When you were first transformed into a beautiful girl after a technological mishap, you were excited that you’d finally get to experience orgasms from the other side. You fully planned to masturbate to your hearts content while researchers looked for a way to change you back.
However, the teasing at school quickly became unbearable. The girls were a little jealous of your new amazing body, and former male friends turned to making jokes at your expense. One classmate in particular was particularly ruthless in his mocking, so you didn’t hesitate to accept his challenge to see who would score higher on the next mid term. Confident in your abilities you agreed that the loser would have to be the servant of the winner for the rest of the school year. You’d make him pay for saying rude things about you.
You were stunned when the test results were posted and he managed to beat you by a single point. The smug look on his face makes you want to punch him. He teases you again and tells you your first job as his servant was to organize his messy locker.
You honor the bet, organizing his notes and books while silently fuming. Then he drops a bombshell. You’re to come back to his house and clean his room the same way. Before you can protest he grabs your arm and forces you to walk with him.
Soon you’re at his house, cleaning his room while he looks at you smugly. As you bend over to arrange some objects on the floor, you’re startled as a hand slips under your skirt and gropes your panty covered ass. Too stunned to move, your brief hesitation allows him to reach up and slide his hand under the waistband of your panties to massage your bare ass. You start to verbalize your protest, but he is unwilling to hear it. Your panties are quickly yanked to the ground and he pushes you so that you must brace against the wall to avoid falling over, flipping your skirt up and exposing your asshole and pussy. He drops to his knees and buries his face between your cheeks, running his tongue up and down the entire length of your ass crack, from your asshole to pussy.
It feels amazing, way better than all the masturbation you’ve been doing. He strips you naked and leads you over to the bed, pushing you face down and spreading your legs. You plead with him to stop but your new female body quivers in anticipation, your clear arousal as your pussy gets incredibly wet on full display. He reaches over to the nightstand and grabs something as he rubs the head of his swollen prick up and down the hot wet crack of your pussy. You think he’s about to take you, but suddenly your ass cheeks are spread, and he pours some lotion all over your ass crack.
Your eyes go wide when suddenly the head of his prick is pressing up against your asshole. You yell at him to stop but the copious lubrication and the pressure from his push has your butthole yielding to his cock almost instantly. You hiss in surprise as he slowly slides the entire length up your well lubricated rectum in one deep slow stroke. He doesn’t stop until you can feel his balls pressed to your wet pussy, his cock fully inside you. It hurts, he’s big and stretching you but he remains motionless, holding himself deep as your bowels adjust to the invader. He reaches underneath of you and plays with your big tits, squeezing your nipples to distract you. Suddenly he begins to move. Slow at first, but faster as you loosen up to him. Pain turns to pleasure as he snakes his hand underneath you to rub your clit while continuing to fuck your ass and your grunts and groans every time he bottoms out inside you fill the room.
It catches you by surprise when he finally cums. His steady thrusting suddenly becomes erratic before you hear him groan loudly and shove himself as deep as possible. Your eyes widen as you feel the powerful throbbing of his cock, feeling his massive load of hot cum splattering against the walls of your rectum. You reach down and rub your clit furiously, the pleasant sensation of being filled with his hot seed quickly making you cum as his orgasm finally trails off.
He pulls out of you with a grunt, and tosses your clothes back to you. You hear a car in the driveway, one of his parents is finally home from work. You don’t even have time to clean up as you hastily get dressed, pulling up your thin cotton panties to catch the cum leaking out of your ass and down your legs. You have to leave by climbing out his window to avoid being seen. By the time you’re finished walking home, the crotch of your panties is soaked through with his sticky cum, translucent and clinging to your pussy and the cool air chills the cum that had dripped down your leg.
Even though you can feel your wet panties clinging to you and your ass is a sticky mess, you’re too tried to do anything but collapse on your bed. A vibration from your phone alerts you to a text message. As you look, its a message from him. “see you tomorrow for more of the same.” As you feel his seed still leaking from your well used asshole, you have a thought. You’re only 1/3 the way through the school year and you realize that for the next 6 months you’re going to be getting your ass fucked a lot.
Its been three weeks since your first encounter with your classmate. You were correct in your assumption. Every day after school for the last three weeks he’s dragged you back to his house and fucked your ass until his parents come home. Every day you’re out the window like a criminal when they pull up, gingerly walking home, his cum dripping out of you and soiling your panties. It still feels like his big cock is moving in and out of you 20 minutes afterward.
As you strip off your clothes in the bathroom and finally peel off your cum soaked underwear, it goes into the hamper with the rest of the week’s laundry. You discovered after the first week that unless washed immediately, it leaves permanent stains. After three weeks most of the panties you own that were bought to get you through your unexpected gender change are permanently stained from his cum, a reminder of your encounters and his ownership of you every time you get dressed.
