Drilling the Captain

by Synesisbassist

First published

You are a Wonderbolt in training, a cadet if you will. You may not be the fastest but you sure as hell are the most determined.The training has been hard, tiring, and pushing you to the breaking point. But the icing on the cake... Is Spitfire.

You're already two weeks in and you're not sure how much more you can take. You are a normal Wonderbolt Cadet. While pretty average across the board when you started, you've quickly shown that your will to improve is strong. Though a few have already broken down under the hard stare of the Captain, you have been undeterred so far. Well, that is until Spitfire started picking on you.

The mare is hard, she's tough. And quite frankly? She's one hell of a bitch. She would always call you out in front of the others with quips and comments that would make any normal stallion snap like a twig under a earth pony. But you held on strong through extra laps and missed dinners. But a pony can only take so much before they lose it and do something they've always dreamed of. Lucky for you, she likes it a little rough.



Contains: Anthro, (right off the bat) slight choking, dubcon, standing missionary, cunnilingus, mare squirt, anal and anal creampie. With a bit of cuddles and pizza at the end!

Featured: 17/09/2018-18/09/18. Thank you all so much! :pinkiehappy:

Thanks for checking this out, I hope you enjoy it! As always, special thanks to my editor BlazingMoon for doing the editing!

Also thanks to two pre-readers, for helping a lot with the story content! Wouldn't have been as polished without them!:yay:
Duskhoof
Miles Skywalker

Lesson One

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“Come on maggot! Move your ass! The clock is ticking!!” You grumble under your breath, your eyes narrowing as you kept running. The sun had long since started to set, the glowing orange ball sinking lower into the horizon. There were no other sounds, aside from your hooves hitting the concrete. Your ragged breaths barely registered as you ran faster than you ever thought you could. Everypony else had the chance to hit the showers already. Hell, they were probably all in the mess hall enjoying a nice hearty dinner right now. Talking their day away with laughter and jokes.

But not you. You were still outside, running the track while your legs begged for forgiveness. Your wings tried flapping to assist you, but you resisted. Spitfire would add at least four more laps if even one feather caught a bit of air. Speaking of the air, it burned your lungs, your nose and your chest. She thought it would be a ‘great workout’ to make you run shirtless, in the cold evening. While she wasn’t wrong, any sweat that dared to trickle down, almost froze right on your black fur. Tartarus, the grass on the inside of the track had already started to freeze itself!

A pony’s short coat was not designed for this, it barely protected your insides from the nipping air. Your fingers felt numb, your ears felt like somepony had lit them on fire and you’re sure your balls retracted inside your body. “Enough daydreaming Cadet! Get your sorry flank in gear before you get a swift kick upside them! Let’s move!” Gritting your teeth, a growl escapes your lips before you put on a fresh burst of speed.

Stupid Spitfire… Thinks she's hot shit… With arms pumping, hooves clacking loudly against the ground, you hunker down and sprint the last hundred meters as quickly as you can. You’re practically a blur as you almost lose your balance. The taste of blood in your mouth, a pain fills your side as you blow past the finish and slow to a stop.

Hands on your knees, you pant hard while clenching your eyes shut. You’re so light headed that a simple breeze would have been enough to blow you over. “Huh, that's your fastest lap yet. Next time, do the same but without me having to yell at you.” The yellow mare smugly grins. Walking past you, one of her wings snaps itself open to slap your rump. “Alright rookie, hit the showers, let's go. If you're quick enough, you might be able to get something to eat tonight.” Growling under your breath, you rub your stinging flank.

The way she says it though, just pisses you off to no end. Like fuck, you're not going to bed hungry again. Unfurling your wings, you take off like a bullet towards the showers. Touching down just outside the shower hall, you see the sun has set. Only the final few rays of sun light up the sky in twilight. Your nipples are rock hard from the cold as you push your way into the changing room. Snatching a towel from your locker, you quickly strip out of your sweaty outfit. Light blue sweatpants reveal a pair of black, skin tight briefs. Though those quickly add to the pile of dirty clothes on the floor.

