“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...