IML is over. There’s still one more post I need to put together – my one real S/M experience (other than the one where I mostly just watched), but it contains video, so I need to edit the video first.

Expectations vs. Reality

For starters the hotel wasn’t exactly a bathhouse. VERY sexual, but different than a bathhouse. I didn’t see any open doors or anything like that. I did see one cumhole that put a sticky note in the elevator lobby for each floor saying he was taking loads, but that’s about all I saw. Instead it was like a buffet. Login to your favorite hookup site, look for guys 0 miles away and have them come to your room. It was also a lot about private sex parties and gangbangs. The trick was 1) finding them, and 2) getting invited.

Going into it I had hopes of how many guys I’d fuck and how many I’d seed. I got my raw dick in 12 different holes and seeded 4 of them. It’s not bad, but I was hoping for a lot more than that. But it was my first time, and I know how I’d improve those numbers next time…

I was also suprised with how many native Chicago guys wanted to hookup. I guess I expected it to be mostly guys attending IML. When I wanted hole right then and there, it always seemed like the guy was 5 miles away and not at the hotel.

Highlights

Top three sexual experiences (in no particular order):

• Fucking the little kid. Probably one of my favorite fucks. It was vanilla, but he was close to my ideal cumhole…
• Whipping and fucking the sub bottom and having him drink my piss. Been WAY too long since I really inflicted some pain on a bottom. I liked it…
• The “tussle” with the forceful top. It opened my eyes to a different way of thinking about sex – in a good way…

It’s interesting that only one of those three involved cumming in a guy’s ass…

Fucking Jarod Steel was definitely notable, but not in the top three… Also notable was fucking the young little guy in the backroom of the Eagle.

I really liked Lake Shore Drive. I could see myself living on it, which says a lot… I also liked getting out and seeing some Frank Lloyd Wright stuff in Oak Park one afternoon…

Things I’d Do Differently

I didn’t expect to get things perfect the first time around. I went to see how it would be. But having seen it, there are things I’d do next time to make the most of it…

Next time I go I want to go with a “partner in crime”. Not that that I’d want to be joined at the hip or anything – but just someone to hang out with in the off hours. If it’s a top – someone to share bottoms with, if it’s a bottom someone to fuck when I need a nice wet hole… Nothing too serious, definitely not a pretend boyfriend for the week.

Spend less money. What this past week cost me is a bit crazy. The hotel (and parking) bill was $1,600. Then there was gas money of probably $300+, then Flex for $80, plus food, etc. I guess that’s not all that crazy, but it can be done less expensively and still have just as good of a time. I’d rather put the money toward more leather gear.

Having the partner in crime be a roommate would help a lot – half the room bill. Not driving would help as well. I had never been to Indiana and Illinois, and it had been ages since I was in Ohio and northern Pennsylvania. I’m glad I drove, but don’t feel the need to do it again next time. The stop over at Flex Cleveland was definitely something that could be dropped.

I’d eat better. There were some days when I only had one meal. Or one day my two meals consisted of a roast beef wrap and a big slice of pizza. My intestinal track was a complete mess and I had the runs by the end of the week from not eating properly. Once I had some decent food in me on a regular basis everything went back to normal – so I definitely need to eat better next time. I did lose 3 pounds this past week though.

I’d also skip the last day. There was a nice vibe the last evening, but all in all, it didn’t seem worth it to stay the extra day. However, I did meet the straight, forceful top – that was one really good thing that came out of it. He called today to talk… It’s not an anal sex thing with him, but I like where his mind’s at – a mix of desire and resistance…

I’d be more focused on one of the recon sites rather than BarebackRT. The point of the event is leather and fetish and the guys on BarebackRT are too vanilla.

I’d seek out and go to some sex parties next time as well. There were some guys who were going to two or more a night… Don’t know I’d do that many, but one a night (plus maybe a piss party) would be nice.

Next time I’ll do a lot more watersports… There were enough guys there who liked drinking piss, I really should have done more of that…

I’d force myself to go to all the competition events next time. I felt like I got disconnected from the actual contest and wish I had been more connected. Just a bad choice on my part…

I’d get a haircut before I went. IML just seems to prefer guys with really short hair…

I’d have fewer, but larger bags… I packed completely wrong for getting in and out of the hotel… Need more bags with wheels, etc.