Coming back from breakfast this guy comes onto me in the elevator. He’s flagging whipping top. He asks if I want to hang out and i say sure… He’s a hot, lean, older guy who looks “complicated”…

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…