Disappointing Hookup With Long-Time Fuckbud

29 January 2012 | 3 Comments

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I wasn’t going to write up this hookup, but I’ve got a little time to kill, so why not…

latin fuckbud14+ years ago, a few weeks after I met my current boyfriend, I wasn’t exclusive with my bf yet and I had gone out to the bars. It was early December and cold and I was walking home from a bar in full leather. Leather is cold in the winter and hot in the summer and I was freezing my ass off. I had leather pants on, motorcycle boots, and a my favorite motorcycle jacket on. I sorta remember not having much of anything on under that – maybe the leather bodice thing that covered just the upper part of my torso.

Anyway, I was walking up 7th Avenue south of 14th Street when this hot little Latino came up to me. He was SO cute. He was wearing this little red Santa hat. He tried really hard to get me to let him go home with me, but I wasn’t in the mood (forget why). We exchanged phone numbers and then fucked a week or so later.

At one point he mentioned he had done some porn and for a while I was a bit obsessed with him – buying every video and magazine that I could find with him in it. The picture to the right his him from back then. Obviously he was really hot! He’s got a big dick too – which you can sorta see hanging down between his legs.

So a year or so later my bf and I move uptown and who do I run into – the little Latino who’d picked me up that night. Over the years we’ve fucked on and off. I’ve fucked him in the bathroom at his school. I’ve fucked him in the park near us. I’ve fucked bottoms with him, etc. It’s been pretty hot.

At some point he became poz and age and possibly the meds seem to have had an impact on his body. Believe it or not he’s considerably thinner than he was back then – he’s almost frail looking now, but I find that pretty hot. I like really little guys.

Just after New Years I’m online and see him online so I send him a message. An hour or so after that I’m at his place (I needed to eat something first). He loves sex. He put me on my back and sucked my dick, got me hard, and then sat on my dick and rode me. Like he’s done with me before, he came on my belly without touching himself.

Getting ridden doesn’t make me cum, so I put him on his belly and started fucking him. For whatever reason I couldn’t cum, so I kept fucking him and fucking him. It just went on and on… At some point I must have cum ’cause my dick started going down – like it does when I cum.

When it was all over I was sorta disappointed I hadn’t felt myself cum, and while he didn’t say it, I got the impression the fuck was a bit too long hard and rough for him. Plus my dinner had included a dish with onions – which was a mistake – I think I had onion breath even though I had brushed my teeth before going over (oops).

We laid there sorta spooning and I was feeling his body. He was SO thin and so little. I asked how much he weighed. He said 120. My bf is the same height and he’s usually 127 to 130ish. There was no way this guy was just 5 or 10 pounds lighter – every part of him was noticeably thinner than my bf. He had to be more like 110. He did say he was self-conscious about his size and weight. I told him I loved it – but I don’t think he quite believed me. But he was so tiny – it really was pretty hot.

All in all it seemed like a bit of a disappointing fuck for both of us. I’m moving out of his neighborhood in a couple of months – it sorta felt like a final fuck with him… Which is sorta too bad. Maybe we can do one more and have it go better so we end on a better note – who knows?

I’m starting to think poz bottoms are better bottoms…

22 November 2010 | 25 Comments

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Fantasy-wise it’s hot to breed neg bottoms, but honestly I’m starting to think poz bottoms are just better bottoms. A little over 2 weeks ago the neg bottom who last time asked my status after I fucked him said he wanted me to come over and fuck him again. Needless to say I wanted to complete my mission and actually get a load up his ass, so I said yes…

I show up at his place, we chat a little. I was a little earlier than he was expecting so he jumped into the shower after I got there. He seemed a little hesitant to just walk around in a towel after showering (he’s seriously inhibited), but I convinced him it was no big deal. After chatting a little more we moved into the bedroom. He sucked my dick and did a horrible job of it. He was going a million miles an hour on my dick when a nice slow, relaxed blowjob would have been so much more erotic.

I really wasn’t interested in his dick so went straight for his ass… He seemed a little shocked by my getting right to the point – I think he wanted it to be slower and more romantic or something… But he still liked being rimmed… 🙂

Eventually (after doing some kissing to get him “ready”) I lubed up and got into him. He kept wanting to change positions and when I’d start getting in a groove he’d start squirming. It was really frustrating and at one point I had to tell him to stop squirming. Not squirming seemed like a revelation to him… Later he said he wasn’t a very good bottom because in the past he’d mostly topped. But honestly if he’d topped enough he’d know what turns a top on – and he’d know that squirming is counter productive. And for god’s sake I even wonder how many blowjobs he’s gotten in the past – I mean he doesn’t even understand the basics of sucking dick.

