Looking back, it’s not hard to see where you fucked up.
You had done fine for most of your high school career. You had made the Honor Roll, you’re fairly popular, and you never got into any trouble. When you enrolled in Crystal Prep Academy, you were only concerned with doing well and getting out of school without causing a fuss. You played by the book, never skipped school, never even missed a day. You were content with your life of good grades and no conflict whatsoever. Then came last year’s Friendship Games. You didn’t participate, but you saw what happened. How could you not? And, seeing your school’s very own Twilight Sparkle turn into that weird magical demon thing made you realize something.
You were boring! Nobody would remember you for being a perfect student, because CPA was filled with perfect students. If you weren’t perfect, you attended CHS instead. Perfection was the norm, and you were about as perfect as can be. But that sucks. If everyone is perfect, then perfect means average, and who wants to be average? Not you, that’s for sure.
So, the next year, your last year of high school, you decide to tap into your inner bad boy. You only get one senior year, why not make it memorable? Your plan was to TP Dean Cadance’s house. Dean Cadance normally had a pretty decent sense of humor about this sort of thing. You figured that she’d be mad at first, but wouldn’t really try to kill you. The two of you would probably be laughing about it by the end of the week. So, you watched Dean Cadance come and go from school for a week to make sure you were hitting the right house, then you went to do the deed.
Right there. That’s where you fucked up.
Because, in your lust for high school infamy, you didn’t realize that Dean Cadance wasn’t going to her house that week. She was going to Principal Cinch’s, whom she was house sitting for while the principal was away visiting family for the week. So, when Cinch arrived to her house covered in toilet paper, she basically tore CPA apart to find the culprit. It wasn’t long before she found you, and threatened to have you expelled. Obviously, you couldn’t let that happen, not when graduation was so nearly in your grasp, so you bargained for your life. Eventually, she conceded that you could stay, if you cleaned her house for the next week. Top to bottom, inside and out.
Ordinarily, you would think that this was cruel, unusual punishment, but, from Cinch, you felt like that was pretty fair. Not only was she the queen of hardasses, with legends told about her vile detentions, but she was also about seven months pregnant. So cleaning her house for her, the house you messed up in the first place, doesn’t seem that shitty.
That’s what brings you here, to Principal Cinch’s personal home. You look up the house over, it’s deep blue exterior almost entirely hidden by the toilet paper you covered it in. You really got the place good. You splurged on the heavier, two-ply, name-brand toilet paper, too, so none of it had been displaced by the wind. Leave it to you to overachieve, even in your delinquency.
You meet the principal at her door, and she looks mad. Cinch has this snarl on her face, as if she smells something rotten. You try not to look at her belly. Or anything, really. Nowhere is safe. Her eyes are currently beaming with the rage of Satan himself, so that’s a no-go, and you can’t bring yourself to look at her body. Especially not how she’s dressed now. Cinch is normally never seen without a nice, prim, proper suit and skirt, but today she’s wearing yoga pants and a stretchy blue sweater to accommodate her round, pregnant belly. She looks comfortable, albeit mad as a badger and twice as scary. You have to admit, Cinch looks good for her age. She’s gotta be somewhere north of forty-five, but she’s got the legs, breasts, and ass of someone just hitting thirty. If she just smiled every now and then, she’d probably be pretty good-looking. Hot, even.
Not that you’re one to check out your principal. You’re just very observant, the sort of guy to pick up on things like that.
“Good of you to finally make it,” says Cinch. She sounds like she’s talking to her child who was out past curfew. “There’s a ladder in the backyard which you can use to reach the higher places of interest. I left out trash bags there as well, and I expect those bags in the can and the can to the curb before you get to work on the interior.” Her glare on you tightens. “Do I make myself clear, Mr. Anon?”
“Yes, ma’am,” you say, trying not to let on how truly intimidated you are.
“Good. I expect you done and working inside within the hour.”
Your eyes go wide. The entire house is covered in toilet paper, there’s no chance in hell you’ll be done in an hour! But Cinch didn’t bring you here to listen to excuses, which she shows by turning her back to you before you could even form words in your brain. She disappears into her home and shuts the door behind her, leaving you to get to cleaning. It’s a drag, but it’s the bed you made for yourself. Time to sleep where you shit.
