My Trans Sex Life

Okay. Here goes.

You can call me Ezra. I'm 25 years old and I live in a medium-sized city, in a Western country. (That's all the detail you're getting - I don't want any creeps showing up on my doorstep 'cause I decided to put the details of my sex life on the internet.) I'm a trans guy. I've been on testosterone for two and a half years, and I just got top surgery last year. For the most part, I look like your average guy: I'm not exceedingly short, I can grow a semi-decent beard. I might be a little bit pretty, but I still pass as male 99.9% of the time.

Recently I got out of a long term relationship. How long? Long enough that when we got together we were both girls. I thought I was a lesbian. Then I realised I was a guy, but I thought I was still only into women. It was only after I started hormone treatment that I realised... hey, guys are kind of sexy. I realised that I'd always been attracted to men and just hid it because I was "too masculine to like boys."

Anyway, up until a couple of nights ago, I'd never had sex with a man. I figured, what time to experiment than when you're freshly single? And I decided, fuck it, I might as well document my sexcapades... and put 'em on the internet as well. What have I got to lose?

So I downloaded a bunch of hook-up apps a week or so ago and started swiping. I decided to be up-front about being trans, seeing that I'm mostly looking for sex, and I don't really want to be having that conversation over and over with each person I meet. As well as having that on my profile, I decided to be one of Those Guys, and have a shirtless selfie as one of my profile pictures... I mean, I spent a LOT of money on this chest. Might as well show it off, right?

I was surprised (and flattered!) at how many matches and messages I got, pretty much from the moment I signed up for each app. A lot of those were people confused about whether or not I had a dick (I have several, but none are permanently attached to my body), and even more were people who just wanted to show me THEIR dick. But there was still a decent amount of legitimately cool, good-looking guys who actually wanted to talk to me (and not just send me dick pics) though.

One of those guys was M. M was a few years older than me, with a sort of rugged, outdoorsy look - his main profile pic showed off a full beard and the kind of chest and arms you'd expect to see in a Marvel movie, and subsequent photos on his profile showed him hiking, mountain biking, and drinking beer in front of a campfire. He was super hot - did I mention those arms? DAMN.

We exchanged a few messages. Turns out he was really funny, and, as a bonus, had been with a trans guy before! I told him I'd never fucked a dude (I was kind of worried about not being any good) and he told me it didn't matter. Being new to the hook-up thing, I asked if we could meet in public first, and he was cool with it, so we made plans to meet up at a local bar that Friday night after we were both done with work.

I got to the bar around seven thirty. He was already there, and I was kind of surprised to find he looked just as good as he did in his profile pictures. He was tall, too - I'm not a short guy (before my transition I was 'tall for a girl'), but he had a good six inches on me, at least.

M bought me a drink, and we sat and talked for a bit, the usual small talk topics - work, movies, plans for the weekend. I'd been a little anxious that M was going to be a completely different person to the guy I'd been chatting to, like, some dirty old man with a fetish for trans boys; either that or he'd look like his profile pic but be super creepy. But he wasn't! He was fun to talk to, and VERY nice to look at, and I wasn't getting any weird vibes from him. (I still had Find My Friends turned on as a precaution, though.)

Once we finished our drinks, we walked back to his place, as it was only a couple of blocks away. I was still kind of nervous, even though I'd had a beer and M had turned out to be cool. I mean, you know, right? I'd never fucked a guy before! I'd never even seen a dick that didn't have to be strapped on outside of porn!

I was lucky that M was so cool. He told me we didn't have to do anything I wasn't comfortable with, and that if it turned out I wasn't into it he'd call me an Uber, no hard feelings. "I don't think that's going to happen," I told him. Like I said: M was HOT.

We started out just kissing for a while, both of us fully-clothed. He was a good bit taller than me, so he had to lean down and I had to lean up. Even this was a new experience for me - I'd kissed a lot of girls, but they were all around my height or shorter. As well as that, I hadn't realised how different kissing someone with a beard would be!

Eventually we ended up on the sofa, sort of half-sitting, half-lying down, with me on top of him. I could feel him starting to get hard, his cock pressing against my stomach through his jeans and my t-shirt. It made my mouth water like I was about to get it on something delicious. (I guess I was, in a manner of speaking.)

I put my hand on him over his jeans, just to see what it felt like. I don't know how to describe it, but something about it went straight to my cunt. I kept my hand there, feeling his dick grow harder, maybe petting it a little, maybe squeezing slightly. I wanted to get my hand on it properly, skin on skin, so I shuffled back so I could undo his jeans, and he helped me pull them down a little, just enough for him to get his dick out.

I think I might have made a noise, or maybe I was making some sort of weird face, because he laughed, but not in a mean way. He asked if I was okay, and I said yes, and he asked if I wanted to touch it, and I said I did. And then, embarrassingly, I asked, "Is it... are you... big...ger? Than average?"

