I breathed deeply as I looked at the skirt in my hands. Looking up at the mirror, I found myself wondering how the hell I had ended up in this situation in the first place.

----------

I found my roommate on Facebook, which I'll admit can be a little sketchy, but I totally lucked out! He's very neat, does his dishes, and is genuinely a really chill guy. We've ended up talking in the kitchen till the early hours of the morning many times now, just laughing and passing a joint back and forth. The only thing about him is the way he... dresses? Dresses isn't even the right word; it's more like his whole vibe. I guess you could say he's a bit of a femboy.

Sure, he wears skirts and thigh highs and walks around the house in this big, oversized Metallica t-shirt, but he also kinda talks and acts like a cute girl too. He's super friendly and cuddly, and you'd think this would get in the way of his dating life, but this dude brings home way more girls than I do. Not just girls too, guys, other femboys, basically everyone seems to want him. I have no idea how he does it!

Earlier, we were playing Mario Kart on the couch, a pretty typical night for us actually. He tends to be a bit of a homebody, but I had recently broken up with my girlfriend and didn't really feel like dealing with going out. He had been teaching me to play, and honestly, I'd been getting pretty good! I knew some of the routes by heart at this point, and I was starting to beat him pretty regularly. After a couple of rounds, I noticed he seemed a little distant, he kept shifting uncomfortably on his end of the couch, not really sitting still. Suddenly he turned to me:

"Hey, wanna play for stakes this time?" he said.

"Oh, you're on!" I replied, grinning. 

"What do you want to play for? I can't do cash since I'm kinda broke, but we could say loser has to do the other's laundry for a month or something?"

"Eh, that's boring," he said, flicking through the track menu options. "How about… loser has to do whatever the other person says for the rest of the night?"

"Bet," I said simply. "Flip a coin for who gets to pick the track?"

"Nah, you pick," he said, yawning, the hint of a smile on the corners of his lips.

As soon as we started playing, it became abundantly clear he had been going easy on me this whole time. Very easy. He absolutely destroyed me in every race. I didn't even come close! The weird part is that he wasn't bantering like we usually did when we played, playfully poking each other as a distraction. It was just pure laser focus as he dominated the whole time.

"Best two out of three?" I said weakly when I finally crossed the finish line of the last lap.

"You wish," he said, grinning. "I'll be right back."

He walked to his room and came back holding some clothes and accessories in a little pile, which he handed to me.

"Go put these on," he said, gesturing to the bathroom down the hall.

"Bro, what the fuck? No way," I spluttered indignantly. "I'm not wearing that."

"Oh, grow up," he said, rolling his eyes and flopping back on the couch. "You lost, and rules are rules. Plus, it's just for tonight."

—-------

I took a deep breath and set the skirt down on the counter, then proceeded to take my shirt off.

"Stupid bet," I muttered to myself as I tugged my jeans off, hopping on one foot.

"Stupid sissy clothes."

I threw my clothes in a heap in the corner and stared trepidatiously at the clothes he had given me. It suddenly struck me how quickly he had been able to grab them… almost like he'd had this ready.

"Nah, that's dumb," I thought as I slipped on the crop top, the hem revealing my smooth midriff.

Luckily, I was the right size to fit his stuff. I was a little more toned since I liked to work out and play sports. The skirt fit just fine around my hips.

"Huh," I thought, looking at myself in the mirror. "From the waist down, I just kinda look like a hot girl. Like if I saw a girl wearing this with legs like these, I'd—"

I stopped myself there and shook my head. What was I thinking? Better just get this over with. After wrestling on the thigh-high socks (kinda tight) and the choker (felt weird but had this cool chain thing in the middle), I was left with the part that I was most dreading. There on the counter was the last article of clothing he had left me: a pair of lacy black panties.

"I could just wear my boxers instead," I thought to myself. "He'd never know." But even as I thought it, I was reaching down and stepping into them, pulling them up my thighs under my skirt. There, I encountered a bit of a hiccup.

I don't mean to brag (okay, maybe I do a little), but I have a pretty big cock. It's not like massive or anything, but it's above average and thick, and I had definitely made my girlfriends in the past pretty happy. The cute lacy panties were simply not equipped to handle something of that size, and so, even soft, I bulged visibly through them.

"That's kinda hot," I thought, absently rubbing my cock through the panties, loving the friction of the fabric against my sensitive skin. I jumped suddenly as I heard a knock at the bathroom door.

"Everything okay in there?" my roommate yelled. "You're taking fucking forever."

"Oh, screw you," I laughed, snapping out of the reverie I had just been in, and walked out to meet him. This may be dumb, but it was mostly over, and he'd probably just make me go get him drinks and stuff the rest of the night.

