2012-21

Saturday morning I was supposed to hook up with this pain pig off Recon. He had been really pushy to have a whipping session with me the week before and mildly upset when I canceled. So we scheduled it in advance for a week later. He somewhat sensibly wanted it early in the weekend so he had time to recover before Monday morning. We chatted the night before online and then I texted him in the morning to confirm and he said he was still coming so I gave him my address. It’s been a while since I had done a proper S/M session and I had to get set up. That took a while and got me all sweaty and finally the time came and I sat down and waited for him to show up. And I waited and waited. Finally after 30 minutes I realized I’d been stood up. I text him and message him on Recon and give up. [He never did get in contact with me and explain himself.]

At that point I needed to find a hole. One guy nearby indicated he was up for it, but needed to clean out. I waited 45 minutes and finally gave up on him too (it only takes 30 min to clean out). While I had been waiting for that guy another guy had contacted me who had been messaging me a fair amount lately. When I gave up on the other guy I contacted him and asked if he was cleaned out and ready to go. He was, but then he asked if I could help with subway fare. I told him no problem.

Thinking about it, every time I take the subway to a trick’s place it’s $2.25 each way – so fucks cost me (or the trick) $4.50. I see that as pretty cost effective, though of course a trick I that’s within walking distance is better yet… So as I got ready for the guy to come over I took out a $5 bill and threw it on the bed.

He arrives and he’s pretty cute – late 20s, skinny, a bit hairy – basically a cute little otter (though not over the top hairy). We stripped down – he had underwear over a jockstrap, so I had him keep the jockstrap on.

Honestly, I’m a little hazy on the details – I don’t think he sucked my cock first, but he might have. Anyway, I tell him to get on the bed on all fours and I start eating out his hole. Given that I had taken a Cialis that morning it didn’t take long to get hard – I was sporting a hardon most of the morning… As I lube my dick and start to shove in I’m thinking about how prevalent completely anonymous sex is these days. I mean yet again here’s a bottom bending over and taking my dick with zero conversation. Maybe it’s just me, but it feels like more and more bottoms will take raw dick and loads literally with no questions asked.

Given how hard and thick I was I knew it wouldn’t take long to cum. He felt good. I put his legs together and rode him like a log. It was one of my favorite ways to fuck back when I was just starting out many moons ago… It’s especially hot with thin guys…

As I said, it didn’t take long to cum and since I had just taken a pill I stayed hard after cumming so I fucked him a little bit afterwards and then rolled him over on his side and kept pumping in and out of his ass. When I do that I tend to lightly touch the bottom – sorta caressing him… Bottoms who like intimacy love it, but this guy seemed uncertain how to respond. He tried to reciprocate, but it was awkward…

We talked a bit after I got soft and my dick popped out of his ass. Nice guy – seems like he’s still finding himself, which is completely OK at his age…

As he left, he grabbed the $5 bill… It did feel a bit like he was a cheap hooker, but nothing wrong with that 🙂