Written by Mattrichards

BDSM
3 Sep 2008


For some time I had been sitting in the chatrooms of a website aimed at transvestites. I can’t say why, exactly. I can’t even remember how I had come across the site originally. But I did, and I joined, using a false name and email address. I just liked to listen to the conversations in the chatrooms. The site had a variety of users. I’d guess about half were transvestites. The rest were “admirers”, escorts looking for business and, I suppose, men who were curious to see what went on, much like myself. I never posted messages or tried to chat with anyone myself. I just liked to watch.

A couple of months after I started, I was sitting watching the chat when a private message came through. It was from a guy called Andy, requesting I join him in a private room. I looked at his profile. It said he was an admirer. It made it clear what he wanted “Not into guys as guys. Like TV`s only but will take part in 3somes with other guys as long as we both fuck the TV only. 5ft 10, 13st, VWE, average build.” It seemed a bit weird, but I thought why not!

It was a guy who lived in a small town about twenty miles away from me. He said it was good to see someone local and that he thought he’d just say hello. We chatted for a bit. He asked me what kind of things I was into. I told him I was straight and told him about my fairly limited experience. I used to have a girlfriend who I visited a swinging club with. He was very interested in this and asked me all kind of questions. Asked me if I was still with her – seemed disappointed that I wasn’t, although told him we were still friends.

He asked me if I had ever sucked a cock. I told him I had and he asked me for details. I told him my very limited history. He asked me if I had ever been fucked. Again, I told him the truth – once by a TV. He asked me if I enjoyed that sort of thing. I realised I had told him all kinds of things I had never told anyone else. But I thought, since he didn’t have a clue who I was, it didn’t matter.

I asked him about his experiences and he detailed all kinds of encounters with transvestites. He seemed very experienced and I felt a bit out of my depth. He then told me he’d met a guy off the site the previous day. Just a guy he said, not a TV. He said he didn’t normally do that, but the guy had sounded keen so he’d thought why not. Apparently the guy had come to his house, sucked him for a while and then licked his arse. He said finally he’d fucked the guy and finished off by coming in his mouth.

I found myself getting a little turned on which was weird, but it was all starting to get a bit heavy. I asked him how he met the bloke and all the TV’s he’d told me about. He said he’d just picked them up in the chatrooms. I asked him how he did that. And he said, “same way I picked you up”. A jolt went up my spine. I hadn’t thought of this as being a pick up. I realised I had an erection. He started asking me more questions about my experiences and I answered them in slightly more detail. All the time I was aware that the power in the conversation had moved totally to him and this was a real turn-on.

Then he asked me what I was looking for on the site. I didn’t know. I said something about new experiences. He latched on and asked me if I was looking for a TV. I said I might be interested and he asked me what I’d like to do. Did I want to fuck a TV. And I said probably not. I said I guessed I was a bit on the submissive side. So he asked me if I wanted to suck a TV. I’d already told him my limited experience in this area, so he knew the answer. I said yes. He asked if I wanted a TV to fuck me again. I said I didn’t think so – not really my thing.

Then he asked me if I’d like to suck his cock. I didn’t answer. After a few moments of silence, he asked me something else. We carried on chatting. He told me another story about another TV. I asked for details, he supplied them. Then he asked me if I’d ever swallowed. Then he asked: “if you suck my cock, can I cum in your mouth?” I said I didn’t know. “So you’ll suck me off then, just don’t know whether you’ll swallow?” A moment’s silence. “Yes”. “Yes you’ll suck me off, or yes you’ll swallow?” A moment’s silence. “Both”.

The he said he had to go. Said we must chat again sometime. And he was gone. Leaving me very confused and with a massive erection to deal with!

I went on the site the same time the next day, but no sign of him. Same the day after. I sort of forgot about him after that. Then about a week later I got a message – meet him in the chatroom that afternoon at half three. Half three and I log in. Immediately a request for a private. He says hello. Then straight in, first question: “Did you have a wank after we finished chatting last week?” Pause. “Yes”. “LOL!!” I hate that computer speak stuff.

He asks me about the conversation we’d had the week before. Had I been waiting for a contact like that? I answered him honestly, “No”. “So what made you say yes?” I told him I thought it was the idea I’d been “picked up”. “LOL!!” Then: “you’re a bit of a tart, aren’t you?” I didn’t answer, but was turned on by the cheapness in the suggestion.