As I stepped out of the bathroom, I was conscious of a slight breeze coming in through the window that ruffled my skirt, the fabric feeling soft and cool against my thighs. I blushed a little as I turned to face my roommate, preparing myself for a snide comment or a jab about "femboy supremacy."

Instead, he just stared at me with a strange intensity, his eyes tracing every inch of my body. I had caught him looking at me once or twice like this before, always when he thought I wasn't looking. I didn't think much of it; I knew he was bi and figured he was just checking me out the way I would check out a girl roommate, but this time felt different.

"Come here," he said, his voice steady and warm. "Turn around for me."

I rolled my eyes and gave him a little spin, my skirt lifting slightly as I did so.

"Walk around the room a little, nice and slow," he said.

This was a little weird, but I figured he was just getting his money's worth from this bet. Next time, I was definitely only taking him on in Smash, that I knew I could beat him in for sure... probably. As I walked around the room, I could feel the intensity of his gaze still on me, even when I had my back turned to him.

"Stop," he said suddenly as I walked up to him. "Run your hands down your body."

"Dude, I'm not—" I started, but he quickly cut me off.

"Do it," he said firmly, a thickness to his voice I had never heard before.

I found myself slowly tracing the contours of my body, feeling all the exposed skin this outfit provided. It felt good, but I was still unsure of what was happening. As I got to my thighs, he spoke again:

"Lift your skirt up," he said simply, his voice a little softer than last time.

I paused briefly but then complied, thinking it was better to just get this over with so we could pretend it never happened. To my horror, I found myself growing hard in my little panties, my cock straining against the bounds of the fabric. Slowly, he walked forward and gently traced the outline of my cock, his soft fingers sending jolts of energy through my body. He reached down and pulled out my now throbbing cock, stroking it gently in a way that told me he had done this before.

"What a nice big cock you have," he said, continuing to stroke me as my breath caught, the feeling of his warm hands around my shaft sending me spinning.

"But I'm afraid I'm bigger," he said, smiling, and reached down to pull up his own skirt.

I was so caught up in the feeling of my cock being stroked that I almost didn't register what he said, but then I looked down and saw what he had been hiding this whole time. Swinging gently between his thighs was the biggest cock I had ever seen. Easily several inches longer and thicker than mine, his pink panties had stood no chance of containing that monster as it hung proudly out the sides, his thick balls straining out as well.

Smiling, he reached down with his other hand and started stroking himself, and I realized with horror that he wasn't even fully hard. He brought his thick, smooth cock against mine and proceeded to press them against each other, his huge shaft dwarfing mine. He slapped my cock around a little with his, then held his up against mine so I could watch it droop over the top. Holding both our cocks together, he began to stroke, frotting us gently as he let out a little moan.

I couldn't believe how unbelievably turned on by his big dick I was, the sheer size and weight of it alone making me even harder. I had never been particularly interested in men before, I identified as straight, had only had girlfriends, and never thought that much about guys in the locker room, but this? This was something different.

"Looks like I beat you again," he said, chuckling, still stroking our cocks together like it was the most natural thing in the world. I didn't trust myself to speak, so I just whimpered softly, a sound I don't think I'd ever made before in my life.

"Time for my prize, then: get on your knees." 

With a gentle push on my shoulder, he had me on my knees, my body acting completely independently of my mind. From down there, his now hard cock loomed above me, thick and heavy as it swayed and twitched in front of my face. I could feel the heat radiating off of it as he jerked himself off in front of me, using one hand though he could have easily used two... or three... or four.

Suddenly, he let his cock drop down on my face with a meaty "thwack." The impossible weight of it rested on me as he rubbed himself against me, slapping me gently with his thick shaft. Then, in a moment I knew was coming, he pulled back and lined the tip up in front of my mouth, waiting patiently as my lips parted of their own accord. I didn't look up at him as I took him into my mouth, not wanting to break the spell by looking into his familiar eyes. With my gaze fixed on his length, I began sucking his tip, bobbing my head gently as I tried to take more and more of him into me.

He moaned as I let him in deeper, my mouth struggling to accommodate his prodigious girth. I curled my lips around my teeth like an old girlfriend of mine used to, and focused on relaxing my throat as I proceeded to take him in. He let out a soft moan as I proceeded to blow his huge cock, his hand on my head in my hair as I did my best to pleasure him. At around halfway down, I finally hit my limit as I began to gag, my body unable to take any more of him. I tried valiantly, but he was just too big; this is as far as I could get.

Suddenly, from nowhere, I heard a click. I looked up to find him holding a leash, the other end attached to the little chain loop on my choker.

"Oh, so that's what that's for," I thought absently, my mouth full of cock. "But why does he need a—"

With a sudden tug, he yanked my throat and face further down his cock, one hand in my hair and the other on the leash as he pulled me into him. At the same time, he began thrusting into me, using my throat as a hole for his pleasure and leaving me fighting for my life as I tried to hold on to his hips.

