• I visited a theater friend of mine in Queens one morning before work. He likes giving me head usually at my place, so it was fun to see where he and his partner live. He gave great head as usual, and I helped him cum by sucking his cock and playing with his hyper-sensitive nipples. He made coffee too, so it was nice to hang out and catch up afterwards.
• I had a second date with D, which had no anal but did include a sleep over and playing with my favorite Tenga masturbation sleeve. We both came a couple of times and had a lot of intimate fun and a little horsing around, too. I put the whole (long) story in a new community I made: !gonewildstoriesgay@lemmynsfw.com. Please share feedback to help me become a better writer.
• I had some more fun (solo) with the same toy later that day.

I think I'm getting some of my mojo back, or maybe just getting better at knowing what I want, and when I want it?

• Finally met this guy from Beirut. I literally got into the city, reached my place, and I had an hour to kill before meeting friends. A Lebanon-based Polish tourist who regularly visits NYC finally coincided and wanted to finally bottom for me. Very slim, tall, smooth twinky type. I told him I don't have much time, wouldn't want to top but we should have some quick fun.
  • But nah, once we got into it, we both wanted to fuck - he wanted it bad.
  • The mechanics were great, loved his moaning. Wanted to kiss more while I was fucking, but also wanted to hear him moan, so did a bit of each until I came in him and I had him jack off while I was still fucking.
  • Had a nice little chat, too. He's a nice guy <3
• Fun-sized bottom friend came over for slow oral, with unexpected ending. He's a small young shaved twinky guy, and it's fun to watch him do his thing. Smaller mouth and hands struggling with my dick are fun, too :-)
  • And for the second time now, he ended up cumming from just the pleasure of sucking my cock and friction as he was rubbing on my bed. And wow cheers to him, it was a massive puddle of semen!
  • He needed a little break, and we cuddled, and ultimately he felt bad but didn't have it in him to continue. Sad for me, but happy he really enjoyed.
  • Which led to me still looking and…
• Extended oral worship the same night. Finally connected with a guy in my neighborhood who has wanted to really take his time and suck my cock for a long time. Said he really wants to "serve" and I was happy to oblige. We had a drink and a little weed together, and he put on a playlist and went to work.
  • Brilliant oralist. I don't know what he was doing with his mouth, I felt like I left my body at times. It was fun how we was sucking to the beat of the music at times. And barely/strategically using hands, which is exactly how I like it.
  • This edging lasted over an hour. With me sitting on his couch and him down on the floor, head buried between my legs. It only ended when he finally decided to shift his pace/intensity, and he swallowed my load. It took me a while to catch my breath! Hung out, and we both appreciated getting to know each other, he says I can come by any time :-D

The cum must flow.

A few days in the city, action packed with fun lol. I think after the cruise I had to get it out of my system.

• Monday I wasn't planning to cum so I would remain energized for Wednesday. Met a guy I've been chatting with for months finally at his place in Brooklyn. We made out, sucked each other off, and rimmed each other. He ended up making me cum, and I spent the night. Rimmed me for about an hour before falling asleep. Guy is hung like a porn star lol, must be somewhere over 9". Nice guy, made avocado toast for me with homemade bread for breakfast.
• Tuesday afternoon got a hung guy from Grindr to come over for a blowjob. I let him know I'm good to bottom, and we did that instead, and he bred me. Fun verbal play, and felt very good. No cumming for me, remember Wednesday.
• Tuesday evening visited a British tourist at his nearby hotel room. We mostly just cuddled, joked, made out and watched a terrible movie naked. Bottomed for him first with a condom (his ask), then later we went bareback and he came in me. Just more fun cuddles for a bit, as well. He was the first average-to-small top, and I learned that I really do need a big one to enjoy myself while bottoming.
• Wednesday @joshoff@lemmynsfw.com came over to my place :-) I think we're the first two guys, and maybe even the first two people(!) to meet up from lemmynsfw.com. Months of posting little messages and we finally decided to meet since we both live in NYC and our preferences are pretty compatible. I just posted another clip in !gaybrosgonewild@lemmynsfw.com. More clips will come in the coming days as I keep working through almost 2 hours of footage. Some highlights and reflections:
  • This dude is fucking gorgeous. I could stare into his eyes all day. Started nervous, but got comfortable after a nice chat.
  • We were making out on the couch, with him straddling me, his hands on my shoulders. And I kind of just went for it, and carried him from the couch to my bedroom, and threw him down on the bed. He weighs 160lbs, and in hindsight it's kind of crazy and so hot that I was able to carry him like that. Will do more.
  • Holding his head down on my cock, either with my hands or with my feet. Having him keep my dick clean if he gagged a little too hard on it. Gives great head. Fun to watch him struggle to fit my balls in his mouth, too. Rode his face for a while like that, too.
  • I was so worked up, I barely had him riding me before I came the first time! He's a champ. We'll have to practice this more for sure. Fucked him for a while in that position, anyway. So many more positions to try together.
  • I fingered him and had him riding the prostate orgasm wave for minutes continuously. Awesome how sensitive he is, and I could have just kept that up forever while making out.
  • I came again while jacking off/having him suck me. So he got one load in each end -- my favorite.
  • I've never been this rough or verbal before, and I really enjoyed it. He's a good boy, and I'm excited to schedule something with him again.

