Yes, twice, in my early twenties. I was single and it was something I wanted to try. I had money I did not need to live and could put towards futile things. And both times were complete disasters.
The first was out of the spur of the moment. The escort was an older woman, cold, distant and sincerely rude. It felt obviously mechanical and detached. I barely managed to get erect and did not finish. It was paid disappointment.
The second time, I took the time and patience to call some escorts and check if the posture was more in tune with what I was looking for. I eventually found a person within my age range, that at least seemed nice and welcoming. I made an appointment and went. I got a nice shower, followed by a massage, but again something felt off.
When I looked into that woman’s eyes, which I still had not touched, I felt horrible about myself. An abuser. I apologized, got dressed and excused myself. What it has remained with me up until this day was a passing comment from her that I was “not bad at all”, as I got undressed. I’m plain, unremarkable. I can’t imagine the men she had already catered to.
A friend of mine has been a prostitute. She said it was the most fulfilling and fun job she has ever had. She loved all the different kinds of people she met. Plus being able to get tax rebates on underwear was nice.
Years after my two failed experiences I met with a former school colleague and after a long night and a few drinks, reminiscing of what had happened in our lives up to that moment, I had the honour to be confided that she was an escort.
She was adamant on how she had been lucky and how so many girls she’d met throughout the years had had terrible fates, to depression, alcohol, drugs, etc. She enjoyed what she did, it had allowed her to reach things she otherwise would have never been able to, including a college education, in an area she was passionate about, in the school she had always wanted, but a slight mistep and she could have had the same fate as others.