by D. L. Savage
Finally! He had the whole afternoon to himself.
Tony felt his stomach flutter with excitement as he realized just what he was about to do.
First he closed the curtains, and then he pulled out that package from under his bed. He took out its contents, laying the items one by one on the bed. Then, his heart absolutely pounding with a mixture of nervousness and excitement, he began to get undressed, slowly uncovering his slim, pale, almost completely hairless body.
He’d never been at all interested in macho pursuits and sometimes he wondered if he lacked testosterone or something, because his body still seemed waiting to finish going through puberty. Sure, he had some pubic hair, but not that much, and there were just a few silky browny-blonde tufts growing from under his arms, too. But his legs were almost completely hairless, if you didn’t count the blonde downy peach fuzz that covered his shins. And his chest and back were smooth, too. Even his feet were small and girly: never growing past a pathetic size 6.
Once he was completely naked, the first thing Tony pulled on were the stockings, feeling their tight fabric move snugly over his feet, his ankles, then pulling them further, up over his knees and stretching them up onto his mid thigh. They made his legs look surprisingly slim and — he noted with a shiver of surprise — actually kind of girly. Wow. Was it really that easy? Yeah, if he squinted down at his own legs a certain way, there’d be no difference if they belonged to that of a slim, sexy girl. He felt pleased and surprised, eager to transform further ...
Next he tried on the bra.
He’d seen something on TV perhaps about how girls put these on correctly, and so he copied what he’d remembered: fastening it first around his waist like a belt, and then shuffling it up and into place. It felt so weird, and kind of dug into his back and shoulders in places. But it wasn’t an especially painful feeling though, just ever so slightly uncomfortable. He looked down at the small cups, that were hanging open, his own flat chest exposed beneath.
Didn’t girls sometimes pad their bras? he thought.
At this, Tony went over to his desk and took out the roll of toilet paper that he kept in there for secret clean up operations, after watching porn on his computer. He tore off two long rolls of paper, scrunched them up and then stuffed the cups of his bra with them, until, as long as you didn’t peer directly down the front, it actually kind of looked like he really did have two small, pert breasts. He guessed Bethany must be A- or B-cup.
Tony could feel his cock kind of swelling, just a little, at the completely odd, unusual feel of the bra and the stockings, but he ignored the horny, tingling feeling as much as he was able, as he didn’t want to get hard before he’d at least got the panties on, otherwise he’d never fit his cock neatly inside them.
He went back over to the bed and picked up the tiny pink thong, holding it up to his face again, his hands trembling a little with excitement as he once more sniffed in a deep breath of Bethany’s musky scent, so excited to feel the very same panties that she’d worn slipping between his ass cheeks. This was the part he’d been looking forward to the most for some reason.
He bent over and placed first one, then two feet through the thong. Then he pulled it upwards, over his legs, his thighs, then further, until the waistband was in place. He felt that thin strip of fabric slide up between his buttocks and, with surprise, he realized that the panties must be made of some sort of elasticated material that actually stretched to accommodate the prominent bulge at the front too: his cock and balls creating a smooth round lump in the pink fabric. He felt his cock grow a little more, but luckily it stayed tucked down, just making the bulge get a little more prominent.
Next he stepped into the skirt and pulled this up around his waist too. It felt so revealing and floaty, hardly covering anything at all. He zipped up the zipper at the side, then smoothed it down, but he could still feel cool air all around his buttocks. Wow. He felt so fucking exposed. So flirty and sexy and weird. It was such a strange feeling; and he was kind of getting turned on at the idea of how open and accessible he was beneath this tiny little pleated skirt. Because all he would need to do was bend forward, or catch the slightest gust of wind, and you would be able to see absolutely everything: the smooth roundness of his bare buttocks, and the hot pink flash of his thong, cupping his balls and cock so tightly and disappearing snugly between his tender ass cheeks.
Next Tony pulled on the vest top, smoothing it down over his flat tummy, marveling at just how real his brand new breasts looked now, beneath it.
It was time for the final piece of the puzzle, Tony realized with another shiver of expectation and excitement.
He picked up that silky, shiny black wig and pulled it onto his head, feeling the netting hug his scalp and the ends of his new long hair swishing around, tickling a little against his bare shoulders. As he padded over to the full length mirror in Mike’s side of the room to see his new reflection, Tony felt his skirt floating around, dancing at his thighs, and he felt the thong, so tight and snug, rubbing softly against his asshole as he walked, and the cool air on his bare upper thighs. He felt so pretty kinky and horny by now; turned on by a newfound sexiness that he didn’t even know he had!
So this is what it feels like to be a girl, Tony thought, and he found a part of himself even wishing there was someone else there to see him like this: wanting to turn someone else on with this new sexy side of himself, just as much as he was getting turned on alone.
When he saw his reflection, he couldn’t quite believe what he was seeing.
Fuck!
He actually looked good!
* * *
Tony gasped, feeling his cock swell and twitch beneath the snug elastic material of his pink panties. He drank in his own reflection, and for the first time in his adult life, he didn’t completely hate what he saw. Sure, there were still little imperfections here and there: his eyes still looked tired, for instance, and his brows were maybe a tiny bit unruly and his skin on his face was kind of blotchy, but apart from that, he actually felt like he could almost pass for a girl!
