Trying Too Hard To Please

13 August 2012 | No Comments

Load 2012-37

There’s a bottom who I’ve been in a lot of contact with lately, but timing always sucks. Well, Saturday morning things worked and I went over to his place. He told me he’d have the door unlocked and he’d be on the bed face down, ass up. It all sounded pretty good, but honestly I was sorta in the mood for something a little more relaxed. Still, anonymous is always a good way to start…

I got to his place, the door wasn’t ajar, but since the doorman had just called his number and he had told me he’d be waiting on his bed, I tried the knob and it was unlocked. Usually in anonymous pump & dumps the lighting is pretty low, but all the blinds were open and there was tons of light (not a problem – just more of an observation). He had an alcove studio, so I went over to the alcove and there he was just as he said he would be.

I wasn’t in a rush so I took off all my clothes and got down on my knees to rim his hole. The hole was a little musky, but seemed pretty clean so I had some fun with it – sucking on it, etc. Too bad there weren’t other loads in there. I love when I suck on a guys ass and he can push out cum from other tops. That got me hard, so I stood up and went to fuck him. There were several bottles of poppers around, but I didn’t see any lube, so I got things as wet as I could with spit and pushed in.

Long story, but I had pushed stretching my Prince Albert too far to quickly (ball stretching & PA stretching at the same time is a bad idea) and then slept in the bigger ring which irritated it, so I had to take it out, give it a few days of nothing and then start all over. I had just put the curved barbell back in the day before and even it was pretty sore and irritated. But he took the extra ball on the bottom of my dick without a problem.

He had a nice tight hole – I almost wonder if he was clenching to give me a good fuck. But what was interesting was that I seemed to hit bottom in his ass really easily. That doesn’t usually happen unless the guy is around 5’4″ and this guy was maybe 6 inches taller than that. Usually I love hitting bottom but every time I did my PA would shoot out a bit of pain. It wasn’t particularly happy about fucking when it was so tender.

I lasted maybe a little bit longer than usual, but still came pretty quickly. It was at this point that the bottom said “stay inside me” – which I intended to do anyway, but the problem was one of position. I tried briefly to lay on top of him, but I’m a big guy and didn’t know whether my weight was too much for him. I went to roll us over one way but didn’t want to be looking into the mirrored all (too much looking at each other for an anonymous fuck). So I rolled the other way, but it was a little awkward – like he didn’t really want to or he wasn’t expecting it or something.

There was just something a little off with the chemistry at this point. Best I can describe it is the bottom wasn’t relaxing and just being in the moment. Still, I pumped my dick in an out of his hole. Since I had cum I wasn’t 100% hard, and with the position we were in my dick was a bit bent. But I found if I pushed with my fingers where the bend was that I could continue to fuck him pretty well.

One thing I did was pull my cock so it would almost come out. This was the thing that caused the bottom so much pain a could weeks before – when the ball on my PA repeatedly gets inside the sphincter it can be painful. Though a couple weeks ago i was really slamming into the guy’s ass – this was just a relaxed, slow fuck. I chatted briefly with him afterwards and he didn’t mention any pain – so I don’t think that was the case this time. Still, I imagine he got the sensation of feeling the ball on the PA every time I pulled out.

As I was starting to get soft I pulled out. I really wanted him to clean off my dick, but he didn’t volunteer and I didn’t force the issue. I got up and felt his cummy ass.  I couldn’t resist so I licked some of the cum up (tasted good!). All in all the bottom seemed to want a quickie pump-n-dump, so I figured I’d leave. He said I could take a shower or whatever, so I went into the bathroom and tried to clean my dick – not because he was dirty, but because I knew my PA needed the cleaning. I pissed a little in his sink and then used soap and water for the rest.

When I came out he said I could stay longer, but I wasn’t really feeling that vibe. Honestly I think he read the blog saw some of the pump-n-dump hookups I’ve been having lately and tried really hard to give me what he thought I wanted. You can’t fault a bottom for that, but I sorta wish he hadn’t tried so hard.

As I was dressing he apologized – he had looked back and seen me. Clearly he was trying to live by a rulebook he got off the blog. Guess he missed the part about how I like to start pretty anonymous, but the ending doesn’t have to be. Then I realized my keys weren’t in my pocket, so we looked around for them a little (turns out I had left them at home). Then I was off.

All in all a good fuck…. While the bottom tried to hard to please, what he proved to me is he’ll probably give me whatever I want. I could probably rough fuck him with my big PA, or even get into BDSM with him and he’d take it light a champ – ’cause he works so hard to please. So in the end it’s all good…

There was a little funny incident as I left the building. As I came in I saw what I thought was an older leather queen on his Harley outside the building. He had the leather vest on with pins all over it – very old school leather bar. Then as I was coming down the elevator these two guys were talking and by the conversation it seemed one was the coop board president. I walked behind the president as he left the building and the old leather queen was still outside and they started chatting about how he didn’t know if he was going to go for a ride upstate because it might rain. I just thought “only in New York” are regular people so accepting of difference. I mean there’s a chance the guy wasn’t gay – that he was straight and part of some aging motorcycle club, but it was the West Village and the guy looked 110% like the old guys you used to see at the LURE on a Saturday night. I mean full leather with all the pins stuff to prove their track record in the community. And here was this older (probably) Jewish guy who probably had 2 kids, 4 grandkids treating the leather queen and his issues like they were completely normal. THAT is why I live in New York.