You turn on the shower and carefully step in. The hot water feels good against your body. After a moment of relaxation you squat in the tub and push. You can hear the splatter of the rest of his cum dripping out of your ass and hitting the bottom of the tub, watching as it mixes with the water and swirls down the drain. His loads are huge and if you don’t try to get it out you’ve found you’ll usually be leaking for hours.
After 5 minutes of squatting you’re sure its all out and finish the rest of the shower. As you dry off another text message causes your phone to buzz. Its him. “Be at my house Sunday morning at 8, my parents will be gone for the day” it reads. You nearly panic. Its Friday, so your abuse is over for the week. He’s left you alone on Saturday and Sunday but now he’s changing the game. Another message comes through. “Don’t even think about ditching, wouldn’t want anyone to find out how much you’ve come to enjoy getting your ass fucked.”
Your cheeks burn in shame. The first week you’d been so resistant, trying to get out of your deal, and generally being nasty to him for tormenting you so. By the second week your ass had started to become accustomed to his huge cock, the initial pain of penetration and stretching yielding quicker to pleasure each time as he trains your ass to take dick. By the third week, much to your shame, the idea of him forcing you down on the bed and taking your ass starts to make you wet. This past Wednesday you had cum for the first time just from anal. He loves taking you when you’re face down on the bed, in complete control. You couldn’t help it, the angle of his thrusting and the position had both your nipples and your pussy rubbing up against his dirty, balled up sheets and comforter. His mocking was unbearable when he realized you’d cum, and it had excited him so much that he instantly shoved himself deep and hard and unloaded a massive wad of spunk into your hot rectum.
You knew you were caught. You could hardly sleep that night. You set your alarm for 7, despite it being a Sunday, so you wouldn’t be late.
When you arrive at his house the driveway is empty. You knock on the door and it quickly opens. You can’t meet his eyes as you step inside. He grabs your arm and leads you to his bedroom. Once inside he picks up a package and tosses it to you.
“Put this on” he commands.
Puzzled you open the package. Inside is the tiniest bikini top you’ve ever seen in your life, and a miniskirt that won’t even fully cover your ass or pussy. He looks at you expectantly as you stare dumbfounded at the attire, tapping his foot impatiently.
“Hurry up.”
With a grimace you start to remove your clothes. He forces you to face him as you do so, delighted by the embarrassed look as you lose your shirt, your skirt, and finally your bra, exposing your big tits to him. The mishap had worked wonders, you’d been blessed with triple D sized breasts when you changed, with all the perkiness and firmness of a teenager. He grabs them roughly and paws at them, leaning forward to suck on your nipples before handing you the top. You put it on, the thin triangles of fabric barely covering your nipples and offering minimal support for your heavy breasts as you tie the string behind your back.
You move to step into the skirt but he stops you. He tells you to lose the panties. You close your eyes, dropping the cotton undergarments to the floor and stepping into to much too tiny skirt and swiftly pull it up. His teasing is relentless. Just as you thought the skirt barely comes halfway down your ass and your pussy is completely exposed to him. You’d learned quickly how to shave, and kept your lips smooth and bare with a small, well trimmed bikini line bush above. Whatever the machine had done to you had also made your skin flawless, and you never had to worry much about razor burn on your pubic area or legs. Just a little lotion and you were smooth as silk after a shave.
He cups your mound, commenting appreciatively on its smoothness as he probes with his fingers before backing away and leading you out the door. You’re to spend the next hour doing his chores, dressed like that, as he watches. You can see the massive hard on straining his shorts as you’re forced to bend over and clean, exposing yourself completely to his hungry eyes.
You’re polishing the dining room table when suddenly he’s behind you, pushing you down so that you’re bent over it. You’re pinned against it, unable to escape as you hear him moan that he can’t wait anymore. Quickly he yanks off his shorts and spreads your ass, coating your butthole and his cock with lotion. You brace yourself as you know what is coming next, holding tightly onto the table and spreading your legs slightly to give him easier access to you. You’re resigned to your fate as his bulbous head presses against your sphincter, smearing the lubrication all over your opening before pushing inside.
You push out to loosen yourself as he grabs your hips and pushes forward, your body quickly accepting cock once again. He gives a few short slow strokes to let you adjust and then one long slow one, pushing forward while pulling you back until his thighs are pressed against your ass and his rock hard maleness is fully embedded in you. It doesn’t take very long before it starts to feel good with your training, and in two minutes he’s pounding you deep and fast.
Your big tits are squashed against the table as you reach under and furiously rub your clit, your moans and his grunts echoing in the large but sparsely furnished room. You hear him telling you to take his load as he groans loudly, cock throbbing powerfully and spewing hot cum deep in your bowels. You cry out as you cum with him, your female juices dripping down your legs as you enjoy being filled with his seed.
