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…

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…

After the disaster early yesterday evening, which followed the uneventful night the night before (thanks to the same person), I pretty much took control of things and made sure I had a decent night last night…

I determined that drinking alcohol was a recipe for disaster for my cock, so I went down to the bar in the lobby and had a ginger ale, then had a slice of pizza and then headed back to the Eagle since it had shown some promise the night before. I got to the Eagle a little early – like 9:30 and there were only maybe 15 or 20 customers there, so after drinking a Coke I decided to go next door to Man’s Country.

Man’s Country is a really old (and old-style) bathhouse. The room had chipboard on the walls (cheap plywood) that had been worn really smooth and darkened over the years. The crowd wasn’t nearly as attractive as Steamworks. IMHO, the primary reason to go to Man’s Country is because it’s next door to the Eagle…

I got a room, which turned out to be a good thing since all evening I’d rest a little in the room with the door shut and jack my dick until it got hard, put a cock ring on it, and then sit in the room showing my cock which stayed nice and hard. When I got bored sitting there I’d take a walk around to see who there was to fuck.

On my first walk around I saw this muscular, light-skinned black guy laying on his stomach face towards the door. I went into his room, rimmed his ass, then when we stood up and he did this awkward thing to get me to suck his nipple I realized he was a bit of a freak. But he had a really nice, tight, muscular body so I put up with it. Long story short we fooled around and then he grabbed a condom at which point I said “no condoms” and that was pretty much the end of it. As I was putting my towel on he was sitting on the bed and did this thing with his leg to figuratively kick me out of the room. It came off as very prissy queen…

There were a lot of guys who just blew me. In some cases I didn’t really want to pursue anything further with them, in one case I didn’t really want to fuck him and on top of it he kept pushing a condom almost the point of being funny – he bent over and put the condom on his back just above his ass…

Then this guy came by who blew me for about 5 seconds and then said, “Do you like to fuck?” I said “yes”, so he got on all fours on the bed and presented his ass for me. I got up, inserted my dick and fucked him. He had a good hole and was telling me to breed him. I asked him whether he had loads in him already – since it sorta felt like it, and he said he had three in there. I pulled out my dick and rimmed him, but couldn’t taste any cum, and he made it clear he wanted to get fucked, not rimmed, so I went back to fucking. It was my first fuck of the night and didn’t really want to cum yet so when he asked if I could cum I said I wasn’t ready to yet… He understood, but that was pretty much the end of it…

Later in the evening, between blowjobs, I was walking around and saw this tall black guy on his stomach. I went in, he blew me to get me hard, and then I fucked him. He was really into getting fucked raw and taking loads (especially from big white guys). I gave him a good fuck, but didn’t cum.

There were a few other guys laying on their stomachs, but with the ones I was interested in, none of them wanted to hookup with me, which was OK… Whatever. There was also this chalkboard in the bathroom and people put messages there if they were taking loads. The funny part was when I first saw it another guy commented that there wasn’t any chalk to write messages, which means the bottoms bring their own chalk (sorta funny). Thing was, none of the cumholes on the message board really did it for me, so never did even try to fuck any of them.

So around 2am I knew the Eagle had been busy for a while (the room I was in was under the Eagle and I could hear the people moving around in the bar like a herd of cattle over my head). I had fucked two guys and gotten blown by probably a half dozen more. There weren’t that many new guys coming in, so I figured I’d head to the Eagle.

The Eagle was really busy when I got there. I went into the back bar area and saw guys getting sucked and one guy getting fucked. Then I headed into the small dark room area where I saw this guy I had fooled around with the night before having sex. He was getting blown and I spotted him when he was in the middle of his orgasm. He recognized me and we sorta felt each other up as he was leaving the room. I tried to get into the room but it was too crowded and hot, so I turned around and walked around a little before.

When I tried again I was able to work my way into the room and saw this short, thin, young, black guy bent over, giving head. I felt up his ass and his body and he was really hot. He was dark-skinned and had a harnass on. When I got close enough, things wrapped up with the top he was sucking and he turned his attention to me. I really wanted to fuck him, but he seemed like he just wanted to give me head, which he did for a while. Then when he stood up one time he finally got the point that I wanted to fuck him. He turned around and presented his ass to me. I got down and started rimming him… Then stood up an fucked him.