Gingerly stepping on the damp, tiled ground. The showers greet you with a welcomed silence, it seems that you were here alone, which suits you best anyways. The Wonderbolts didn’t segregate the showers here, not like there would be enough anyways. There were only usually only ten cadets anyways, and with only one other stallion in the mix, it just didn't make sense. Though the cadets are separated from the actual Bolts, something about a scandal a long time ago. But you never really cared for gossip anyways. You were here to prove yourself, not idly pass rumors along…. But you heard it was an ex-captain, getting it on with a cadet. The thought occasionally ran though your mind, but you always remembered why you were here. To win, not for poon.

With the water on and steam rising, you step into the wonderful stream. The warm water felt heavenly on your frozen body. Your silver mane clung to your neck, reminding you that you probably should get a manecut sooner rather than later. Scrubbing your athletic body, your mind strayed back to Spitfire.

From her fiery mane to her slender and toned legs, she was, on all counts, a beautiful mare. On top of her good looks, she was one of the best fliers the Wonderbolts had ever seen. Her wings were like razors to the air, slicing through it with more precision than a doctor, to propel her to the top of the team at a young age. Though she was a bit older, she could still hold her own very well. Every time you watched the Bolts practice, you could see she put as much effort into it as if she was performing for Celestia herself. A playful grin on her muzzle, those eyes sealed behind her goggles as her and the rest would display things you and the other cadets could only dream of.

But this was only one side of her. The other was a teacher, and a hard ass at that. That tight uniform hugged her body, showing off every single curve she worked so hard to get. From her slim tummy to those slender legs. Her tiny bust and those pretty lips hiding the smile she desperately wanted to show more.

Her fiery mane was, admittedly whimsical as it whipped behind her head at breakneck speeds. Those burning orange eyes always seemed serious, with a hint of playfulness that yearned to come out. But you knew what sacrifices that job came with. As did she. And Spitfire took her job very seriously. Her officer uniform clung to her slim body, her red whistle would bounce off of what you could call tits, but honestly they looked more like peaches. She didn't have a thick figure, but her tiny hourglass shape was perfect for slicing through the air. Her little shorts where always hiked up, showing as much of her legs off as possible.

Come on, think of something else. Think of…. Damn it… Frowning, you realize your ‘little stallion’ has risen to the occasion. Well, more figuratively than literally. It hung limply, slowly filling with blood at the thoughts that swam around in your head. “Stop it.” You scold, but it has a mind if it's own. It gives a small twitch before you let out a sad sigh. “Tonight. I promise.” Though you've said that for the past week and a half. By time lights out comes around, you're usually pretty tired. And there's not exactly a lot of places to jerk off around here. But you digress, and continue washing.

It takes minimal time to get soaped up and rinsed off, the worries and stress of the day feel like they wash right down the drain along with the dirt and sweat. Drying yourself off, you step back into the change room. With your towel around your neck, you whistle a small tune to yourself. It actually manages to make you smile for the first time in a few days. You put on a pink shirt and a pair of black sweatpants, and you are about to head out into the hallway when you notice the door.

It looks like it was stuck slightly open, but you were sure you closed it behind you. Shaking that thought from your mind, you put your bag over your shoulder and step outside. “You're late, Cadet.” Nearly jumping out of your skin, you see Spitfire standing there. The yellow Pegasus is still in her uniform, her eyes are narrowed as she looks at the watch on her wrist. “Took you seventeen minutes, and forty seven seconds. What were you doing in there Cadet?”

And there goes the good feeling from the shower. “I was washing myself, ma'am.” Throwing on a quick salute for good measure to hopefully please her.

However, Spitfire doesn't seem impressed. She narrows her eyes and steps closer to you. “Somehow I don't believe you. Now, what were you doing? I bet you were in there, jerking off like a pathetic little runt.” Wow, ok. Things got turned up to twelve.

You barely hold your neutral gaze. “No ma’am! I was taking the time to enjoy a nice, relaxing shower after a hard training day.”

“Hard day? Cadet, you haven't begun to see what I will do to you here. If you think this is hard, you might as well pack up and head home. No one will judge you for it. Many ponies have come and gone because they thought it would be easy.” The mare crosses her arms with a smirk.

She's got to be fucking with you now. And, though you hate to admit it, it's pissing you off. “Ma’am, no ma’am. I'm staying put and giving it my all.”

Spitfire took a second to examine your face, your icy blue eyes met her orange ones. “Whatever you say rookie. But that still doesn't explain just what took you so long in the showers.”

