Archive for the 'Friends' Category

Twinky 3 and 4-ways @ chilloutboys.com

Just not meant to be…

Last night “friend of a friend” came over for dinner. For all you guys who say I don’t care about bottoms - well, there are some I care about and I can truly say I love this guy and think the world of him. I’ve fucked him two (or three?) times but I hadn’t been able to cum in his ass… This time I figured I’d give it another shot - I had a 3 day load and figured I should be able to cum this time…

Since my bf was taking a nap on the couch we went into the bedroom where I had pulled out some leather gear I figured he’d be into. Turns out he hadn’t done much of any BDSM before, but he was game. After a quick blow job I put a collar on him. Then I gave him a choice of a spandex hood or a leather hood (he chose spandex). And then once he was hooded I put puppy mitts and ankle restraints on him. Then I locked the puppy mitts together with a really heavy lock. I did this in part to make things less personal and more sexual. I hate to say I tried to make a piece of meat out of him, but if you took a coarse view of it you could say that. I wondered whether the reason I couldn’t cum before was because of the personal connection - so I wanted to remove that from the equation…

It was hot seeing him on all fours on the bed. I ate out his hole for a while and then went to fuck him. Earlier that day I had gone downtown and picked up a new 2 gauge PA to replace the one I had dropped on the sidewalk and scratched one time when I took it off before going through a metal detector. One of the other times I had fucked him I fucked him with a PA - so I knew he was OK with it. I had to manually shove the PA into his ass ’cause he was pretty tight and then once it was in there it hurt a little bit (but not as much as the one time with the black guy a year ago), so I figured I’d pull out, take it off and continue on without it…

When I pulled out it had some shit on it, so I went into the bathroom to quickly clean up. I also brought out a wet wash cloth to clean him up with since he couldn’t do much for himself - being hooded and with no use of his hands…

Long story short, things were difficult after that point. I kept trying different things, but nothing was really working for me… Finally, I sorta gave up, and we just laid next to each other cuddling.

I took off his hood (he was cuter with it off), and had him give me a blowjob (with the PA out). I had one of those spongy rubber cock rings on and got a nice big fat hardon from the blowjob. I had him get back on his knees and gave him a nice long, hard fuck. It went on and on, but somehow “that spot” on my dick that, when massaged just right makes me cum, wasn’t getting rubbed the right way… So after a while I could tell it just wasn’t going to happen - as much as I wanted it to… Finally, I tried with him on his back, but it just wasn’t happening…

We wrapped things up (sexually) and then had a great dinner and sat around (with my head in his lap) and watched a foreign film he brought over… All in all a great evening… I wish I could give him a load, but it seems like it’s just not meant to be…

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Something Good Came Out Of A Pump-And-Dump (sorta)

Load 2007-23

Tonight a guy in the neighborhood sent me a message on Manhunt saying “seed me”. I first fucked him 10 years ago this month - a few times, and then a few years later - once in the bathroom of a school he was going to. He was wearing sweat pants and no underwear. He took my load and then went to class where my load seeped out… But I digress…

So we arrange a quick pump-and-dump in the park next to where we live, while I’m out walking the dogs. We meet up, go down to the end of a dead-end trail, tie up the dogs, he sucks my dick a little, then pulls down his pants and I start fucking him. It’s freezing out with icy snow on the ground, but I don’t care… I had put one of those soft rubber cock rings on so I had a nice chubby.

I was fucking a bit like a jack rabbit - quick and hard. He asked me to slow down and do long strokes. Normally I don’t like bottoms calling the shots, but I’ve always had a thing for this guy… I slow down, it feels good. I had been on the edge of cumming earlier that night and knew it wouldn’t take much for me to cum, and sure enough after a little bit I let loose in his ass - nice big load too.

I put my dick back into my pants, he wipes his butt with a paper towel, mentions how much I cam and we split. (I saw him walking off deeper into the park - probably looking for more loads - the park here is pretty cruisy)…

I get home and when I got to the bathroom and notice my boxers are a bit “dirty”, which means he must have been as well. So I decide to take a shower before bed. That breaks my routine of going directly to bed when I get back from the dog walk. I then lay down on the couch and channel surf. There’s a 24 hour news channel here in NY (local news, not CNN). I flip to it at the top of the hour and do something I almost never do - watch the 11:00 news. One of the top stories was about a big high profile accident downtown. I recognized some of the details of the accident and got online to verify that our friend wasn’t hurt…

But he was hurt, and after a lot of phone calls we found out that it looks like he’ll be paralyzed from the waist down. While that’s horrible news, if I hadn’t hooked up tonight we wouldn’t have known about it - it would have been another normal night where I went right to bed after walking the dogs.

