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’m pretty late writing this up, but 3 weeks ago now I hooked up 3 days in a row and never got around to writing up the 3rd hookup…

The third hookup was with this 40-something lean guy not too far from me. It was middle of the day and I was horny, so after a little chatting I told him I’d walk over to his place. Took about 25 minutes to walk over to him and when I get there he’s got this great little tight body and a sexy accent I wasn’t expecting. After some sucking we get down to fucking and we started on his couch, but it just wasn’t working so I asked if we could go to his bed. He apologized for a messy bedroom that wasn’t all that messy and the change of venue was a big help.

I fucked him pretty long and hard but even though he was pretty much exactly my type body-wise I wasn’t cumming. It was just one of those days. I kept hoping I’d get my nutt – about half the time in situations like this I do, but it just wasn’t happening. I was starting to overheat ’cause it was a warm day and he didn’t have A/C on, so we took a bit of a break.

After the break we resumed but I just wasn’t able to cum though I was able to fuck him pretty well. Actually, it was well enough that he came without touching himself. But finally I sorta just gave up trying to cum. Then I realized he had cum and since he had cum and I was wiped out that was sorta the end of it…

The whole time I wasn’t all that sure I was his type. He wasn’t really giving me any signals. I could tell he wasn’t repulsed by me or anything, but it was unclear how into me me really was. When we were done he then told me he really liked guys with my build and thought my belly was sexy. So if the opportunity arises I think he’s worth a 2nd shot… I do like his tight little body…

A funny thing happened as I was leaving. As I exited the front of his building I realized I had put my shirt on backwards. I looked around to make sure no one was looking and then took my shirt off and put it on properly… Guess it just wasn’t my day.

Hooked up last night with the Italian daddy I fuck sometimes. Just before he came over I had been running around the neighborhood and at one point had to go pick something up at a friend’s place (down one huge hill, up another, then up 4 flights of stairs, then back down the hill, up the other big hill)… It was a celebration of sorts for him. That day he started a new job after being unemployed for a over a year…

He started by giving me a blowjob but his teeth were hitting my dick, so I switched to fucking him. Problem was I was tired and I sorta gave out before I was able to cum. Plus the room got hot (which is always bad in my case), and his hole just didn’t feel the same as it had in the past (looser – not sure why)…

Anyway, I tried, but it just didn’t happen. He wasn’t going to accept failure, so he had me lay down. I was such a sweaty mess I had to make sure there was a towel under me – everything I touched got wet. He went to work, and cleaned off my dick with a blowjob (much better this time). He worked and worked and worked and tried everything in the book. I got hard for a bit and fucked him some more, but then it was just clear it wasn’t going to happen. He tried a little more, but finally I just put an end to it.

Too bad, would have been nice to give him a special reward for finding a job…

I was about to apologize for not posting more here, but it wouldn’t be right to apologize. My life is crazy right now – good things are in the works, but they’re just not related to sex. When I was a kid there was one and only one thing I wanted to be when I grew up – then I realized that the day-to-day business of it wasn’t really what I thought it would be so I gave up on that dream. Well, I’m getting to work on a project related to it right now and I’m having a blast doing it. However, I’m stretched really thin and feel like I’m beyond burning the candle at both ends, but it’s good stress and a lot of fun.

Thing is, the project keeps me so busy sex really isn’t on my mind. At the end of the day I sorta just collapse in exhaustion. I get horny sometimes, but only have enough energy to jack off. I guess the lesson in all of this is that there are times when life just isn’t about sex – and that’s not a bad thing…

The project is going to go on until at least the end of the year, but I’ll still try now and then to hookup and post things here – it’s just going to be a lot less frequent than normal. If you’re hitting me up on the hookup sites – don’t take it personally if I don’t get back to you or I’m never available…

Two weeks ago I had to go downtown for a meeting (related to the project). I hadn’t fucked in a while and felt like I should try to hookup. I looked during the day for someone to hookup with, but by the time when I needed to leave none of the people I was chatting with could hookup. Then this guy hit me up and he was available and could host. He wasn’t my usual type, but he was sexy and I had always wanted to hookup with him. In his pics he looked a bit severe. He was muscular, heavily tattooed and looked like he could beat you up if he got in the mood. He listed himself as a versatile top, but wanted to bottom for me.