You find the ladder in the backyard, gazing up at the mess you made. You shake your head, not entirely sure if this whole thing was worth it anymore, and you scale the ladder to get to work. Truth be told, it’s really not that bad. It’s tedious, annoying, and absolutely, brain-numbingly boring, but that’s the sort of thing any CPA student worth their salt is good at. You just slip in your earbuds and melt your brain with hard rock and heavy metal while you clean up your mess.
You actually make pretty short work of things. It only takes you about half the time you thought to get all of the toilet paper down off of the roof, and then only another five or so minutes to stuff them all into trash bags. The whole affair turns out pretty painless. After dumping the bags into the trashcan, and pulling the can to the curb as Cinch instructed, you make your way for the door. Nervously, you turn the knob and step into Cinch’s house.
It’s a nice place. You don’t know a whole lot about interior design or anything, but you get the sense that Cinch does. She has paintings lining the wall of her foyer, leading you into the living room. Cinch is waiting for you, sitting comfortably in her armchair reading quietly.
“Shoes off, please,” she says, not bothering to look up from her novel. You do as you’re told and pull off your shoes, placing them beside her own just next to the wall. “You may begin here. Dust and vacuum, then move on to the kitchen. My dishwasher is in need of repair, unfortunately, so I’ll need you to wash my dishes by hand. Then, upstairs is my study, just a quick sweep will do fine. You needn’t worry about the bathroom, or my bedroom. Can you handle that?”
“Y-yes, ma’am,” you say, unsure as to why you feel so nervous. Sure, Cinch is a spooky lady, but you normally hold your own against her. It’s something about how casual the situation is. Seeing Cinch just lounging about, her hair down from her typical neat bun, makes you a bit jumpy.
“Good. Get to work.” Cinch shuts her book and carefully stands herself up, one hand on the precious cargo she’s carrying. You think about offering a hand, but she’s up before you even take a step forward. “Now, if you excuse me, I’m going to take a long, hot shower. If you somehow finish before I’m done, take a seat and wait for me. I’m sure you can keep yourself occupied until then?”
She doesn’t wait for you to answer. She moves out of the living with a speed you wouldn’t expect from a woman as pregnant as she is. You try not to stare as she walks away, but it’s difficult. You’re not sure if Cinch has put on a few pounds because of the pregnancy or if your eyes are playing tricks on you, but she looks decidedly thicker than you remember. Her ass seems rounder, her legs a bit meatier. You are in no way opposed to this.
You turn your eyes away, feeling a heavy blush warm your face. TPing your principal’s house is one thing. Staring at her ass is something entirely different. Not okay, dude. You shake your head and go to find the things you need. Cinch was prepared for this, having earlier laid out the duster and vacuum in a corner of the living room.
As you begin dusting, you hear the water for Cinch’s shower faintly through the floor. Immediately, your brain is bombarded by the image of Cinch undressing, baring her legs and ass before pulling her sweater up over her round, pregnant belly and past her tits, noticeably larger than they used to be. You bite your lip as you imagine how good it would be to squeeze the soft, supple titflesh in your hands, tweaking her undoubtedly sensitive nipples until they leak their milk down your fingers…
And now your dick is hard. Fucking perfect.
“Really, dude?” you say to your penis. “Now? You can’t wait an hour til we get home?”
Your penis doesn’t answer you, though, both because it’s an organ and can’t speak and because it’s gone rogue and is doing whatever the hell it wants.
You groan in frustration, but persevere in your cleaning. Your dick is annoyed at you, but there’s not a whole lot you can do about it. You can’t exactly whip out your cock and rub one out in your principal’s living room. So, with a raging stiffy in your pants, you go about fulfilling the rest of your punishment.
Dusting is quick, only about five or so minutes of your time. Cinch keeps her house pretty clean, it would appear, even in her state. You wonder why she even bothered asking you to clean for her. Probably just to make you suffer, which, even you have to admit, you kind of deserve. Vacuuming followed soon after dusting, and it doesn’t take you very long either. At this rate, you’ll be finished before Cinch even thinks about getting out of her shower.
