My Trans Sex Life Ch. 04

So I went to a party last weekend! It was my buddy's birthday, and it happens to coincide with Halloween, so he always does something fun. Last year a group of us got together, got tipsy, and went to a haunted house. The year before that a whole lot of us dressed up and went to see Happy Death Day (which honestly is a way better movie than we were expecting it to be). This year, though, he threw a good old-fashioned Halloween party, complete with creepy decorations, Halloween-themed food (including extremely boozy blood-red punch), and, of course, compulsory costumes.

I had two requirements for my costume: it had to be (a) at least a little spooky and (b) extremely slutty.

It used to be that my choice for slutty Halloween costumes was unlimited -- at least, if I wanted to suck it up and wear a dress, which I never did. But I never really wanted to do the 'sexy Halloween costume' thing when I was a 'girl.' I was more into dressing up as various slasher movie antagonists, especially ones that wear masks.

Now, though? I love the idea of wearing a slutty Halloween costume, the kind that screams "I'm not straight! And yes, that's an invitation!"

So yeah, I did a whole slutty male witch thing. I didn't go to an awful lot of effort or anything, like, it was pretty 'closet cosplay' type stuff: I already had a pair of booty shorts that say 'creepy' on the butt because that's just who I am as a person, a pair of mean-looking Doc Martens, and a black crop top . Then all I had to do was spend a combined total of like ten bucks on a pair of red and black striped knee socks, a pointy witch's hat, and a broomstick.

I think I looked pretty fucking hot. I definitely FELT hot. It's a lot easier to love my body now that I have a flat chest, broader shoulders and a treasure trail. (It's entirely possible I only wore that crop top to show off my treasure trail...)

I got to the party just after nine p.m., right when things were starting to pick up. I said hi and happy birthday to my buddy, had some drinks, did the whole mingling thing.

I met B in the kitchen when we were both getting more drinks. He was dressed entirely in drag -- and not straight drag, where the guy in the dress is clearly doing it as a joke, but in a carefully coordinated outfit, wig and makeup. He'd brought a women's 'slutty sailor' outfit, a little blue-and-white dress with buttons down the front and a sailor-style collar, and paired it with a sleek black wig and blue stiletto heels.

So I was getting a drink, and he was getting a drink, and we had that moment where we both recognised each other as being Part Of The Club, and we started talking. And flirting. Good lord did B flirt with me. He almost made an art form of it, one of those people who seem like 'flirty' is a core tenet of their personality. I assumed at first that he flirted with everyone like he was flirting with me, but as people passed through the kitchen for drinks, some of them stopping to talk, I saw he wasn't. He was friendly, and called every guy "sweetheart" and every girl "honey," but he wasn't out-and-out flirting like he was with me.

After a while he asked me if I wanted to go somewhere quieter, looking me up and down like he was picturing me already naked. I opened my mouth to say something smooth in agreement, but I was kind of drunk, and instead I blurted "I don't have a dick!"

There was a long moment where neither of us said anything. I felt my face flush with embarrassment. Then B was like, "oh, are you trans?" and I told him yeah, and he was like "that's cool, I've never fucked a trans guy before," and I was like "...oh?" and he was like, "you still want to get out of here?" and I was like "fuck yeah," and he laughed and told me he knew how to get onto the roof.

So we left my friend's apartment and took the elevator to the top floor. When the elevator doors slid shut, B pushed me against the wall and kissed me, slipping his tongue into my mouth immediately. His thigh pushed between my legs and his hands found my ass, squeezing lightly as his thigh rubbed at my dick through my shorts.

The elevator stopped, and he pulled back, grinning at me. He grabbed my hand, and I followed him out of the elevator and through a door, up another flight of stairs, and out onto the roof of the apartment building. B wedged the door open with a brick to keep us from getting locked up there, then led me around the side of the stairwell. It was the only part of the roof that wasn't just flat concrete.

He pushed me against the wall again, his mouth meeting mine at the same time as his hand slid down the front of my shorts. I gasped as his fingers quickly found my cock. "Huh," he said. "From the way straight guys talk, I thought that'd be harder to find."

"The testosterone made it bigger," I managed to say as he touched my cock inquisitively. "But also, yeah, they're not that hard to find. Straight guys are just weak."

B laughed, then bent his head to lick and suck at my throat as he kept touching my dick, stroking it with two fingers against the sides, jerking it slowly like you'd jerk a cis guy's dick. I bit my lip as he rubbed me, feeling the arousal start to spark at the base of my spine.

I put my hand up his skirt to touch his own rapidly hardening dick, stroking it through his underwear, which were, like the rest of his outfit, made for women; they were mostly lace, and his cock probably barely fit in them when it was soft. Now that it was getting hard the tip of it was poking out of the top of the panties, trapped against his abdomen by the waistband. I tugged his panties down at the front, freeing his dick so I could curl my fingers around it and jerk him off as slow as he was touching me.

B's fingers slipped lower between my legs, against my cunt. "Oh," he said, "you're wet," and I was like "yeah... that happens." He slid his fingers back up to my cock, rubbing against it with newly slick fingers, then back down to dip into my cunt. He repeated this a few times, spreading my wetness around. The light touches at the very entrance of my cunt were driving me crazy, a tease of what it felt like to actually get fucked, but his fingers were firm against my cock, sending shocks of pleasure through my lower body, and the combination of teasing and direct stimulation was maddening.

