, thought my dad made it as a joke.”
Your eyes fully focused themselves as you now found yourself back in the basement with Applejack and Derpy surrounding you.
“Jesus, that was on hell of a trip,” you said as you stretched your muscles. “What the hell happened?”
“You… just proved my dad’s machine there actually works!” Derpy exclaimed in astonishment. “Where did you go to?
You explained your case and told her where you went and that you thought it was a joke. However, you didn’t tell her specifically what you did for obvious reasons. So, you just told them that you just wandered around town for four hours until you could come home.
“Well, you have a habit of getting into crazy spots there, Calc.” Applejack chuckled as she gave your arm a playful jab. “It reminds me of how mah ma would tell stories of mah pa when they were datin’.” That was something new for you as you never heard Applejack talk much about her parents. Could something have happened to them?
“Your parents?” You asked. Applejack then pulled out a picture. Apart from a very young Applejack being in it, it looked… an awful lot… like… a certain photo you’ve seen before. “What are their names?” You asked out of cautious curiosity. You heard Applejack sigh a bit before she spoke up.
“Mah dad is Bright Mac and Mah ma is Pear Butter.” She explained, getting slightly teary eyed. “I’ve never seen them since they went on that cruise. What happened to them?”
The last part of the first bit hit you like big pallet of bricks. It took you a few moments to process what you’ve just learned. Pear Butter was Applejack’s mother and you could very well be her actual biological father. Your heart began to race and you struggled not to panic over the revelation that one of your best friends was really your daughter. Thinking quick, you decide to excuse yourself to think about it all.
“Hey girls, mind if I go use the bathroom really quick,” You asked while keep your emotions veiled.
“Sure but don’t be too long. The truck will be here soon and we’ll need your muscles to help us.”
Making a hurried walk to the bathroom, you shut and locked the door. Hyperventilating and panicking, you whispered a stream of curses and various obscenities with the occasional banging of your head against the wall. You could hardly believe it that messing with time would result in such an awkward situation like this. You altered time and the result was Applejack being a daughter of yours. You’ve fucked up and now you’ll have to live with that fact for the rest of your life.
“Okay, okay,” you said as you splashed water on your face to snap out of your state. “Just forget it ever happened and don’t tell her ANYTHING! I hate to see what’ll happen if I told her the truth.”
“Hey Calc, the truck is here! Let’s get moving!”
There comes the distraction you’ve hoped for. You walked out to help your friends hauling heavy antiques to be stored, including the thing that was responsible for your predicament. You can only hope that no one will use it and that it’ll remain forgotten. Eventually, you’ll forget what happened to a degree…
..but it still happened.
“I need a drink.”
Author's Note
Well, here marks the end of the 2 Weeks off sub arc... and one of the craziest chapters I've written. When I started writing this chapter, I wanted it to end the sub arc in a way that was insane and also hve fun with it. Anyways, I'm glad that you enjoy the series so far because it'll only be getting more lewd.
Also, Calc's alias, Iron Wingheart, is a reference to my OC, one of them anyway.
View Online
Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars
A Boss's Adoration (Ms. Harshwhinny Revisited)
You wake up, looking out the window of your room. Clean and serene, it was a beautiful complement to the rising sun. The many get well cards from your family and various loved ones still stood atop the drawer on your left. As you sat up, The phone next to you began to ring. Answering it, you were greeted by a familiar voice.
“I take it that you’re awake by now,” Ms. Harshwhinny said.
“That I am, Julia,” you replied. It was always a pleasure for Ms. Harshwhinny to look out for you, being her assistant and all that. Still, it was an unusual departure from her strict and stern demeanor. All in all, you take it as you see it. But today, you were in a good mood that you’re being released from the hospital. “So, the docs are cutting me loose. Though I still have this damn cast.”
“No need to be so upset about it. Within a few weeks, you’ll be back to your old self. I’m just letting you know that I’ll be picking you up within a few hours.”
“Ah, wonderful,” you breathed with jubilation. “So, I can expect to see you her at around noonish?”
“Correct,” replied Harshwhinny. “No need to rush things. Just take it easy and you’ll be fine. As I’ve said before, you’re in good hands. I’ll see you soon. Take care!” With that last part, her voice carried a sing-songy tune to it. Part of you wonders about her change in attitude, whether it be her pregnancy throwing her hormones out of whack or genuine gratitude for helping her have a child. Still, you consider her a pleasure to work with, thankful for giving you a position worthy of your skills.