Your mind wanders as you head for the kitchen, your brain focusing way more on Principal Cinch than you want it to. You just can’t help it. You blame it on hormones. A teenage boy like you has a brain that’s basically just a pool of chemicals and perverted thoughts. Of course you would steer towards the idea of your unnecessarily fuckable principal nude and lathering herself from head to toe. Watching her caress her belly, run her hands down her luscious legs and her bountiful titties, and…
Fuck. This erection of yours is now an ordeal. It throbs angrily in your pants, yelling at you to do something about it. You try to explain that now is not the time, that you’ll give him the attention he deserves when you’re safely away from Cinch’s house, but your dick refuses to hear it. Some dicks aren’t after logical things. They can't be bought, bullied, reasoned, or negotiated with.
Some dicks just want to watch the world burn.
You try not to think about Cinch, or your raging erection, as you approach the sink. There’s only a few dishes in there, a couple of plates, maybe a glass or two. Even with your incredibly distracting boner, it’s easy to get this done. Just another five minutes of your day sacrificed to sate Principal Cinch’s wrath. You figure you may as well go above and beyond, and you quickly wipe down her countertops with some kitchen cleaner you find underneath the sink. You consider it a peace offering of sorts, just to show her that this whole TP thing wasn’t a personal attack on her.
When you finish with downstairs, you’re left only with the study. By this point, your dick has given up and reverted to half-chub in surrender. It’s about damn time. The last thing you needed was an erection as you walk past Cinch’s bathroom, where you could hear the sound of her shower pattering down onto the floor of the tub, and the soft sound of Cinch singing to herself…
Wait, what?
You double back to the bathroom, the door accidentally left cracked. You bring your ear close to the door and listen in. Just as you thought, Cinch is singing. And, major shocker, she actually has a really nice voice. Strong, but gentle, and almost velvety in her melody. You lean closer to get a better listen, and you accidentally nudge the door with your ear. Your heart stops as the door slowly creaks open, but it seems your fear is unfounded. Cinch obviously didn’t hear, as evidenced by the fact that her singing continues. You wonder what to do next. You should really get to work on the study, but, at the same time, Cinch’s impressive singing leaves you wanting more. You decide to chance it, and slip into the bathroom quietly.
Your eyes go wide at what you see. Cinch’s shower curtains are semi-transparent, so you can see her form, albeit a bit hazily. She has her back to you as she shampoos her hair, letting you gawk and stare at her round, perfect ass, and her thick, wonderful thighs through the shower curtain. Your dick returns from the grave, hard as can be. Cinch still doesn’t seem to notice you. In fact, her singing seems to have gotten louder. Her voice has you in its spell, making Cinch seem even more beautiful than she already was.
Fuck it. You unbutton your jeans and slowly pull your cock from your boxers. You’re not thinking straight, the throbbing in your dick utterly distracting. This is probably a really bad idea, but you find it hard to care. You just start stroking your cock to the super-hot, super-pregnant woman before you. Just as before, your mind starts to wander. You wonder what it would feel like to touch her, feel the smooth roundness of her stomach. Electric twangs of pleasure shiver up your cock, so stunning that you have to bite your lip to stifle a moan. You never knew it before, but you want to fuck Cinch. You jerk your dick harder, the tip of your cock drooling precum as you imagine what you’d do to her. You want to bend her over and ram her from behind, fondling her tits while you do. Your dick throbs at the thought, clearly pleased with your imagination.
“I take it you’ve finished cleaning, Mr. Anon?”
Your heart stops in your chest (yet, somehow, you keep on beating your dick. Funny how the body works). Cinch hasn’t turned, nor has she stopped shampooing her hair, but she’s definitely noticed you. Maybe she heard you beating your meat in her bathroom, or maybe she just has some sort of principal’s Sixth Sense for dirty perverts. Either way, she’s onto you, and you need to get the hell out of dodge.
“For shame, Anon. I would have thought that you knew your manners,” says Cinch. “If you’re going to walk in on a lady while she’s showering and start jerking that cock of yours, the least you can do is say hello.”