I know it's a stupid question, and I probably turned bright red after I asked. I have a dick bigger than his was, but it's bright purple and made of silicone, and I've only really used it a couple of times, and never on myself. The dick I usually wear (a super fancy 4-in-1 packer) isn't what I would consider small, but it's definitely quite a bit smaller than M's. And when I was still with my ex, and I was on the receiving end (which wasn't a lot), she would usually wear one of my smaller dicks.

What I'm trying to say is, even though I had no frame of reference for exactly what size constituted a 'big dick' outside of porn, I was pretty sure M's was big.

He shrugged, and said, "yeah, I guess," and then, "oh, shit. Are you worried it won't fit?" and then, "Jesus Christ, I can't believe I just said that." He actually kind of babbled a bit about how he should probably have said something and if I didn't want to keep going that was okay and that is when I realised:

M was actually a giant dork.

I probably said something like "oh my god," and I think he realised what he sounded like because he started laughing, and then I started laughing, and we just cracked up for a little bit, which was nice, because it meant I immediately felt less nervous. Then, once we'd finally stopped laughing and before I could start to second-guess myself, I put my hand on his cock.

If you're reading this, I don't know if you've like, touched a dick before or whatever. I guess most of you have? Like, most of the world is straight and cis, right, and if you're a straight woman there's a decent chance you've touched a dick, and if you're a cis man you've definitely touched a dick. So there's probably no point in describing how dick feels. But I'm going to anyway, because it's my blog and I'm going to write what I want.

It was hot. Like, not just in the sense that it was really fucking turning me on, but warm, a lot warmer than I was expecting. And it was kind of... silky, if that's the right word? I stroked it slowly and the skin was maybe softer than I thought it would be, even though the rest of his dick was pretty hard already. When I stroked downwards the foreskin pulled back from the tip a little, which was red and a little shiny, and seeing that made me really want to know what it tasted like.

When I looked up at M he was looking down at my hand on his cock, which for some reason turned me on even more. I kept stroking him slowly, keeping my hand loose. I think I asked him if it felt good, and he said yes but give me your hand a second, so I did, and he licked my palm then said "okay, now go." With my hand wet it slid more on his cock instead of dragging. He told me to go a little tighter, and then, after a short while, to speed up a little. By this time he was breathing hard, making aborted thrusts up into my hand. I don't know if he liked that he got to teach me something as simple as how to give a handjob, or if he was just really into handjobs in general, but he was clearly enjoying himself.

I couldn't keep my eyes off his dick. I kept wondering how it would feel in my mouth, how much I would be able to fit before I choked. It's something I've always loved doing for women, using my mouth, and I like to think I've gotten pretty good at it. I wanted to know what it felt like to go down on a guy. So I asked him, "Can I suck it?" and he made this noise, like he'd started to moan then cut it off.

Side-note: is this one of those guy things I don't know about? Are we not supposed to make noise during sex? Most women I've been with, even if they don't scream like porn stars, they usually make some sort of noise, gasps or quiet moans or (and I'm thinking of one particular girl here) squeaks. All of M's noises sounded like he was trying to hold them back. Is it some kind of macho thing? Or is it like, a top thing? I guess I'll just have to fuck more dudes and find out.

Anyway. He said yeah, if you're sure? And I said I was sure, and he said okay, but the condoms are in the bedroom. I felt a little disappointed that I wouldn't get to find out what it tasted like, but if he hadn't mentioned condoms I sure would have, so I can't complain I guess.

So we went through into his bedroom. He got a string of three or four condoms out of his bedside cabinet, and a squeeze-bottle of lube, and tossed both on the bed. Then he was like, "I'm gonna get naked now," so I figured I might as well show some skin too.

I'll be honest: I was nervous about him seeing my body. I was worried he might think it was too feminine, and then at the same time I still have this leftover angst about not being feminine enough. M had told me he was bi, and that he'd slept with a trans guy before, but I was worried he wanted to fuck some cis guy's ideal of a twinky, hairless, feminine trans guy, or else he'd see me naked and realise he didn't want to fuck a dude with no dick.

But I took off my shirt and glanced up at him to see if he was watching me, if he was going to react in any way, and he was looking at me like I was the one who was six foot something with a huge dick and arms like Chris Hemsworth's. So I took off my jeans as well. When I was standing there in my underwear he said, "fuck, you look good," and I had to laugh, because that wasn't what I was expecting to hear at all.

Anyway, he got on the bed, with his back against the headboard, and was like, "come here." His cock was sort of curving up, almost against his belly, and my mouth was watering like crazy. Like, I don't know if I can explain just how badly I wanted to suck his cock in that moment. He rolled a condom on, and then looked up at me.

I didn't know what I was supposed to do, and I told him so. He told me there was no such thing as a bad blowjob (which I'm 100% certain is a lie), and that he'd talk me through it if I wanted, which I did.

I put a hand on the base of his cock and leaned down to lick it. It was weird, tasting latex instead of skin, but I could feel the heat of him through the condom, and how hard he was. I licked him again, up the underside of it - there was a vein standing out there, and I traced it all the way to the tip. He told me not to worry about getting spit everywhere, that it felt better wet, which was good, because I was practically fucking drooling to get my mouth on him.