So I headed down to his place. I had 45 minutes which should have been plenty of time and really I was mostly in the mood for a pump and dump. I got there and there was another guy who was leaving (putting on his shoes). My trick introduced him as his ex-boyfriend. We went into the next room, his bedroom, and closed the door. I started taking off my clothes and he wanted to take off my boots. It was a nice, submissive gesture. Then we felt each other up, and I sucked his dick a bit. But then he started directing the scene. He wanted me to lay back on the bed and let him do the work.

Back almost 20 years ago when I was versatile I remember one guy I hooked up with who was what I’d call a “do me” top. He just laid there and wanted me to do all the work. I didn’t enjoy it. In this situation the roles were reversed and I was being asked to be a “do me” top. I figured I’d give it a try, but it was clear this wasn’t going to be a quick pump-and-dump and I was little worried about the time.

It was nice just laying there being serviced, but oddly he didn’t suck my dick. It was all about me, but I wasn’t really in control of the situation. The guy was bigger than me and he got on top of me and I felt a bit trapped – it wasn’t a bad experience – not at all, but he was in control. Then he got a bottle of lube and put some on my crotch and started rubbing his dick in it. Again, a 20 year-old memory came to mind… I used to really be into frottage and that’s exactly what I used to do back in the day. Then, like I used to do, he put his dick between my legs and started sorta play fucking me. I knew where it was leading and asked him “You wanna fuck me, don’t you?” That sorta weirded him out and he kept saying he didn’t want to fuck me, while he was basically play fucking me. Thing is, he could have taken it further and I would have been fine with it, but it was just awkward since he clearly wanted to fuck me, but wouldn’t own up to it.

I wasn’t sure what he really wanted. I was there to fuck him, but he was basically overpowering me and not even sitting on my dick. If you’re playing power games with a top and in control – at least make it clear to the top you want to get fucked by putting his dick up your ass… On the other hand I was wondering whether he wanted me to turn the tables on him and overpower him… It was all pretty unclear.

I should probably stop for a second and describe him a bit. He had even more tattoos than I thought he would – he was almost covered in them. And when you felt his body there were scars you couldn’t see ’cause they were covered with tattoos. He was very masculine, but with me it was an odd mix of him being in control but still being very submissive toward me. It was all very interesting, but it was throwing me off my game a bit.

Finally, I decided I want to fuck, said as much, got up and fucked him. He wasn’t adverse to it (at all)… The problem was – like a lot of guys with his body type, his hole just wasn’t grabbing my dick the way I like. I still fucked him, but it was sorta clear to me I probably wasn’t going to cum. Every now and then I get a second wind and can cum, but eventually I just started going soft.

At this point he started getting self-conscious about the situation and that I wasn’t staying hard and wasn’t able to cum. He finally sucks my dick and tries to get it fully hard. Then he takes off my leather cockring and puts on one of his soft rubber cock rings on me. I used to like those things, but they now sorta scare the shit out of me. With those things my veins burst and I get ugly bloody spots on my dick. Hell, because of one of those I didn’t get into a Treasure Island video. I was worried, but let it go. He really put it on tight – twisted it a 2nd time around my balls. That got my dick hard, purple and veiny and I did finally get hard enough to fuck again. The 2nd time I got closer to cumming, but the worry of the cockring doing weird things to my dick set in, and I lost it.

At this point time was a factor and it was clear I wasn’t going to cum, I checked the time and it was a couple minutes after I was supposed to leave, so I wrapped things up as quickly as I could and left. He took it all pretty hard. It was like my not cumming was a personal failure and he just couldn’t understand why it happened. Here was this big butch guy completely devastated by a hookup that wasn’t all that bad. I mean it was different and generally pretty fun – it’s not like it was bad sex – it just didn’t quite work. Oh well… His issue, not mine…

Given a different bottom and more time I could totally get into just laying back and being a “do me” sorta top and let the bottom dote on me… Maybe another time…

I woke up earlier than I wanted to on Sunday, but then tried to stay in bed and rest. When I did finally get up my bottom and I went to breakfast. It was better than the day before – the eggs weren’t runny and the hot food was actually hot (and it was free for me since I had bought the weekend pass).