Uh… The fuck?
“H-hello?” you say, dick still hard and in your grasp. Cinch is being uncharacteristically cool about this situation. Instead of screaming at you, or calling the police, she’s just reprimanding you. Not even that, really. The word “tease” comes to mind, and you’re pretty sure that “tease” is not the appropriate thing for her to be doing in this scenario.
“Good boy. So, have you?” says Cinch. She correctly takes your silence for stunned confusion. “Finished. Have you finished cleaning?”
Your brain was in no way ready for this conversation to take place under these circumstances, so it takes you a second to form a coherent thought.
“Uh… I still have to… Study… Clean…” You essentially vomit these words with all the inflection and clear delivery of a man having a stroke.
“Hmph. The study never really needed much cleaning in the first place.” Cinch washes the shampoo out of her hair, wringing it dry. “Well? You’ve already started undressing. You may as well finish the job.” Your eyes go wide. Is she serious? There’s no way in hell she’s serious. This has to be some sort of cruel, sadistic trick. It’d be foolish to risk it.
Unfortunately for you, your dick is calling the shots now, and he compels you to kick off your shoes and socks, then step out of your pants and boxers. You pull your shirt over your head and drop it to the ground, then carefully slip into the shower behind Cinch. You feel like a zookeeper entering a tiger’s cage.
Though, now that you think on it, cougar is probably more accurate.
“How nice of you to finally join me,” Cinch remarks. You’re standing just behind her, the hot water cascading down her body and yours. You can smell her soap, the lavender in her shampoo, and it starts to drive you just a touch crazy. You reach your hand forward carefully, reaching slowly around Cinch and doing what you’ve been fantasizing about doing all day; You gently grasp her breasts, and nearly have a conniption at how awesome they feel. They’re soft and warm, and, just like you fantasized, yield a little trickling of breast milk as you squeeze them.
“Boys. So quick to get grabby.” Cinch sounds a touch annoyed, but she doesn’t do anything to stop you. You decide to keep going, kneading her tits and gently teasing her nipples between your thumb and index finger. “You’re supposed to take a moment to admire your woman, appreciate her body, yet here you go. Straight for squishing and squeezing.” You don’t stop, instead digging your fingers into her soft titflesh a bit deeper. You continue teasing her nipples, eventually getting a soft, breathy moan from your principal.
“Holy shit, this is awesome,” you find yourself saying. “Holy fucking sh—”
Cinch turns her head and shuts you up with a kiss. You thought kissing was easy, simple, but Cinch proves you wrong. Her experienced tongue works its way into your mouth and sends a tingle down your spine. Too soon for your liking, Cinch breaks away, smirking at your breathless, dazed expression.
“I expect my students to keep a civil tongue, Mr. Anon,” says Cinch, chuckling to herself. “And, despite the… unorthodox nature of our meeting… You are still my student, and I demand that you show me respect.”
“S-sorry, ma’am,” you stammer. “Won't happen again…”
“Good. Wouldn't want to cut our time together short because of your foul language.” Cinch turns to face you, brushing your throbbing erection with her belly and sending a shiver through your body. “Hm, you dirty, dirty boy. You like the way my big, round stomach makes you feel?”
“Uh… I…” Words fail you, which seems to amuse Cinch. She smirks at your discomfort, then leans in to give you another deep, passionate kiss. She grabs your wrists and brings them to her chest, urging you to continue playing with her tits. You happily comply, squishing and squeezing to your perverted heart’s content.
“It’s okay, Anon. I see the way you looked at me before I was pregnant.” Cinch breathes her words out in between dives into your mouth. She nibbled gently on your lip, sending your heart pounding even harder than before, a feat you thought impossible. “You clearly thought me attractive. How about now, Anon? Do you still think I’m beautiful?”
“Y-yes,” you gasp. It’s hard to think under these conditions, but you manage to get the truth out, at least. “You’re the most beautiful woman I’ve ever seen.”
“Even seven months pregnant?” Cinch smirks at you, as if she’s caught you in her trap. Again, your head is swimming, but you manage to squeak out the truth.