Bi male mostly top. I'm okay with being ridden until they're used to my size. After that it's missionary or mating press for me. The eye contact. The shock on the receiving partner's face when they realize there's more cock still going in. I love it. Sometimes I can kiss while doing it too.

Even on bottom I prefer that position.

You sound like such a good bottom buddy. Did you expect to bottom for him that night? Were you hoping he would ask?

Dang, nice. So smooth and touchable, yet still intact. All these guys posting lately have such good-looking cocks; it gets me feeling more self-conscious :-)

I was mostly busy with a hectic return to work, and then Thursday night got super busy because my contractor was coming Friday morning to start renovating my apartment. Now I'm on Long Island living with my family for the next few weeks, so I think I will have very little naughty fun for a while :-(

• All week my boy J in LA and I have msg'ed back and forth about both sexy and non-sexy stuff. Once I get back in my apartment we're going to do a holiday cookie swap. Very late Sunday night he let me know he'd be open to jerk off on facetime together some times. He also let me know that he went to a baby shower happening in the family of the guy he's dating 🫠
• Friday afternoon had a quick hookup. Before going to my family home on Long Island, found a guy near my office and we 69'ed and he ended up making me cum by mouth and hand. He is very new to doing stuff with guys, and worried about STDs, so I pointed him to good resources to be more safe. Nice guy, not a great kisser, nice uncut cock, good to chat with before/after.
• Sunday night I was really horny but couldn't make a hookup happen. Connected with a hot local guy on Grindr and we video chatted on Snapchat while he jerked off. We both live with family so we kept it totally quiet. It was so hot to watch him jack off at the same time as me.

Well fuck this was another interesting week. So much to share. tl;dr on my new first-time experiences:

• Fucking a more fem guy
• Being invited to a girl's place for a party she's hosting instead of a date (read below omg)
• Guy cumming in my mouth after 30 seconds of bj
• Can't stay hard when trying to fuck a guy
• Cumming from pure oral, no hands
• Visit to a glory hole

Full stories below:

• Thursday back in NYC. My hot male Tinder match had to reschedule our hookup, so I found a very muscular vers guy on Grindr looking to bottom for me. So smooth and muscley. Turns out he is more fem, and super hot. I was planning to take this one slow, but when we really get into it, he lets me fuck him missionary. I haven't been able to do that for a while, with partners preferring to control the ride by being on top. I went hard. It was intense, it was primal. His facial expressions and vocalization drove me to fuck him even harder. It was only a few minutes of this ferocity before I unloaded everything I had in him. Got his dick leaking a mess from how hard I could hit his prostate. Cuddled for a while, but when I was hard for round 2 he kicked me out because he had to wake up at 5:30am. Funny story, it took forever to find one of my socks, it was hiding in my pant leg, he was giving me one of his pairs to go home before we found it. It was hilarious!
• Friday I didn't get him to orgasm, so I still wanted to make someone reach climax. Guy says it's his birthday and wants head. Sure! Kind of lied about his body type. He was way heavier than "normal" but whatever. Says he might facefuck me hanging off the side of the bed, and i'd like that. We start to heat up, and within 30 seconds of a regular blowjob, he cums in my mouth. I was expecting a bit longer.
• Friday bonus since he came (and left) early, I actually got a reply from one of the girls from last week!!! She invited me last-minute to a party at her place. We're both Indian, and it's a Diwali party with a bunch of her friends. Great group! We eat, drink, dance, sing. She is super flirty with me I think. Light touches, eye contact, slightly suggestive dialog. Her friends are really encouraging and supportive of us, too. She's out of town and I'm out of town for the next two weeks, but I'm trying to stay in touch over text until we find a time to meet. She's really hot, especially in those tight revealing Indian clothes she wore, and also mysterious I am so into her.
• Saturday friends hosted a halloween party which was fun. As I was leaving I decided to walk 50 minutes home since the weather is nice and everyone was out in costume and enjoying themselves. A guy messages me on Grindr offering a bj, and he's on my route home, so sure! I send pics and he assures me he can handle my size and curve. I get to his apartment building, and ask which apt # and he blocks me!! omg!
• Sunday A lanky twink (5'11", 115 pounds) and I plan to meet today to fuck. We want to try some more athletic things like impaling him while holding him or holding him up against the wall. He's light enough that we can do it. Have a coffee together, and I'm not feeling much but I don't overthink it. Make out and he's an okay kisser, but nothing is happening down there for me. He gets me hard with a few touches, we get a condom on, and after he sits on my cock and we fuck for a few seconds I go soft, and I don't really get hard again. I've never had this happen before. I guess I really didn't feel anything for him. In hindsight I should have seen the signs earlier and peaced out and saved us both two hours. He really really tried to make it work, too. I feel bad for him, he must be taking it personally. He, by the way, stayed totally rock hard the whole time. Is this what people refer to as "chemistry" or lack thereof??
• Sunday bonus horny and my backup bottom also had to reschedule. I finally go to visit a guy that runs a local glory hole. GOD DAMN THAT WAS THE BEST BLOWJOB OF MY LIFE 10/10, 12/10 with rice. This guy is a real pro. I have no idea what he was doing with his mouth to create those sensations. He did not use his hands at all. I got distracted a few times and went soft and he powered through it and got me going again. I really thought he might give up or use his hands but he didn't and it was amazing. The climax was deep and he got that load after a lot of hard work. I've never cum from a blowjob without either using hands or facefucking. I think I need to work on getting better at receiving pleasure (BJ) and not just taking pleasure (facefucking, fucking). Taking pleasure is easier because you have to focus on what you're doing. With a BJ the mind can wander. He liked sucking me, so he said I can practice receiving pleasure with him, and next time he'd want the curtain down so I can see how he works his magic.
• Sunday double bonus the other girl from the fancy party with my sister also got back to me about yes wanting to go on a date and we're going to figure it out!

