I almost had sex with a Formerly Male But Hence Undergone A Gender Operation Which Made Him Look Like A Woman Person (is that politically correct enough? and am I allowed to say “prostitute”?). It was not out of choice and in the end nothing happened.
It was my 21st birthday and I was flying through Athens, going from one concert to another. My manager picked me up at the airport and since we had several hours to kill and it was my birthday, he insisted that we do two things I’d never done before: drink beer and have sex with a prostitute. Both were a disaster.
Even though I drank a lot of alcohol at the time, beer was never my thing (I still hate it). But I was forced to drink a whole bottle, which tasted like urine mixed with tonic water. It was supposed to be a good brand.
Then we went looking for prostitutes, except that we were too late and all the good ones were gone. The ones we did see were so old and ugly, that I said “I’m not paying for that! I wouldn’t have sex with her even if she had to pay me”. Eventually we see two gorgeous girls in a car (and yes, you know where this is going). We were not sure if they were prostitutes or just two girls waiting for their boyfriends. We didn’t want to offend anyone, so we just parked behind them and waited, and sure enough, men would come up to the car and talk business. To cut a long story short, a few minutes later we end up in the dirtiest hotel I’ve ever seen, one of those where you get charged by the hour, and I’m naked with a condom in my hands but erection. I don’t know whether it was because it was paid sex (I’ve always felt that you need the romanticism even for a one-night-stand) or whether I had felt that something was wrong with that woman with the perfect breasts (that would not take off the bottom yet). I just couldn’t do it, so I paid her and put my clothes back on. It was only then that I realised she was a he, through a comment (s)he made.
The funny bit is when my manager came out, more than half an hour later. As we left I whispered: “did you notice anything weird about yours?”
“no idea. It was great”
“is it possible that…”
“who cares? A hole is a hole”
which tells you all you need to know about his sexual preferences lol