“Especially seven months pregnant,” you say. Cinch grins at you, then reaches over and shuts off the water. You’re so distracted by the two handfuls of titties you’ve got that you barely even notice.
“Last door on the right at the end of the hall,” says Cinch. You tilt your head in confusion. “My bedroom, Anon. I’d like to get somewhere a bit more comfortable.”
You followed Cinch’s instructions to her bedroom and, just like before, she has you right where she wants you. She all but shoves you onto the mattress and crawl up to you. You try to sit up, only to be pushed down back on your back again. You’re not exactly sure what’s about to happen, but you can make a few guesses. You’ve seen enough porn to know where this is going.
To your surprise, Cinch doesn’t lower her head down to wrap her lips around your fat cock. No, this is arguably better. She strokes your cock, keeping it at attention, then presses it up to your stomach. Then, with a sexy grin she rubs her belly up and down the length of your cock. The smooth, round warmth of Cinch’s pregnant stomach is almost too much to bear. You start to tremble, trying to hold still so as to not hurt Cinch or her baby. The principal of CPA just keeps smirking at you as she teases you with her ultimate womanhood.
“I’ve always thought you were exceptional, Anon,” says Cinch, any remnant of her stern demeanor gone for the time being. “I’ve been waiting for an excuse to make this happen for a long time. Ideally, this wouldn’t be happening while I’m pregnant. In a perfect world, you would’ve earned yourself detention last year, and this baby would be yours.”
Your cock twitches at the idea of dumping a load of cum into Cinch’s fertile womb, knocking her up and claiming her as yours. As sexy as you find the idea, the real world still leaks in through your fantasies, and a question occurs to you.
“Who’s… the daddy?” You can barely talk on account of how good Cinch’s belly feels on your cock. Suddenly, she stops, her sultry, sexy grin becoming an annoyed snarl.
“That son of a bitch, Mr. Turner from Griffonstone High…” growls Cinch. “We got a bit out of our heads at a Christmas Party and the bastard refuses to take responsibility for… You know what? It’s not important. I didn’t call you here to talk about Turner.”
Cinch removes her belly from your dick, much to your dick’s protest. Those protests turn into cheers of joy as Cinch turns herself on all fours, her head stooped down and her rear raised. You can see her dripping lower lips, and, past that, the curve of her pregnancy. You know what she wants. Your dick knows what she wants. Anyone with two brain cells to rub together would know what she wants. But you still wait for her to give you the word.
“Come on, Anon. Fuck me,” whispers Cinch. Your eyes light up, like Christmas Eve for pervs, and you immediately approach your prize. You lick your lips and grab Cinch gently by the hips, bringing your dick closer to her hot, dripping cunt. But, before you can go for the gold, you have a sudden, potentially heart-breaking epiphany.
“I… I don’t have a condom,” you say, blushing to yourself. Cinch turns to look at you as if you’re a complete fucking idiot, which, to be fair, you are. It takes you about a full moment to truly understand why Cinch was looking at you, and, when you finally figure it out, you facepalm with enough force to break concrete.
“I’m pregnant, Anon,” says Cinch, clearly trying not to laugh at you. “I am quite sure that you’re safe.”
Right. You shake your head firmly. Get your shit together, Anon.
You position your dick before Cinch’s dripping honeypot, feeling her heat radiate onto you. This is happening. You’re about to have sex with your principal. You didn’t even know that you wanted to do that until today, but now you don’t know how you were able contain yourself for this long. You slowly ease your dick into Cinch, groaning as her warm, wet, puffy lower lips accepts you, all but sucking you in. You let out a groan, the feel of Cinch’s velvety walls grip your cock almost enough to finish you off early.
But you’re no one-pump chump. Fuck that. You’re determined to please this older, mature, experienced, pregnant woman if it kills you. You start off with slow, shallow thrusts. You worry about Cinch’s baby, which is partly why you’re going so slow. If you’re gonna fuck this kid’s mom, you should at least give them a minute to come to grips with that fact.
