I was debating whether to hookup last night when this bottom contacted me on BarebackRT. Early 40s, Latino, and just a few blocks from me. His profile said he was neg, which I thought was odd for a bareback bottom in his 40s. He says he’s up for coming over and I tell him to come over in an hour. Then he’s late and I ask if he’s going to come over. He says he was vacuuming his place and wanted to finish then he’d be over. Weird response, but he does finally arrive.

When he comes in I recognize him from pics I’ve seen before (which were more accurate than the pic in his profile). He had wanted me to be in leather when I fucked him, so I was in leather chaps, leather vest and boots… We get things started and he sucks my dick briefly and then asks me how I want him and proceeds to lay face down on the bed. It was obvious he wanted to just get fucked. I tried rimming him, but the position was weird, so I just lubed up my dick and climbed on him.

As I’m shoving in he says he’s tight and he was right. Then he asked me if I liked to talk dirty. I can get into it a bit, so I tried to get into it and asked him things like “you like to get bred boy”? And he said “no, but can you pull out and cum on my face?” I just flatly said I like to cum in a guy’s ass. Then he asked me if I had my hood handy and I told him it was too much trouble to get and asked him if he liked anonymous fucks where he can’t see the guy’s face. Again, he wasn’t playing along with my attempts to talk dirty and said “no”. (Then why did he ask me to wear my hood?)

Then he started changing positions and generally disrupting things. In the course of things my dick started going soft (I don’t like bottoms trying to control the scene), but I did learn one important thing. He really liked feeling my full weight on him.

At one point I told him I didn’t think it was going to work and he asked if he had ruined the mood. I just said “whatever” and tried to pass it off. He didn’t seem to want to leave, so we laid there a bit and I jacked my dick. I asked him to suck my dick and he did a half hearted suck for 30 seconds and stopped. Finally I got hard again and climbed on top of him and continued to fuck him. He asked if I just wanted him to be quiet and I said yes…

So I’m fucking him on his belly putting all my weight on him. When I don’t have all my weight on him (supporting my upper body on the bed) he tries to get me to change things up and put my weight on his arms. It’s really clear what he wants - he wants to feel trapped and sorta helpless as he’s getting fucked. He suggests I pull out and cum on his back. And every time my breathing changes a bit or I slow down he asks if I’ve cum in him. While he never says not to cum in him, I can tell he doesn’t want it, but I can tell he also likes tops to overpower him…

So I just use all my weight and pin him to the bed and fuck him. He couldn’t have moved if he wanted to, and it was sorta like he was just a hole in the mattress. When I feel like I’m about to cum I keep my breathing and strokes steady until he’s got most of my load then I slow down. He asks if I came and I say yes. I keep him pinned to the bed for a while and slowly fuck his cummy ass (which he really seems to like).

As I expected, shortly after I get off him he starts wrapping it up and wants to go use the bathroom. I knew he was in there shitting my cum out of his ass, but he still got plenty of cum up there since he got a 4 day load up his butt.

He didn’t seem mad or anything for me not pulling out. Hopefully he’ll come back for more… The moral of the story is that if you get fucked bareback, you will get cum in your ass… Some of us just don’t pull out.

Walking down the hall he asks me what I like and I say I’m a top. He’s a top as well (obviously), so I wasn’t quite sure how it would go. The maid was cleaning my room when we got there, so after making out a little he splits and says he’ll be back in 5 or 10 when the maid is done. I lay down on the bed thinking he probably won’t be back, but then there’s a knock at the door and he’s back.

It was weird hooking up with him… He was really forceful and physical. When I put puppy mitts on him it was like I was wrestling him to put them on, but he was perfectly willing to have them on. Then I locked the puppy mitts together with a heavy lock. Shortly after I did that I realized it wasn’t necessarily a good thing to do. He put a puppy mitt on each side of my throat and it was clear he could have choked me if he wanted to, and given how forceful and strong he was it wouldn’t have gone well for me if he had had his mind set on hurting me.

But he didn’t. I could tell he liked dominating me, he liked the power and control aspect of what was going on. He was hard the entire time. It wasn’t really my style of sex at all, and I definitely wasn’t in control of the scene, but then again it’s not like he was in complete control either.

At certain points I tried to make it about his hole - fingering it, rimming it a little, but he didn’t really want that (not that his dick got soft or anything)… I knew he was into spanking (at least as a top) since he had asked me early on if I liked to get spanked. When I spanked him he had a strong reaction - he was totally turned on, but also didn’t like it. He liked to kiss, but almost never on the lips. The whole scene was a weird combination of tenderness and force. Which is what S/M is all about anyway, right?

When I had his pants down he wanted me to lick his balls. I did, but then I brought out my cock and ball whip and he was in heaven. He really got off on that. He asked what else I had, and I showed him a few paddles and used those on him briefly.

Then he wanted to use them on me. By this point I was pretty comfortable with him. I knew he wasn’t going to hurt me - he just liked things a little rough, so I took the puppy mitts off and told him he could do what he wanted if he was gentle. He was actually too gentle - I had to tell him he could go harder…

Then he wanted to ride me like a pony. He got on my back and I took him around the room, then got on all fours on the bed and he rode me there.

It then sorta wound down. I think part of it was he liked it better when I fought back and towards the end there I was more submissive than he liked.

So after yesterday’s experience, I guess I have to revise what I said. I can be a bottom. Never for anything anal, but there’s a lot of other things in the S/M experience and if I trust the top, I’m good… It’s not like I’m going to want it constantly (I never got hard in the scene with this guy), but I gotta say it’s an interesting change from the ordinary.

As he was leaving he asked where I was from and what I did. I found out he’s a married “straight” lawyer who likes hooking up with guys behind his wife’s back. He had to leave to get back to work, where his wife thought he was. As he left he rolled his pants over his big shiny boots, to blend in more on the street… Curious guy…

Oh yeah, he left me the home-made whip he had been carrying around. It’s made out of plastic coated wire and has knots in it. I tried it out on myself after he left and it’s actually a pretty good whip. Stings a little, but is still pretty “soft”...

UPDATE: Later that evening I noticed the message light was flashing on my phone in the hotel room. Turned out the guy wants to hook up again when he’s in New York. Gave me his number so I could call him. I texted him instead, and he took a while to get back to me, but he did. I think it could be interesting… If nothing else, it’s different and by playing with him, it’ll expand how I use sub bottoms…