Okay, here we go! By the way my goal after this past week is to take the next week as a pause from naughty fun and really recenter myself. I think things swung a little too far towards sex.
Lots of fun this week! Almost all of it was very good to excellent! Apologies it’s long, I’ve been busy.
tl;dr: a bunch of new firsts, summarized here:
being gently dominated
having a toy used on me
fingering a guy while he cums
feeding someone my cum by hand
fingering a guy for his first time
being the first cock in someone’s mouth
Now the details:
Monday Grindr bi bro fun I got back to the city and was feeling pretty horny for a quick hookup. My neighborhood is filled with hotels so there’s always someone around. I was thinking about a quick mutual bj or something. Found a slightly older married bi guy a block away. He said he was 6.5" hard, but was way smaller – didn’t really care, he could have just told the truth. He had a dominant streak, and held my arms over my head a few times. This was new to me, and that gentle dom felt kind of nice. I’m usually the dominant partner. I teased his cock with my hole, and came in that position from him jerking me off. He said he never fucked a guy before, and I didn’t have the heart to tell him that he still hasn’t :-) said it was the best sex he’s ever had with a guy.
Wednesday Scruff traveler pain Hooked up with a different guy in a different nearby hotel for work. I was still just looking for a bj, but guy was bottom and really wanted the D. Also a little older, but very smooth and nice body. Great cock, too. At one point he got so excited, he grabbed my cock from the base so tightly that it really hurt. It actually hurt for days after that. I couldn’t stay very hard after that, and definitely wasn’t interested in fucking. I had him blow me, take my load, and let him take care of himself. It really hurt guys.
Thursday Grindr pleasure dom for bottom My cock was out of commission today, but I still wanted to make someone feel good. I offered a bj to a bottom, and he came over on his way home from work. I ended up giving him a prostate massage while sucking him off. Once we really got started, he came so so fast. Uncut cock which was a lot of fun to suck and swallow. Also a nice size where I wasn’t choking on it. He works in the neighborhood, quite handsome, and wants to meet up for the same or more. This was the first time I had a guy cum with my finger up his ass! Also yeah, I’m more dominant, but I think I’m more of a pleasure dom than a “mean” dom kind of guy…
Friday afternoon tanatric lesson #2 I met up with my local tantric expert to learn about tantric massage. Our time was limited, so we focused instead on having some fun and working on tanatric lingam (penis) and prostate massage. I first showed him what I did to the bottom yesterday, and he then showed my a proper massage technique by demonstrating on me. My prostate is unusually far up inside me, so I brought an nJoy wand for him to use instead of trying to use his finger. It felt very good, so relaxing and arousing at the same time. Neither of us came, and with tantric that’s totally fine. In fact, I stayed really soft the whole time!
Friday evening reconnect with my power bottom boy Power Bottom and I had been planning this meet for a while, and even if I was sore he still wanted to come over. We had a really nice time just being intimate to start. He shared his past trauma with me, so I let him blindfold me and explore my body. Maybe one day we’ll build up to blindfolding him and doing the same. I was also really excited to bring him to the bedroom and show him the new tantric techniques I was learning. I did a combo of lingam and prostate massage at the same time, and with that I brought him to an incredible intense internal orgasm. We started at 9pm and it was almost 3 when we were done, so I had him spend the night. He hadn’t eaten, so I whipped up some quick high protein (Vite) ramen for him. I actually haven’t had an overnight guest in a long time! Slept decent, and got really horny in the morning. After some warmup, I was feeling pretty good. So we were gentle, but did end up fucking at that point. We ended up taking two showers together over the course of the day. I can tell he’s catching feelings, I’m not sure I feel the same way, but he’s a lot of fun to spend time with!
