I had a pretty good date with a woman last week. We spent the afternoon together then she came back to my house. It was my first time having sex with a trans woman - although I’ve been with men and cis women before. I really wanted to suck some dick (it’s been a while!) so I started by giving her a blowjob for a while before she returned the favour. It was really intense and I had to tell her a couple of times to slow down. We calmed down for a bit with just some hugging and touching / stroking and grinding. She bit me a lot and left some big bruises on my neck, which really enhanced the pleasure of her hands on my dick and made it a whole-body feeling. She then straddled me and started face-fucking me, which I’ve never done before. I don’t know that I liked it, but I was masturbating as she did so and I came incredibly hard, so part of me must have enjoyed it! I cleaned myself up (there was a lot of cum) and watched as she finished herself. Very successful date overall :)

As a slight aside, I was really happy with myself. I felt I communicated really well and although I felt she did less well there, we both really enjoyed ourselves. It’s something that I’ve been working on and I think I nailed it :)

I stayed up late! 1 hour! Then, I had CAKE before bed! Man, it was crazy.

I made some significant progress in opening up to my partner and had some fun along the way.

First off, I put on my chastity cage and sent her a snapchat (captioned with the location of the key) from bed where the cage was visible. She took the key and told me next time I need to ask to be locked up for her, which I liked. She asked me if I wanted to touch her or if I wanted to cum. Of course, as a good sub, my answer was to touch her.

I ate her out and made her cum twice, then she asked me to pick a number 1-3. I chose 2, which meant 2 more days locked up before I could cum. Which is the longest I’ve ever been in chastity and was very hot! She even went to the gym with the key around her neck and said everyone was going to see the key…

I got her off a few more times over the next couple days. We had a good, long chat about our D/S dynamics and what each of us wanted, though I didn’t really disclose much in the way of crossdressing during this. We talked about things like collaring, names, punishment, etc. Very good talk.

Sunday came along and I didn’t know what the plan was but was obviously very excited. She asked me to shower beforehand, so I was released from my cage. After I asked her if I should re-lock myself to which she replied “do you think you should?”. Obviously the answer was yes. But from there, I took a risk. While she was getting ready, I put on my lacy bodysuit (the same one from my profile pic). She didn’t know I had this (or any lingerie), so my heart was beating out of my chest as I walked through the door.

Luckily, she loved it. She even helped me to one of the back straps that I couldn’t get myself 😅 after that, she put on her strap-on, put me on my knees, and made me suck it. It was really hot and I got it down the deepest I’d ever taken it thanks to her help. She kept telling me what a pretty mouth I have and how I was born to suck cock. Needless to say, I leaked a LOT of precum during this.

After that I got down to business as she showed off her new crotchless panties. I ate her ass for a bit before starting in on her pussy and making her cum twice, getting a moaned “good boy” each time. From there, we 69’d. I was a bit too focused on her pleasure during this but still enjoyed it very much. Then she asked how I wanted to cum, from fucking her or from a hand job. I asked her to make me eat my cum after, so she chose fucking.

We did a few minutes of doggy style before I came HARD in her. Suffice to say, there was a lot. I thanked her for letting me fuck her and she told me to clean her up, which I did. My cum doesn’t taste great, but it was still hot, and something I’m bad at doing on my own after I’ve came.

Basking in the afterglow, we talked a bit about what we did, and she asked a couple questions about the bodysuit. One of which was “was that in the men’s/unisex section?” to which I replied “I don’t think so but I don’t care”, which was a fine response. She brought up the idea of buying me lacy panties and making me wear them (would not require any convincing from me, hehe). I still haven’t told her everything, but she now also knows I want to wear makeup sometimes, so I’ve made a lot of progress!

Pushing for the most orgasms in one go with no toys! Currently at 3 but 4 seems achievable.

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.

The 13th was the last day my friend with benefits was around I don’t get to see her very often so I Saw her for like three days straight and we ended up going at it several several different times. I had never had sex without a condom before but she took one of those morning after pills and so I got to experience that for the first time and that was really good.

No real fun in the past few months, but I’ve been having interesting conversations with my queer acquaintances. A surprising number of people are ace. Celibacy makes me sad, and I’m starting to see the point of stuff like Grindr/Scruff/Recon. The trouble is that I’d really like to bottom for younger boys, and at the same time I need the emotional/sexual security that comes with a long-term relationship. So many people have never even done anal and are only “queer” in the sense of bicurious or whatever. I’m 31, I’m past that shit, and I’m seriously not happy in my own skin and need that external stimulus to get past my own complexes, and it’s damaging to be alone for too long for real.

My ex/fwb came to visit again. I was really submissive, and he did some CBT on me before we went out for the evening with some friends. We were on the smokers patio at the bar alone and he made me his ashtray which is something I’ve always wanted to try. Turns out I really like it.

Once we got back to his hotel, he teased me relentlessly. We have a fun switch dynamic, so I used his trigger to make him go into subspace and gave him 5 forced orgasms until he was a begging mess.

The next morning I made him cum once more and I didn’t cum at all by choice. Great time.