You rest for a few moments before he pulls out, and you clench your ass to keep his cum inside so you won’t have to clean the floor again. He drags you into the bedroom and tosses you on the bed, pulling the tiny fabric of the bikini aside so he can suck on your nipples.
In minutes he’s hard again. The next three hours go by in a haze of deep hard anal. He’s more adventurous this time, and makes you try all sorts of positions. On your side, spooning you and groping your tits while fucking you slow. His previous load makes a great lubricant as he continues to use your ass. Next he makes you climb on top and ride him, your big tits bouncing up and down as you rock your hips back and forth, taking him deep. It allows you to control the depth and angle of penetration and it quickly becomes your new favorite position. After bringing you off by rubbing your clit, you don’t even mind when he grabs your hips and holds you all the way down on him, his big cock shooting you full of cum for the second time, his second load joining whats left of the first deep inside you.
The minutes tick by as he continues to take you. You’re on your hands and knees when he cums inside for the third time, his hard thrusting making you hold on to the bed tightly, tits swinging wildly. You’re completely loose now, and you no longer feel any shame at the hard fucking you’re receiving. You’re not quite sure how to feel about that.
By noon your asshole is starting to get a little sore. This time you’re on your back with a pillow underneath your hips, legs up on his shoulders as he continues to pound you deep and hard. As the minutes tick by you beg him to hurry up and cum so you can rest. He’s already cum three times and its taking him forever. He redoubles his efforts, and then does something unexpected. He leans forward, all the way, pushing your feet up by your head as he nearly folds you in half. Your tits are pressed to his chest as he leans in and kisses you. He had never done this before, and your shock lets him slip his tongue in your mouth. Its ironic that he’d been fucking your butt for three weeks but never kissed you or done anything else. You close your eyes, letting him explore your mouth. Moments later he groans while kissing you deeply, thrusting to maximum depth. You can feel every twitch of his cock as he unloads in you yet again, your rectum taking its fourth load of cum in three hours.
He breaks the kiss and moves back to a kneeling position, keeping his cock buried in you. You watch as he leans over and goes into the drawer of his nightstand. You’re shocked as he pulls out a six inch long butt plug. He lubes it with the lotion and pulls out of you, the plug quickly taking his place as it slips easily into your well used depths.
“Don’t want you leaking cum all over my bed and the house” he says, grinning tired and sweaty.
He then collapses next to you, pulling you so that he’s spooning you, one arm draped across your slender waist. You’re too exhausted to complain as you lie there and close your eyes, and soon you drift off to sleep after getting almost none the night before.
Several hours later you’re shaken awake. His parents are home, and the adrenaline hits you as you scramble to find your clothes. You strip off the bikini top and skirt, moving to remove the plug thats been buried in your ass for hours.
“Leave it” he says, tossing your clothes at you. “When I bring you here tomorrow after school it better still be in your ass, or else.”
You grimace at his threat as you step into your panties and pull them up, covering the flat flange of the long hard plug. You finish getting dressed as you hear him leave his room and talk to his parents. You hear them compliment him on cleaning he’s done. The praise he receives annoys you greatly as you gingerly climb out the window thanks to the invader currently filling you. You can feel it, along with the massive amount of cum trapped in your ass with every step you take. How you’ll make it through the day at school tomorrow is anybody’s guess.
Its a rough day going to school the next morning. You hardly slept. You’ve gotten used to the plug, except when you sit directly down, as you have to do during class. You squirm in your chair as you try to get comfortable while listening to teachers drone on. Your attention isn’t focused on them, but the invader lodged inside you. You look over and see your tormenter smile at you ever so often, obviously enjoying your discomfort.
You’re actually relieved when he drags you to his house like every other day after school now. He doesn’t waste any time in forcing you down on the bed. He tugs your panties down and flips up your skirt, massaging your ass with both hands. He grins as he pushes on the plug, eliciting a grunt from you in response. Much to your relief, he grabs the edge of the plug and slowly starts to pull it out. Just before its half way out, he suddenly lets go, and you sphincter unexpectedly sucks it back in.
“Looks like your ass likes it so much it wants to keep it. What a slut you are” he taunts you, slapping your ass and repeating the process.
Finally after some begging and pleading he removes the plug. The minute he does you have the sudden urge to go to the bathroom. All that cum trapped in you wants to make its way out and you nearly trip on your half pulled down panties as you race to the bathroom to expel all the loads pumped into you yesterday.
You sit there for a good five minutes as it drips out of you, your ass feeling relaxingly empty after your ordeal. After you clean up you head back to his bedroom, miserable, and expecting to be taken by him yet again.
Shockingly enough he gives you an odd look, and tells you that you’ve endured enough for one day and sends you home without any further molestation. You quickly exit the house before he can change his mind, thankful for this stroke of luck.