Saturday Grindr random bj finally! Yet another guy in town for work, hotel 2 blocks away. We chit chatted on the street for a bit while he smoked a joint. Turns out he’s basically on the same career path I am, and we have A TON in common. Super cute guy, too. He understands I’m really just looking to give a bj, but we still end up getting really intimate and connected in the process. He has a nice thick and long cock, probably about the same size as mine, which is both challenging and fun to suck. I really take my time going slow and working him over, until finally he gives me a nice big load. We spend a long time cuddling, and I enjoy massaging his body while we embrace. He’s been swimming, and it really shows from his well defined back and shoulders – very sexy. He’s pretty much ready for round two and wants to reciprocate, so we jack off together. As I’m getting close, he says he’ll cum once I’ve fed him my cum. Once he said that I climaxed pretty quickly :-) I should be exhausted by somehow a decent load comes out, which I collect in my hand and feed to him. I’ve never done that before! We kiss and he ends up cumming, too. We’ve swapped numbers since he’ll be coming to NYC from time to time, even if we don’t have more sexy times (but we will) he’s a great guy and it’s good for us to know each other. He messaged me a lot later at night that he was still feeling this great energy, and I was too. For me, that’s the sign of having actually good sex! He started dating a guy, and told me it doesn’t feel that way with him, and we agreed that might be a sign it’s not really working with him. We spent about 2.5 hours together. He really wants to take my load, so maybe one day?
Saturday dinner party girl update I went on a first date with this girl a few weeks ago, and I thought she really didn’t like me for a few reasons. I learned from the hosts of a dinner party that she actually does want to see me again, and is just waiting for me to ask! I’m giving myself a day to figure out if I want to or not. Maybe the vibe I got was my own sense of not feeling really connected with her.
Sunday Grindr inexperienced guy many firsts I really thought I was done after Saturday, but this morning an inexperienced top finally reached out to me and was free. He has wanted me to be the first guy to top him, and our schedules have never matched up for like a month. But oh no, he is only free for 1.5 hours! That’s not enough time to start from nothing and get to first penetration enjoyably. I still go over. He’s a super sweet guy, younger grad student, with incredible soft lips. We make out, enjoy each others’ bodies, and explore our manhoods. He wants to suck me for a while. Apparently it’s his first time sucking dick! For a first timer, he’s really quite good, I’m above average, and many guys (and all girls) struggle. He was great. His is smaller and uncut, and so a lot of fun for me to suck on, too. He knew we aren’t getting to penetration, but I do offer to finger him. I rim him for a while first, which is his first time being rimmed! I get one finger and eventually two fingers in to massage his prostate. It’s his first time being fingered by someone, too! He’s really sensitive, and really good about providing feedback. I keep checking in with him, and he’s absolutely in heaven. Eyes rolling back as I finger him and jerk him off or massage his taint at the same time. Eventually he cums while I’m fingering him, and shoots all the way up to his neck :-) Apparently he never shoots that far – that’s the magic of prostate massage! We enjoy his afterglow for a while, then offers to jack me off, which wasn’t necessary but appreciated. I also manage a decent load, which was surprising. Cuddle and chat a bit more, and are ready and clean with 5 minutes to spare on his timeline! He still really does want me to fuck him, and I think that will be easier for both of us now that we’ve connected and enjoyed our time together.
It’s been interesting reading about your experiences these past few weeks and thanks for sharing! I’ve been amazed at the sheer number of reasonably positive encounters you seem to have had in such a short period of time. Just to be clear I don’t say that as a statement of judgement, but coming from the perspective of an introvert who if I meet one new person a month I’m exhausted!
Thanks so much! Guys are so horny and also comfortable hooking up, so even my shyness is trumped by horny energy :-)
In terms of mostly positive, I think Scruff is much better than Grindr for that purpose. I usually take time (days or more) chatting with guys before I’m going to meet. I also look for guys that have well written profiles and ideally have at least one pic with a genuine smile.
As a fellow penis-owner you don’t need to explain horny energy 😁
I get the impression that you’re around the City or maybe LI so you probably will have a lot better luck with any app in general than I ever would. One of the fun things about living rural is that your options are usually pretty limited.
A confession: as you’re (probably) bi I looked through your comment history to try and guess your sex. I only posted that line because I found myself totally unsure 🙂
And yes you’re right I’m on NY Metro so yeah options are amazing. Maybe too amazing. I might need to become more picky 😅
A reasonable and tactful approach as not everyone simply posts pictures of themselves to make things easy 😝. I will confirm for you that I am a bi man haha.