That minute ends pretty soon, though. Cinch’s hot insides are too good for this slow and steady bullshit. You adopt a quicker pace, developing a rhythm of quick thrusts. Every plunge into Cinch’s snatch is heaven, making your head swim. Nothing in life even comes close to how good it feels to fuck a pregnant principal. It’s incredible, and you have no intentions of stopping anytime soon.
“Mmm, there’s a good boy.” Cinch purrs out words of encouragement, which really sparks a fire inside you. “Come on, Anon, harder! I’m not made of glass, dear.” You can’t exactly ignore an order from your principal, so you do as you’re told and fuck her harder, pounding her cunt as hard as you can. You knead her ass with your fingers as you work, Cinch’s moans and pants driving you wild.
“W-wait.” Cinch stops you with a hand to your chest. “I need to switch positions. I’m starting to lean on my stomach, and the baby…”
“Oh! I’m sorry! Okay. You wanna… Like, spoon?” you suggest. Cinch nods to you and repositions herself, laying on her side. You slide up to her back and raise her leg to create entry, and ease back into Cinch. Somehow, this is even better. You still get good penetration, and you’re closer to Cinch than before. It feels more intimate. You can smell her hair again, like in the shower, and it’s nice. Soothing. This is way better than you ever could have imagined. Cinch is a strong, powerful woman, just the way you like, but she’s also got a soft, tender side. She exemplifies this by grabbing your wrist and placing your hand on her belly so you can feel the warmth and life she carries with her. You imagine that she’d make a damn good mother. Still, it’s a shame that she’d be going through it alone.
She leans her head back and kisses you, melting you into ecstasy. This is perfect. In your wildest dreams, you couldn’t imagine things going this well. You find yourself swooning over this woman that, just earlier today, you found utterly terrifying.
Your bliss reaches a peak, and you erupt in Cinch’s snatch. She moans faintly as you cum, milking you with her pussy. You set her leg down shakily, and wrap your arm around her middle. You decide not to pull out, not yet, and Cinch doesn’t make you. For the time being, it seemed you both were content with some post-coital cuddling.
“Next time, I’d like a bit of warning, Mr. Anon,” says Cinch tiredly. “If it’s all the same to you, a surprise orgasm is what got me into this predicament to begin with.”
“Right. Sorry.” You rub her belly softly, concerned for the cargo she carries. “Can I… Can I ask about the baby?”
“I suppose. What do you want to know?”
“Are you gonna be okay taking care of it?” Your concern for Cinch’s child is genuine, of course. As much of a hardass as she could be, you actually always liked Cinch. Even before she let you fuck her. She was an incredibly admirable woman, despite her faults, and she doesn’t deserve the shit hand that life dealt her.
“I can manage. Dean Cadance so graciously offered to assist me, if it comes down to it. And, besides, I have family,” says Cinch. “My sister and her daughter wouldn’t hesitate to come to my aid if I asked them to.”
“Well… Uh, I… If you want…” You grapple with your words for a bit, unsure how to say it. “I just mean, if you ever need some help… I come from a big family. I’m the oldest of six, so I know a thing or two about dealing with babies.”
“Are you volunteering to be my child’s stepfather?” Cinch snickers. You laugh as well. When she phrases it like that, you do sound a little silly.
“Kinda.”
“And are you offering so you have an excuse to come back over here and fuck me again?” Cinch raises an eyebrow at you, bringing back some of her stern power that you know her for.
“Kinda,” you repeat. “But I’m serious. I don’t know if you… You know, want me, but… Like you said, you wanted to have my baby anyway. If Turner won’t be here for you, then I will.”
It gets quiet for a moment, and you have to pray that you didn’t kill the moment. Slowly, Cinch turns her head and kisses you. The silence persists for some time as you kiss passionately. You break away, and Cinch smiles at you.
“Well, then, I suppose we’ll need a name for the little bundle of joy,” she says.
You smirk at Cinch, and the two of you begin brainstorming baby names. It’s strange. You didn’t think you’d be ready to commit yourself so soon, or so intensely. You couldn’t even settle on a girlfriend during high school, but here you are pledging to help a woman twice your age raise a baby. You’re not sure how things will play out from here, but you’re certain of one thing.
This was the best detention ever.
