My Trans Sex Life Ch. 03

You guys. I went on a date the other night. Like an actual, honest-to-god date, with like, dressing up nice and dinner and expensive wine and all that jazz. It was way fancier than I'm used to, and the whole time I was worrying that I was making a fool of myself with like, my lowly normal person manners and inability to talk about The Economy or whatever it is rich people talk about, but I guess I did okay because after the date we went back to his place and proceeded to have the most mind-blowing sex I've had in my entire life.

L messaged me online a few days ago. That's relevant because that app isn't one of those apps where you can only message someone if you match with them - you can pretty much message whoever you want as long as they haven't blocked you. I don't think I would have matched with L on other apps. On the surface he didn't seem like my type (not that I know exactly what my type is when it comes to men, but whatever).

That's not to say that L's not hot, because he definitely is. He's just... well, for one thing, he's a good ten years older than me, in his mid-thirties. And he's very clean-cut, a real Professor type - blazer, tie, thick-rimmed glasses. He has the kind of job you have to go to school for a long time to even be considered for, and he's clearly raking it in because (a) he paid for my dinner and drinks and told me to not even worry about how much they cost, which is a thing I'm really not used to doing, (b) we drove back to his place in a fucking Mercedes, and (c) his house (not an apartment) is one of those ultra-modern glass-and-concrete ones that I couldn't ever afford to rent, let alone buy.

He was cool, though. Interesting, easy to talk to, and not at all condescending like I was sort of scared he would be. We spent longer at dinner than I was really expecting - by the time we were done with desert it was well past ten, and I hadn't even noticed, I was having such a good time.

Back at his place he poured us both a drink and put on a record (like a literal vinyl record on a turntable and everything) and we sat in his living room and talked a little longer. I was getting kind of impatient, though - by this point it was around eleven and I had been thinking about getting fucked all evening. It didn't help that L kept making innuendos so subtle I wasn't sure if he'd meant them at all, and looking at me like he wanted to eat me alive.

So I threw back my drink and climbed onto his lap and kissed him. He took charge immediately, his fingers digging into my hips as he licked into my mouth. I may have been on top of him, but there were no illusions about who was directing this.

He tipped me onto the sofa on my back and immediately started to unbutton my slacks, pulling them down and off. I was wearing my packer that night (I like to wear it when I dress up nice) and he put his hand on it and pressed down so the base of it rubbed against my real cock, making me gasp. He asked if I wanted to leave it on and I said no, so he took it off along with my underwear, before crawling between my spread legs.

L put his thumb at the base of my cock, pulling the hood back so the hard tip of it was exposed, and then he leaned down to lick it, his eyes not leaving mine the whole time. I jolted when his tongue touched my sensitive dick, and then again when he repeated the action, lapping at it flatly. I bit my lip, fighting to keep my breathing under control as he dragged his tongue lazily across my cock over and over.

He teased me like that for what felt like forever, alternating between those long, slow licks and flicking his tongue over the tip of my cock until I was gasping and writhing under his mouth. Then he put his lips around it and sucked, hard. He was still playing with the tip of it with his tongue as he sucked, teasing it back and forth. It was intense, each lick sending something akin to an electric shock through my body.

Every time I felt I was on the edge of orgasm he would retreat, go back to lapping gently around the base until I relaxed and my breathing evened out, and then start his torture again.

Eventually he slipped two fingers inside me, curling them to press against my g-spot immediately, making me cry out. He rubbed them rhythmically over that spot inside me, pressing firmly with each pass, forcing desperate noises out of my mouth as he did so. It was almost overwhelming, his fingers inside me finding my most sensitive spot with laser-precision as his lips worked my cock. My whole body was trembling with pent-up pleasure.

He thrust his fingers into me faster and harder, the pressure in my belly building as his fingertips thudded against my g-spot. I was so wet his fingers were making loud squelching sounds inside me, and I put my hands over my face, embarrassed.

He kept it up, never once stopping his assault on my g-spot. When I started to feel my orgasm rising in me again, instead of withdrawing like he had been, he doubled down, his tongue flickering fast against the tip of my dick as his fingers worked hard against my insides. I'd been biting my lip so as not to make so much noise, but now I couldn't hold back, moaning loudly as he took me higher and higher.

There was one horrible moment where I thought I was about to piss myself, but then something shifted inside me and that feeling turned to intense pleasure. I screamed, and L shifted, pulling his mouth off of my cock and sliding his fingers out of me to instead rub them fast and hard against it, and I...