The door then opened and through it stepped Redheart. She looks upon you with lidded eyes, the same eyes you’re familiar with. Ever since last week that you’ve started sharing lustful nights during your sponge baths, she gives you that look every single time. But that look soon gave way to that of professionalism as Dr. Horace entered the room.
“Good morning, Mr. Crunch. How are you feeling today?” Horace asked, breaking the silence.
“Damned happy that I’m going home,” you shot back.
“Heh, I can certainly tell,” he said as he flipped through his clipboard “Well, all you really need to do is to get ready for the day, sign some discharge papers, and you’ll be good to go.”
“Done deal,” you muttered.
“Okay. Well, get ready for the day. Redheart will wheel you out to the front desk when you’re ready.”
“Alright. Thanks, doc.”
Once Dr. Horace left, Redheart helped you out of the bed and into the bathroom. As before, she washed every inch of your body, including your junk. Even though the moment gave you a raging stiffy, you both thought it best to not to start screwing then and there, as much as you both want it. Like always, she did a good job and helped you into your casual wear. It felt good to be in nice and comfy clothes after weeks of being in a patient’s gown.
Before you knew it, another nurse arrived with a wheelchair and a pair of crutches. With assistance from both her and Redheart, you were seated on the wheelchair, relieved at your change in mobility. But still, you had to stay put until your boss arrived.
As you were busy watching TV, staving off the long crawl of boredom, you heard a familiar click-clack of steps from down the hall. Turning around and facing the door, your sight was soon greeted by a familiar blonde-haired sight. Right away, she rushed over to give you a hug, pressing her rotund belly against you.
“Good to see you, Julia,” you whispered as she broke the hug.
“Likewise,” she replied, dusting herself off. “Now, let’s get you out of here.”
With the aid of some nurses, you were pushed to the front desk in the lobby. Once there, you’ve signed the papers, setting you free after weeks of confinement. From there, you were helped into Harshwhinny’s SUV along with all of your stuff and you were soon off and away.
“So, how does it feel to finally be out and about?” Harshwhinny asked.
“Good,” you replied. “But damn, I absolutely hate hospital food.”
“Well, you be pleased to know that we’re stopping at my place for lunch. We’re having butternut squash ravioli with a creamy garlic sauce. It was a recipe from my mother.”
“Please, you’re making me hungry, Julia.” You laughed, as does she. For the rest of the trip, the two of you made pleasant conversation with the occasional talk about work. From what she told you, you were granted the go-ahead to work out of your house until your leg was fully healed. All it will amount to is answering calls and e-mails from the financial department with the occasional meeting. Thank goodness for video conference technology.
Soon enough, she pulled up to a modest looking place with an orderly looking garden at the front. Being helped inside through your crutches, the interior shared the same aesthetics as the exterior. You’d figure for a woman as rich as Ms. Harshwhinny would live in a lavish place. But hey, to each their own.
“Come, sit down on the couch” said Ms. Harshwhinny. “I’ll be right back with lunch.”
Nodding, you carefully seated yourself on the couch with your crutches as support. It felt good to sit upright on something that wasn’t a hospital bed. You leaned back, closing your eyes as you took in the atmosphere. It felt tranquil, peaceful, and cozy enough that you could just fall asleep with not a care in the world. However, the scent of butternut squash and garlic kept your senses alert and your hunger growing.
“Lunch is up,” Harshwhinny sang, walking in with two plates of creamy pasta goodness. You both chowed down on the plate of pure comfort. Sweet and savory, it was amazing, reminding you of Sunny Flare’s stir fry. Every bite and morsel brought warmth to your soul. The best part of it was the creamy garlic sauce that had notes of parmesan. It certainly was better than the stuff that you had for weeks.
“Gotta say, never thought I’d like butternut squash,” you said, wiping bits of sauce from your lips. “I’m honestly very surprised.”
“Well, my mother knew cookery like it was at the top of her head.” Mused Harshwhinny. She then scooched closer to you. Your face grew a little red but it wasn’t anything out of the ordinary between you two. Carefully, she placed your hand on her belly, running it across its surface. Soft and smooth, it felt warm to the touch. As you ran your hand across her tummy, you felt a slight bit of force pushing against it. It was clear the life growing inside was getting antsy.