"Oh fuck yeah," he moaned as he fucked my face with his huge cock. "You take it like such a good boy. Look me in the eyes while you suck me"

I looked up and met his gaze, my cock throbbing wildly at the intensity I saw there. We kept going like this for God knows how long. He would occasionally give me breaks as he pulled out of my mouth, letting me catch my breath as he pumped his cock with both hands. Soon enough, though, I would feel a tug at my leash as he thrust himself back into my mouth, forcing himself deeper into my throat. Finally, after what felt like ages, he began to quicken his pace, thrusting more and more desperately into my throat. Even after all of this, I had yet to make it further than three-quarters of the way down before I hit my limit, but suddenly he was thrusting harder and deeper, claiming inch after inch.

"Oh fuck, baby, I'm about to cum. Take it like a good boy, take my big dick. Oh fuck, oh fuck, oh FUCK."

With that, he grabbed my head with both hands and forced himself into me fully, my face pressing against his body as I took every inch of him. He came hard down my throat, his cock throbbing and pulsing wildly as he dumped wave after wave of cum into me. Eventually, he pulled out and stroked himself off to finish his orgasm, thick, milky white ropes that on their own could have been one of my climaxes covering my face. I sat there with my mouth open and tongue out, too shocked to do much else as he used me to get himself off. Finally, he slowed down and stopped, thick globs of semen dripping down his shaft. Panting slightly, he looked down at me, his cock hanging ponderously between his soft thighs.

"What a great warmup," he said, smiling, all the characteristic pep and joy back in his voice. "Now let's have some real fun!"

I was about to object, exhausted from being facefucked into oblivion, but I could still feel my own cock throbbing against my panties, yearning for release.

"A deal's a deal," I said, shrugging. "What's next?"

—---------------------

He pushed me gently back on the floor so I was lying down. It's not that he was necessarily stronger than me; it's that my body seemed to have completely accepted that it was made to submit to him, to do whatever he asked. I lay down as he moved to kneel in front of me, leaning down and gently tracing up and down my body with his fingers. My whole body ached and shivered at his touch, his wet cock twitching slightly as he took in the sight of me in thigh highs and a skirt. He pulled up my crop top and traced my nipples, my cock throbbing hard as he proceeded to pinch and play with them. Finally, he moved his fingers up to my lips and pushed them gently into my mouth. I was primed to accept whatever he wanted to put in there, and so I accepted easily, sucking them eagerly. As he did so, he gently placed his cock on top of mine, thrusting slightly as I felt the slippery wetness of it against mine. Even semi-soft, he was bigger than me, which only made me harder as I sucked his fingers greedily.

"I would split you in half if I tried to fuck you like this," he said casually, like he was discussing the weather or what happened on the news. "I'm going to have to warm you up so I can take you without hurting you."

I couldn't say much with my mouth occupied, but at that point, I wouldn't have cared if he broke me; I needed him inside me so badly. I gave him a little moan of affirmation, and he smiled, pulling his fingers out and moving them down to my ass. With his other hand, he pulled my legs up to my chest and then slowly stroked my cock, while his wet fingers rubbed the entrance to my hole. I had heard that it could feel good to be touched there, but I was always too scared to try, too scared about what it might mean if I liked it. Right now, though, all that fear was gone; all I felt was desire.

"I'll start with one," he said gently, his other hand still fondling my cock, so I had a constant supply of pleasure as I got used to this new sensation.

He slowly slid his index finger into my tight hole, my spit lubricating him as I took him in easily. The sensation was strange, but pleasurable, especially when he reached up far enough to find a spot that made my head spin every time he touched it.

"That's your prostate," he explained. "It's important to massage it once in a while for health, and also because it can feel very, very good."

With that, he started applying slow and gradual pressure there, stroking and pushing it with practiced motions. I recognized what was happening as what I did when I was fingering a girl, but it felt different somehow, like the feeling was more intense, more sensual. I felt a pressure start to build inside me, a warmth in my core that spread throughout my body. He kept going like this, stroking my cock while massaging my prostate and making me feel like my whole body was on fire. I didn't realize I could feel this good; it was like I was a whole new person in that moment.

He slowly slid in one more finger, the intensity increasing as he stroked me a little faster. I began to feel the pressure build more and more, the feeling of his hand on my cock making me feel sharp spikes of pleasure when he touched me.

"I could cum like this," I realized as he continued. "I could cum like this, and it would feel really, really good."

As if reading my mind, he suddenly stopped and pulled his fingers out, my hole throbbing and aching to be filled and stretched as it just was.

