Well, guys, last Thursday I finally broke my dry streak.
I finally got sick of being strung along (or just ignored) on the usual dating sites. I did what I almost never do anymore: I went on Craigslist. The reason I don't make a habit out of going on Craigslist is because, for the last few years in Ohio the site has been all flakes and spambots. I don't know what the Maine one has been like, but I figured I'd give it a shot.
I found an add right away that had been posted recently titled, "Where are all the tops?" and inside were four pictures of a tan ass looking invitingly at the camera. If you don't think an ass can give you an inviting look, you aren't staring at them enough. The text of the post said that the guy needed to be topped and wanted it bareback. That was enough for me. I sent him an email with my stats, a few pics, and said, "I'm a top. Let me fuck your hole."
Very soon I had his address which was about a five minute drive from me. He wanted me to get there soon because he needed to be at a meeting in an hour and a half. I told him that I'd be there and gone with enough time for him to get clean if I left right then. He told me to come.
I pulled up to his house and parked in the street. He had said the side door would be open and he would be in the back bedroom. Both things were true, though the layout of the house made finding the bedroom kind of hard. He was laying face down and I took off my clothes and put on my cock ring. I knew he wanted anon play, but he wasn't blindfolded so that meant he was ok with looking. I walked up and stuck my half-hard cock at his mouth, noting that he was much more pale and grey than in the pictures. To be fair, in his emails he had warned me he was older, and I'd told him I didn't care. I still didn't. I just like it when the pictures tell the truth.
After he got me hard with a mouth that hardly impressed me, I said, "Let me get at that ass."
He rolled onto his back and pulled his legs up, and I just shoved myself all the way in. He closed his eyes and clenched his jaw in either pain or pleasure. I didn't really care which. I started fucking him right away, only opening my mouth to tell him how great his ass was (it was clenching in all the right ways) or to nibble on his collar. He moaned and sighed under me, letting me know I was doing my job right.
When I came it wasn't as much as I can usually come in a good session, but I also hadn't been working that hard. Part of the problem too was he had grabbed my nipples really roughly and now they were bleeding, which pissed me off. I came in him, fucked him for a little while longer, but there was no way this man was going to get a second load from me by just staying still like his was, so I pulled out. I looked down at his sheets as saw where my cum had leaked out with a little bit of shit in it, which made any desire I'd had to felch him shoot far away. I just pulled my shorts up and made a mental note to take a shower the moment I got home.
I was no longer worried about the dry spell, and that night I even began to get emails and messages from guys looking to hook up. Sadly I was leaving for the Boston area and a trip to Province town for the long weekend, and couldn't meet any. I still had a great weekend though, and I'll tell you about it soon.
On a side note: the trip to Boston is why I haven't been posting as much or replying to comments. This may happen again in the future as I am still apartment hunting in Boston and I'll have to make trips down to view apartments. Once I settle on one and move in, I should be able to post regularly again, I'm just letting you all know that in the near future I may have periods of no posts. Thanks for reading.