I might make another comment here with a longer story but here’s a quick one:

Second, after it had been about 2 weeks since I’d came (sickness + a houseguest), my goddess decided it had been too long. Of course, I made her cum before she even touched me. Then she edged me a good ~10 times. She called me “good” after each time I told her I was getting close, which I thanked her for. It was the most I’ve ever been edged, I was making some really pathetic moans at the end. She climbed on top to finish me off inside of her. I kept getting too into it and moving my hips too much, which meant I fell out of her a couple times. I had to learn to let her do her thing and not give into the urges. Eventually came inside her and thanked her.

Some nice naughty fun, but also a good chunk of way more chaste dating fun to share!

Naughty:

• A younger tall lean muscle guy was going for a jog in the neighborhood, invited him over to get a bj. Fun cock to suck on, not too big. He had a rough/dom side which was fun for our play. He needed to cum by jacking off, which I’m not a fan of, but I understand some guys have difficulty with that. Decent range
• My well-hung sub neighborhood friend really wanted us to get together again. I went over and locked him in chastity again, then had him suck on my cock for about 40 minutes. I would play with his balls or his hole at times. Feed him poppers, make out with him a little, too. He’s been locked up for a week now while I was out of town. I told him to go to the gym and sauna and show off a little, just like he normally does. I’m waiting to hear back on how it went.
• Later that day, I went to visit a new friend in Brooklyn. Tall, blond, nicely muscled. We hung out in his apartment, played with his dog, made out, and got naked. Very fun to rim him. He wanted to bottom for me, but he didn’t have any lube!! We tried without lube, but I could feel skin on my penis beginning to tear. So instead I had him finish the blowjob my sub friend started, and played with his nipples while he jacked off.

Nice, a bunch of first dates:

• Met a younger guy to check out Fotografiska, a photography museum which is closing in a couple of months. Had a yummy lunch at a nearby diner afterwards, including some legendary onion rings omg. He’s cute, otter-type, nice legs, definitely would like to see again.
• Met a Long Island woman for coffee and snacks at this weird eclectic middle eastern + south asian + north african cafe. Nice conversation. Not sure if we’re a good personality fit, but I asked her out to dinner next, and let’s see. Gorgeous legs, sweet smile, and razor sharp intellect.
• Met a nurse in his neighborhood in Brooklyn for lunch. He showed me this cool cafe with some awesome local art and sculpture for sale. I’m tempted to be naughty and go buy this expensive vase I like. We chatted some more outside and had a few smooches. It was really fun to feel that even a couple of light kisses were enough to start getting me hard :-)

Observations:

• I do enjoy being dominant and a little rough. A lot. I don’t need it for sure, but it’s fun. A willing sub is an opportunity for me to be creative.
• Dates are really fun for me right now - whether they get physical or not. Though if they also get physical that’s even better :-)
• I am getting aroused way more easily recently. I think I’m getting more comfortable with my own sexuality and vulnerability and it’s paying off in how I feel and express affection and arousal. A few light kisses have never affected me like that so easily before.

2 weeks ago I met a chastity bottom and stayed the night at his place. Ate his beautiful ass that tasted like strawberries. He’s a gorgeous femboy type who takes good care of himself, and looks younger despite being my age. Too bad he ghosted me.

Now I’m in touch with a similar type of guy, potentially to meet in the next week or two. Frustrated that I can’t make it an ongoing thing with my exact type. This new guy wants me to piss on him and calls me “master”, so maybe he’s kinky enough to not get scared off.

Last night, me and my occasional FWB had sex. We started with me lying in the armchair while he rubbed his cockhead all round the area turning me on and coating my entrance with his sweet precum till I was really very wet and slippery. He milked my precum into the mix too. Eventually I was jst desperate and got him to sit down on a seat and then I slowly sat on his cock. The feeling of his cock inside me! We took it slow and it was intense. I could tell when he was about to cum and everything speeded up a bit even though we were really trying to take it slow and sensual, and I started cumming, so did he and I knew his sperm was being pumped inside me. Usually he pulls out and cums pressed against my crack, but last night I wanted him to stay inside me while he came. We’re pretty good at cumming together, mainly because I can really tell when he’s close and it’s the sexiest thing in the world to know he’s gonna cum.

I’ve been horny all day now!

Very little unfortunately on my front. I’ve been stroking to porn quite a bit but nothing outside of that. The orgasms have been pretty good though. Wouldn’t mind more than just porn.