Your First Time...'Fess Up
farmerart
For me, I was such a workaholic that it didn't happen until I was 37. One of my guys brought his girlfriend to a Christmas party I threw for my employees. Both of them got roaring drunk, had a screaming spat, and the guy split on the girl. I taxied the girl to her home and walked her to the door. She was a crying, sloppy drunk and was all over me as soon as I was able to get her door open for her. Nice Christmas present for me! I tried to see her again but it was a one-timer only.
Two decades of lost sex; I had better live to a sexually active 95 years of age to catch up.
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My first actual FS sex with a sex-worker was at an onsite "massage" place in Philly, oh so many years ago. She was black, skinny, and didn't take off her top. She just slipped off her panties, leaned back on the bed, raised her legs in the air, and I was in. It wasn't much, but for $60 at the time, it worked for me.
Angelique at H8S last Summer!
First time with a "sex worker": 1978, 17 in a club in Ft. Erie. That *was* something (several somethings, fact) to write home about, though perhaps unsurprisingly, I didn't write home about it...
I went to a MP in Indianapolis many years ago expecting a HJ or maybe a BJ at best. She asked me to go down on her first, then she sucked my dick, and I thought that's it. But she suddenly stopped and got on top of me for FS. That's not why I went in, but who's to complain?
First time with a sex worker was a black girl I met at the Lariat Club in Fremont, Nebraska, back when Fremont had strip clubs, shortly after I moved here to the Omaha area. We ended up in a motel room in Fremont (I can't remember what the name of the place was, but it was a chain motel). This experience could have turned me off on sex with sex workers for life, but it didn't, somehow. Someone once told me once you go black, you never go back, but if they had had sex with this particular black girl, they wouldn't say that. She mostly just sat there and seemed to be going thru the motions the whole time. It's possible this experience made me suspicious of black dancers ever after.