So hot. You kind of buried the lede on messing around with a trans woman. The communication and such was great. Do you have any other notes on the experience? Would you do it again? How far do you think you'd go with her? :-)
dazedandconfused
joined 2 years ago
Nice, thanks for posting! I think we should include today (Monday) since it was part of a long holiday weekend here in the US, too.
Two weeks ago I was in Florida for a gay Disney wedding. I thought there would be more fun amongst the wedding guests, but everyone was straight and in couples. That didn't stop me from having some fun in the three days I was there (Friday, Saturday, Sunday):
Friday
- Conference hotel guest quickie bj for him, on drugs? - kind of weird behavior. Also weird was his scrotum was kind of empty. Very average dick which is fun to suck and suck on without worrying about breathing/gagging. Wanted me to bottom for him, but frankly I don't bottom for average sized guys - I just don't get much out of it. Later his profile name had balloon emoji, so I think he does some kind of drugs...
- 20 yo Indian Australian tourist bj for me. Staying in a hotel room with his Mom from India and his brother from Pennsylvania lol. Came over to my room at night. Really had trouble sucking my whole cock. With some warmup he was able to take most of it down his throat, and it started to feel really good, like his throat was squeezing my head as I thrust in deeper. Always kind of fun when I see guys tearing up while deepthroating me :-) he was amazed by my rimming skills, and ultimately swallowed my load and went back to his family. He had told them he was out "finding something to eat" which was kind of true ;p
Saturday after a whole day in the heat for the wedding
- Disney resort employee came by after his shift. wanted to get "sloppy head" - sent me some examples of porn stars sucking dick. He said he has never done any kind of sex with a guy before. I'm skeptical of this claim, but okay sure. Challenge accepted. He's really thick and decently hung. Got him to cum once deep down my throat and then a second time while showering in my mouth. I had to manage my gag reflex, but after some warmup it was really manageable. He said it was so much better than women, and I agree. Men are better at sucking dick.
- Younger curly haired, amazing ass for late night cuddles - Nice making out. Straddled him on top of his big firm/squishy bubble butt and massaged him for a while. Enjoyed getting head and rimming him. Massaged his prostate and sucked his nice dick at the same time. He wanted me to top him, but at that point it was 3:30am, and I just didn't have it in me. He had to leave at 6am to get his flight. I had him cum while I massaged his prostate. I love feeling the prostate harden as a guy orgasms.
Sunday last full day in Florida
- Marriott corporate employee quickie bj for him - he was there for a conference. a little older than me, very very thick, average length. Very tender and positive/welcoming. A lot of fun to do something like that with a nice guy.
- Local guy doing idk what but it was amazing - went over to his place. he said no promises about bottoming but he really wanted my dick in his mouth. We have a good 40 minutes of him sucking, me rimming, and me face fucking him. He's so cute, and he looks even cuter with his mouth full of my dick. While rimming him, he asks me to tease his hole, and we have another 40+ minutes of me teasing his hole by rubbing my hard cock against it. And then even teasing by just inserting the tip and holding it there and removing it. It was primal. There was only lust when I looked at him, feeling his hole like that was such a turn on, coupled with his responses and moans. I was so close to just ramming it all the way in a few times, but I managed to keep it under control. He leaks a lot of precum, and the wet sound of him jacking off while I'm on his ass made it all even hotter. Sweaty, hot, grunts, moans. It was intense. Finally when it was just too much, I gave him the requested facial and he jacked off and came at the same time. He's a really smart grad student, and we had some great chit-chat for like half an hour after that. It was the perfectly satisfying conclusion to a busy weekend.
Two more things in the last week/days
- Weird doctor hookup - idk, pretty good looking, but his apartment was totally empty. We ended up taking a curtain off the wall so we had something soft to lay on while we fooled around. Quick to rinse his mouth and ask me to rinse mine after even a tiny bit of oral fun (no semen or anything). Wanted to make me cum, but didn't do anything at all with my cum once it sprayed everywhere. Not even playing with it...
- Cute cub-type for Broadway show fun :-) - nice funny local LI guy on Scruff invited me to a preview screening of a broadway show in the city. He's in media and is kind of an "influencer" so he gets invited to stuff like this. His pics and stats suggested an otter, but in person he was a lot heavier :-\ we enjoyed the show and Q&A with cast and crew, then had dinner and went back to my place. He wanted to bottom for me, and I was nicely aroused for it, but I didn't feel the kind of attraction that would have me really enjoy it. So we had oral fun. His dick is significantly below average, but very leaky and fun to play with. He enjoyed getting me to cum, and I was surprised when he came and shot like 6-7 feet, and ended up spray a bunch all over my headboard lol. We had ice cream at the train station before we both boarded our different trains back to Long Island. We'll stay in touch and be friends and maybe hook up from time to time idk.
Dang based on your post history I'm really interested in finding out 😏
To be fair I couldn't stop either. The absurdity of it all. His computer was set to french so even though I was using it he had to sometimes translate the Apple website forms for me.
There are many fun ways to masturbate to keep it interesting. As someone who has gone many years between sexual encounters, trust me. 😉
I love the lust and anticipation in his eyes.
For all to see? 😏 Do you have a little exhibitionist streak?
Thank you, great wise sage of outdoor sex ♥️
Nice. "Womanizer" like ikr Britney Spears song…?
Outside inside cumming. Hot. I've never done sex outdoors in any form. Any notes?
To "cum" (orgasm) from prostate play alone requires regular practice and focus on the sensations that your prostate is giving you. In my experience, I had to work at it to take it from "interesting" to "oh woah that's amazing". And even the, I need to be in the right mindset to really enjoy it. Don't give up! It's something we get to enjoy that women don't, as they don't have a prostate :-)
I'm pretty nervous about unprotected sex with women. I can only imagine how different it would feel. You're getting me jealous <3