You bite your tongue, resisting the urge to yell. “Ma’am, as I said…”

She cuts you off when her finger presses into your chest. “Stop lying to me. I know exactly what you were doing in there.” The biggest shit eating grin came across her face. “Don't worry rookie, little dicks need love too.”

By now you're just pissed. Sure, you're not monstrous down there, but you sure as hell don't have a tiny dick. “Looks like I struck a nerve- Oh, you also missed dinner time. Lights out in two hours.” That's it, this mare has pushed you too far.

“Fuck you.”

The words seep from your lips, a growl arising as well. Spitfire seems a bit taken back, the grin all but gone. “What did you just say to me?”

You take a step towards her, your frame towering over hers by a good few inches. “I said fuck you, Spitfire.”

Though she's undeterred by your intimidation act. “See, that's what I thought you said. But I figured I should give you the chance to correct it before you got into trouble. Ten laps around the track.”

“Fuck you, and fuck your track.” That seemed to piss her off. Spitfire narrows her eyes and puts her face in yours.

“Fuck me? Fuck me, huh? You would like that, wouldn't you? You worthless newbie! Get the fuck off my training ground!” She grabs your shirt and in an instant, your hand is around her throat and she's pressed against the far wall.

Your bag drops to the floor as you focus solely on her strained face. “Don't you dare touch me Spitfire.” The adrenaline is pumping hard, the mare lets out a squeak but other than that, she stays silent. “I'm sick and tired of getting shit from you. It's been day in, day out for the past two weeks!”

As she struggles for breath, she smiles. “You always had girly hands, Cadet.” Of course, she had to get in another quip.

With a fresh surge of anger, you clench your hand tighter. She gags a bit, her cheeks flushing pink as her hands grab your arm. “You're a cunt. Maybe if you weren't such a bitch, you could actually get laid by a real stallion.” She goes a bit wide eyed as you grin. “Oh yeah, I saw you leave with Soarin at that little celebration you had for the last show of the season.” You can almost see the daggers in her eyes as Spitfire let's out a snarl. “I'm guessing that he was too sloshed for any fun, eh?” Faust above it felt good to get back at her, even for just a moment.

“F-Fuck you…” She manages to squeak out, her right hand grabbing your shirt. It was then that a thought came to mind, a thought so small, so… Brief, you second guess yourself if you actually thought of it.

“Oh Spitfire my dear, that can be arranged.” The mare lets out another squeak as her wings spread wide. Now she's actually fighting you, her hands and hooves flail to push you away from her. But sadly for her, you’re physically stronger then she is.

Firmly pushing her into the wall, you bring your chest to hers and feel her tiny tits inside her shirt. You slide your free hand down her belly and into her shorts. “N-no!” Nothing separates your fingers and the rough patch of fur above her marehood, which surprises you.

“No panties, Captain?” Your heart’s racing, hands shaking as the mare struggles. This will most certainly get you not only kicked out, but probably arrested! But you can't stop, your hand slithers down as she clenches her eyes shut and whimpers.

Your fingers trail through her patch before… Wet. Holy fuck is she wet. You almost recoil at the sensation, but instead you press on. The tip of your middle finger slides up and down her soaked labia a few times, feeling the warmth that her pussy gives off. The pegasus spreads her legs, panting a bit and you fumble around to find her clit. Though the throbbing nub is not hard to find, the fleshy protrusion throbs as you fingertips graze it. Giving it a few rubs and a squeeze, you pull your hand from her shorts.

Bringing your fluid covered fingers to your mouth, you quickly lick her juices off. It’s tasty. A little tangy with a spicy aftertaste, but still good. Taking a good look at the panting pegasus, you see her cheeks are flushed red and she trembles slightly. Thankfully for her, you let up a bit on her neck, but you still hold her in place tightly.

You grab her hand and smile before bringing it to the bulge in your pants. Once her slender fingers feel it, she latches on like it was about to give her the keys to the universe. “F-fuck you're actually pretty big.” Spitfire bites her lip as she gently kneads your rapidly growing stallionhood. The smell of an aroused mare, the feeling of her hand on your dick, it's all too much.

