Building on the last encounter where the straight lawyer did sort of a dominance battle with me where neither one of us was exactly in control, I contacted the bottom I’d hooked up with a couple times so far - he was my first load at IML, and then later I fucked him with 3 other guys plus watched a dom top use him. Anway, I contacted him to see if he wanted to hang out and have drinks at the bar. He said yes, so I went up to his room. We chatted briefly, I told him I hadn’t cum in a while and didn’t know if I could, but if he wanted to work for it he might get it. As you might expect he did want to work for it…

He unbuttons my pants and just as he starts sucking my dick my phone rings. It’s my bf. I answer (while the guy is sucking my dick), and chat with my bf a little and then he asks what I’m doing later and I tell him I’m going down to the bar to have drinks. He asks with who, I tell him, and then say I should probably go, ’cause the guy is sucking my dick. My bf takes it in good stride and I hang up the phone and get down to business.

Long story short (’cause this is just the beginning), I give him a half way decent fuck. Pound him pretty hard, but just can’t cum (in hindsight, since this post has taken a while to get up, I had the beginnings of a cold and was feeling run down). So we wind it up and head downstairs to the bar.

Most of the people going to IML had left earlier in the day - the crowd at the bar was pretty sparse. There’s a bunch of Treasure Island guys there, including Brad McGuire. In general the mood at the bar is about the best I had seen it all weekend. Guys were happy, goofing around (one group kept throwing each other over their shoulders and horsing around). It was groups of friends, things were over and everything was really relaxed.

After two pints of beer I had to piss, so we headed upstairs. As soon as we got to my room there was no need to go to the bathroom - the bottom just got on his knees and drank every drop. Since it was beer piss he said it tasted better than the other night - less rank. Right after he drank my piss he got up and wanted to kiss. I wasn’t so sure about that one (didn’t really want to taste my own piss) and made the kiss pretty superficial.

Then I showed him the whip the top from earlier in the day had left, and we decided to start playing again… I had the puppy mitts out from the session with the top, so I put them on him (he hadn’t worn puppy mitts before), then we tried on a few hoods. The bottom really doesn’t like hoods - he had told me as much before. So I tried to start with a really thin spandex hood, but it was too small for him. Then we tried the thicker spandex hood and that worked, but since we were trying things out I put the leather hood on him next.

I knew being hooded was a big step for him, so we took it really slow and easy, and it was good I was someone he trusted… His initial panic subsided and I decided since he was hooded I’d take advantage of the situation, take pictures, use him, and videotape it. I put his legs in the air, pull down his pants, exposed his butt and well, the rest you can see in the video below… It’s probably my best video yet - nearly 18 minutes long… Basically I fuck him, spank him, and whip him, and paddle him…

I didn’t realize at the time exactly how stinging the other top’s whip was, but I paid attention to the bottom and his reactions to what I was doing and managed to not go past his thresholds… Still what you saw in the video above hurts like hell. It’s just the bottom likes a certain level of pain - earlier at the bar he had been showing me the bruises he got that weekend and remarking how he wished he had gotten more and bigger ones.

So what you see in the video was my most S/M experience at IML - glad I got it on tape! And next time I want a lot more like that - and even before next time I’ll be looking for bottoms who get into this stuff… I’ve got the one sub bottom who will let me go there (he’s load #30 that I still haven’t gotten up yet), but if any of you want to volunteer, let me know…

The bottom and I got to be pretty good friends at IML - we even met for lunch the next day and went to the Art Institute of Chicago before we left town… He’s got an interesting story to tell and I’m hoping he’ll write up his thoughts so I can share them here… Let’s just say he’s pretty much given up with risk reduction and knows full well what that means… He’s a sane, rational guy in a long-term relationship and is completely responsible in just about every other aspect of his life… He’s not what you’d expect of some one taking such a big risk…

UPDATE: Well, the bottom liked the video…

the video is great. it’s almost exhilarating watching my ass get redder and redder as you’re beating it, knowing how much it was hurting me and how much i was enjoying it. and yet watching it as a viewer, detached from the pain now, is an interesting experience. i think it is a good video and a good scene, it’s not all the same thing, it shows a good view of my red ass, it shows you off well and shows you very much in control, and it succeeds in dehumanizing me by hiding my face and head almost all the time, while focusing on my ass.

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…