“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.