I'm 28, a moderately successful and over-educated white guy and I've been seeing prostitutes for about 2 years now.
It started after a really horrible break-up, a death in my family and a job loss all occurred within the same 3 month period. I was dealing with things that were just awful and horrid (wakes, unemployment, depression, relationship dramatics) all the time and I was on the verge of losing it. I did have an inheritance so money wasn't tight at least.
I was on Craigslist one night, bored, lonely and horny. So I wandered to the Erotic Services section. I was pretty put off by most of the ads. I consider myself very liberal and think of the sex industry as generally pretty exploitive and cruel. Seeing all the ads that were clearly put up by very desperate women was anti-arousing really.
Then I saw B's posting. She was a curvy artist who described herself as a 'courtesan'. She posted a Jean-Leon Gerome painting of a reclining Harem girl instead of a face picture. I was curious, called her and booked a session.
She came to my place and was absolutely wonderful. We talked about art, music sex-positive porn, genderfucking, queer theory and BDSM. I've always had kink in my heart but hearing someone so open, so free in expressing it was wonderful. She was an amazing lover and I enjoyed her company as much as the sex. I felt free to experiment, to play and because it was a professional exchange I didn't feel as shy. Not that I was disrespectful of her, but asking your girlfriend to us a strap-on has a lot more nuances to it than asking your 'courtesan'.
I started seeing her once or twice a month and have kept on doing so even though I've been in relationships. I won't lie and say I don't think of it as cheating, it is. I finally stopped when I met a woman who, to be honest, shared a lot of similarities with B. I told B about this and she wished me nothing but happiness. We've spoken a few times since and seen each other socially. It's a bit like work friends after one person has moved to a different job.
B was an eye-opener in a lot of ways. Most of all, she showed me what I really wanted in a partner. My girlfriends before had been very much the type of women I thought my family or friends would approve of. After B I knew I wanted someone who shared not only my kinks but my passions as well. I'm really grateful to her. I've had friends comment on how I've changed and how I've become so much more confident and assured. In no small measure, B is responsible for that.