It was really crowded in there, and difficult to get in a good position for fucking, but we finally got things pretty well sorted out. He was bent over a long urinal (which reaked of piss) and I pounded him. I should mention there was this latin (?) kid in there who was watching everything. When I was getting blown I tried to feel him up, but he would push my had away, but as soon as I started fucking the black kid the latin kid got interested and started trying to feel my dick in the black kid’s ass, and feeling me up… I fucked the black kid for a while (for fucking in a dark room), but wasn’t able to cum before he had had enough. When we stopped we kissed and he thanked me before leaving.

Then, next to me, there was big white guy getting fucked. I’m pretty sure he was the same guy who was getting fucked in the bar area when I first came in. When the top was done with him, he blew my dick briefly before turning around and giving me his ass. His legs were considerably taller than mine and his ass was shall we say “meaty”, so it wasn’t the best fit. I had to stand on my toes to fuck him. I did it for a while, but could see it wasn’t going anywhere, so quit. He then turned around and let another guy fuck him. I held his head on my shoulder and whispered in his ear how he was a good boy getting fucked and taking loads. When that guy was done with him, he turned around and I fucked him a little more, but again, not the right “fit”, so it didn’t last long.

Meanwhile the little latin guy was still standing there and seemed somewhat interested, but nothing came of it. The big cumhole blew him about the time I wanted to get out. I was hot and drenched in sweat. It felt good to get out into main area where it was nice and cool.

I started talking with the Latin guy I had seen the night before. He had also been in the dark room and saw me fucking the little black kid. He said he wanted me to fuck him, so after we both had a drink we went into the backroom and after rimming him briefly, I tried to fuck him, but I just wasn’t hard enough. It was a combination of a lot of things, but it just didn’t happen right then and there, so we gave up and got out of the dark room.

I told him I wanted to bring him back to the hotel and fuck him. I even waited around for a while while he said he was going to go tell his friends he was leaving, but when push came to shove he didn’t really want to do it and said since I hadn’t been hard enough to fuck him I must not be into him. I hadn’t been all that hard when I was fooling around with him the night before, so I could see his perspective. I knew it would go well if we weren’t trying to do it in a backroom, but he didn’t know that and I wasn’t going to try to convince him.

So I left. On my way home I ran into a guy who wanted a lift to the hotel. He comes regularly and said this IML hasn’t been as good as others. A lot of people stayed home for financial reasons and he didn’t think things were as crowded as they had been in the past. It was an interesting comment. The funny part was when we got to the hotel he wanted to give me a kiss. When he was done I realized my beard probably smelled of ass – wonder what he thought…

When I got back to my room I was still horny and didn’t have any problem getting a full hardon, so I got onto BarebackRT and looked for someone to take my load. After a few messages I found a guy who was a few floors above me and came over.

The guy was a hot, beefy, shortish white guy. Had a nice body on him and was pretty attractive – even cute in a rough around the edges sort of way… It was late and we both knew what we wanted, so we got down to business pretty quickly. I rimmed him and then fucked him – on all fours, then on his belly, then all fours, then on his belly and then on his back… Problem was, there was a point I could tell I wasn’t going to be able to cum, so we finally just wrapped it up and he left. Even so, it was a good fuck…

And even though I didn’t actually seed any ass, it was a good night. Got my dick in 5 raw holes, and had a bunch of blowjobs. It was certainly a lot better than the night before or what happened earlier in the evening.

Wow… Haven’t had a post like this one in a while. Back when I started the blog it was really introspective. Unfortunately I lost a lot of those posts when I did a stupid mistake when migrating the blog off blogspot.com… This is another one of those introspective posts – haven’t done one of them in a while…

I ran into the guy who I was hanging around last night. He and his friends were looking around the leather mart… Anyway, we started talking, then went up to their room where a half dozen of us were drinking (from a big bottle of Captain Morgan). When they went downstairs to the bar I wanted to put my camera I away, so he and I went to my room. When we got there we started fooling around. Thing was I just wasn’t all that into it. I was in a mellow mood, and not particularly horny, plus he’s not really my type…

I’ll skip most of the details, but suffice it to say that we played around a little, I tried, but the more I did the less I wanted to do. My dick was getting smaller by the minute…

Thing was, he was drunk and horny. He was having a great time and I don’t think he really sensed that the situation was going bad for me quickly. Then he reached for his drink and managed to spill some of it. I was laying down, face up, and he was straddling me. I wanted to get up to get the towel and he didn’t want to let me up. That was it – I pushed him to get him off me (not too hard), and he still didn’t get the hint. Finally I just said, “Would you leave?” I didn’t want take it to that but what were my choices? He was a messy drunk who had a little too much “captain in him” (actually way more than a little too much).