As I mentioned last week, I took this week off from sex. Some of the guys and gals online did a great job of teasing me with some very naughty chats, pics, and videos. Basically had me constantly hard and wanting to fuck. I think I had gotten used to being really sexual because I had to jack off up to three or four times a day to feel normal!

On a cleaner note, I went to a black tie benefit event with my sister. She's a great wingman. With her support, I got the phone numbers of two really sexy, beautiful, and smart women! I haven't picked someone up like that in a long time. I'm making plans with each of them (separately!). Let's see where it goes!

I just signed up for Tinder, and listed myself as bi. It's kind of annoying that I'm matching like 90% with guys and maybe 10% women. I would like a more even split. I guess this is why some other bi guys told me they use those apps for women only...

edit: I guess at least there are a lot of very attractive people in general on there.

If I need to be quiet I can be completely silent. However lately any moaning or heavy breathing has also included some growling and grunting too. It can get pretty loud when I'm completely in the moment with a partner. I don't actually know how loud as I'm not paying attention at the time. I really really love when women moan with pleasure.

Men are good, too, of course. I think they can be more shy.

Bonus: yeah it's only polite that way if they want it somewhere specific I can try try oblige.

Okay you really want to know, then I’ll tell you. Has gay stuff so don’t read if you’re a prude. But if you’re a prude, why are you here?

I signed up on Scruff, and my phone has been BLOWING UP. I will skip the dozens of explicit chats, image swaps, custom videos, etc. and just tell you about this one:

• A sub bottom reached out to me around 4pm on Friday. I’m not really dom/sub, but it’s fun to mess with people, and I can give it a try. So I mention chastity and he is REALLY into the idea. He has to meet friends for dinner and hanging out at 7, so he comes to my place, and I put my chastity cage on him for the first time in his life.
• It’s his first time, so I use a cut-able travel lock and tell him what to watch out for in case it’s too tight or painful.
• The whole time he’s at dinner we have absolute FILTHY dom/sub texts back and forth about how it’s not his cock anymore, it’s my clit, etc. and every time he feels it, he feels my hand tightening around him, because it’s mine. My god he LOVES this. Periodically while at his friend’s apartment, he goes into the bathroom to take a video showing me his cage is still on and huffing poppers. HE BROUGHT A FUCKING BOTTLE OF POPPERS with him from his house to my place, to dinner, to his friend’s apartment.
• After dinner probably around 1am or so he wants to come back to my place to show off his cage but I know he wants more. He comes over, pulls down his pants, takes off his shirt, and shows me his whole body. He was leaking precum all over himself all evening and had made a huge mess in his pants.
• He then worships my body and my cock until finally he gets to swallow my cum. He did a good job. Once I’m finished, I open up his lock, and let him take care of himself, while I hold and kiss him in my lap. We clean up and he heads home by 2am.
• TODAY (Sunday) he came back to get locked up again. This time he has the key, and I taught him how to put on/remove the cage. That’s his responsibility now. I’m still not having sex with him, so he has another random hookup come and facefuck him. I told him not to tell his hookup about the cage in advance. The guy was so surprised but LOVED how much of a pig this sub bottom is. They both had a good time, and the sub bottom realized he really is so much more focused on pleasing the cock in his mouth rather than his own useless nub when he has it locked away. He’s going to make sure he likes it then probably buy his own. He can’t have mine. That things was expensive around $150.

So here’s the thing about all that, by the way. It’s fun for me to roleplay, but I’ve learned I’m really not part of this whole dom/sub dynamic. I can play the part, but for me it’s just play. These guys LIVE it.

Edit: why do you have a chastity cage? It makes it a lot easier for me to enjoy my dildos without immediately cumming myself from masturbation.

Edit 2: a shorter story from this week: a gay couple reached out to me to see if we have chemistry. They’re cute. The wild thing is the partner that reached out to me is BLIND and the audio of the video of me cumming turned him on so much he wanted to reach out. Isn’t that crazy?! (that video is posted here on Lemmy)