My sexy fun for the year seemed to start and end in July. It seems I can’t get much, but that doesn’t stop me from trying. I brought a gay friend to a BDSM group a couple days ago, and he politely observed and listened to people talk. Very quiet and non-confrontational sort of guy. I don’t think he’s interested in me.

I’ve also taken an interest in niche dating sites - made an account on Duolicious and managed to make contact with a metrosexual 24-year-old, but he’s so incredibly shy and reserved that I don’t think it’s going anywhere. I also found a site called Sissy Island, but they’re having server errors. If I could date only in femboy and sissy circles, especially if the crowd skews more to Gen Y, I couldn’t ask for more. My sexuality is abnormal, and I guess I’m going against the grain by avoiding people I’m not attracted to, since the standard for my generation seems to be having no standards.

Since Lemmy didn’t have one yet, I created !gonewildstoriesgay@lemmynsfw.com. In the future, I might type of some of these experiences as longer stories there, and just link them here with a short tl;dr: summary. But also feel free to post your own stories there ;-)

I’ve been sick for about a week, but I’m finally starting to feel better tonight! However, last week I was up in Boston. And while I was traveling with family, I still had my own hotel room, soo… why not have a little fun right? But just a little:

• NYC Hinge date + sexy fun! Before I left the city I had a Hinge first date with a vers guy. I invited him to a museum invite I could take a +1 to. A lot of fun to have some cheese and champagne on the museum’s dime :-P We had dinner in the neighborhood, and headed back to my place.
  • Pretty quickly things got steamy, with lot of touching, and pretty good kissing.
  • Guys about my size, a little leaner, a little less muscular. Still a nice chest to hold onto ;-)
  • Moved to the bedroom. He isn’t quite as hung as I am, but plenty big enough for a fun time.
  • We start with him riding me, but I think after all the drinks I had had (2 + 2 + 1) that afternoon/evening, I wasn’t really feeling it, so we just flipped.
  • Our boy can go hard and just keep going. He was fantastic with topping. A lot of energy, and just hard enough to hit the right spots once I gave him some encouragement. It was inspiring. I lost track of time for how long he went at it. Eventually we both were feeling stiff so went for a more relaxing and intimate side-by-side thing.
  • Like me, he’s really into smiling, laughing, and even joking during sex. He remarked about that in the middle of fucking. It adds a lot to our chemistry together.
  • We finished by touching each other, kissing, and getting down to swallow each others’ loads when it was time.
  • Was going to see him this week, but I’m still too sickkk :-(
• Oral fun night 1: a nice product designer who’s been visiting Boston for a month from Mexico city came over to my hotel room well after midnight. Normal build, cute face. Enjoyed giving each other blowjobs – his was not too too big, so it was easy for me to focus on technique and practice more ways for him to get new pleasurable sensations. Big balls too. We share some pretty big loads with each other. Just hung out and shared Boston/Cambridge travels tips and restaurant/ice cream recommendations for another hour or so :-)
• Oral fun morning 3: I woke up really early, and this guy showed up as just 83ft away on grindr. Tags hung, vers top, oral. I offered to come over and say a quick hello, and he asked, “How? With your mouth? :-)” and sure why not !
  • Handsome guy visiting from Philadelphia for a work conference, who had just gotten in last night.
  • Excellent kisser!
  • Really nice and rock hard throughout our time together, which was a real delight. He’s a bit bigger than me, so yeah he deserved to call himself hung ;-) it was more of a challenge than my friend on night 1.
  • We kind of switched between who was in charge, which was fun for me, too.
  • He was gently jacking me off while I sucked him, which turned me on even more. After he came and I swallowed his (surprisingly sweet) cum, he took him time focused on returning the favor :-D
  • We exchanged info, apparently he comes to NYC a lot. We should probably flip fuck.

I got my first really significant pegging 👀

I’d been pegged before with a toy that was about 4"-5" and pretty slim, which was nice but obviously didn’t hit the spot. This time we used my trusty 7"-8" dildo of average thickness, which was an EXPERIENCE. I didn’t take it quite as well as I’d hoped, and she couldn’t bottom out in me without a little bit of pain. But it was still awesome.

I was caged for most of it, but after I apparently made pathetic enough noises and pleas, my goddess let me out to cum. She wasn’t planning to do so in the first place, so I guess I must have been VERY pitiful.

Otherwise, I also got a knockoff Aneros toy and tried it out. It was fun! I can see the appeal, but I’m a bit intimidated by the amount of effort and information. Just have to practice more!