My Trans Sex Life Ch. 02

After my encounter with M, I couldn't stop thinking about it. Rather, I couldn't stop thinking about dick.

There's a joke among trans guys about the three H's of testosterone treatment: hot, hungry, and horny. I had thought that I'd experienced all three of them to the fullest extent. When I was around eight months on T, I was so turned on all the time - I was literally always wet, and jerked off at a bare minimum twice a day. I had thought my ex had a high sex drive, but suddenly, I was insatiable, waking her up with my mouth on her cunt or begging her to put her fingers inside me before we went to bed. I would jerk off in the shower before work, in the living room in the evening when my ex was out, in bed while she was in the bathroom taking her makeup off; even, more times than I care to admit, in the single-stall gender neutral bathroom at work. When I say I was horny all the time, I mean ALL. The. Time.

That was nothing compared to how fucking horny I am now.

After I wrote my last post, I went straight to my toy box and picked out the biggest cock I own - eight and a half insertable inches of bright purple plastic. I got on my knees on the floor of my bedroom and fucked myself with it until I came. Then I did it again.

Needless to say, my purple dick has now taken up permanent residence in my bedside table, rather than relegated to the toy box in the closet that I only really open when I have company. Almost every night this past week I've used it, fucking myself with one hand while I stroke my cock with the other. Every time I was remembering how it felt to get fucked by M, how good it was to be filled up like that, the half-noises he made as he moved inside me, the hot splash of his cum against the skin of my back.

It wasn't long - barely a week had passed - but I felt like I hadn't been fucked in aeons. I hate to say it, but... I was (and am still) kind of desperate for it. I can't believe I went so long thinking I didn't even like guys.

M had told me to text him if I ever wanted a repeat performance, and I probably will eventually, but I wanted to try out something different... maybe something a little more dangerous. Vanilla is nice, but there's way more to taste.

Z was definitely not vanilla. His profile photo was him in dangerously low leather pants, smirking at the camera in a way that probably should have been infuriating - he knew full well how hot he was. He messaged me first, a generic 'how's it going, sexy' that should have been uninteresting, but his profile intrigued me, so I replied. We exchanged a few arbitrary messages before it quickly devolved into obscenities.

Him: so if i was going to fuck you

Him: which hole do you like it in

Me: actually... i've never tried anal

Him: seriously?

Him: you look like youd love it

Him: like youd be begging for it the moment i touched your hole

Him: and im real good at it

Me: i've always wanted to try

Me: just never had the chance

Him: id get you nice and wet

Him: eat your ass until you were trembling

Him: stretch your hole nice and slow

Me: so... are you free tonight?

I took a shower. A thorough one. I soaped up my index finger and circled my asshole with it, prodding gently at the entrance before I took a deep breath and slowly pushed in. It felt... weird. Not mind-blowingly amazing, but not bad, either. Just different. I wriggled my finger a little bit, tried to push it deeper, but the angle was all wrong and my hole was very tight and I couldn't do all that much. I was kind of disappointed, and worried that maybe I wouldn't like it. But I figured that Z probably knew more about anal sex than I did, and I might as well try it - plus, I'd been dreaming about cock all week, and I wasn't about to pass up this opportunity to get it.

Z told me to just come to his place, so I flicked my buddy a text telling him where I was going and to check in on me if I didn't text him back before one a.m. before I ordered an Uber. Z lived across town, in a ground-floor apartment. There was a motorbike parked out front.

Z answered the door in a tight tank top that showed off his tattoos and sweatpants that showed off his half-hard dick. I had a sudden flashback to having a mouth full of M's cock, how thoroughly soaked just getting it in my mouth had made me. I licked my lips. Z noticed me looking, and smirked that same infuriating smirk that was in his profile pic.

It wasn't long before I was on my knees, licking and sucking at Z's cock. I slurped wetly at the head before taking it into my mouth as far as I could without choking, then pulled back to suck at the tip again. He tangled his hands in my hair, tugging gently at first, then firmer when I moaned at the sting of it. The feeling of his cock siding between my lips and across my tongue, filling my mouth, went straight to my cunt, just like I knew it would. I rubbed at my own hard dick through my underwear as I sucked him.

His fists tightened in my hair and he started thrusting shallowly into my mouth. He was talking, growling meaningless dirty phrases at me as he did so: "Yeah, take it. Fuck yeah. Suck my cock. That's it." Stuff that should sound ridiculous, imitation pornography, but in his voice, and with his cock in my mouth, it was hot as fuck.

Finally he dragged me off his cock, drooling and gasping. "Come on. This way." And he pulled me to my feet and down the hall to his bedroom.

He bent me over the bed and slowly pulled my jeans and underwear down over my ass. He groped and squeezed it, pulling the cheeks apart, then spanked me - not too hard, but enough to make me gasp. He didn't pull my jeans down all the way, kept them around my thighs so it was impossible for me to spread my legs. Instead, he kept his hands on my ass, pulling the cheeks apart so he could see both of my holes.

When he licked me I swear my brain shorted out for a moment. It felt wrong, having somebody's tongue touching me there, and I almost tried to jerk away, but at the same time it felt so good I couldn't even think. He started out licking long, flat stripes over my asshole, before tracing increasingly smaller circles around it until finally he was teasing my hole open with the tip of his tongue.

I couldn't believe what was happening, or how good it felt. He kept prodding at my hole with his tongue, then pulling back to lap at it with the flat of his tongue before wriggling it a little way inside again. I was gasping at the sensation, shivering every time his tongue found its way further inside me.

I was so lost in the feeling that I hardly noticed when he pushed a finger inside me. It was slick with spit and slid up to the knuckle, no problem. He kept licking around it, holding it still inside me, for a while longer, and then he started slowly moving inside me.