Then he tells me a story. He’d met up with a TV. He’d fucked her a few times before. He gave me the details of their meet. All pretty ordinary really. I asked him what she looked like and he said her picture was on the site. He gave me her name and I had a look at her profile. He said that one of the pictures on her profile was of her sucking his cock. I looked at the picture. That confirmed his VWE claim from his profile! He said I know what you’re thinking. “What? I asked. “You’re thinking how much you’d like that in your mouth.” Pause. “Aren’t you?” “Yes” I replied. “Or up your arse?” “No”. “You sure about that?” “Positive”. “Just the blow job then!” “Yes”. “I’d invite you today, But I’m a bit busy. Talk again.” And he was gone.

A few days later, same sort of thing. He private’s me, get’s me to admit that I’ll suck his cock, taunts me a bit on other things I might do, then he has to go. Same pattern every three or four days. For a few weeks. Maybe half a dozen chats in total. Then I went on holiday for a fortnight.

Now it’s important to realise that all this time I haven’t actually decided to do anything. This is all cyber chat. He asks me questions, I answer. But this isn’t me, this is a false name typing messages into the ether. I don’t even know if this guy is who he says he is. It’s all just titillation really. If he’d said come round now, I don’t know what I’d have done. But he didn’t. Assuming of course it is really him. Because that’s the nature of the internet. Just as I’m not who I’ve told him I am, he’s probably not who he say’s he is. For all I know he could be anywhere in the world, rather than just round the corner, and he could be any age and either sex. Or it could be more than one person – a group of students having a laugh. But interestingly, I did think it was one man living a few miles away. And I did wonder – what would I do if he was to say: “okay, come round now”. And quite honestly I didn’t know the answer.

When I got back from holiday I went onto the site again. After a few minutes I got a request to private. He asked me where I’d been. Told him I’d been away. Asked him if he’d had much action recently. He said not, but he had something planned for later that day. A threesome with a TV and a guy. He’d had them both before, but not together. He asked me what I thought. I said it sounded fun. I asked him what he planned to do but he said he hadn’t planned anything, he’d see how it went.

That afternoon I wondered what he might be up to. I went back onto the site mid-afternoon and he was there. I asked him what had happened. Apparently the TV hadn’t turned up so it had just been him and the guy. Bit of oral, then he’d fucked the guy, finished up coming in his mouth. Said the guy had left sore but satisfied!

Then he asked me if I was still keen to suck his cock. I said yes. There was something different about the questions which made it more real this time. Then he said he was still in the mood and did I want to come straight over. Suddenly then it was make or break. A quick decision. Go for it, or forget about it. I said okay. He said, very simply: “arrive, suck, swallow, leave. You up for that?” I said yes. He gave me his address. About twenty minutes away.

So what seems like a few moments later, I’m parking outside his house. I knock on the door and he opens it. I follow him in. He is a little older than I am expecting, I think, although I’m not really sure what I am expecting anyway. He is dressed in a pair of shorts and a T-shirt. He walks across the room to a spiral staircase and climbs. I follow. He walks into a bedroom at the top of the stairs. He takes off his shorts and sits down on the edge of the bed. I stand still for just a moment, uncertainly. Then I kneel down on the floor between his legs. Gently I kiss the end. Then lick the shaft slowly. It twitches slightly and begins to grow. I put it into my mouth and feel it swelling inside. I suck and kiss and lick. I find the taste not unpleasant. He seems to be enjoying it, which encourages me more. After a while I start to use my hand as well, wanking him whilst sucking on the end. This seems to go down well and he seems to be getting more excited. I continue sucking, and I start to think about him cumming in my mouth. Will I swallow? Then he starts to wank himself into my mouth. Clearly he’s nearly there. He takes his hand away and pushes himself into my mouth again. I suck harder, then I feel him cum in my mouth. Not a huge volume, but enough for me to get a taste. I swallow every drop, licking around the head to make sure I haven’t missed any. Then I get up, walk downstairs and out of the door. Not a word spoken.

I go back to my computer and send him an email. “I did it! I'm not sure what I was expecting, but I have no complaints. I wanted to feel like a tart. Be completely in somebody's power, and that's what I got.” And that was it, out of my system. I could forget about it all.

I got a response to my email a day or so later: “Yes thanks - it was good. You suck cock very well. I don't know whether you got a sufficient load of cum this time but hopefully next time there'll be a better load!” Next time? I wasn’t entirely sure about next time.