Out of nowhere, you lock lips with Spitfire. She gives no resistance as you kiss her deeply, your hand grabbing roughly at her chest. Her nimble hand slips into your pants and underwear, wrapping her own fingers around the base of your dick. Spitfire squeezes it none too gently, but you're already hard enough that it only adds to the building pleasure.

With a quick move, you let go of her neck and rip her shirt wide open, sending a few buttons flying off the process. “You’re gonna have to fix that.” Revealing her bare chest to your praying eye. Her tiny tits jiggle slightly as they’re released from their tight prision. Though not a second is wasted and your hands are all over them, rubbing, squeezing, pinching, everything you can think about. Everything you’ve always wanted to do to them, you do. “Not so rough.” Spitfire’s complaint barely reaches you, you're too far lost in the heat of the moment.

Suddenly, you grab her by the back of her head and pull her inside the locker room. Pushing her back up against the lockers, you kiss her hard again. With a quick sleight of hand, she pulls your pants down around your knees and quickly starts rubbing your hard cock. The nine inches of onyx black horsecock twitches proudly in her hands. “Damn Cadet, didn’t know you were into older mares.” Older? She’s not that much older than you, maybe ten years, tops. But you don’t even care, your hands make their way to her ass and give her cheeks a firm squeeze.

“Maybe, but you still got a sexy body, Spits.” Spitfire moans sharply before you tug her shorts down. This is it, no turning back. You push your chest to hers as you spread those legs apart slightly. She stares up into your eyes as your head touches her soaked nethers.

“Well? Are you going to fuck me or not, Cadet?” With a small frown, a small push, your head slips inside her. “A-ah~” The yellow pegasus inhales sharply, her walls clench down hard, making you bite your lip before sliding in more.

“F-fuck.” You can’t help but groan as your length pushes into her, her pussy is wet, tight, and begging for more. With a quick stroke back, you thrust into her again. Stars flash into your vision, sweet Celestia her pussy almost makes you nut right then.

But you can't, you have to get her off first. Spitfire would never let you live it down, for the rest of your life. Slowly you begin to fuck her, trying as hard as you can not to lose yourself. Spitfire’s hands trail down your sides, holding onto you gently as you bury your dick into her over and over. “That's right Cadet, you're doing juuuuust fine~” Whimpering, you brace your hands onto the lockers behind the mare, your belly touching hers each time you bottom out.

The velvet interior of her pussy feels like fine silk on your dick. She’s wet and only getting wetter as you continue to fuck her with reckless abandon. You can’t help it anymore, her insides are begging to be filled. You’re more than happy to oblige. “S-Spitfire…. I’m gonna c-cum!” Your hands move to her hips, holding her tightly as you quiver.

Her eyes snap up from your crotch to your face. “Don’t cum inside me Cadet, we’re just getting started.” The mare pushes your back, your length sliping from her hole with a slurp. The bench in the middle of the room catches you behind the knees, forcing you to land hard on it. Spitfire takes your cock in hand, her fingers delicately holding it as she stands on the bench. Her hooves resting on either side of you, while her trimmed pussy is right at face level. “Lesson one, always make sure your mate gets off before you do. Now, I want you to eat my pussy like a good little colt.” Her free hand grabs the back of your head while bringing her box to your face.

She didn’t need to tell you twice. Grabbing her thighs, you bury your mouth into those sweet lips. Her scent and taste floods your senses, your tongue lashing with a deep hunger. “Mmmpf~” Faust above she tastes amazing, her fluids are even better from the source. Spitfire’s fingers grab a fistful of your mane, urging you to go deeper.

“Oh fuck yeah, that’s right.” Grinding her hips onto your face, she covers your mouth and nose with her mare juice. Wiggling your tongue past her folds, you feel and taste her deep insides. A sharp inhale comes from the mare above you, while a smile works its way onto your muzzle. She reluctantly lets go of your shaft, both her hands now holding your head. “D-damn, where did you learn to eat p-pus ahha!~” Pushing past her lips and with your snout now pushed inside her hole, your lips part and your tongue comes out to lash at anything it can.

But it only takes a few swipes of your tongue to push her over the edge. Spitfire’s walls clenched around your muzzle, a rush of her marecum flooded your nose almost choking you. Pulling back sharply for air, you cough and sputter as her fluids squirt from her lips and onto your face and chest. One of her hands rubs her slit quickly spraying even more of her essence over your chest and stomach. “Oh fuckkkk!!!”

