We had an interesting Saturday night. We went out with a friend who’s going through a messy divorce. Said friend is also quite wealthy and has a bit of a phobia about women who are after him just for his money. And well within reason, I’ve seen the way women lose their goddamn minds around him. It gets nasty, women swooping in to sit next to him as soon as another girl’s gone to the bathroom. Said girl gets back and stares daggers at the girl who’s ‘stolen’ her spot. He had one girl talking dirty to him while her boyfriend was on the other side of the room – and was a friend of his. So fucked up.
Anyway, long story short, he’s developed a bit of a thing for high class escorts. I first witnessed this quite a few months ago, we were out one night with a group of friends (three guys, two girls) and the subject came up. Next thing I know, he’s booked a hotel and the two of us are picking the girls and I booked them on his card over the phone. The first two girls were not that attractive or fun so we didn’t extend. But the next two were hot and fun and they basically just partied with us all night. I think my friend may have tried to have sex with one of them but was too drunk.
This weekend was a bit different. For one thing, I got to do all the ‘girl shopping’, which was fun. The girls joined us at the nightclub we were at and then we all went back to our house. I don’t know when the decision was made to take one of the girls to our room or when we decided who went with who but it happened pretty quickly. Our friend stayed out on the couch with the other girl. An awkward moment ensued when the agency called and I had to run my phone out to him and I walked in on him mid-fuck. Definitely not something I needed to see and I doubt he was enthused about having a phone shoved in his face at such a moment. Ahhh, so many adventures.
On a side note, I escorted for maybe six months in my wild and crazy youth but, aside from when I was working as well, I’ve never actually been with one (although I did contemplate hiring a male escort). I’m not sure I’d make it a regular occurrence. She was very nice and she sat and chatted with us afterwards but it was quite impersonal. I can’t remember her face and I doubt I’d recognise her in a crowd (granted, I wasn’t sober).
I’m not ashamed or regretful but I probably wouldn’t rush to repeat the experience. I want everyone to be a willing and enthusiastic participant and I think, as soon as you’re paying for someone’s time, that line becomes blurry and it’s hard to know if they’re into it. Of course, she could have had a great time but the cynical part of me thinks probably not.