The next day has you relieved. You start to wonder if maybe he’s feeling guilty for using you as his personal cum dump. Things are looking up, until lunch. No sooner have you finished eating and moved to dispose of your trash than he catches you alone and tugs your arm and pulls you out of the cafeteria and into the bare hallway. He pulls you along, holding your hand. You quickly follow praying no one sees him touching you like that.
He shoves you into one of the lesser used restrooms. The second you’re inside and he makes sure its empty one hand slides under your shirt to cup your large bra covered tits, and the other snakes down your panties and grabs your ass. You can’t believe he’s actually doing this in school. A sense of dread of anyone finding out about what you’ve been doing chills you to the core as he pulls you into a stall.
He tugs down his pants and underwear, exposing his rock hard dick which proudly juts into the air. He sits on the toilet and leans back. He looks at his watch briefly and then pulls a bottle of lubricant out of his bag and hands it to you.
“We don’t have much time until class so you better hurry. It would be a shame if you didn’t make me cum and everyone found out what a cock loving slut you’ve become since you were turned into a girl.”
You grimace as you yank the bottle of lotion out of his hand. You don’t need to be told what to do at this point. His smug looks as you pour some lubricant on your hand and stroke his cock makes you want to hit him.
“Better hurry, you got 10 minutes.”
Once his cock is wet and glistening from the lubricant, you turn around, pull your panties down to your knees, hitch your skirt up around your waist, and pour some more lube on your hand which you quickly use to grease your asshole until its nice and slimy just like his cock. A moments hesitation from nervousness at actually doing this in school as you wipe your hands off on some toilet paper has him growling with impatience.
“Sit on it” he commands you, pulling your hips backwards and nearly causing you to fall.
You give him a nasty look as you turn around to face away from him and lower yourself, reaching down and grabbing his greased cock and holding it tightly. You guide your hips while holding him in position until the head of big prick slides between your cheeks and gently presses against your asshole. You take a deep breath and push out as you sink further down, your well lubed anus parting swiftly as the head pops inside you. You grimace a bit from the initial penetration, your legs burning from squatting at such an awkward angle. Eager for relief, his cock slides into you as you slowly sit down, the feel of his thighs supporting you and taking the strain off your legs a welcome respite. You wiggle your hips, satisfied when you’re in a position to take his cock all the way.
He slaps your ass and tells you to ride him as you start to rock back and forth. After the other day’s long butt plug session there’s no pain as you take him fully. You let out an involuntary groan ass your ass is filled again. You’re glad he can’t see the blush on your face as you bounce up and down, panties at your knees and your legs together tightly so that you can fit between his open legs. If there wasn’t such a high chance of the two of you getting caught you would enjoy this a lot more.
Two minutes tick by as you pick up the pace. You have to make him cum quickly and clean up before class. As you’re starting to bounce hard, taking him deep and trying to make him cum, he reaches around and starts to massage your clit. Another groan escapes your mouth and he takes obvious enjoyment at your pleasure. He’s become quite good at it, and the feel of his cock in you combined with you rubbing is going to make you cum quickly.
Just as you’re about to cum you hear the door open to the bathroom. You freeze in panic as you hear male voices but he continues his assault on you. You’re too close, and despite hearing a zipper and several guys start to piss in the urinals his deftly working fingers send you over the edge. Your body goes rigid as your eyes widen and you clamp your hand over your mouth to prevent anyone from hearing you. You arch your back and push down, fully penetrating yourself and enjoying the feel of his cock deep in your ass as you cum hard.
Your body is literally trembling from such a tremendous orgasm, the quivering and squeezing milking his cock. You feel him push up into you, grabbing your hips and holding you tightly as he rocks you back and forth on him. A sudden powerful throbbing lets you know what’s happening as the warmth of his cum spreads through you deep in your ass.
You close your eyes and do everything in your power to remain quiet as your twitching body is filled with his semen. You’re vaguely aware of the sound of fading voices and a door closing shut as you enjoy the feel of him cumming in you. As he finishes you sag down on him, his cock starting to go soft in your ass.
After a few moments rest, you’re about to stand when you hear the bell. You only have a few minutes to make it to your next class. You still have to clean up and grab your stuff! Suddenly your torturer stands up and pulls out of you, reaching down and pulling your panties back up into place before his cum starts to leak.
“Looks like you don’t have any time to clean up if you don’t want to be late” he says, looking positively satisfied as he quickly wipes his cock and tucks it back into his boxers and pants.
You want to hit him as you grab your bag and storm out headed for your next class, already feeling the cum and lube start to leak out of you and stain your panties. You know you’ll be leaking his cum and dealing with sticky wet panties for the rest of the day.
Source: reddit.com/r/eroticliterature/comments/8ewpow/man_transforms_into_a_woman_and_gets_to_explore
If you manage to finish here’s the rest of the story: https://pastebin.com/1QxRRxGK
It’d take 7 more posts if I were to paste it, so just read from there.