I came harder than I thought possible, my pussy throbbing as my body seized with pleasure. I could feel my abdomen clenching and releasing, clenching and releasing as I came, practically fucking wailing with how good it felt. In the moment I didn't notice much more than the all-consuming feeling of pleasure flooding my body, but as I slowly came back to myself I realised that the insides of my thighs were soaked.

Dazedly, I looked up at L. His face was flushed and his eyes were dark with lust, his chin slick from my cunt, his shirt damp. "Good?" he asked.

"Uh huh." I couldn't really form more words than that.

"Again?"

"Oh my god," I said, but I didn't say no. He slid his fingers back inside me - three of them, this time - and immediately started rubbing them hard against that spot inside me. He leaned down to suck my cock into his mouth. No more teasing - this time he seemed to be determined to make me cum in as little time possible. He sucked hard at my little dick as his fingers drummed against my g-spot, and in no time at all I was writhing and moaning, my legs shaking with it as he worked his fingers inside me.

This time when I felt it building he said, "keep your eyes open," and grabbed my hair with his free hand to tilt my head down to look between my legs. He pulled his fingers out of my pussy and jerked my cock fast, and as the pleasure overtook me and my body jolted I saw liquid gush from between my legs, further soaking my thighs and L's arm and shirt.

"Oh my god!" I moaned. I was shocked - I'd never squirted before, I wasn't even aware that I was capable of it. I'd had one girlfriend previously who squirted every time she came, and I thought that the world was sort of divided into those who squirted every time and those who weren't able to squirt. It was like L had unlocked this whole new world of bliss I'd thought I'd never have access to.

"One more," he said, and I nodded, my eyes wide as he plunged his fingers back into my now sopping pussy. I didn't know if I could cum that much in such a short period of time, but holy shit did I want to find out. This time I rubbed at my cock while L finger-fucked my cunt. It almost hurt to touch, so I kind of squeezed the base of it between my first two fingers and jerked it like a cis guy's dick instead of touching the oversensitive tip.

It took a while longer to get me there. L massaged my g-spot like he was being paid to do it, and I almost didn't want to cum again it felt so good. I wanted him to keep touching me like that until I couldn't think anymore, until I was just a puddle of nerves on the floor. I didn't care about cumming, I just wanted him to keep up the pressure against my g-spot, keep the warm waves of pleasure washing over me.

But soon enough those warm waves of pleasure gave way to a building desperation as my third orgasm of the night started to curl in my gut. I rubbed myself faster, feeling my belly tighten, and begged L to fuck me harder, told him I was close, that I was going to -

"Yeah, do it, squirt for me," L said, and I wailed and obeyed, cumming so hard my eyes practically crossed. This time there was less of it, but it still came, spraying from my cunt, across my thighs, dripping down my legs.

I lay there, draped over the couch, shaking while I came down from my orgasm. L was still fully dressed, hadn't even taken his shoes off, but he didn't look so put-together anymore: his hair was dishevelled, his shirt was soaked with my cum, and his erection was making a tent of his slacks. Still, I felt like a debauched mess in front of him, naked and wet from the waist down with my shirt rucked up around my chest.

L stood and started to undo his slacks. Finally! I'm not complaining about cumming three times in like half an hour or anything, but I was wondering if he was actually going to fuck me or if he'd just wanted to watch me cum. As someone who is well on his way to becoming a cockslut I was going to be a little disappointed if I didn't get to at least see it.

He pulled his cock out and stroked it, watching me. I licked my lips at the sight of it, thick and hard in his hand. I asked if he was going to fuck me, and he asked if I wanted to get fucked, and I almost laughed - how could he not see how badly I wanted a cock in me?

He produced a condom from somewhere, rolled it on and knelt on the sofa between my spread legs. He guided his cock to the drenched entrance of my cunt. We both watched as he finally, FINALLY slid inside me. I was so wet that he slid all the way in in one go, filling me up, and we both moaned.

He fucked me in slow, languid thrusts at first, long rolls of his hips. I didn't think I was going to cum again, and I wasn't trying to, happy to just lay back and feel his big dick moving inside me. But he kept it up, rocking into me like he had all the time in the world, like he wasn't trying to cum or make me cum or do anything but what he was doing.

I felt hot all over, each thrust of his cock inside me sending more heat skittering along my skin. It built inside me, this restless energy, until I felt like if I didn't do something to let off the excess I might spontaneously burst into flame. I couldn't stop moving, my fingers scrabbling over L's back and my legs kicking as he continued fucking me slow and deep, gasping and twisting as the heat built and built.