When we got back to the room I thought it was odd that tops would come to the door hoping to fuck the bottom and he’d answer the door and say he wasn’t up for being fucked. His rib was still hurting from the rough fuck at the gangbang the prior day, but I got the sense that it was more than that.

Then he mentioned that the hot vers top jock who was at the gangbang wanted to come and “hang out” with us. He then mentioned that he had stayed up late IMing him and had been IMing in the morning as well. I could tell he was infatuated with him. Honestly, I think it’s great if a cumdump finds a gangbang top and falls in love. It’s sorta the perfect combination. Far better than meeting someone socially who’s going to freak out when they find out you like being an anonymous bareback gangbang bottom.

I said yes to the guy coming over, but I was apprehensive. There were a number of scenarios where it could work out great, and a few that would be a problem. It would have worked if he had come over, thrown the bottom on the bed, fucked him, and then spent the afternoon hunting for more tops to fuck the bottom. Or since he’s vers, maybe he’d spend the afternoon taking loads with my bottom – that would have been cool too… But there was something in the bottom’s eyes that worried me – love.

The guy came over and I was busy writing up the first blog post about Friday night. They laid on the bed and talked and sometimes would involve me in the discussion, but then things got more intense between them. They were kissing and cuddling and making out… Frankly, it was just the wrong time and place for that. I got to the end of my blog post and wondered what in the fuck I was supposed to do. It wasn’t comfortable sitting in the chair and I really wanted to be doing some filming – that was one of my primary objectives for the weekend and I hadn’t done any of it yet.

There was an older bottom online who wanted to come over and was up for being videotaped. I pushed him off a bit thinking I’d give the two love birds time to finish what they started, but when the bottom showed up they were taking things so slow they had just gotten naked and were getting ready to fuck. The trick took off his clothes and the two of them on the bed suddenly realized that it wasn’t just about the two of them any more. “My bottom” (I’m using those words loosely) asked “Should we leave” and I just said “Yeah”. I was fuming by this point because things had gotten so awkward. They got their clothes on while I got the camera and lights ready and then they left.

I had an interesting hookup with the trick in which I fisted him. It was my first time fisting and I got totally boned doing it – but I’ll save that for a separate blog post.

When the trick was gone I texted “my bottom” and told him I wanted to talk face to face. He was eating and got there like 30 minutes later. We had what I thought was a really good, honest talk. A lot of issues came out and I thought everything was back on track by the end of it.

A little after we were done talking this young sub texted me. He’d been wanting to hookup for a while and it just hadn’t happened, and he was interested in having sex with both me and “my bottom” even though he swore he was neg and he knew “my bottom” was a cum dump.

“My bottom” started cleaning up a bit (said it was in preparation for the gangbang), and then the young sub bottom showed up. He liked being a puppy and started nuzzling his head on my belly and getting me to pet him. He was really sweet and while he wasn’t very verbal, he did a fair amount of non-verbal communication (“my bottom” could have learned a lot from the kid). The young sub started sucking my dick and I got “my bottom” to come over and the puppy seemed really excited to service him.

I got behind the puppy and he pulled down his pants and exposed his hole for me. Then he took off his pants and shoes completely as it got more serious. I fucked him a bit, but the position was a little awkward. I knew the perfect position would be doggy style (how appropriate) with the puppy on all fours, one of us behind and one of us on his knees in front. So I got up and figured I’d switch with “my bottom”. I got on my knees and got the puppy on all fours and “my bottom” started to fuck him. It seemed like just a minute or two later when “my bottom” announced he was really close and about to blow his load. I just asked “so you’re going to lube his hole for me?”, and then he blew his load up the puppy’s ass. [The sub bottom knew it was happening, knew he was about to take a load from a cumhole bottom and didn’t do anything to say or indicate ‘no’.]