It also points out the fragility and unpredictability of life… But that’s a whole other topic…

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Quick Pump-And-Dump

Load 2007-22

Been chatting with a guy I’ve known casually for a while now who lives really close to me. He’s not really my type, but did a quickie pump and dump with him last night - kept it pretty impersonal, even though we knew each other and it only took a few minutes… Hadn’t cum in days and really needed to seed some ass. It’s sorta funny. He probably wouldn’t have taken me for a pump-and-dump top, and I wouldn’t have thought of him as a cumhole…

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Fuck and suck while a bit drunk…

Along the lines of “Don’t hookup when you’re not feeling well” is don’t expect to cum when you’re drunk…

I’ve been wanting to get back to fucking the friend of a friend I fucked back in December, but for one reason or another it just wasn’t happening. First my bf thought he was competition since it was the first time I’ve really had a “friend with benefits” and my bf didn’t know what to make of it… Then life was busy and I wasn’t hooking up with anyone, then I didn’t see him on-line much… You get the picture - a thousand excuses…

Then, he put two and two together and figured out I was the person behind this blog, which was a little weird since someone in my circle of friends now knows the sordid details of my sex life. Then again, he’s participating in them…

Since the details of my hookups with him all got trashed when i managed to delete my blog a few months ago, I just sum it up by saying we fucked three times and I never could cum with him. He’s a good bottom, eager to please, nice clean hole, but his body type is the type I find it difficult to cum with. But I still really like to fuck him - just wish I could give him my load.

So yesterday I had saved up a 3 day load for him and we were going to hookup after work. Then there were some complications, and he wound up just coming over for drinks with me and my bf. By the time he got here I had had about a shot’s worth of Glenlivet. I made him and my bf a margarita and myself another scotch… By the time my bf went out of the room and he started giving me a blow job, it all felt good, but I wasn’t at my peak…

Anyway, my bf came back into the room while I was getting blown. He sat down and watched for a little bit, but he hasn’t had much of a libido the last few weeks. Even though he’s been warming up to the idea of having sex with the guy, he hasn’t had much of a libido the last few weeks, so he went out for a smoke while the two of us had some fun.

We progressed from a blow job to him on his knees bent over the living room couch with my raw dick in his ass. His hole was a little dry, so we moved to the bedroom and I lubed up with Gun Oil and fuck him for a while standing up with him bent over the bed, and then we moved up onto the bed and had him on his stomach… The whole time I was fucking him, he was sorta whimpering…

It felt good barebacking him, but between the fact that I still need to find the right position with him, and the fact that I was a bit drunk, and I hadn’t eaten in hours, I started getting soft. So I rolled over and we kissed and cuddled briefly until we figured we should wrap it up before my bf got back…

We then sat around and had another round of drinks and talked…

Now I’ve got a 4 day load and need to find a hole to deposit it in…

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More Recognition + News on the Gangbang Slut…

Well, “the friend of a friend” figured out this is my blog. It’s a little weird being “friends with benefits”, but even more so now that he can read all the details about my sex life… Oh well, I knew it could happen, and it really doesn’t bother me that much since I always figured someone who’d be looking for blogs like this wouldn’t be one to “throw stones” and that’s generally the case with him. Now I just gotta get my dick in his hole again and finally get some cum up there. (I would link to the hookups with him, but they all got lost when fucked up and manage to delete my blog.)

So, the guy I fucked back in January and February who likes to get gangbanged had another gangbang Tuesday, which isn’t such big news - he has one about every two weeks. What is news is that he’s set up a Yahoo! Group to facilitate him getting cum in his ass, and it already has 77 ‘members’. Good for him - but one of the comments on the group was from a guy who showed up at 8:30 (gangbang was supposed to run from 6-9) and he had stopped getting fucked. Wonder what was up with that? BTW, his profile on Adam4Adam still says he’s neg…

Otherwise, I’ve been working like a dog, but really need to find a good hole this weekend…

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Smoking Man

Last night, the guy who used to clean for us came over. He's moved on in his life and doesn't clean apartments anymore, but the industry he's in now is pretty calm in January, so he said if we needed him to come over and clean a few times this month, he'd be happy to.

So I come home to him cleaning and after I grab myself a glass of wine and relax a bit I go into the bedroom where he's cleaning my bf's desk. I initiate and we play around just a little… The guy is a smoker - a serious smoker (unfiltered cigarettes he rolls himself). He's tried to mask it by chewing gum or something, but it's not all that effective - and the issue is that he likes to frenchh kiss with tounge and it's just not working for me. I like the guy and think of him as a friend, so I play along a little. About the time he's sucking my dick my bf comes in to see what we're up to, and gets his dick sucked a bit too before he has to go back and check on dinner that's cooking on the stove.

We play a bit more - I feel up his hole and when I get to his dick I realize he's into CBT 'cause he's got a neoprene ring around his dick and balls. Then my bf wants a cigarette which is a production since he rolls them, so we take a break and then have dinner…

After dinner he's cleaning a bit more and we play some more. I finally get my cock in his ass, but I'm not totally hard 'cause the chemistry is off for me. My bf didn't join us this time so he went out and got him. My bf wasn't totally into the situation so he did like I did the other day and just layed there and was one of those "do me" tops… I got it up enough to fuck him while he was sucking my bf, but it didn't last all that long and I didn't cum. After that he rode my bf but my dick never got hard again…

So, it was and OK experience, and I don't mind a little affection and maybe a blowjob next time he comes over, but that's about all I'm interested in…

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