I was still face-down on the bed with my jeans and underwear trapping my legs together, moaning into the sheets. He pulled his finger out of me and poured a stream of lube over my hole, pushing it inside me with first one, then two fingers. They were longer than my own, reaching deeper inside me.

It felt way better than when I'd tried the same in the shower. The drag of his fingers against my insides sent white-hot sparks up my spine, making my cunt twitch with every careful twist of his fingers. Then he leaned back in and resumed his earlier activity, licking around his fingers, or slowly stretching them apart and licking between them, thrusting his tongue as far into my ass as he could. I was making way too much noise, muffling my loud moans in the blankets. He pulled his fingers out and actually fucking sucked at my rim before plunging them back in - three of them this time, coated in more lube.

He kept fingering my asshole, occasionally leaning back in to lick into me, for what felt like a very long time. I could feel my cunt dripping down the insides of my thighs, mixing with spit and lube and probably making a mess of my underwear. The longer he kept at it, the more amazing I felt, relaxed and loose as he took me higher and higher.

Finally he pulled away entirely. I stayed where I was, gasping for air, my whole body feeling like it was melting into the bed. I heard the noise of a condom wrapper behind me, and then more cold lube hit my asshole, dripping down over my cunt.

He rubbed the head of his cock over my dripping pussy, almost slipping inside before dragging it over my taint to press at the slicked entrance of my ass. There was a long moment where I thought it wasn't going to happen, that despite the thorough stretching he'd given me that my virgin asshole would still be too tight, but as soon as I had the thought the head of his cock popped through the ring of muscle.

It... didn't hurt, exactly. But I was very aware of how much bigger his cock was than his fingers, how much bigger it was than my asshole, that it was making space for itself inside me. He asked how I was doing, and I must have forgotten how to form words, because all I could do was nod.

His hands were on my ass cheeks, holding me open for him. He thrust forward, a few more inches of dick entering my hole, and paused for a moment, letting me adjust. And again - until his hips were flush against my ass and his cock was deep inside me.

It was unlike anything I've ever felt before. This strange feeling of 'wait, that shouldn't be there' combined with 'holy shit yes yes yes!' He started to thrust shallowly into me and my whole body lit up with pleasure, the drag of his cock in my ass sending lightning through my veins. The deeper he went the more amazing it felt, like I was being stuffed full of cock in the best possible way. I swear I could feel it in my stomach. Fuck, I could practically feel it in my throat, every thrust of his hips punching another gasp out of me.

He talked as he fucked me, more of that porn star talk from earlier. "Yeah, you love it, don't you? You're so fucking tight... can't believe nobody's fucked such a perfect ass before. Look at you, you're gagging for it." And I realised, eventually, that I was talking too - moaning out "yes yes yes" and "fuck me fuck me" and "oh god oh god it's so fucking good!"

He told me to touch myself, and I did, managing to get my hand between me and the mattress so I could jerk myself off. It was an awkward position but if I shoved my ass back against Z I could move my fingers the way I needed to, and I rubbed desperately at my cock, my hips jerking as he drove into my ass again and again.

When I came it was different to anything I've felt before. You know how you'll be watching porn and the girl will be getting fucked in the ass and she'll start yelling "My asshole is cumming! I'm cumming with my ass!"? I always HATED that. Like, an orgasm is an orgasm, right? How can you cum with your ass? (I'd understand if it was someone with a prostate - but in gay porn none of the bottoms ever yell anything about how their ass is cumming, it's all just cursing and moaning.)

But... it definitely felt different to cumming when you're being fucked in the pussy, or just rubbing yourself off. I could actually feel my asshole pulsing just before I started to cum, could feel it clamping down around Z's dick. And every thrust seemed not just to draw it out longer, but to start it anew.

As soon as I started to cum Z started pounding into me harder, faster, chasing his own orgasm. I wasn't complaining - like I said, every time he shoved into me a fresh wave of pleasure rushed through me, until my body just couldn't keep it up, and then I just laid there, aftershocks jolting my body as he rutted into me.

He came with a grunt, his hips jerking against mine. When he pulled out I could actually feel how loose my asshole was from being fucked. I reached back to feel it - it wasn't gaping, but it was puffy and soft and three of my fingers sank in easily. I was so hot and tight inside, and still slick with lube. I started to ease my fingers in and out of myself slowly in a poor recreation of being fucked. The angle was terrible and my shoulder was straining, but I couldn't get enough - of the sensation of my hole being stretched around my fingers, or of how I felt inside.

"Fuck," Z moaned behind me. I'd almost forgotten he was there. "That's so hot."

I went to pull my fingers out of me, but Z stopped me with a hand on my wrist and told me to keep going. I bit my lip and did as he said, slowly fingering my well-fucked asshole.

I put on a bit of a show for him, wriggling and moaning as I fucked myself. I was still hard, still had at least another orgasm in me, but the position was all wrong for me to be able to rub off against the bed or to jerk myself with my other hand, and I couldn't get my fingers as deep as I needed them or fuck myself as hard as I wanted to.

"Please," I gasped, as I twisted my wrist to try and force my fingers just that little bit deeper. "Please, it's not enough."

Z teased me, pretending he didn't know what I was asking for. He kept asking me questions, making me beg for it, until finally he took pity on me and plunged two fingers into me alongside my own.

I pulled my own fingers from my hole and shoved my hand between my legs so I could rock against the hard line of my fist as he thrust his fingers into me over and over until I came again, my hole squeezing around his fingers.

Later that night, when I was back home, I put in an order for a set of anal training butt plugs on my favourite sex toy site. I have a feeling I'll be needing them.