There was one time when I felt like I was about to cum but then didn’t feel the squirt. Thing is, all of a sudden his ass felt all wet and some fluid spurted out of his hole. Then I realized that I had cum and he had finally gotten my load – but I wasn’t quite sure. I was also disappointed that I didn’t actually feel the ejaculation. Still, it made me wonder how many other bottoms I’ve cum in where I thought I hadn’t cum… Maybe my batting average is better than I think. After “cumming” I kept fucking him. But eventually my dick sorta just ran out of steam (like it would if I had cum – which reinforced the fact that I had cum).

So we laid there and chatted a little and he’d suck on my dick a little every now and then, etc. I asked him what he meant last time by “that was a first for me in many ways”. He said it was the first time he got barebacked, but he sorta alluded to the fact that it might have been the first time he got fucked. He tried to pass it off that he had been a top in the past, but I just don’t believe him. I think the guy is pretty new to gay sex. Maybe he’s sucked a few dicks or something, but that’s about all… He once again asked if I was negative, etc. I told him the truth (again) but went into as little detail as possible.

I wasn’t 100% sure I had cum, so I went back to fucking him when I got my second wind. He did better (didn’t squirm too much), but I still wouldn’t call him a good bottom. Once again I didn’t feel an ejaculation, but who knows… Maybe I gave him another load… Eventually I was done so I wrapped things up an left.

A day later I get a text message from him…

I freaked out today and got myself tested… Thank God it’s Negative.

My Dr is asking me to do this 28 day medical program which has a lot of side effects… Can I speak with U?

I responded…

It’s called PEP. Personally I don’t recommend it. But it’s up to you. I haven’t used a condom in 6 years and only used them occasionally before that. It would be crazy for me to run to the doctor in a panic every time I have sex. I’m OK with the risk I take. Only you can say what’s right for you.

Then he responded…

I appreciate your response… I was at emergency for 3 hrs… I really like you and thought that I can have this conv with you.. Hope u understand.

OMG… That is just totally fucked up… I mean he knew what I was about and he invited me back to get fucked raw and take a load, then he can’t deal with it and spends 3 hours in an emergency room?That’s just too much drama. A poz bottom would just take the load and want you to come back and give him another load.

I never got back to him so I don’t know how it all turned out. Hopefully he’ll get over his inhibitions and just enjoy sex. But I have a feeling that’s not going to happen any time soon – he’s going to have this tortured sex life until he becomes poz… Maybe then he’ll relax and enjoy getting fucked.

Thank god for poz bottoms!

Catching Up…

26 October 2010 | 1 Comment

I’ve started getting “are you OK?” e-mails and I’m way behind in posting… Life’s been busy – very busy… For the most part it’s all good, but sometimes it’s all a bit much and I just sorta check out. I try to get the things done that have to get done, and then when I just can’t do any more I just collapse in front of the TV or maybe go out and have a drink…

BTW, one thing I realized this morning was all those times I didn’t think I came – I probably actually came. I was jacking off this morning. Actually, as a kid I never jacked off like other guys – I’d pretty much hump the bed – which is what I was doing this morning (sorta frottage without the other person). Anyway, I was having difficulty cumming and finally it felt like I was having a dry orgasm. I didn’t think I came, but then I checked and I had cum – not a huge load, but a decent amount. So all those times I didn’t think I came – I probably did cum in a fair number of them… Go figure.