"Now you're ready," he said, smiling, as I looked down to find him rock hard again. I gulped nervously as I eyed his cock, suddenly very aware of how much bigger it was than a few fingers.

"Don't worry," he said softly as he pumped himself with both hands, lining himself up with my hole. "I'll be gentle."

That was the last thing I heard before my whole world spun. The feeling of him pressing his tip into me was so intense, a whole new level from just the fingers. True to his word, he went slowly, inch by inch, allowing me to get used to his outrageous girth. The feeling of being filled up and stretched out was something I never knew I needed. It was like being hugged from the inside, like being complete in a way I never knew I needed. He began to fuck himself into me deeper and deeper, his brow furrowed in concentration as he did his best not to just rail me like he wanted to.

"Oh fuck, you're so tight," he moaned, the sounds of his soft, girly voice making me throb even harder. I felt like I could feel every vein, every contour of his cock. I was his completely, and he knew it. We continued like this for some time, him working himself deeper and deeper into me as I gradually relaxed and allowed more of myself to be taken by him. At one point, he stopped and pulled me up gently by my chain, flipping me over without bothering to pull out. Laying flat on my stomach, I could feel him go even deeper, my cock rubbing against the floor in a way that made me feel incredible.

“This must be heaven,” I thought to myself as I felt his weight comfortingly on top of me, his gentle rhythmic thrusts producing a wet thumping sound and eliciting little breathy gasps and moans from me.

"I'm sorry," he said suddenly, stopping mid-thrust. "I can't hold back any longer."

"Wha—" is about as far as I got before I felt him grab me by my hips and pull me into doggy style as he began to fuck me the way he really wanted to fuck me. Deep and with an intensity that belied a deep, carnal desire. He fucked me like he wanted me more than anything in the whole world, his cock thrusting deeper and deeper into me as I cried out. Each thrust caused me to dribble out cum, as if he was milking it out of me. It was the strangest sensation, like an orgasm in slow motion, but without the crash that I normally got after I came.

He yanked my collar and pulled me up so I was sitting up on my knees, my cock bouncing wildly as he pounded me from behind. He pulled me up further so we were standing and proceeded to walk/fuck me around the apartment, occasionally stopping to bend me over one surface or the other. It was, and I say this without reservation, the hottest thing that's ever happened to me. I felt like a little toy to be used for his pleasure, nothing more than a hole for him. At first, I was too distracted by the feeling of such a large object inside of me to process what I was feeling, but now that I got used to it, I began to be aware of just how good it felt. He claimed me completely as his, pressing me against the wall as he thrust deeper and deeper into me.

"Come here," he said breathily as he walked me over to the mirror we kept by the front door. 

"For outfit checks before leaving the house," he had said innocently when I asked him why he put it there. "Yeah, right," I thought as he fucked me standing in front of it, the perfect view of me getting railed.

"I'm getting close," he moaned into my ear, the leash and choker applying slight pressure against my neck. "So am I," I thought, feeling that familiar build of tension and warmth from earlier.

"Touch your nipples," he suggested as he pounded me. "It'll feel good." I would have done whatever he told me at that point, but this sounded like a particularly good idea. I reached up with my hands and started pinching and rubbing my nipples, the sensation adding yet another harmony to the orchestra of pleasure I was experiencing. 

I suddenly realized that completely involuntarily, without meaning to, I was moaning like a girl. The sounds that came out of me were sounds I had never made before, but they felt so natural, the only possible response to being railed so thoroughly.

"Oh FUCK," I gasped as the additional sensation pushed me towards the crest of something I had never experienced before. 

“Oh God, oh God, I think I’m going to, oh God, YES-”

With one hard twist of each nipple and a particularly deep thrust from him, I came, hard. My cock shot cum straight at the mirror as I experienced the greatest orgasm of my life. My ass and cock throbbed so intensely, I felt like I was going to pass out, and all the while, he rode me through my orgasm, whispering in my ear what a good little slut I was for him.

The sensation of me cumming was enough to set him off too, as I felt him throb and burst inside of me. We both stood there, fucking each other through our orgasms, the warmth of his cum filling me up inside. I can't tell you how good it felt to feel him throb inside of me, his breathy, desperate moans mixing with mine as we became a single entity, bound by the pleasure of the moment.

We collapsed back onto the couch with him still inside me, cuddled against each other as we fought to catch our breath. I felt so safe in that moment, wrapped in his arms, the warmth of him flowing in and through me. We lay there together for some time, breathing softly in time with one another and feeling so content with all that life had to offer in that moment. I felt, for the first time in my life, complete.

"So," he said softly while he played with my hair, "you wanna play some more Mario Kart?"

I turned around and kissed him then and there, our lips melting into each other as his shock faded into a soft, serene pleasure. I pulled back slightly and smiled:

"I have a better idea."