Her smell fills your nose, nostrils flaring while your length grows even harder. “Damn Spitfire. Didn’t know you were that pent up.” The yellow mare pants above you, her legs shaking, struggling to hold her body up.

“S-shut it Cadet.” She collapses onto your belly, your length riding up between her butt cheeks. “And you’re as hard as ever. So don’t even go there with me.” Her hands hold onto your shoulders, a grin slowly spreading across her muzzle. “Well, I had my fun. Hit the shower Cadet, you kinda reek.” With a small grind back, the mare swings her hooves around and gets up from your lap. Leaving junior feeling quite left out. Spitfire swished her tail while she discarded her top and made her way back into the shower room.

D-did she? Yup. She did. Grumbling as your aching length throbs for release, you quickly strip what little clothes you had left on you and head into the showers as well. Steam fills the room as the slender mare bends over, arms braced against the wall with her rear out. “About time Cadet. Come on, I’m not that much of a cunt. Come finish what you started.” Her ass doesn’t even get to wiggle a second time. In a split second, you cross the room and grab her cheeks with a hard squeeze.

“Don’t ever tease me like that again.” You mutter as you press your tip against her lips, but a yellow hand reaches back and pulls it up against her tight pucker. Oh fuck yes!

“Oh? And you expect this to happen again?” There’s a spark in her eyes as you push forward, Spitfire biting her lip gently. Your precum soaked tip presses into it and with a pop, the head slips inside the forbidden tunnel.

“Ohh~” You groan loudly, it’s even tighter than her pussy was. “Y-you’re fucking right Spits. I’ll make you c-crave my cock,” The tight ring clenches as you give a shallow thrust into her ass.

The yellow mare moans loudly, her hands pulling apart her cheeks as you continue to push deeper. “I’ll hold ya to that, Cadet! Now fuck me!” Tightening your fingers onto her hips, you push as hard as you can and pull her back to your crotch.

SMACK!

Both of you moan in pleasure as you completely bury your cock inside her ass. The tight ring clenches hard around your dick, making you groan in pleasure. “Hot damn Captain~ Never took it up the ass before?” Cracking open an eye, you see Spitfire gritting her teeth. Her cheeks are flushed while her head is turned to look back at you.

Shaking her head quickly, Spitfire groans loudly as you pull back. “N-no. I’ve always wanted to try though.” You know you’re not going to last long, not with this tight hole begging for a filling. Like Tartarus you’re not going to comply either. Grabbing her hips tightly, you thrust all the way back inside her. A loud gasp escaped from Spitfire’s throat, her eyes clenching shut as you rail her ponut.

Hips meet ass with a smack, the lewd noises of her hole clenching to your length as you pull back, a moan of pleasure and the cycle repeats over and over. Balls pulling tight, your length throbbing and jerking a few times. “S-Spits, I’m gonna cum!” You try to warn the pegasus but it’s too late. As soon as the words are out of your mouth, you erupt inside her.

In your last moment of awareness, you try to pull back only to be stopped by her hand. Spitfire gently holds your hip, as the first rope fires inside her ass. “It’s so hot~” The mare gently rides your dick as you fill her rear with your spooge, the warm goo filling her bowels quickly and flowing back against your member. You weakly hold her hips as the white fluid seeps around your dick, making your final few thrusts extra wet. That familiar warm, tingly feeling wells up inside you, spreading from your crotch and flowing into your entire body.

Spitfire shivers, her hips gently pulling away from yours as your deflating dick slips from her warm confines with a wet slurp. “Damn Cadet, you did better than I gave you credit for.” The tired pegasus stands under the stream of water long forgotten, her eyes staring into yours. She’s smiling. Like, for real. Not a smug grin but a true, honest smile. It’s refreshing to see on her, in your eyes.

Throwing up a small salute, you can’t keep the big grin off your face. You just fucked the Captain. “I aim to please, ma’am!” A yellow hand wraps around your wrist and pulls you against her, those tiny tits pushing against your chest.

“Call me Spitfire, Cadet. You earned it.” Spitfire leans in and kisses you gently. Those lips are soft and gentle as the mare kisses you. Honestly, you’re a bit surprised she can be so gentle, but you promptly kiss her back, cupping her cheeks in the process. If you went back in time and told yourself that tonight you’d get to fuck Spitfire, before sharing a kiss in the shower… Well, you’d probably piss yourself laughing.