Anyway, here’s a run down of my fucks lately. Usually I do one fuck per post, but I need to catch up so I’ll just give basic details…

The messy sub…

The first fuck I skipped and didn’t write up was a 3way that we videotaped with his messy submissive bottom. I have mixed feelings about him. The best way to describe him is “inferior”. But he was so eager to please and I think in many ways he knew his place. He liked being abused by superior men. He wanted it to hurt. He actually wanted to get fucked so hard that he’d bleed. The problem was he wasn’t very well trained. He tried so hard, but he fucked up in a major way. He was cheating on his boyfriend on top of everything else, so he skipped out of work early and came over. He actually brought alcohol and mix, but he hadn’t cleaned out and the enemas he brought didn’t do the trick. I hooded him, and flogged him. He didn’t want me to leave marks ’cause he was afraid his boyfriend would see the marks, but his skin was so sensitive I wound up leaving them by accident. I stopped as soon as I realized, but it was too late. Then I went to fuck him I sorta tore him up a bit ’cause I had my PA in. When I stopped to let another (poz) top have a go at his ass you could see blood. I told the other top that’s what he wanted and so he went ahead with the fuck. But then he got dirty pretty quickly so everything stopped. He went into the bathroom and I had him use my showershot but after about 10 minutes he was still having this reddish brown stream come out of his ass. By that point the moment had been lost, so I told him it was time to leave – and he left (with a bleeding ass).

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Honestly, this was one of the best sexual experiences I’ve had in a long time. It was the day after the messy sub and once again I had a bottom who was willing to do whatever I wanted. My bf videotaped it. I flogged him, and then fucked him. He was hotter than the guy the day before. What got on video was pretty routine, but after videotaping had stopped and my boyfriend had left I just lay on the bed and he started massaging me and softly playing with my dick. It was tender and loving and submissive. He was clearly there to serve – anything I wanted he would do. I just laid back and enjoyed the experience. It was pretty incredible. I fucked him a bit more at one point, but I just really liked the peaceful nature of the whole thing. I’ve been wanting to hookup with him again, but it hasn’t happened (yet).

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About a week later I had another hookup with Ian Cody (the Samoan-looking guy). It was a good fuck, then his roommate came home. Then I learned his roommate was his jealous ex-boyfriend and I had to sneak out of the apartment… Sorta funny…

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Then a couple weeks later there was the hookup with the little Latino in the hot apartment with no A/C (and the other top with the HUGE dick)…

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The day after fucking the little Latino I fucked Jayson Park. He came over and we alternately fucked and talked about a project he was working on. We stayed in bed so long and my position in bed was a little weird and I wound up fucking up my back somehow.

The neg bottom…

Then a couple weeks later (when my back stopped hurting) I fucked up with the neg guy who asked my status after I fucked him. At the time I didn’t think I came in him, but now I’m thinking I did. Other than not feeling the cum, otherwise it felt totally like an orgasm.

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Then a week later I fucked the hot, tattooed, 20-something Latino I’ve fucked before. He was rushed for time ’cause his brother was coming over to go out for dinner. Thanks to subway problems I was late getting there. I think the whole thing took less than 5 minutes. For a while I didn’t think I could cum, but he did get my load. Then I had to rush out ’cause his brother would be there in a couple minutes.

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Two and a half weeks later I was in California for a conference. I was thinking I’d fuck a lot while I was there, but it didn’t work out that way. I only  managed to get two fucks in before the conference started. The first was the night before the conference. He was a nice guy, but there wasn’t much in the way of real chemistry. He was a hungry hole. I needed a hole and he was hungry for the load.

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The next morning I woke up early (I was still on east coast time). Turns out there was this Asian guy in the hotel next to mine who was looking for a load. He reminded me a lot of Ian Cody (the Samoan-looking guy). He was sorta an interesting fuck. He was a civilian who was working for the military. The military guy he worked for was in the next room and there were paper thin walls. He was pretty sure his boss had left by then, but as I got to the elevator there were uniformed military guys around. Hope he didn’t get in trouble for the fuck. He’s technically covered by non-discrimination policies, but his bosses have made it clear that they’ll fire anyone they find out is gay.

I did have a rather interesting conversation with a gay guy I knew at the conference. He went into all sorts of details about how he’s now in a 3 way relationship. He’s a top with his “husband” (they’re married). But he’s a VERY submissive BDSM bottom for his “master” (who also has a boyfriend). The other day he texted me pics of the whipping marks from their latest play session… 🙂

That was almost two weeks ago now. Haven’t had sex since then in part because right after I got back from California I had a cold for a bit over a week. I’m just now starting to feel like I’m getting back to my normal self. Now I’ve got a crazy amount of work to catch up on. And on top of everything else we got notice that a contractor who worked for us 5+ years ago is suing us. His lawsuit is a joke, but it’s just one more thing I have to deal with…

Going forward, I’ll try to post right after I hookup, but no promises…

Sorta A Forgettable Hookup…

18 July 2010 | 4 Comments

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Had sorta a weird hookup the other day… This guy hit me up on BBRT and despite my effort to get to the point and hookup, he was asking all these other questions. Finally I had to ask – did he want to fuck or not? If he wasn’t really into it I’d move onto someone else. He said yes. We agreed on a time and he came over.

