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 :)
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? :-)
No other notes really. It was nice. We're almost certainly going to go on more dates together, but having sex is tricky logistically because we both live with other people. I did want to bottom for her but I hadn't prepared so yeah.. she did lie behind me at one point and just grind against me while giving a reach-around, which was a good alternative. TBH, I don't know if she'd want to top me. We did originally plan for anal (me fucking her) but I got overexcited with the face-fuck so we didn't get that far 😅. We'd been going for about an hour at that point so we were both happy to call it quits there for that day
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!
Wow your story helps me understand that I'm not really that subby, at least not in a BDSM sense. Thank you for sharing! And congrats on opening up to your partner. I hope this openness will help you both become even closer to each other! ♥️
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
Saturday after a whole day in the heat for the wedding
Sunday last full day in Florida
Two more things in the last week/days
I am always in awe when I read your posts. How do you have time and energy for all this sex with so many partners?? As usual, I really enjoyed reading your adventures ;)
I think a few things:
Pushing for the most orgasms in one go with no toys! Currently at 3 but 4 seems achievable.
That sounds fun!
I remember trying something similar when I was younger but my arm just got tired haha
How deep of a puddle do you melt into after that many orgasms? I'd fall asleep that instant.
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.
I'm pretty nervous about unprotected sex with women. I can only imagine how different it would feel. You're getting me jealous <3
Yeah, I've known her for a long time and I watched her take the pill so I knew she actually did and didn't just tell me she did it. You have to have a lot of trust in her to be able to do that.
There are some good short medium and permanent options out there. But not really recommended for hookups.
A copper coil worked great for us before we decided on no more kids. They come with or without hormones and will make periods worse, but then all the creampies one could dream of!
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.
Where you are matters I guess. I have many younger boys who want to top/flip for me. But some of them are too young for me, like 19 lol. Recon seems kind of intense, and even Grindr can be a lot for me. Scruff has good guys that you can know a bit before you get in bed for some fun. Would that be enough? It sounds like maybe you're looking for some fwbs.
Friends with benefits and romance. Ideally, I'd like openly queer and kinky partners who are openly queer and kinky everywhere and don't try to hide it, and for those relationships to last, and if they don't I need valid reasons why not. Maybe even marriage one day.
In terms of Recon being intense, I very much need that BDSM dynamic. I don't have to call him "master" when we're at a coffee shop because that might be weird for the other guests, but I've been a part of the kink scene for a while and see no reason to hide it. 19 can be too young depending on their level of experience. I dated a 19-year-old transgirl a few years ago who was more mature than I am now. Of course, the hillbilly community college crowd has a mental age of about 10. It's hell here.
I don't mean to complain. I very much want a hardcore sadist partner or two who participate in the community, and if 10% of the population fits the description then everyone I know is playing coy.
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.
Wow that's something I'd never heard of before. Glad you liked being his ashtray 😁
In general there were a lot of very kinky updates from folks this time. Cool to see people being more open with their partners, and with us. Thanks for sharing!