Last night I was down in Chelsea with some time to kill. So I got on the web (via my cell phone) and saw a listing on Craigslist by a guy who had literally begged me to fuck him previously…

Me: “Where are you located?” (since his ad just said “downtown”)

Him: “im in chelsea teens/7th ave you and your stats”

Me: “39, 6′, 230, 8″, white. we’ve corresponded before-check past emails for my pics. I’m close and can stop by in a little bit if you want…””

Him: “hey dont see an old email from you but im HOT and HORNY you wanna CUM over or send me a DICK pic… do you know what I look like?”

Me: “What’s you address – I’ll be there in a few minutes… and yeah, I know what you look like you sent me a lot of emails trying to get me to fuck you… ;)”

Him (again): “hey im ready where r u CUM and Get it”

Me: “16 & 7 what’s your address?“

Him: “Kewl its 6pm now what time,I will send you my addy”

Me: “Not asking a third time… I WAS looking for NOW. the games are really tiring…”

I give up, sign out of mail and send a text message to a guy who gave me his cell number and told me to call him whenever I was looking to fuck, but he texts back that he’s off to a Project Runway party (which I didn’t really understand until I got home and my boyfriend was watching the first show of the new season – great crop of designers BTW).

So I check my e-mail one more time and he had finally sent me his address… I send a message back saying I’ll be there in a bit.

I arrive and it’s a ‘modest’ apartment (nothing particularly wrong with that- some cumholes live in real dives) . In the pic he had sent me he had really short hair, but now it was really long. We played around a bit, he sucked my cock. I wanted to rim him and he cleaned off the lube he had put on his hole. The whole time he’s trying to talk dirty and a lot of what he’s saying is focused on the fact that he’s black and I’m white. I can definitely get into the whole racial thing, but the way he was going about it wasn’t really doing it for me.

Then I went to fuck him… We’re both standing – he’s bent over a desk. Thing is his legs are longer than mine and my dick comes to a point about 2 inches below his hole. I can get in his hole, but not comfortably and I’m not in the mood to stand on my tip toes to fuck him (been there, done that – no fun…) I ask him to lower his ass, he doesn’t get it. I then push down (pretty hard) on his lower back and he stays right where he is. I move him around to the couch thinking that might be better. No luck. I have him lay on his stomach and he manages to lay in a way that’s awkward for me.

I’m so over the hookup and my dick is almost too soft to fuck. Then he says (still talking dirty) “You like your hard dick in a black hole, don’t you?” I’m thinking – Guy, can’t you notice I’m soft? What’s the talk about my hard dick? It’s not hard!

At that point I give up. I say “it’s not working for me”, pull up my pants, put on my jacket, grab my bag and leave…

For someone who I think (based on his Craigslist postings) gets fucked a lot – he’s a really bad bottom…