Trying too hard

Sometimes, when I like someone too much, I think I try too hard and fuck it up...

I met someone cool a few days ago. She was staying with me and we were talking about BDSM relationships, so I made a proposal. I dug out my PA5000 and suggested I wear it and give her the key for the duration of her stay. Since her planned visit was barely even 24 hours, it wasn't really much of a hardship.

I think she was initially sceptical. But I assured her that I had no expectations - and that even if she held on to the key and did nothing with it, then it would still add a little extra colour to her visit. I let her know I had no expectations, other than getting the key returned to me at some point. Even if that happened just before she boarded her train, it would still be cool.

No expectations, but plenty of hopes.

She asked a couple of questions, clarified what I was getting at, then went for it. I went for a shower, she made sure the belt was secure, then we got dressed and went out.

We had a cool time. We stopped at the protest on St Andrew Square and she revealed how politically aware she was, when she got into a debate with the people there, while I revealed how clueless I was by standing in the background being quietly impressed. At one point I picked up and thumbed through a copy of Ayn Rand's Atlas shrugged - and Christ only knows what that book was doing lying around there. But mostly I was painfully aware that I would have nothing sensible to contribute to this conversation.

I took her around the Grassmarket and into Greyfriar's Kirk and a couple of places in the general neighbourhood - and eventually we ended up in the Banshee's Labyrinth, where I wanted to show her the free cinema. A great concept - it's like a student pub - but with a cinema. It's on Niddrie Street, if you're ever in Edinburgh... go and check it out.

The Dark Knight was playing, and it was at this point that we really started getting into the full spirit of the tease. She sat between my thighs and I gave her an acupressure massage in the back row of the cinema, and she reached back and tickled my balls gently, until I got her to stop - not because I didn't like being teased into that semi-painful erection, but because while she had her arm reaching back, her scapula was in the wrong position for me to massage her properly.

Then we started kissing and fondling each other properly. I stroked her pussy through her jeans and was delighted when she opened her thighs to let me in. And before long, I had her jeans open and my fingers inside her properly. She showed me how to stroke her the way she liked it.

And then she started telling me what she liked. Her voice was soft, but still... the people in the row in front of us must have heard some of what she said. And by now, I'm hard enough that I'm actually squirming a bit. My cock is really starting to be constricted by the bars of this cage it's locked up in. We decided we'd had enough and went back to mine.

It's still going well. We've agreed by now that if I get any release at all, then I'm going to earn it. And so, when we get in, I take her to my room, and start to eat her cunt. And at this point, it's still going well. I'm having a great time.

It's when the belt came off that it started going wrong. That's when I started to be less passive and more proactive. And normally that's cool. Most of the girls I've been with before now have liked when I've been proactive. And I've liked it, because it's allowed me to set a pace I'm more comfortable with - so if I'm not getting hard quickly enough, I can disguise it by doing something else so they don't get near my cock until it's ready for them.

Not this time, though. She wanted to go on top. And my two main problems started to kick in. A combination of performance anxiety and (I'm not kidding here, though it'll probably sound that way) condoms that are restrictive. Seriously. I know that most men out there claim that they're bigger than they really are, but I do have a bit of a problem with condoms. I don't want to fuck without them, but they definitely impede the blood flow. And that kicks in the performance anxiety. And that exacerbates the problem. Oh, and I'd wanked off twice that morning, before I met her - something I'd never have done if I'd known we might end up fucking. Anyway, she was on top and trying to cram a half-hard cock inside her and I was fully aware of my deficiency.

So... it went badly from then on. And the following morning, when I woke up and found that she'd gone to the spare room, I knew that I'd done something wrong. I could remember some of it vaguely - just enough to make me cringe a little. And then, bit by bit, over the course of the day, the rest of it came back to me, accompanied by a cringe-inducing sense of horror.

As we left the flat to go for another walk into town, I remembered pushing her off me and trying to take her doggy-style. I felt my cock thickening up again when I was more in control and setting the pace, but it was definitely the wrong thing to do. I know I was too rough at that point, because she winced and snarled over her shoulder at me.

As we sat down in a shop in the Grassmarket, I remembered thinking that she just wanted it over with and trying to end it. Probably the biggest misjudgement of all. I actually knelt over her and started wanking - trying to cum over her tits. In my head this seemed like a good idea. I genuinely thought that I was doing her a favour.

As we watched a couple of short films in an art gallery, more and more details came back. And the whole time, I just kept on cringing.

Later, I tried to talk about it, but she wasn't interested in that conversation. I hoped that if I acknowledged my misjudgements and accepted them, and that if I let it be known that I had learned from my mistakes, then - if she came back to Edinburgh and stayed with me again, then she might give me a second chance. After all, I genuinely did like her.

She told me I was a great tour guide, though. So at least I got that much right. Nothing else, though.