“Heh, I think it knows who you are,” she chuckled.
“You’re going to be a great mother, Julia,” you replied with a tender voice. Still, some thought kept eating at you. After your vacation months ago, she treated you as if you were a business colleague. Now, it’s as if she views you as something beyond all that. It only really happened after your accident when she would visit you every other day. For you, it could be anything. “But, why are you acting so friendly towards me?”
“Well,” she started, clearing her throat “I suppose I’ll be honest with you. I would’ve attributed my behavior to my fluctuating hormones but that would be an excuse. Ever since you impregnated me months ago, I’ve felt this sense of gratitude towards you. As for our arrangement, I was right to pick you. Your skills have proved most useful. When that accident happened…”
There was a hitch in her voice as she took a small pause. At a glance, she appeared to be calm and collected like she always was. Tilting your head, you noticed something small traveling down her cheek, a tear. Why was she crying? Was it for you? If her earlier statement was an indication, you knew right away what she meant.
Resting your arm on her shoulders, you gently pulled her into a hug, taking care to not hurt her baby. Rubbing her back, you gently rocked her as she cried a bit in your shoulder. Shushing her, you reassured her that everything was alright. Still, she was uneasy.
“I just… I didn’t want to lose you! I’m carrying your child and you’ve been the best assistant I've had! I’ve grown fond of you and I wasn’t about to let you go!” If there were anything you’ve learned since you started working for Harshwhinny is that she always meant what she says. Here, she’s spilling her guts to you, her assistant that makes sure nothing is wrong in the workplace. Still, it was a terrible sight to see her upset, knowing the effects it had on her baby.
When all seemed calm and peaceful, a hand gently reached for your cheek and you were pulled into a kiss with a blink of an eye. This one felt different than the last time you both did it months ago. It lacked purpose, fueled purely by emotion. It was also easy enough to lose yourself in the moment. Though you couldn’t move, Harshwhinny was kind enough to climb onto your lap. For the next few moments, you shared a silent yet powerful moment of intimacy. It felt so sudden yet it felt so right.
“Do you feel better, Julia?” you whispered.
“Much better,” she replied, “Don’t ever scare me like that again.”
“Well, I know better to not piss my boss off.”
“Good. But as much as I like our little moment, I would like to go somewhere more comfortable for both of us, like my room.”
“Good idea.” With her assistance, you got on your crutches and followed Harshwhinny to her room down a short hall. Her bed was a large one, no doubt could fit two or more people. At its head was a mountain of pillows of varying shapes and sizes. It looked like a big fluffy cloud to you. You carefully lowered yourself on it, slow and steady. Just when you thought that she would join you, she does the opposite and retreats to her bathroom. For moments, you wondered what she was up to before your answer walked back out.
Ms. Harshwhinny stood there, completely naked and holding a bottle of oil. Putting two together, your dick tingled at the thought. She wanted a massage, to have your hands spread a relaxing oil all over her pregnant body.
“Heh, I know you’re excited but I would much rather you be nude for this.” Following her orders, you removed your shirt while she took care of your undergarments. Once those were off, your cock sprang tall and proud. Harshwhinny smiled at the sight of it, recognizing it. “It’s been a while since I’ve had that cock of yours. I hope you won’t disappoint.”
“You know me, I never do.”
Handing you the bottle of oil, Harshwhinny laid back on you and spread her legs. Pouring a small amount of the liquid on her rotund belly, you worked your magic as you gently massaged the oil into her skin. Without much friction, it felt like a nice slide. Judging by her resting her head on your shoulders and a relaxed sigh, she dearly wanted this, especially from you.
“Ooooohhh yeeeesssssss,” Harshwhinny moaned, “that’s the ticket. As much as you like my belly, my breasts would like some love.”
Shifting your hands upwards, you gently caressed her milk engorged mounds. With the oil, it was like they melted to your touch. Every squeeze and rub earned you a breathy moan and a trickle of her milk. As kinky as you were, consideration for your boss stopped you from playing with her puffy nipples. You wanted to be sensual but not rough. Your efforts were rewarded with a slow kiss to your lips, making your dick tingle with excitement. As you stared down her belly, your mind hatched a devious plan and her being lost in pleasure offered you a window.