The main thing to his advantage was that his figure was just right for this kind of outfit.
Okay, he might not look totally curvy and voluptuous, but he did kind of look like a skinny, slim-hipped sporty type of girl, just like Bethany in fact! It was only now that Tony realized just how similar their figures were. Tony was only a couple of inches taller than her, if that, and as a result her clothes seemed to fit him so well, so perfectly.
He turned his back to the mirror and looked at himself over his own shoulder, feeling another horny twinge in his cock as he slid his skirt up over his thighs and bent forward, letting his smooth pale buttocks slowly and sensuously emerge from beneath the hem of the miniskirt: and apart from the soft round bulge of his balls, which was somewhat bigger than that of a girl’s pussy lips, the view was otherwise the same. He had a hot ass, he realized with delight. A hot, full. round ass, just as smooth and toned and sexy as Bethany's!
He reached around behind himself, running his fingers over the smoothness of his buttocks, feeling his skin tingle, feeling so horny and sexy, wanting to watch his body move and write and wriggle in its new, purely female state: wanting to watch himself be as sexy and as feminine as he possibly could …
The video, he remembered.
If he filmed himself on his computer, using the very same webcam that had got himself into this mess in the first place, then he could also watch himself on the screen as he made his movie, killing two birds with one stone: not only would he fulfill his side of the bargain and video himself for Bethany, but secretly he realized that he actually wanted to do it no matter what … He wanted to see himself.
As the computer booted up, Tony selected one of Mike’s ‘sex mix’ CDs — the ones full of r’n’b slowjams that he always put on when he wanted to try and get a girl, those same nights that Tony was always kicked out of the room, and forced to wait around studying in the library or one of the computer clusters.
The sultry, sexy music filled the room, urging Tony to move his body, to feel that skirt brushing around his thighs and ass, to move his hands up his figure, cupping his new breasts …
Finally the computer was up and running, and Tony quickly set the webcam recording, the image of his new girly self now filling his monitor screen.
Wow!
He looked even hotter on the screen — due to the lower resolution and the cameras other settings, his skin looked much softer and purer, and there was now almost nothing to distinguish his feminine physique and appearance from that of a real girl. His long black hair sparkled in the dim light, and he began to slowly dance to the sexy beat of the music, running his hands up and down his body, turning around, steadying himself on the chair and arching his back, thrusting his ass out for the camera, feeling his miniskirt riding up around his bare butt cheeks.
He ran his hand between his legs, his fingers lightly brushing against the tingling swollen lump of his cock and balls beneath the stretchy hot pink fabric of the thong. He moaned a little, desperate to release his cock from its restrictive stretchy sheath, but also kind of savoring the pleasurable discomfort, too. His small cock was fully hard by now, but still curled around on itself, kept snug and tight by Bethany’s panties.
Tony glanced over at the bed, the pale pink dildo now catching his eye.
It was time.
He picked it up and brought it near to his face. It was so big, much bigger than his cock. It was totally realistic too, even down to tiny little details like folds of skin and veins running up its large thick shaft. It was kind of soft and hard at the same time, pretty much like a real cock, and Tony wondered what it might feel like in his mouth.
Before this moment, he’d never ever thought about the idea of sucking a cock, but now the thought of it really turned him on. It seemed to fit in with this sexy new feminine side of himself: what seemed to get him most horny how was the idea of getting someone else off.
He parted his full lips and brought the dildo up to his mouth, gently sucking on its big bulbous head. He could taste the faintly sweet-yet-salty tang of Bethany's pussy juice on the dildo as he sucked it, taking more and more of it into his mouth, savoring this weird new feeling, his cock throbbing in his panties as he began to slowly fuck his own mouth.
He moaned a little, closing his eyes, wishing that this was a real cock instead of just a rubber one. Man, how nice it would feel to have some hot thick meat sliding in and out of his mouth, twitching and pulsing and then finally spurting its thick creamy cum deep into his throat …
Tony pulled the dildo from his mouth with a slick wet pop, then pressed it against the seat of his chair, so it stuck there by its suction cup, all shiny and wet with his own saliva.
He felt overcome with an almost animal horniness now. His whole body was shivering and trembling as he positioned himself over the dildo, parting his legs wide, his skirt bunched up around his waist, reaching behind himself and tugging the thong slightly to one side to uncover his tight little asshole, which he lowered down onto the dildo, until the large wet head of it was touching right against his puckered button.
He tried to relax his ass muscles as best he could, and then, with a grunt, he let the first bit of the dildo slip inside him. Fuck. It felt absolutely huge, and the feeling was somewhere right between pleasure and pain. He paused where he was, unsure if he could take any more of this big hard shaft inside him. He reached down and touched it with his fingers, trying to work out how much he’d fit inside himself so far. Not much at all, by the feel of it.
