Last night “friend of a friend” came over for dinner. For all you guys who say I don’t care about bottoms – well, there are some I care about and I can truly say I love this guy and think the world of him. I’ve fucked him two (or three?) times but I hadn’t been able to cum in his ass… This time I figured I’d give it another shot – I had a 3 day load and figured I should be able to cum this time…

Since my bf was taking a nap on the couch we went into the bedroom where I had pulled out some leather gear I figured he’d be into. Turns out he hadn’t done much of any BDSM before, but he was game. After a quick blow job I put a collar on him. Then I gave him a choice of a spandex hood or a leather hood (he chose spandex). And then once he was hooded I put puppy mitts and ankle restraints on him. Then I locked the puppy mitts together with a really heavy lock. I did this in part to make things less personal and more sexual. I hate to say I tried to make a piece of meat out of him, but if you took a coarse view of it you could say that. I wondered whether the reason I couldn’t cum before was because of the personal connection – so I wanted to remove that from the equation…

It was hot seeing him on all fours on the bed. I ate out his hole for a while and then went to fuck him. Earlier that day I had gone downtown and picked up a new 2 gauge PA to replace the one I had dropped on the sidewalk and scratched one time when I took it off before going through a metal detector. One of the other times I had fucked him I fucked him with a PA – so I knew he was OK with it. I had to manually shove the PA into his ass ’cause he was pretty tight and then once it was in there it hurt a little bit (but not as much as the one time with the black guy a year ago), so I figured I’d pull out, take it off and continue on without it…

When I pulled out it had some shit on it, so I went into the bathroom to quickly clean up. I also brought out a wet wash cloth to clean him up with since he couldn’t do much for himself – being hooded and with no use of his hands…

Long story short, things were difficult after that point. I kept trying different things, but nothing was really working for me… Finally, I sorta gave up, and we just laid next to each other cuddling.

I took off his hood (he was cuter with it off), and had him give me a blowjob (with the PA out). I had one of those spongy rubber cock rings on and got a nice big fat hardon from the blowjob. I had him get back on his knees and gave him a nice long, hard fuck. It went on and on, but somehow “that spot” on my dick that, when massaged just right makes me cum, wasn’t getting rubbed the right way… So after a while I could tell it just wasn’t going to happen – as much as I wanted it to… Finally, I tried with him on his back, but it just wasn’t happening…

We wrapped things up (sexually) and then had a great dinner and sat around (with my head in his lap) and watched a foreign film he brought over… All in all a great evening… I wish I could give him a load, but it seems like it’s just not meant to be…