But here you were, holding the hot Captain in your arms as you both shared the most intimate kiss of your life. She took the lead quickly, her tongue slipping into your muzzle to dance the dance with yours. Her hands run over your pecs, lightly ruffling the hair there while her head tilts to the side. Holding her chin with one hand, you pull her hips closer and lose yourself in the moment.

But the need for air is strong and although you’re strong willed, you need to breathe. Your lips part and you exhale deeply, as does she. Her cheeks are flushed and you know yours are as well, the burning feeling behind them only intensifies as you stare into her orange orbs. “Y-you know. You could, I dunno, come back to my pad for some pizza? It’s the least I could do for being such a cunt to you, Cadet.”

Your stomach decides you’ve had your fun, and that food sounds good to it right now. So, taking matters into its own hands, it lets out a loud growl. “That sounds like an amazing time, Spits.” With new found energy, the two of you quickly wash up, making sure to get any and all remnants of your ‘activities’ removed and washed down the drain. A quick phone call from an ‘emergency’ phone in the locker room to the pizza shop later, and you both quickly get dressed.

Thanks to you ripping her shirt open, you let her borrow a sweater that she could wear. Honestly, she looked damn adorable in it. The grey black sweater honestly looked pretty good against her yellow fur. Though the ‘<3 THE PLOT’ across the back in white lettering did make you chuckle a bit. She had her head leaned into your shoulder the entire time, your arm wrapped around her shoulder as you both walked across the frost covered grass.

“C-Cadet?” Spitfire broke the silence as you approached her personal quarters. It was almost like a mini mansion to be honest.

“Mmm hmm?” You don’t want to speak, mostly because you’re afraid of what she’s going to say. And because you don’t want this moment to end anytime soon.

Spitfire stops you just before you both reach her door. “Look, no pony is going to be happy if word gets out what we did, alright? Honestly, we both broke protocol. Enough to get BOTH of us kicked out.” Your heart stops for a moment as she takes a breath. Then, a sly grin spreads across her face as she leanes up to kiss you once again. “And I’d fucking do it again and again~ Damn, you shoulda seen the LOOK on your face!”

“You’re fucking with me, right?” You deadpan, not really finding it as funny as she was.

The mare giggled like a little filly and kissed you again. “Of course! We’re an inactive branch. The only way we could get in trouble is if you decide to open your mouth, or Equestria goes to war.” Just then, the sound of flapping came behind you.

“Delivery for Captain Spitfire!” The slightly younger delivery stallion held a satchel that he opened and slid out two, large pizzas. Spitfire smiled before paying for them, adding a few bits for a tip and the quick delivery before he took off once more. Only giving a small glance back that could only be described as ‘you lucky bastard.’

Sliding the piping hot boxes into your hands, Spitfire opens the door and lets you inside. “Come on, Cadet! Don’t let the pizza get cold!” You walk inside and are greeted with, honestly the cleanest house you’ve ever seen. “Brr, better turn the heat up. I normally don’t even stay here. I’ll grab a few beers and we can watch a movie or something.”

“Sounds good!” You walk over to the couch and place the boxes down onto an expensive looking glass table. Spitfire quickly returns with a couple of cold beers and flops down into your lap. She pops the top off the table and hands you one. “Thanks, Spits.” Bringing the cold bottle to your lips, you relish in the taste of a frosty cold one after such a long day.

“Hey. To new friendships, and hopefully even more beyond that.” Spitfire pushes her bottle against yours and takes a long drink before grabbing a slice of very cheesy pizza. Butterflies fill your stomach as you grab a slice as well. You lean down to kiss her, when there’s the sound of wings flapping, and somepony else flops down onto the couch beside you.

“Awesome! Pizza!” Sitting there, is the blue furred pegasus herself, Fleetfoot. The mare is almost in the nude, except a pair of pink panties and a small, white tank top. She happily noms on her own slice of the pizza before looking between you both. “Wfat? I miff somfehing?” After a few moments of silence, she shrugs and turns on the TV, munching away.

“So,” Fleetfoot paused as she swallowed her mouth of pizza. “Does he have a big dick or what, Captain?”