He closed his eyes, relaxed again, and let himself slip a little further down the dildo. Again he groaned and grimaced, feeling another intense flash of pain, mixed in with a deep, horny pleasure at the thought that this too was exactly how a girl would feel, if she were to have anal sex, which he’d heard a lot of girls enjoyed ...
Instead of sliding any further down the dildo though, Tony lifted himself up it again, then pushed back down, slowly but surely building up a bouncing rhythm on it. And with each bounce, he let a little more of the thick rubber cock slip up inside his tight quivering ass.
Tony gasped as he found himself actually riding the dildo finally, his silky black hair beginning to dance around his bare shoulders, his pert little breasts staying firmly in place, his long legs helping him bounce up and down. And on screen he looked so fucking sexy: just like a real girl, the only difference being that hard swollen bulge in the front of his panties.
As Tony continued to ride his rubber cock, he felt the strangest thing. He felt urgent fluttering tingles building up in his stomach, stronger and stronger, and at first he wasn’t sure exactly what this new sensation even was. And then he realized. It was the start of an orgasm!
What the fuck? he thought. But I’m not even touching myself!
And slowly but surely he felt the sensation get stronger and stronger, and as it did, Tony rode harder and faster on the dildo, gasping and whimpering as the feeling grew and grew, flashing out around his body now.
Fuck, he really was about to come!
He reached down between his legs and tugged the gusset of his thong to one side, his cock springing free just in time to spurt the first in a series of long hard jets, the cum spattering all over his tummy and thighs as he continued to ride the dildo, his cock swinging up and down freely as it squirted, and he felt his ass clenching tight around the dildo too, his whole body now shuddering from the sheer force of his orgasm: so much more intense than anything he’d experienced before now.
It took a moment for him to come back down to earth afterwards. Tony’s trembling legs felt like jelly as he slowly lifted himself up and off the dildo, feeling it slip from his quivering ass, his soft cock still dripping with the final globs of his gooey white cum. And his head was still so busy spinning and whirling, it took him another moment before he remembered that he’d recorded the whole thing too!
* * *
Tony clicked ‘send’, then sat back in his chair, his mind still spinning with all kinds of conflicting feelings. A part of him was totally disgusted with what he’d just done. Another part was worried — did this mean he was gay? Bi? A cross-dressed? A sissy? A girl trapped inside a boy’s body? Or something else entirely? Maybe there wasn’t even a name for what he was …
And then another part of him was just plain excited, too: both for what he’d discovered about himself and his sexuality and also for what Bethany would say when she saw his brand new movie. If she thought he was kind of ‘pretty’ as a guy, just wait until she saw him completely transformed!
And then another thought entered Tony’s mind too.
What if his video actually turned her on? What if she masturbated when she watched it, just like she had that night on webcam. What if she toyed with her small breasts and her tight hairy pussy again, sucking her lip into her mouth and shivering as she came, squirting while watching Tony spurt his own cum, hands free? Holy shit. The idea of that – of Bethany playing with herself while watching his video – made him want to cum all over again.
But instead, he waited.
He denied himself any more pleasure until he heard back from Bethany, who he’d been kind of secretly thinking of since her email as his ‘mistress’ — it seemed a fitting title for her, because she was cruel and strict and cold with him. She wanted to teach him a lesson, to teach him how to be a good little obedient slut. And more and more, Tony was beginning to realize that this was exactly what he needed …
* * *
Bethany's email arrived that same evening. Luckily Mike was out once again, this time on another date with Stephanie, his casual on/off girlfriend (or ‘fuck buddy’ as Mike always called her to Tony), and so Tony was able to take his time opening and reading the email, savoring the strange new feelings he was experiencing — fear and excitement and anticipation all rolled into one inside him.
With a deep breath, he opened the email:
That was hot, Bethany's reply read. You really are a ho
rny, kinky little slut, aren’t you? I was right about you: I just knew you’d make a pretty little girl. I especially liked the part where you came without touching yourself. I knew then just how much you were enjoying that dildo, pounding your tight asshole.
But don’t get too pleased with yourself, slut. The fun’s not over just yet. You’ve still got a long way to go before I let you off the hook. I want you to come to my dorm, tonight — Block D, Room 4F, 10 p.m. sharp — and I’ll teach you a lesson you’ll never forget. And before you come round: make sure you shower and shave under your arms, as well as your legs and balls and ass. And don’t forget to bring all the items I sent you.
L x
Tony read over the email again and again, his mind whirring. Why was she doing this? Some part of her must be getting off on it: on humiliating him, on telling him what to do, on dominating him completely. This was no longer about the money, Tony realized. Something else was going on here, he just couldn’t quite work out what.
And the strangest part of all was just how much he was enjoying being humiliated. He had to admit that to himself now. He was actually relishing being made to feel small and worthless by this strict bitch of a mistress — by cruel, sexy, horny, green-eyed Bethany, who seemed to embody all those nasty bratty high school girls that had turned their noses up at him all this time, dressed in their figure-hugging yoga pants and thong panties, their hair done up in ponytails, chewing gum, their lips full and glossy, their breasts small and pert, their hard little nipples tantalizingly visible through their shirts and blouses …
It was almost too much to take in in one go.