I should backup and mention that my doc gave me a prescription for Viagra this past week and this was the first time trying it out. I cut the pill in two and took the small half – probably about a 40% dose. I was curious to see how it would work. An hour went by and nothing. Then at about and hour and 20 minutes it started kicking in. I felt really hot and flushed – uncomfortably so. I remember feeling the same way the first time I used the herbal stuff I normally use.

When I answered the door I had this raging, rock hard hardon in my pants. I’ll give Viagra definite points for hardness.

When we got to the bedroom he was pretty submissive. Didn’t do anything without being told. I was sorta expecting that since he had said he wanted to be tied up and used. I told him to get on his knees and he started sucking my dick. I put a collar on him as he was sucking my cock and then when he stood up and I took off his clothes, I put on wrist restraints which I locked together with a nice heavy lock.

I then told him to get on all fours on the bed. He was bit beefier than I usually hookup with, but I wanted to rim his ass. When he got on all fours I noticed his ass crack was darker than the rest of his ass (why are some guys like that?) and he smelled a bit funky. Not horrible, but a bit too far from squeaky clean for me to really get into rimming him. Needless to say I didn’t rim very enthusiastically and ended it pretty quickly.

I then pulled out the Wet Platinum, lubed up my dick and went to fuck him. He was 3 or 4 inches taller than me and bent over  on the bed his hole was 6 to 8 inches above my dick. There was no way I was going to be able to fuck him like that. I pushed him forward onto his belly and shoved my dick in. He was beefier than the guys I usually hookup with, but I found that if I was at a bit of an angle his hole felt pretty good on my dick.

This whole time he never really gave any positive feedback. It was like he really didn’t care who I was, and probably didn’t care if he even got fucked. It was like he was getting fucked to pass the time. He seemed sorta bored or like his his head was off somewhere else thinking about something. All in all he was sorta ‘vacant’ and ‘absent’. Add to that bad breath that I could smell when I was on top of him fucking him (I gotta remember to get guys with bad breath to go gargle with Listerine so I don’t have to smell that).

Then, on top of everything else, he asks for more lube, and when I pause for a second I realize I’m actually about to cum. If I pull out to get more lube I’ll cum while I’m out of his ass. I hadn’t even been fucking him for very long, but I had a 6 day load built up and could have cum in any decent hole that day – and his hole was doing the trick. So I paused, tried not to cum, spit on his hole a couple times and resumed my fucking. I knew it wasn’t going to go on for much longer.

As I was about to blow I was thinking about the fact that his profile said he was neg, yet he had asked no questions and here he was laying there like a piece of meat about to get my load – and totally disconnected from what he was doing. I would have loved to know what he was thinking at that moment. It was like he didn’t care, but there was more to it and I couldn’t tell what that more was…

I blew a decent load up his ass and kept fucking him for a little while – told him I wanted to keep going and give him a second load, but then the Viagra started to fail me and so I pulled out.

It had only been a few minutes at this point. What was I going to do with him? I had him clean off my dick, which given that his ass was a bit musky coulda been a bit disgusting, but he cleaned it right off like it was perfectly clean. I had him suck me some more, but I wasn’t really all that hard, so I stopped.

I asked him if he was into flogging. No. (Forget about asking about whipping if they’re not into flogging). I asked about padding. No. I was staring to run out of options. I played with his nipples and when I sucked on one of them he reacted positively (a first). I could tell he liked that. So then I searched for the suction cups I have for nipples, but couldn’t find them. I got out my nipple clamps and he indicated that he didn’t know if he could take them. I tried to use them gently, but you can’t really use nipple clamps gently – they kept slipping off. I was out of s/m tricks.

The whole time he was jacking his dick, which was a bit distracting. But it wasn’t like he was jacking it ’cause he was turned on – he was jacking it ’cause he seemed embarrassed about having a soft dick. Finally he got hard and stopped jacking. It was like a dog presenting a hard bone to his master – it was sorta cute. Thing was, he was a bottom – I didn’t really care about his cock.

