Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.
I was nineteen when I found the site. Like most male nineteen year olds, in fact like most males past the start of puberty, I had sex on the brain a lot, probably most of the time. In theory, as a bisexual guy, not too bad looking and easy to get on with, it shouldn't have been too hard for me to find a partner if I wanted. Unfortunately, I was far too shy to chat up anyone, male or female. To make matters worse, there was my tendency to fall ridiculously in love with my best friends for ages, which I then wouldn't do anything about either, or if I did things didn't work out.
So, to cut a long story short, I was nineteen, horny, and not getting any, when I came across a free internet adult personals website. It wasn't completely free of course, if you wanted to start messaging someone you had to be a paying member, and also if you wanted to see the details of most people's profiles. But I was feeling horny so I thought I'd give it a try. I posted my ad, saying I was young and bi looking for sex with just about anyone, with a few photos of myself without a face, mainly of my erect cock as that seemed to be what all the other guys there had done. Whenever I was bored I would add some more details, or a fantasy, in the hope that someone would be interested.
Soon some people were, though disappointingly but not really surprisingly, my admirers were exclusively male. Over several months I tried to meet up with some of them, but it always fell through. I didn't blame them, as I was quite nervous about meeting too, and I wasn't sure enough of my housemates to feel comfortable bringing guys back, so it had to be at the other guy's place or a hotel.
Eventually, after several disappointments, I got a message on the site that stood out from the others. The sender, Ed, was eighteen for a change, whereas most of the others were around thirty or even older. Also, for once the message was longer than one sentence and wasn't just complementing me on the photo of my dick. Now, I don't mind being told I have a nice cock, but I know I have a nice cock. Over seven inches long and not much under two inches thick, in internet adult dating world at least, it's above average. In fact it's about the only part of my body I don't have issues about, especially then when I was really skinny with hardly any muscle at all. Still, it gets a bit monotonous when that's all the messages said, especially when they didn't lead to some hot fucking.
What made this one really stand out was that the guy had clearly read all my profile, even the extra bits linked to, and he was responding to a fantasy I'd put on another page. Apparently he also had similar fantasies about crossdressing, and after exchanging a few horny messages we arranged to meet. He lived in a town not far from my university, and although I was home on holiday, I needed to go there for the day and I'd have time after. He said his house would be empty, so finally I had a meeting likely to become reality.
We'd arranged to meet at the train station, so I rang Ed when I arrived and waited for him. A few minutes later a guy about my height with big frizzy hair approached, and as he got closer I recognised him from the pictures of him in women's underwear he'd sent me. We walked back to his house, talking, me a bit nervous as this was my first time with anyone, until we got to his place. It was a big house, with a barn attached that he opened and we entered. It was a bit sparse, but with some sofas and a table, so we sat down and continued talking, listening to music, both a little nervous but also quite horny. He said that he'd wanted to be fucked by a tranny for years, even though he was only eighteen, and I'd wanted to dress as a girl and be screwed for a long while too, although in the end our roles were reversed.
Eventually he couldn't take anymore waiting: "Would you like me to dress as a girl for you then?"
"If you like, yes," I replied, feeling awkward and not sure what else to say.
Ed picked up his bag and left the room, leaving me to fidget and wait, nervous, but very excited, all sorts of thoughts going through my head, thinking of running out on him, what we would do together, and so on. I took my top off as the anticipation was making me hot, so I sat in my tight black t-shirt, which despite being labelled large, I suspected was a girls t-shirt, as the band I got it from were much more popular with girls than boys. Finally I heard his footsteps and he came into the room, wearing a tight pink skirt and a vest top, looking very attractive. As he sat down again in the armchair, I noticed he was well muscled, and in the shade of the skirt I could just make out the shape of his cock.
"What would you like your slut to do then?" he asked. This was actually what we said; after all, it was a bit of an artificial situation, so it was difficult to know what to say.
I simply replied: "Let's start with some oral."
Ed obediently got down on his knees between my legs while I quickly unbuttoned my flies and pulled my trousers and boxers down, taking my limp cock in his mouth while I was still kicking my shoes off. His mouth was hot and wet on my dick, which was quickly getting hard, so I pulled my t-shirt off too and touched his frizzy hair as he bobbed up and down on me. I was getting impatient now, and wanted to get at his cock, so he suggested a sixty-nine. First though, I had to unzip his skirt, pulling it down off his hips so he was just in the top and the black knickers, his hairy genitals poking out from them. I lay back on the sofa and he got on top of me, adjusting his position until he could suck me and he was within my reach.