A few days went by and I went back onto the site. He was there again. This time I contacted him. I asked him if it had been ok. He said yes. He was just sorry he’d been in action earlier in the day so couldn’t give me a full load. Then he said: “I’m full now though. Maybe you’d better come round and suck me right now.” There was a slight pause, then he said “can you get away now?” I said yes.

Half an hour later I’m kneeling in the same place licking and kissing and sucking. I seem to know what he wants more this time. And this time I’m determined that he won’t need to use his hand. He seems to like it when I lick his balls. At one stage he lifts his legs up onto the bed and I think he wants me to lick his arse, but he doesn’t say anything so I don’t. He’s getting more excited and I feel his cock pulsing at the base, then he shoots several jets of cum into my mouth. Again I swallow it all, though this time it’s a full load. I’m pleased with myself. I get up, walk downstairs and go out of the door.

This had been an altogether more satisfying experience than the first time. Less rushed, more complete. But that started me thinking about what next. How to up the stakes. What if he had asked me to lick his arse. Would I have? What if he’d wanted someone else there? Go down on one of his other visitors, a TV or the guy he’d seen before me the other day. What else would I have been prepared to do? Did I want to continue? Did I want it to progress further? I wasn’t sure. Maybe I should just forget all about it…

The next day I logged onto the website and looked for his name in the online list. He was there. I contacted him and we exchanged pleasantries. Then he said “can you come over this lunchtime”. I hesitated – two days running. Then I said yes. He said, “one o’clock, don’t be late” and was gone. I arrive at one o’clock on the dot. I knock on the door and he lets me in. He walks straight across to the stairs and walks up. I follow. When I get to the bedroom, I half expect someone else to be there, but there isn’t anyone. He takes his shorts off and sits on the edge of the bed. I kneel between his legs and start to work on his now familiar cock, which gives it’s now familiar response, swelling in my mouth. I lick the shaft and then lick his balls. Immediately he brings his legs up onto the bed, presenting me with his balls and his arse. Without a word he puts his hand onto my head and pushes it lower, making it clear what he wants. I begin to lick around his arse, relieved to find it clean. I rim him for some time, then go back to his balls and finally his cock. I carry on like the day before, enjoying the fact that I’m able to turn him on like this.

A few moments later he reaches down and holds something in front of my nose. It’s a small bottle of poppers. I inhale several big breaths. I begin to feel a little light-headed and go back to my task with renewed vigour. A few minutes later he gives me another shot of the poppers. Then he reaches down and gently pushes me away. “Stand up.” I do. “Strip from the waste down.” I hesitate. This hadn’t been part of the deal. I’m light-headed and a little confused. “Strip!” I take off my shoes and socks, then my trousers and pants. “Lie down!” I do. He stares straight into my eyes. He reaches down and pushes my legs apart. I try to say this isn’t part of the deal, but no words come out. Then he says “beg”. And I think he’s not going to do it. It’s just a control thing. He wants me to beg him not to. And I’m just about to, when he says “come on, beg me to fuck your arse”. And at that moment we both know it’s going to happen. And from somewhere the words come. And I beg him to fuck me, to push his cock inside me!

He passes me the poppers and I inhale again, deeply. He takes a bottle of baby-oil from the side of the bed and pours some onto his hands. He reached down and starts to apply it to my arse, working in one finger then two. It feels a little uncomfortable. I take more poppers. He inserts a third finger. Then he puts a condom on and kneels between my legs. All this time he’s been staring straight into my eyes. Then he enters me. A look something like triumph in his face. It hurts like hell and I try to push him away. But he begins to move out himself. Then back in and out, gently rocking backwards and forwards, each time getting further inside, each time hurting less than the time before. And he’s completely inside me. I feel his balls against my arse. Gradually the rhythm increases and from the look on his face I know he’s nearly there. Then he tenses up and cums. And it’s all over. He pulls out and takes the used condom to the bathroom.

I feel sore and drained. The poppers have given me a headache. I start to get dressed. He comes back into the room. “Enjoy that?” I mumble a fairly sorry sounding yes. “Good. Ever been spit-roasted?” From the look on my face he knows the answer is no. “I’ve got that guy I told you about coming back on Friday. Be here about eleven.” I stand rooted to the spot. “Off you go then” he says. I finish tying my shoe and go down the stairs. As I open the door he says “See you Friday”. I close the door behind me.


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