I felt up his cummy ass and thought about fucking him some more, but my dick wasn’t really cooperating. Finally I just wrapped things up by taking off his collar and wrist restraints. He got the hint, got dressed and took off. We did talk a little as he was getting dressed. It wasn’t completely awkward, but I still have no clue where his mind was while we were having sex…

As a first time using Viagra it was a bit disappointing. It did get me rock hard, but it didn’t last very long. In some ways I like the herbal stuff I use better. I don’t get quite as hard with it, but I get thicker. I think I’ll use Viagra when I’m not completely horny (’cause that’s when the herbal stuff isn’t sufficient) and I’ll use the herbal stuff when I’m good and horny and just need a boost to make my cock bigger and more sensitive.

Repeat With The Italian Daddy

3 June 2010 | 3 Comments

While some repeats work out well, some don’t… I’ve been off my game lately when I fuck the Italian daddy who likes to take my load. I’ve been hit or miss with him from the beginning – not sure quite why… Sometimes it’s easy to give him a load, other times it’s impossible. Last time he looked like he had gained some weight and I wondered whether that was it, but this time he was looking much hotter. He’d been out in the sun and had a bit of a tan that worked really well on him.

He started by giving me a blowjob. His blowjobs don’t always go well. Early on his teeth would scrape my dick – that’s not such an issue any more. But this time (and others) he managed to suck my dick in a way that the head of my dick was so sensitive it was almost painful. I’m not quite sure how he did it… I think the head of my dick was rubbing on the ridges on the roof of his mouth or something. Anyway, it was distracting and uncomfortable. I tried to move him around to get in a different position, but it just wasn’t working.

Despite the pain I was fairly hard, so I just went to fucking him. I fucked him for a while and pounded him pretty well, but just wasn’t cumming. Finally I sorta lost my hardon. He sucked me some more, and I got hard again and fucked him a little more, but then lost it again. I did have the A/C on but was still feeling a bit overheated. I tried directing the A/C to blow on me, but that didn’t seem to help. At one point we took a break and just cuddled. That actually worked better than him giving me a blowjob. I fucked him a little more, but finally it was just clear I wasn’t cumming. It was first thing in the morning so maybe I was also low on blood sugar. All I knew was that my bf was waiting to go to breakfast and I didn’t want to draw it out too long so I called it quits.

I REALLY want to give him a load, so next time he comes over I’m going to be really horned and we’ll keep it to a pump and dump. That always seems to work best with him…

I Fucked The Cum Out Of Him, Literally…

10 November 2009 | No Comments

This guy came over last night. I’ve fucked him a couple times before. He’s very close to where I live and is a total sub bottom. He even gets into me degrading him and treating him like a piece of meat. I wasn’t 100% horny, so I figured if it didn’t go well at least he didn’t travel far.

He comes over, we head to the bedroom, and just as we get there my real estate broker calls. I answered my phone as the guy was taking off his clothes. While I’m talking to her he gets naked and I get my pants down and I have him suck my dick while I’m talking on the phone. The news wasn’t great – we got an offer turned down and it was as high as we were going to go on that property. So it wasn’t making me think horny thoughts, but I kept him on my dick even though I wasn’t hard.

Once I got off the phone I had to get back in the mood and nothing gets me in the mood faster than rimming a clean hole. So I put him on the bed, put his legs up and started eating him out. Mind you, there’s no real conversation – he’s just a piece of meat to me.

When I’m hard I lube up my dick and stick it in. He says he’s tight and squirms around. We reposition with him on his belly, but his hole is too far from the top of his ass to fuck comfortably. So I put a pillow under his waist and get back to fucking him. It was probably a minute or two later that he says something about slowing down and not cumming. I didn’t hear it clearly and thought he was playing the same “don’t cum in my ass” game he pulled the first time I fucked him. So I kept on fucking him how I wanted.

But then less than a minute later he stops things and says he’s cum. The comment I didn’t fully hear was about him cumming – not me. Problem was he couldn’t keep getting fucked after cumming, so that sorta ended it. I then realized he’d cum all over my pillow, not the towel I had down. Oh well.

Well, I guess it’s good I can fuck the cum out of someone, but I don’t like the fact that I didn’t cum.

 

 

 

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