Load 2008-37

This bottom contacted me this weekend and really wanted to hookup with me. He had contacted me 18 months ago when I posted a Craigslist ad. Back then he really wanted to hookup as well, but didn’t want to take my load. So I filed him away in the “not ready” folder. Then he contacts me about 6 months later – still interested, but it doesn’t happen. Then he contacts me again this past January, and then this weekend. This guy knew what I was about and really wanted to hookup with me…

So tonight he asks if I can travel to Flatiron area, I check with my bf and head over. If you know Manhattan you know getting from Washington Heights to Flatiron takes a good 45 minutes, possibly more. I hurry as much as I can since he’s “staying late at work” to hookup with me.

That’s the other thing I forgot to mention – the guy has a boyfriend and the boyfriend thinks he’s hard at work (on the weekends, late at night, etc.)… When actually the guy has a private office and has people in to have sex…

Anyway, I get outside the building and my cell phone doesn’t have a signal for some reason and I have to call up to find out where he is in the building. Finally I get through and go up. He’s got this somewhat cute, but cramped corner office which is very private.

I unzip and put on one of those soft rubber cockrings. He seems to think it’s weird that I’m not taking off all my clothes, but getting my boots off is just too much trouble…

He’s described himself all sorts of different ways over the years, “Asian”, “Asian/Spanish”, but he looks like a Pacific Islander – nice beefy body – muscular with a bit of beef to him… Not a bad guy to hookup with…

So he gets on his knees and starts sucking me off. I’m nice and hard thanks to the cock ring and having taken a couple pills before leaving. He seemed to just want to suck, but I wanted to move it on to fucking, so I convinced him to let me rim him.

I bend him over a table and start eating out his ass. Nice ass – and he started really getting into it. He actually sorta leaned back into me, which makes it a little difficult for me since I need to come up for air to breathe. So I balance his weight with my hand so I’m able to pull my head away for air…

Things were looking good so far… Mind you he’s jacking his dick the entire time. I’m so hard I don’t even need to touch myself.

I get up, put some spit on his hole and some on my dick and shove in. He had told me it was a while since he’d been fucked and he seemed really tight. I can’t really get in the first or second try, but the third try I get in and just hold him there so he can get used to my dick.

But then the fucker cums and pulls off my dick. After the history with him not wanting to take my load I knew exactly what he had just done. It’s titillating for him to think about getting fucked raw and taking loads, but still, after 18 months, he’s not ready to do it. UGH…

I used his cum to lube up my dick, and tried really hard to convince him to let me fuck him. He asked if I’d fuck him with a condom. “No.” Then, after cleaning his cum off my dick with a paper towel, he got down on his knees and started blowing be again. He didn’t get that I wasn’t going to give him an oral load. I’ve come with blow jobs less than a handful of times in my life and one of those I was paid… I wasn’t going to do it with him after a bait-and-switch.

I’m pissed. I pull up my pants and leave. I should have said something pretty rough to him. If anything guys like that make me want to reveal their identities… But I’m a good guy and don’t (though there are plenty of clues in the description above)…

So then I start wondering who I could text to get a quick hookup. I try a cumhole I’ve been wanting to hookup with for a while, but he’s not available. I try another guy who I’m not sure who he is, but it’s a non-working number. Finally I settle on the guy I fucked the other day – the one who wanted to get an oral load… He had been hitting me up since then for another round. I knew he wanted an oral load, but would take it up the ass.

I get to his place and like before he drops to his knees in the hallway, just inside the door. The guy is an excellent cocksucker. At first I was worried I wasn’t going to get hard enough, but in no time he was choking on my dick. It was fun – I’d go from thrusting into the back of his throat, to holding him on me seeing how long he could take my dick down his throat…

The pig just loves to suck cock and he’s one of the best cocksuckers I’ve had in a while. It went on forever and at one point he said something about trying to get me to cum down his throat. What was so not going to happen – especially not after the first guy.

Eventually I start telling him I want to fuck him and feeling up his ass. It takes a while, but he gets the message. After sticking it in his ass in the hall briefly we move to the bed where he gets on all fours and I push him down on his stomach.

Besides being a good cocksucker the guy is super skinny – like emaciated. I sorta like guys like that, so it didn’t take me long to cum (especially not after the good blow job). The orgasm was sorta weird. I felt it coming, and felt like I was “leaking”, but it didn’t come, didn’t come, and finally sorta came. Then when I finally stopped it really came. Whatever – he got his ass flooded…

I then spent a few minutes slowly pumping in and out of his cummy hole. Felt really good… Then I turned him on his side and held him (in case he wanted to cum)…

It’s weird with him – in some ways he’s my type, in other ways he’s not. When he wanted to kiss (more than a peck on the lips), I tried to make it clear I didn’t want to. When he persisted, I said I had to go…

I washed off my dick, put on my pants and boots, and left…

At least the evening wasn’t a total wash out…

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.

As on my way out to IML, I stopped in Cleveland and stayed at Flex on my return trip. After the uneventful time last time I had pretty low expectations. On top of that it was clear by then that I was coming down with a cold. It started a couple days before and as I write this it’s in full swing… So I was feeling pretty run down and my being there was more as a cheap hotel with the possibility of sex than anything else.

Believe it or not, the place was even more deserted this time than last time. When I went upstairs (where most of the rooms are), there was almost no one there. My first time around upstairs I think I saw one person.

There were 3 or 4 cute guys downstairs in the hot tub and pool, but they were keeping to themselves. All in all there were maybe 8 to 10 other customers I saw around. At one point these two guys were 69ing in the TV/porn room and it looked sorta hot, so I climbed up next to them. I knew they weren’t body beautiful or anything, but whatever. Then one of them wanted to suck my dick while the other guy rimmed his ass. So I let him. Then they changed positions and I had a good look at who had been sucking my dick… UGH! That was the end of that…

Finally I sorta gave up and laid in my room and wrote a blog post. This fairly attractive young-ish (mid to upper 20s) black guy walked by a few times and then stopped. He had a big thick dick that was curved to the right. He wasn’t in great shape. It was like he had lost a lot of weight and was still saggy in parts. The worst part was when he went to kiss he tasted like he’d been eating out some pretty funky ass. So I just tried to avoid kissing him – ’cause it wasn’t like there were many other options…

Since I wasn’t hard and he was, I sucked him a bit to get things started. Then he sucked me. Then I sucked him some more… I had been grabbing for his ass and feeling his hole, so as I sucked him he laid back on the bed and put his legs up. It was clear what he was looking for. So I just went a little lower and rimmed him. That got my dick nice and hard, and I just got up, spit on my dick and shoved in. I loved how there was no discussion of condoms… He just took the raw dick.

I fucked him for a while and really tried to cum, but given how run-down I was feeling from my cold I just couldn’t. I think he was at least wondering whether I came silently in his ass. I could see it in his eyes… We weren’t talking – just fucking. And there were a few times I’d pound him hard and then slow down. The fact that I finally just couldn’t keep it up I think told him I had cum.

With my deflated dick, he knew I was done and so he got his towel and left. It’s funny to think he left thinking I was a stealth breeder…

After that I pretty much went to bed. In the morning there were even fewer people to hookup with, so nothing happened.

So as far as Flex Cleveland, let’s just say there’s a reason why they’re half price during the week… Without going on a weekend, I can’t really say anything conclusively about them, but I can say weeknights are pretty dead.

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.

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…