Then “my bottom” went back to cleaning up the room as I fucked the puppy’s now cummy hole. At least that’s what I thought he was doing.

I was having a great time with the puppy – I loved how submissive he was. I had put a collar on him early on, and then he picked a hood and put that on (he LOVED hoods). I fucked him for quite a while but never did cum. The odd part was that he seemed a little hesitant to take my (neg) load, even though he had been fine taking “my bottom’s” poz load. When I had him on his back he’d stiffen his legs which made it difficult to really fuck him. It’s not like that’s puppy play – if you’ve ever seen a dog roll on his back and be submissive their legs are never straight.

We had a good session that was really tender and intimate. I loved how tactile he was to the point where I’d really love to do more puppy play (hint, hint to any of you in the NY area who identify as puppies).

I tried to get “my bottom” to get back into the play, but he resisted. I suggested having the puppy rim his hole (dogs like ass, right?), but he wasn’t even willing to do that.

As we were winding up “my bottom” left and said he was going downstairs for a drink or something. I was still concentrating on the puppy and didn’t really think twice about it. I asked him to do final approvals for the gangbang and send out the final e-mail with details, which he did before he left.

The puppy took off his hood which was his non-verbal signal that he was done. I took off his collar releasing him and he got ready and went. He had told me that the load he got from “my bottom” was his first one at MAL. I asked him how MAL was going for him and he said something like “it’s going great now” and then rubbed his head in my lap. I was seriously falling for the pup… He said he’d try to come to the gangbang. He’d mentioned hed’ be up for it previously as long as he was hooded since he didn’t want anyone to recognize him.

Then he left and I went and had dinner and a beer with Jayson Park. (Actually, he didn’t have dinner – just drank a beer while he watched me eat).

Then I went back up to the room to prep for the gangbang and “my bottom” wasn’t back and he hadn’t responded to a couple of text messages I had sent. Then about 30 minutes before the gangbang was supposed to start I noticed that his stuff was missing. While I had been fucking the puppy he had packed up and left. How he could sit there and do the final approvals and sent out the confirmation for the gangbang when he knew he was leaving is beyond me.

Later I found he had sent me an e-mail after he left…

On my way back to NYC via train. I just needed to leave…

Thanks for letting me join you this weekend.  Had a blast.

That e-mail sorta sums up his contradictions. He had a great time, but he had to leave without saying anything.

There’s so much I could say about him, but it would all be conjecture. I really don’t feel like I understand him much at all. I know deep down he’s a good guy, but he seems horribly conflicted. I’ve seen his personal Facebook page and in his profile pic he’s this completely normal, happy regular gay guy. But then he likes to get gangbanged, but then he also seems to have issues with getting gangbanged. He seems like he’s got a lot to work out, and I hope for his sake he gets to the bottom of it all.

With everything that had already happened that day I wasn’t really looking forward to the gangbang anyway. I knew Jayson was headed off drinking for the evening so after sending out a cancellation notice on BBRT, I called him up and we went out to the Eagle and then to the Reaction dance party later that night (but that’s another blog post).

And a couple postscripts to this post…

First, when it was done the day was actually a good day. I fisted someone for the first time, and found I really love playing with puppies, and Jayson and I had fun when we went out and a good fuck when we got back. So yeah, there was drama, but the sum total of the day was really good.

Second, the sub bottom texted me later and asked what “my bottom’s” HIV status was. Silly boy. I reiterated what I told him before – that the guy had taken 15 loads so far during the weekend and then later told him the load was “undetectable” but that if he was concerned he should be more careful and tell his limits to his tops. Personally, I think the sub bottom is doing a weird form of bug chasing where he puts himself in situations where he will take poz cum, but he does it in a way which is completely submissive so it’s done to him rather than him actively doing it – which sorta fits with his submissiveness. From my perspective I knew “my bottom” was on meds so there was almost a zero chance the sub bottom would get pozzed.

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.