I didn't realise I was about to cum until it was already happening, a low pulse of pleasure that started in my gut and slowly spread through my body as I shuddered underneath L. It wasn't the kind of orgasm that hits you hard and leaves you gasping; it was more of a slow, sustained buzz of satisfaction, and it lasted for ages.

I was still trembling when L pulled out of me and turned me over so I was bent over the arm of the sofa, then immediately slid back into me. This new position drove his cock directly against my g-spot and I sobbed. It was too much - I wanted more.

He gripped my hips, pulling me back against him as he thrust into me. It wasn't slow any more - now he was fucking me like he meant it, his fingers digging into my skin hard enough that I hoped they would bruise. He was grunting with the effort of it as he pounded into my cunt, and I could feel his breath on the back of my neck, could hear the sloppy noises of his cock inside me and the slap of his skin against mine. I was making noises too, breathless little 'uh uh uh' sounds forced from my mouth with each thrust of his hips.

He tugged my hips back against his, creating enough space between my cunt and the arm of the sofa that he could reach around and play with my cock. I almost told him no - even overwhelmed with sensation like I was I knew that the slightest touch to my oversensitive cock would hurt - but I didn't actually want him to stop, I just wanted to play like I did, and we hadn't talked about anything like that, so I managed to hold back.

It DID hurt, his fingers rough against my poor tender dick, but it felt good, too. Like it was entirely out of my hands what I felt, like it didn't matter what I wanted, L was going to give me what I needed.

He asked me if I thought I could cum again. I couldn't reply - I didn't know if I could. Then he TOLD me he was going to make me cum again, and I cried out "ye-e-es!"

He kept fucking me just like that, pulling me back onto his cock as he played with mine, sometimes circling it without actually touching it, sometimes tugging gently on it, sometimes rubbing it hard. It took a while, but eventually I felt the telltale heat bubbling deep inside me, expanding until it filled up my whole abdomen, and I told him, "Oh my god I'm going to cum again," and then I was, convulsing, pinned between L and the arm of the couch as the pleasure hit my like a punch to the gut.

L drove into me hard a few more times before he stilled deep inside me, his cock twitching as he came into the condom, like he'd been waiting for me to cum a fifth and final time before he did. He leaned hard against me for a few moments, breathing heavily, before slowly pulling out and getting up.

I assume he went to go throw the condom away. I don't know, because as soon as his weight was gone from on top of me I collapsed against the sofa, half-passed out from exhaustion. He really had wrung every ounce of pleasure out of me that he could. I didn't know if I could stand up, let alone find my way back to my apartment.

I know I lay there alone for a bit, but I don't know how long, or what L was doing while I did so. Next thing I remember, L was crouched next to the sofa, offering me a bottle of Gatorade. I took it and thanked him, and my voice was like a stranger's it was so wrecked. I told him I'd be out of his hair as soon as I could figure out how to walk again, and he laughed, his eyes crinkling in this way that made my heart do something it had no right to be doing, and told me to take my time, he didn't mind.

I chugged half of the bottle of Gatorade and lay on his sofa for a while longer, staring up at the ceiling and kind of a little delirious. That was probably the best sex I'd had in my life, and it was with a kind of nerdy-looking rich guy ten years older than me who I'd known barely a few hours. It didn't quite compute until later - at the time I was mostly just replaying key moments from what had just happened in my head and thinking "oh my god" in a loop.

Eventually L appeared again, his hair damp, in a pair of sweatpants and no shirt. He asked if I wanted to take a shower, and I said yes please, so he helped me to my feet (I was a little wobbly) and showed me the bathroom. His shower was huge - like, the size of the entire bathroom in my apartment, huge. He gave me a towel and told me to use whatever I needed. So I took a shower, and washed my hair with his fancy shampoo, and zoned out a little under the hot spray, still stunned from the, I can not stress enough, life-changing sex I'd just had.

When I was done I was feeling a little bit more like a person who could, you know, say words and walk around and stuff. I went to find L to say goodbye, and he was like, "you can stay if you want, it's late and I don't mind," but I felt kind of weird about it, so he was like "at least let me pay for your Uber," which he did.

Before I left he told me he'd like to see me again. I shrugged and told him I wasn't really looking for anything serious even as my mind was screaming "YES! YES! REPEAT PERFORMANCE!" and he was like "that's fine, I'm not really either," and I was like, "cool," and he was like "so, I'll text you," and I was like, "cool," again, and then my Uber was there so I left.

So like. That happened, I guess. I went on a fancy date and had incredible sex with a hot guy who wants to see me again. I'm still kind of processing the sex, honestly. Like. I can't quite believe it. I squirted! I came, like, five times! I'm going to be jerking off to that memory for the next century.

Lucky me.