When I finally got the head of his dick in my mouth - fuck! It felt so good, heavy on my tongue, filling my mouth up. I didn't realise how much I'd love it. I sucked on the tip a bit, and then when M told me to try taking a little more I did. He told me how to do it properly, how to bob my head and keep my tongue pressed against the underneath, and... I might have gotten a little overexcited and tried to take a bit too much and choked on it. Fuck! Even that felt good.

By this point I was dripping wet and hard as hell. I reached down to rub my cock, rolling it between my fingers as I sucked on M. I was so close already just from having my mouth on him, I knew that it would only be a matter of minutes before I was cumming.

"Stop," M said, pulling me off his dick. I might have whined a little - I was REALLY enjoying myself. But then M told me to turn over so he could fuck me and I almost came right then.

I took my underwear off - they were soaked through at the crotch - and got on my hands and knees on the bed. M knelt behind me. I knew he was looking at my wet cunt and hard little cock, and I buried my face in the pillows, as much turned on as I was embarrassed by it.

I felt him stroke gently at my cock before his fingers moved further down. He circled my cunt with his fingers, teasing me and watching me twitch with it, until he finally slid two of his fingers inside. It felt good, but - I mean, I've been fingered before. After all that cock-sucking I was more than ready to get fucked.

"Fuck, just put your cock in me already," I said.

M laughed. I felt him shifting behind me, and then the blunt head of his cock at the entrance to my pussy. He asked me if I was sure and I told him to stop fucking teasing me and then he slowly pressed inside.

I came.

The feeling of my cunt being stretched out and filled up, the drag of his cock inside me, the head of it pressing hard against my g-spot - I was already so close, and I wanted it so bad, and as soon as he was more than halfway inside me I started to cum. I cried out and shoved my hand between my legs again, rubbing desperately at my throbbing cock.

M stilled, deep in my cunt as it clenched around him, and stayed there as I came down. I was gasping for breath, pushing my hips back over and over to get him just that little bit deeper in me, my fingers still against my swollen dick. When I could finally breathe again, and I could think of to say was, "oh my god."

M laughed breathlessly. "Yeah?"

"Oh my god," I said again. I rocked back against him lightly, feeling the hard length of him inside me, and squeezed deliberately around him. I had just cum, but I was nowhere near satisfied. "Fuck me!"

He did, pulling almost all the way out of me before plunging back in with a roll of his hips. I yelled as sensation hit me like a punch to the gut, bursting deep and hot inside me before shooting sparks through my whole body. Again and again he thrust into me, his cock rubbing hard over my g-spot each time, and I couldn't stop making noise, gasping and moaning as he fucked me. I remember thinking, oh my god, I'm getting fucked by a man. It felt sort of surreal, like I might just be fantasising while fucking myself with a dildo, but the smell of sweat and cum and the noise of his hips connecting with my ass reminded me it was real.

He started to speed up, and I started touching myself again, jerking myself with the rhythm of his cock inside me. At one point I reached further back, feeling the place I was stretched around him, slick and open for him. I wondered what it would feel like to slide a finger inside myself next to his cock - I was already so full, but I could imagine how it might feel to stretch just that little bit further, and I shuddered at the thought.

I pinched my dick, rubbing my thumb back and forth over the plump tip of it, feeling M quicken inside me. He was making low noises now, bitten-off moans deep in his throat, and his thrusts came fast and hard, pounding into me. I could feel the pleasure building fast in my gut, and I rubbed my cock faster, clenching around M's cock, desperate for it; when I came again it was intense, one of those heart-pounding, leg-shaking ones that seems like it goes on forever.

I was moaning non-stop like I couldn't stop myself. Maybe I couldn't. M kept driving into me, sending shocks of pleasure just on this side of too intense through my oversensitive system. All I could do was lie there, my ass in the air, making quiet, desperate noises, until he gasped "oh fuck, oh -" and pulled out of me. I looked over my shoulder to see him tear off the condom and jerk himself off fast, only a few short strokes before he was cumming, shooting ropes of cum against my lower back.

After, we dozed for a while. I could barely move, I was so overcome with pleasure. Seriously: I was still shaking for a while after. Eventually, M sat up, stretched, and asked me if I was hungry.

I definitely was. It was after ten, and I hadn't eaten dinner. So M ordered us take-out, and we sat in his bed and watched some stupid Netflix comedy and ate. And then he fucked me again - on my back, almost folded in half, with his hands on my thighs pushing my knees against my chest as he thrust into me. This time when he came he stayed inside me, and I could feel his cock jerking in my cunt. It made me desperate to know what it would have felt like bareback - would I be able to feel his cum in me as he spilled inside me?

He offered to drive me home, but it was late, and he was kind of half-passed out after his second orgasm, so I took an Uber. He gave me his number, though, and said if I wanted to mess around again to text him. So that's cool. I'll probably take him up on it. But I also really want to, well, get slutty, for lack of a better term - you know, sleep around, see what I like and how I like it. Get a little adventurous.

Stick around, if you like. I'll let you know how it goes.