Last night was my last night in Chicago. I did and S/M scene with a bottom in the early evening (got a video of it, so that post will come a little later), and then headed out to the Black & Blue Ball, which is basically a wrap up dance party for IML.

I got there a little early and the crowd was small. It was at a straight club, but one of the bartenders was a cute femmy gay guy who wore a collar, so I got drinks from him all night long.

I was wearing leather chaps over dark jeans, and just a leather bar vest up top (no shirt). The S/M crowd seems to like my belly, so I figured I’d show it off. I had worn pretty much the same thing at the Eagle a few nights before and liked the response I got from it – which is funny ’cause before I thought about going to IML I swore I wouldn’t be showing my bare belly… Now I think I look pretty good bare chested in a leather vest…

Anyway, that was a long diversion to also say I wore the whip I had gotten from the top earlier in the day on a ring on the side of my chaps. So I was dressed head to toe in leather, and was flagging whipping top. While the crowd was sparse and people actually noticed each other, I had a really good response to what I was wearing. One guy gave me a “woof woof”, and another guy stopped me, took a look at the whip and said “you can use that on me anytime.”

I’m not big on dancing – house music is one of the few things I enjoy dancing to. The DJ played some excellent deep house when things were a bit empty and then some good regular house music. So I got some dancing in… There was this hot otter who I really liked to watch dance to house music. Not many gay (white) guys are good at dancing to house, but he was. When the regular dance music came on he did these fan dance things… Otters are sorta cute. They’re an interesting combination of masculine and feminine (and bottoms!)…

Then things got a bit crowded, and I was just hanging around drinking and watching the crowd. As I was standing there this fairly attractive beefy guy comes up to me and tells me out of the thousands of guys he saw that weekend he liked me the most. OK… Let’s just say within 5 minutes of talking to him he used the ‘wife’ word (as in he wanted to be my wife)… He was coming on really strong. I didn’t really know if I even wanted to hookup and this guy had the flowers for the wedding picked out in his head…

We went downstairs to talk and on the way down I saw this guy come up the stairs who I had wanted to hookup with. He was a fisting bottom who said he’d teach me how to fist… We saw each other and then did a double take and each smiled a big smile and waived to each other.

After getting downstairs where it was quieter and hearing more of the guy’s story I started feeling like this was another disaster in the making. He said his friend that he came with was having lots of sex, but he hadn’t done anything and his friend had told him to get busy and hookup with someone… Thing was, he wanted way more than a hookup.

A few minutes after I started wondering how to get out of the situation he notices the wedding band on my finger. His face becomes completely crestfallen. It was like he just got sucker punched. I know it’s horrible, but my mind started turning – this was my way out… So over the next 5 minutes or so I patiently worked him toward the conclusion that I wasn’t the right guy for him – that he needed someone different. He was just about ready to hookup with me anyway, but I didn’t want it…

After getting out of that I roamed around the club a bit looking for the fisting bottom. I didn’t think anything would come of it, but still wanted to at least touch base with him, but I never did see him…

I had told myself I wanted to be in bed by 1am, since I had to drive the next day and driving when you’re tired is miserable (and dangerous – did you know it’s more dangerous to drive tired than drive drunk? Well, maybe not seriously drunk, but what counts for DWI in some states isn’t as bad as driving tired.) So I left around midnight and figured I’d head up to the Eagle again since I knew they were trying to do another big event…

But when I got to the Eagle it was dead. Not dead exactly, but since they had opened up the dance floor upstairs people were so spread out that it felt dead. The dark room had some people in it, but not many. I stood around in the darkroom and a couple guys gave me a blow job, but I didn’t know whether I was up for fucking anyone, and didn’t see anyone that inspired my dick, so I left.

I managed to get back to the hotel at 1am, so I was close to being on schedule. As I was walking down the hall to my room I see this guy in underwear getting ice from the ice machine. He’s acting pretty weird, and pretty quick I realize he’s totally tweaked. Imagine Johnny Depp in “Pirates of the Caribbean” – now image it’s a hot little, somewhat muscular bottom boy who’s tweaked on god knows what… Let’s just say he got my dick hard. After the first interaction, he took the ice back to the room and then came out into the hall again. His friend came out wondering where he was and we met. Then his friend went back to their room and tweaked bottom started feeling me up in the hallway, then I pulled out my dick and he bent over and sucked it a little.

I so wanted him to come into the room so I could fuck him. His body was all sweaty from the drugs, and it’s an under statement to say he was my type… The idea of seeding his hot little ass got me going… I should have just pulled him into the room and fucked him – he was “impressionable” and I probably could have had at least a quick fuck, but he went back to his room and didn’t come out again… Guess someone else got lucky with his ass…

So I got to bed at 1:30…