The thing that flashed through my mind was when I used to escort. There were times when I didn’t like the client, or didn’t like the scene, but I was a good escort and pretended to be enjoying myself so I’d get paid. Suddenly with this guy I felt like I was back in those days where I was pretending to like what was happening to keep him happy. But it’s not like I was getting paid, so what’s the point?

It was actually a really deep emotion all this brought up – not just as simple as feeling like a hooker. I started escorting a year after my first sexual experience, before I really figured out who I was sexually. I have nothing against escorting. If I had it to do all over again I’d probably still want to do some escorting – but would have done it a little later (or better yet, started sex earlier).

But escorting damaged me a bit sexually – that much I know. After it ended I was in a comfortable relationship that was minimally sexual, and after that relationship is when I really figured out what I felt comfortable with was being a top…

The thing I think I realized tonight was that the whole power-and-control aspect of how I have sex, and even being a top, and having short well-defined hookups, probably all stems from escorting. Put another way, I need to be in control because I hate not feeling in control in a sexual encounter, but at the same time I need the bottom to want me to fuck them – I need eagerness. Having been the one who pretended to be enjoying themselves, I don’t want a bottom to have to do that with me. As a result, acting out rape fantasies does nothing for me. I may jack off to them, but in real-life I need the bottom to want it.

And on top of everything else, I just realized that because I was spending time with him I forgot that the big IML contest was on and I missed it… UGH!!! That was one of the things I really wanted to do while I was here and now all the contest activities are over…

Now I have to get myself back in the mood to hookup. This is the last big night of IML (tomorrow will be quieter) and I want tonight to go better than last night.

It’s been a bit weird this week being here at IML for the first time and on my own to boot. I’m not a social butterfly. I do much better if I’m with someone who’s social… Once I get started things are easy, it’s just getting started…

So last night I was down in the hotel bar (which was completely packed) and these two guys come up to me and start chatting. Nice guys – one’s older than me (didn’t ask his age) and the other one is mid-thirties but sorta baby faced. We chat and they seem to really want me to hang out with them, which was cool. We even had dinner together, and afterwards we hung out at the bar some more (some of their friends were REALLY hot – two in particular where these mid-west farm boy types…) I had heard a lot of sex parties were going on and when they wanted to go to a party in the hotel that’s what I assumed it was. When we got there it was a dance party, not a sex party. I wasn’t really in the mood to dance, neither was the older guy and the younger guy seemed a bit ambivalent about it so we just stood around the lobby outside the party and talked to people.

I had sorta wanted to go to The Eagle or The Jackhammer. I knew the Jackhammer was having a sex party in the basement and Treasure Island was having a DVD release party in the main bar. Thing was I hadn’t signed up for the sex party, so didn’t think I could get in, but I still wanted to go out and see what things were like. Oddly enough when I had talked to my bf earlier in the day he told me to see if I could get into the sex party – to make the most of my being here…

It wasn’t readily apparent, but the older guy was into me, but being really discreet about it – not coming on strong at all. I wasn’t quite sure what to make of it. He wasn’t really my type, but I would have gone to bed with him… I asked if they/he wanted to go out to the bars, but he said ‘no’. He started coming onto me a little bit after a while, but it was really subtle. Then there was one point where he and another friend went somewhere (bathroom?) and I felt if I was going to go out, I needed to do it then, so I said goodbye to the younger guy and took off.

