Straight Male / 42
Browsing Led To Buying...
Back when Craigslist personals was a thing, I browsed the Casual Encounters section regularly. I was looking for a real woman to hook up with--hopefully someone discreet with a loveless marriage similar to mine. It only happened once. I got lucky at a conference in Boston and had amazing sex with a grad student who posted an ad for a quick orgasm.
A couple of years ago, I was searching for the next Craigslist, but only finding ads for escorts. I searched all over, and eventually found Skip the Games, which seemed like a pretty straight-up advertising service for working girls. I browsed my area weekly, titillating myself with the possibility. After a while, I noticed the patterns: some ads were too good to be true, some were clearly guys, some were so vague as to be impossible, and some looked legit. Once I found a review site, I took the plunge and met a woman at a hotel on the way to work. For $150, she sucked me almost to the point of orgasm, then slid a condom on me and rode me slow and deep until I exploded. She was good, but not really my type in person, so I thanked her and moved on.
Since that time, I've been scared a couple of times but had no problems. Every couple of months, I try a new woman. I've gotten head in the car at a public beach from a chubby redhead. I've worked hard to get my dick inside a super-skinny tattooed girl in a shabby apartment. I've had several unenthusiastic blowjobs that I had to hand-crank myself just to finish up and get out of there. On two occasions, though, I met happy, beautiful women who seemed to genuinely enjoy their work. I'm not rich enough to make this a more regular thing--it's more a case of stashing 20's periodically than anything--but I love the thrill and the danger.
A couple of years ago, I was searching for the next Craigslist, but only finding ads for escorts. I searched all over, and eventually found Skip the Games, which seemed like a pretty straight-up advertising service for working girls. I browsed my area weekly, titillating myself with the possibility. After a while, I noticed the patterns: some ads were too good to be true, some were clearly guys, some were so vague as to be impossible, and some looked legit. Once I found a review site, I took the plunge and met a woman at a hotel on the way to work. For $150, she sucked me almost to the point of orgasm, then slid a condom on me and rode me slow and deep until I exploded. She was good, but not really my type in person, so I thanked her and moved on.
Since that time, I've been scared a couple of times but had no problems. Every couple of months, I try a new woman. I've gotten head in the car at a public beach from a chubby redhead. I've worked hard to get my dick inside a super-skinny tattooed girl in a shabby apartment. I've had several unenthusiastic blowjobs that I had to hand-crank myself just to finish up and get out of there. On two occasions, though, I met happy, beautiful women who seemed to genuinely enjoy their work. I'm not rich enough to make this a more regular thing--it's more a case of stashing 20's periodically than anything--but I love the thrill and the danger.
- That's Juicy! 24
- Remove It! 2
