I was very recently involved in a hook up with two couples. I subsequently found out that one of the couples was actually not an organic pairing. The guy involved ( Ollie) had brought along a paid escort girl ( going by the name 'Brandy' ) I know Ollie from my social circle but not well so had no idea he was actually single. To be fair he didn't introduce her as a girlfriend just as a friend. In retrospect I am not bothered in the slightest that she was a paid escort but I have never before sexually engaged with a sex worker. ( I have in the past given it consideration though) I only discovered Brandy was actually a paid escort because I asked Ollie if he and Brandy might want to hook up again. He then confessed that she was not actually a friend of his. I am thinking of taking advantage of her possible availability for future fun.
Ollie told me he will contact Brandy and give her my e-dress. I am thinking I may ask her to fuck me with a strap on. She looks a lot like a girl from a place I worked and I have fantasised about being fucked by her.
I think my confession fits here. Many years ago I was seeing a masseuse and I wanted lots of happy touching before the happy ending so anytime what was already feeling good started feeling REALLY good I pretended the stimulation was too much and she switched. It prevented the ejaculation and after a while I would tell her I was able to “take it again”; going back to the way that brought me close to finish. When I could tell she was likely going to get tired or sore I let her finish it. For me the experience was not just the orgasm and ejaculation, it was getting more desired stimulation before the even more desired finish.
I used an escort only once during a trip out of town. I used an app that came recommended by two different friends (one genderqueer and one cis-female.) It was kind of like the OnlyFans of escort apps, where the people all supposedly worked for themselves and it was very safe and sex-positive oriented. The escort profiles all required a screening process that required customers submit proof of a recent STD test and the results. I'd wanted to try it because I was still reeling from a terrible breakup two months later and didn't feel like dating anyone. I thought hooking up with someone under purely transactional circumstances might be a good way for me to start dipping my toe into seeing people again. I was also leaning more and more into my desire to engage in pee-play with a woman and, again, felt a certain amount of safety in trying that in a transactional encounter. But it ended up being a total disaster and did not supply me any kind of relief. The girl was not the one in the pictures. She wasn't ugly, but totally different hair color, and height, and body shape... etc. She was from Kazakhstan and clearly worked for a service that was using the app to post a generic profile, then sending whatever girl was available. I made small talk with her asking how long she'd lived in the city and it was fairly recent. She said she had friends who already lived there and encouraged her to move out too. Which made me uncomfortable, as I got the underlying message this girl's situation was somewhere in a gray area that wasn't exactly forced prostitution or trafficking, but probably wasn't too far off from it either. Where her friends probably moved to the US, got jobs as sex workers and probably encouraged this girl to come out too, possibly because the guys who ran the service asked them to bring in more escorts. On top of that, she did not do pee play and did not let guys eat her out (the only two things I wanted to do.) I didn't want to have sex or get a blow job, nor was I able to get an erection anyway because I in such a fucked up headspace, and the anxiety over ordering an escort and worrying if I was gonna get ripped off made that even worse. So there was this awkward impasse between me and this poor girl who had no clue what to do with a customer who doesn't want the two central services she offers. She was willing to masturbate for me, and did that while I played with my soft penis. I didn't really believe she was getting off so it was not exciting at all. Then she kinda threw me a bone and humped my dick and as she did it, I got semi-hard and managed to cum on my stomach. She asked to use my shower and I said yes and asked if I could shower with her. That also was not on her menu. Which I could understand. So, I asked if I could at least watch and she let me stand in the bathroom while she showered with the curtain open. In another very kind overture, she said, "Look," and held open one of her legs and pee'd in the shower. Which didn't do much for me but it was a very kind way of saying "Sorry I didn't do the stuff you wanted. So, here, I'll give you this." And the sheer thought of it, and her ability to notice I was going through a sad time in my life, did cheer me up a bit. I called her an Uber. Thanked her for coming. Asked if she needed me to wait with her until she got in the car. And she was gone. I basically paid $1,000 to be able to tell myself, "Well... Now I've done that!" Oh, and also have a goddamn week's long panic attack until I was able to get an STD test done, since I didn't have a condom on when she humped me.