Holding his legs with my arms I pulled him closer and began licking his dick, pulling his foreskin back to get at his smooth head, gingerly licking at it with the tip of my tongue until he was hard and then took him into my mouth and began sucking. He tasted good, but he was quite a bit smaller than me in both length and width, and without any difficulty I managed to take the entire length of his penis in my mouth, the head in my throat. I did this a few times, still feeling his warm wet mouth around my cock, his teeth dragging lightly over my shaft, and then I began licking his balls, flattening his pubic hair with my saliva. I was about to start sucking his dick again, when he got up to turn the music off.
I knelt up and asked him if he'd like to fuck my arse, or something along those lines, and reached into my bag to pull out my tube of KY jelly, that so far I'd only been able to use on my own with my dildo and vibrator. I was looking forward to it so much that I forgot to get the condoms out, but luckily Ed reminded me, so while he put one on I spread some of the lubrication on my shaved arse hole, then put a bit on his rubber-coated dick and turned around to face the wall, leaning forwards and pushing my bum out towards him.
He put the end of his knob on my sphincter and began trying to push it in, and I pushed back, as I knew I was supposed to from reading on the internet and my solo experiences, so little by little I felt it edge its way inside. He pushed it in as far as he could in that position and then began thrusting, and it felt good despite not filling me as much as I would have liked, but after a couple of minutes it became clear that this position wasn't the best.
Immediately, I lay down on the sofa and brought my legs up as I'd seen on the internet and in videos, and then Ed, who was now just in a bra, lay on top of me supporting himself on his arms and entered me again. In this position he managed to penetrate me a little further, and he also started to masturbate me. I was no longer as hard as before, even though I loved being fucked by a transvestite like this, his cock thrusting in and out of me, but both of us strangely silent. After a few minutes he said he was going to cum and asked if this was too soon. I said no, but afterwards I wished I'd asked him to cum in my mouth, because I was left wanting to taste cum at the end of the session. Anyway, I didn't, so soon he pulled out, his dick softening and the condom full of his semen.
We got up, and then he took my place, asking me if I wanted to fuck him, which I certainly did, and I put on the other condom while he lubed up his arse, and then I put some KY jelly on my cock, massaging it a bit to get it hard, and got into position. At first I thought I wasn't hard enough, because I was pushing hard against his sphincter, but it wasn't going in, and I suppose I was nervous so I was softening up, but it also became clear that Ed was just too tight for me. So we stopped a bit, he did some poppers and used a fairly small dildo to loosen himself up while I wanked to try and get myself hard again, and we tried again, but still no luck.
Finally, he stood up and bent over, holding on to the arm of the sofa and I went behind him to try again, but still it wouldn't go in, and in the end we decided it must be too big. I was a little surprised, as I didn't think that less than two inches thick and about seven inches long was especially large, just average, but apparently not, which was a nice ego boost, especially after my growing humiliation at not being able to penetrate him!
Anyway, once we'd given up on the idea of me fucking him, I pulled the condom off, and Ed got down on his knees and took my dick in his mouth again, pausing to laugh, probably because of the poppers, at how big it was. As I watched him give me a blow job, I began to relax again after the embarrassment of not being able to fit in his arse, and after a couple of minutes I was rock hard, and we could probably have tried for penetration again, but I decided not to suggest it as the condom had been on the floor. Ed sucked harder, and I could feel his tongue swirling around the head, and I began to murmur that it felt good. Placing my hands on his curly hair, I closed my eyes, enjoying his mouth on me, and eventually felt the pressure building in my balls and the familiar warm tingling in my head.
"I'm going to cum," I warned him, not sure if he wanted me to ejaculate in his mouth, but he just intensified his efforts. I gasped as the orgasm flooded my head, and I could feel my jism spurting into Ed's mouth but he kept sucking, prolonging the climax and increasing my pleasure even more. As it began to fade I looked down and could see drops of cum falling from his mouth to splatter on the floor. He pulled back and asked me how it was.
"That was fantastic," I told him after a pause of shock, not knowing what else to say. Still recovering, I looked around, and Ed passed me a tissue to clean up. Once we'd cleared away the mess and the condoms, we both got dressed and left to get something to eat, both of us pretty satisfied, and much less nervous.
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<a href="https://www.lushstories.com/stories/trans/webmeets-diary-ch-01.aspx">Webmeets Diary Ch. 01</a>