The first time was when I was 19, high on drugs and fed up with being a virgin. I did a lot of stupid stuff when I was a teenager, and this was one of the less stupid things. My parents were out of town, and I called an escort. An hour later a skinny, not unattractive blond woman at least six years older than me stood at my door. She was friendly, erotic and obviously quite experienced. It was good, though I wouldn't call it fantastic, and I wasn't a virgin anymore.
My experiences with paid sex have been varied since then. I don't consider myself a 'regular', as I don't have a fixed agency nor a specific brothel, and I don't do it more than maybe a few times a year. But I'm probably the type of guy the sex industry thrives on.
In my mid twenties I was on anti-depressants for a while. One of the side effects of the drugs was that I was perpetually horny, and ironically enough the drugs also made it very hard for me to reach orgasm. I went to a brothel I'd heard from through an acquaintance, the first time I'd ever been in a brothel. Until then escort agencies had been my suppliers of choice.
The girl was stunning. I could barely believe she was in the industry. She turned out to be distant, however, and a bit too professional. I didn't reach orgasm, which I assured her was no fault on her part, and the look she gave me told me she was well-aware that it wasn't her fault.
I quit the anti-depressants shortly after that, having overcome my demons in a more traditional way - by growing up. I continued with the occasional escapade with working girls, when I could afford it and was sufficiently deprived. As my career advanced and my salary increased, so did my visits to brothels become more frequent. I even gave a friend of mine a brothel-visit as a birthday present. He appreciated it.
In my country prostitution is legal and brothels have standards of safety and hygiene to adhere to. As such I've never been too worried about the health of the working girls I've been with, though of course condoms are always used. I wouldn't want to go without them. The thing is, I like going down on women. I like it a lot. The last time I made a visit, I chose this tall, thin brunette with nipple piercings topping her small breasts and a few tasteful tattoos adorning her lean frame. Her eyes smiled as she was introduced to me, and more than anything else that's why I picked her. I went down on her for a full half hour, and after she came (or expertly faked it) she panted that this didn't happen often to her. Whether it was professional courtesy or not, I appreciated the comment. The subsequent fuck was intense and a lot of fun, as if she wanted to repay me. A memorable experience.
And probably my last one. That visit was made when I'd been dating someone for a few weeks. The sex with my new girlfriend wasn't great and she didn't enjoy receiving oral, hence my urge to visit a brothel again. I cheated on her, and now that our relationship has grown it bothers me more than it did then. The sex is still bland, but that is something we can work on, and our emotional bond is much more valuable to me. She hasn't been with many men, and while she knows I've had a more active sex life than her, I haven't the heart to tell her most of my sexual partners were paid ones. Even in my country that's a taboo, a stigma that marks you as a loser. I disagree with it wholeheartedly, but that doesn't make the prejudice go away.