It was already 2am, I didn’t even know how late the bars would be open. When I was standing waiting for the valet to bring the car around I saw a bunch of Treasure Island guys get out of a cab, so I knew the Treasure Island part of the evening at the Jackhammer was most likely over, but I went there anyway. The bar was mostly a dance bar with a leather store attached. There were stairs down into the basement where the sex party was going on, but just a rope across the stairs with a sign “Closed, Private Party”. As I stood around I saw guys leaving, so I figured the sex party was probably already winding down…

So I headed down the street to The Eagle. It was a far more serious leather bar. And they had a darkish bar area in the back where guys were getting blow jobs from cocksuckers, and then there’s a little dark room as well. Thing was, it wasn’t completely dark, it was totally packed, and there was enough light so I knew the guys weren’t really guys I wanted to have sex with. There was one guy in the corner who I would have fucked. He turned around, but when I felt his hole it was all warty… I wasn’t that desperate to fuck.

When I turned around there was a fairly attractive guy who asked if he could suck my cock. When I said ‘yes’ he said “really?” I didn’t understand why he said that, but he got down on his knees and started blowing me, but he didn’t last long. I wasn’t getting completely hard, and he was probably being jostled by everyone around him. Then he grabbed my waist band and pulled himself up. I thought thought that was odd, but whatever… I then got out of the dark area and walked around and then I recognized the guy who had just blown me in the dark area – and then I noticed his arm was partly amputated. It explained why he pulled himself up using my waistband, and where the “really?” came from (not 100% confident in himself)…

I then spent a little time in the darkish bar area. A Latino came onto me and long story short, we fooled around and he blew me a bit. My dick was only sorta responding. It would get hard for a while and then not so hard. There was a guy standing next to me getting fucked, and I could have fucked the Latin guy if I wanted to, but it was late,I was wiped and not at 100%, so I didn’t even try.

Then just after the Latino guy, this chubby sub wanted to suck my dick. He turned out to be a really good cocksucker, but I knew the evening was ending when he was giving me an excellent blowjob and I wasn’t getting all that hard. Then this other guy wanted to make out with me while the chubby guy gave me a blowjob, etc…

I could just feel that it was time for bed. I went to the front bar and talked to a couple of guys. When a messy drunk that I had had to push off of me earlier in the night collapsed in front of me and spilled his drink all over me, that was sort of the end of it. After cleaning myself off, I just left and went back to the hotel. There was no point in going to the bathhouse next door…

Other than the fact that I didn’t fuck anyone, it was a good night…

Load 2008-36

There’s a guy who was visiting NYC a month or two ago who I really wanted to fuck, but things didn’t work out. Well, he’s here at IML and we just hooked up…

Again, not a leather hookup (oh well), but he’s so totally my type I didn’t care. He’s a 22 y.o., short, black guy who’s got a really lean, slightly muscular body, and a phenomenal ass.

He arrives and he’s shorter and cuter than I was expecting. He was wearing a hoodie, flip flops and the bottoms from hospital scrubs. He started stripping down just inside the door – no shirt, no underwear… I was loving it…

We kiss a bit and then he climbs on the bed and presents his ass to me. It was a truly incredible ass, and a really nice hole. I get down on my knees and rim him, which he seems to really love – it kept him moaning…

After rimming him for a while I got some spit on the head of my dick, stand up and fuck him. His hole felt great – nice and reasonably tight boi hole… He takes the dick really well and after a bit of warm up I fucking him fairly hard. Then I push him forward and fuck him on his belly.

Fucking little lean guys on their bellies almost always gets me to cum, and this time was no exception. It felt really good to give him my load…

I roll him on his side and keep my dick in him. Pumping him a little here and there while we enjoy the moment and talk about stuff… He’s not into leather – just came with a friend ’cause he’d never been before…

After a while of laying there cuddling he got up to look at the view. While he was standing naked in front of the window I started rimming his ass again… Didn’t taste any cum cause I must have cum pretty deep. He asked how the cum tasted and I told him I didn’t taste any. Then when I was taking a brief break he basically farted some of my cum out of his ass and it landed on the carpet. It was sorta funny, but I could also tell it wasn’t all that “clean” (not shitty, but just not clean), so I cleaned it up with a towel and didn’t pursue it further.

All in all a really good fuck. Didn’t capture it on camera ’cause I just wanted to enjoy his body. If he wants to fuck again I’ll see if he wants to videotape it…