Gliding a hand downwards, you began rubbing her puffy vulva with the palm of your hands in a slow and fluid motion. Her breaths soon evolved into a cacophony of yelps, moans, screams, and utterances of your name. For too long, her condition and work schedule filled her with too much tension, begging to be released. A long loud scream echoed in the air as you inserted three fingers inside her moist sex. Using your thumb to give attention to her clit, it wasn’t long before your hand became drenched with an explosion of her essence. Harshwhinny bucked her hips as she rode out the entirety of her orgasm.
“Oh my, you still have your magic.” Harshwhinny moaned as she sat up. “This is bringing back… memories.”
“Memories?” you purred. “That was one hell of an experience and I never thought I’d be one for going to a massage parlor.”
“Well, I had to think of a way of making you mandated vacation start wonderfully.”
“Eh, it wasn’t too bad. A bit boring for sure but not terribly bad.”
“Honestly, I can’t tell if you’re an optimist. But I digress. There’s still the matter of your ‘reward’ for making me feel so good.”
“What reward?”
“Close your eyes, Calculus.”
Doing just that, you expected a nice blowjob from her. But oh no, you were given something far better. The moment you felt slick cold skin touch your shaft, you opened your eyes to see her belly firmly pressed against it. Up and down, it rubbed against your cock. Lord can only describe what you’re feeling in that moment. It was incredible, better than a blowjob. The way her body pressed against you nearly drove you to madness. Yet something other than lust drove her bellyjob. It was pure unchained intimacy.
“You like it, don’t you?” she purred “You like the thought of coating my belly with your big load? Go ahead, cum all over my belly when you want to.”
You desperately endured her motions, enjoying the rapturous feeling of the bellyjob. Bit by bit, you began to feel lightheaded, the signal of your impending orgasm. Once your grunts became more pronounced, Harshwhinny disengaged and started jerking you off. Just before you busted a nut, she aimed it towards her belly, coating it with your hot sticky jizz. Just the thought of cumming all over her figure turned you on immensely, making you shoot more of your load.
“My goodness. I thought you’d be spent after Redheart’s company. Then again, I know you’re not a one-pump chump.” She then crawled to your left and laid on her side, presenting herself to you. Then, she gave her ass a playful slap and a finger gesture that spelled come hither. “Now, you know what to do.”
Nodding, you scooched a bit forward and pulled her the rest of the way. Positioning your dick at her slit, you thrust your hips forward, penetrating her honeypot. You held her tightly as you began thrusting, all while giving her belly the occasional rub. Spooning had always been a favorite of yours ever since you banged Dean Cadence in high school. You always enjoyed the thought of holding a woman in your arms while you railed her from behind. It was the most comforting experience and it held a deeper meaning for you considering she carries your child. She wanted love and you were going to give it to her.
Turning her head around, Harshwhinny latched onto your lips once more in a battle of lips and tongues. She even placed her hands on top of yours as you rubbed away at her swollen abdomen. To think you’d be banging your boss a second time, luck has a way of sticking with you.
“Oh yes!” she moaned loudly. “Oh, I needed this so bad. Fuck me until I can’t feel anything! Fill my pussy with your cum!”
You didn’t need any permission to do so. You doubled your efforts and thrust like a mad man. Evey gyration tightened your balls further and further. Within the span of a few minutes, you shaft quivered and you blew your load in her snatch while still pumping in and out of her. Seconds later, Harshwhinny followed suit, drenching your crotch and the sheets below in ladycum. In the afterglow, a moment of silence was held between the two of you as your eyes made contact. By the time the ecstasy died down, the moon had started to rise and you were both tired.
“Calculus,” she yawned. “I don’t know about you, but I can just sleep in your arms right now.”
“If you want, I’ll be happy to accommodate that.” Reaching over, you pulled the blankets over your bodies, laying snuggly as you both started to feel heavy-eyed. As your senses started to relax and your eyes shut, Ms. Harshwhinny said something that made your heart stand still for a few seconds.
“I love you, Calculus.”
“I… I love you too, Julia.”
Author's Note
Well, the strict but closeted softie Ms. Harshwhinny makes her return. This time, she spills her heart out to her assistant. As always, I hope you all enjoy reading this.