Have your fun while life lets you. Just be safe in the process!
Wednesday dude needs to chill tf out. You can grab people, but if you end up hurting people, then just chill. Good lord!
This week seemed to end a lot more better than last time, so hurrah for that! And party girl might be coming back in the mix, so who knows where that’ll take you!
My heart broke for power bottom dude - he seems so sweet, but at the same time, you got to go with how you’re feeling. Hopefully he doesn’t feel like he’s been strung along - if he’s catching feelings and you aren’t, then it’s probably best to have a conversation (I’ve been on the receiving end of this many times, and while these conversations suck, it ripping off that band aid sooner rather than later helps with the healing process).
Lots of very promising experiences, I hope something blossoms from it!
Oh, and the Monday grinder bro - poor dude. I’m so glad you let him have his moment lol
Thanks and I’m happy you enjoy following my sexploits. I’m all healed now thankfully.
Thanks also for the perspective. It’s really hard for me to develop feelings in general. I’m really hoping I can get Power Bottom to be a fwb. I need to have a chat with him at some point for sure. Same with my Saturday career-parallel bro from LA. We have some good chemistry.
Okay, here we go! By the way my goal after this past week is to take the next week as a pause from naughty fun and really recenter myself. I think things swung a little too far towards sex.
Lots of fun this week! Almost all of it was very good to excellent! Apologies it’s long, I’ve been busy.
tl;dr: a bunch of new firsts, summarized here:
Now the details:
It’s been interesting reading about your experiences these past few weeks and thanks for sharing! I’ve been amazed at the sheer number of reasonably positive encounters you seem to have had in such a short period of time. Just to be clear I don’t say that as a statement of judgement, but coming from the perspective of an introvert who if I meet one new person a month I’m exhausted!
Thanks so much! Guys are so horny and also comfortable hooking up, so even my shyness is trumped by horny energy :-)
In terms of mostly positive, I think Scruff is much better than Grindr for that purpose. I usually take time (days or more) chatting with guys before I’m going to meet. I also look for guys that have well written profiles and ideally have at least one pic with a genuine smile.
As a fellow penis-owner you don’t need to explain horny energy 😁
I get the impression that you’re around the City or maybe LI so you probably will have a lot better luck with any app in general than I ever would. One of the fun things about living rural is that your options are usually pretty limited.
A confession: as you’re (probably) bi I looked through your comment history to try and guess your sex. I only posted that line because I found myself totally unsure 🙂
And yes you’re right I’m on NY Metro so yeah options are amazing. Maybe too amazing. I might need to become more picky 😅
A reasonable and tactful approach as not everyone simply posts pictures of themselves to make things easy 😝. I will confirm for you that I am a bi man haha.
Have your fun while life lets you. Just be safe in the process!
Wednesday dude needs to chill tf out. You can grab people, but if you end up hurting people, then just chill. Good lord!
This week seemed to end a lot more better than last time, so hurrah for that! And party girl might be coming back in the mix, so who knows where that’ll take you!
My heart broke for power bottom dude - he seems so sweet, but at the same time, you got to go with how you’re feeling. Hopefully he doesn’t feel like he’s been strung along - if he’s catching feelings and you aren’t, then it’s probably best to have a conversation (I’ve been on the receiving end of this many times, and while these conversations suck, it ripping off that band aid sooner rather than later helps with the healing process).
Lots of very promising experiences, I hope something blossoms from it!
Oh, and the Monday grinder bro - poor dude. I’m so glad you let him have his moment lol
Thanks and I’m happy you enjoy following my sexploits. I’m all healed now thankfully.
Thanks also for the perspective. It’s really hard for me to develop feelings in general. I’m really hoping I can get Power Bottom to be a fwb. I need to have a chat with him at some point for sure. Same with my Saturday career-parallel bro from LA. We have some good chemistry.
lol Monday bro 🙃
Sounds like an ace plan!