After a while of this I'd had enough, and I told him to put his fingers in me. He slid two of them into my cunt at once, and I sighed, happy to finally have something inside me. He fucked me slowly with his fingers, sliding them all the way out before carefully pushing them back in again, and it felt good, but I needed more. I told him how to curl his fingers to find my g-spot, and he did, and once he'd found it he kept thrusting his fingers against it on each glide in.

His fingers inside me were incredibly distracting, and I kept forgetting to jerk him off, my hand stilling on his cock for several long moments as I got lost in my own pleasure before I realised what I'd done and started stroking again.

I asked him if he had a condom, and he did, so I said, "great! Now fuck me already." I pulled my shorts down, kicking them off one leg but letting them stay tangled around the boot on my other leg, and I turned around, bracing myself against the wall with my hands. I heard the crinkling sound of a condom wrapper opening, and then he pressed himself against me, rubbing his dick along my cunt before guiding it into my hole.

I groaned with satisfaction as I felt his cock filling me up. He was nice and thick, just enough for it to feel like a bit of a stretch, and in this position, with me bent over slightly and him fucking me from behind, the head of his cock grazed my g-spot as he thrust in. When he was all the way inside me he paused for a moment and asked, "you good?" In reply I rocked forward a little, then shoved myself back onto his cock. He laughed breathlessly, and started to fuck me.

He built a steady rhythm, not too slow, fucking me nice and deep, and hard enough that I was rocking forward with every thrust. I tried not to get too loud, not wanting to alert any of the upper floor tenants to our activities, but moans kept escaping, especially when he'd occasionally grind in deeper as he bottomed out, getting that little bit further inside me. Then he reached around to rub slowly at my cock as he fucked me, and I couldn't stop the embarrassingly high-pitched noise I made.

He wasn't touching my dick like he wanted to make me cum faster, he was sort of just... playing with it, pinching it lightly between his thumb and forefinger, or rolling his finger around the tip in a light circle. Then he'd take it between two fingers and jerk it fast for several long seconds, winding me up until I was clenching around his cock, feeling the beginnings of an orgasm stirring in my belly, before he'd stop and go back to playing with it gently.

He'd just started to fuck me faster when we heard voices and footsteps echoing through the open door. There was no time to move before a group of six party-goers spilled out onto the roof. I recognised my friend whose birthday it was. I felt frozen in place, worried that they might turn and see me with my pants around my ankles, getting fucked from behind. But they disappeared around the other side of the stairwell, still talking and laughing. I felt a weird surge of... disappointment?

Before I could do anything else, B started to thrust slowly into me again. I turned to look at him over my shoulder, my eyes wide, and he just smirked at me and winked. I bit my lip. The thought of the others catching us in the act made my stomach twist with anxiety, my face flush with embarrassment - and an odd sort of excitement spark between my legs.

I could hear every word the others were saying, every footstep they took as they walked across the rooftop. For a while it was all I could focus on, even with B moving inside me. They were gossiping, joking around. There was the click of a lighter, and the smell of pot started to drift through the air.

"Fuck," I mouthed. What if they heard us? What would they think of me, if they caught me like this? They'd probably think I was a slut, spreading my legs for some guy I'd just met. Would B even stop if they saw us, or would he keep fucking me with an audience?

I shoved my hand into my mouth, biting down to stop the moan that threatened to erupt from my mouth at the thought. I could still hear them talking like they were right next to us, but it wasn't the only thing I was focused on anymore. B was fucking me with steady, hard thrusts, his hips meeting my ass with every thrust in. I was hyper aware of the quiet noise it made every time his hips connected with me, of the wet sounds of him moving inside me and of our combined heavy breathing. It seemed impossible that they couldn't hear us, but they kept talking amongst themselves, making no indication that they could hear me getting fucked.

B was rubbing my cock again, with a purpose this time, his fingers flying over my hard little dick as he drove into me again and again. I was doing my best to stay quiet, to keep my noises muffled, but the combination of B's cock moving inside me, his fingers on my dick, and the idea that the others might hear us at any time was making it very hard to hold back my moans.

I hadn't thought I'd had an exhibition kink before this. But fuck, the idea of being caught was so hot, the thought of people seeing me like this, bent over with a dick in my cunt and desperate for more... god, I was so turned on I'd probably have let them have their way with me as well, once B was done with me...

I bit down hard on my hand and came, barely muffling a yell as heat burst in my gut and sent a pulse of pleasure through my body. I convulsed, my legs shaking hard enough that I might have fallen if B hadn't been holding me up, my whole body tensing as I rode out my orgasm.

B yanked my hips back against him, grinding into me as I came, clenching around his dick. A few more hard thrusts and he stilled, buried deep in my pussy as he came too.

We stayed there for a moment, still, catching our breath. Then he pulled out of me, leaving me feeling wet and empty and used in the best kind of way. I quickly pulled my shorts back on. My legs were still shaking a bit.

We went around the side of the stairwell again, coming into view of the others on the roof. They were sitting in a circle, smoking and talking. My friend smiled when he saw me, and called, "Ezra! Where were you? We were looking for you!" He held out a joint in invitation, so B and I joined the rest of them in the circle.

I shrugged in response to my friend's question, told him something like, "I was around."

He looked between me and B and back again. "Oh my god. Were you guys fucking?"