Fun with Pros

The first experience I had with a sex worker (from an escort service) was in 1986. For the next six years, I probably had such an encounter about 4 times a year. At the time, I lived in a city where streetwalkers were plentiful, and was fairly close to the Bay Area (San Francisco/Oakland) where "massage" parlors and strip clubs (with private rooms) were easy to find. Of course, every time I went on a business trip, I checked out the local action, whether incall in some form or fashion, or outcall via the friendly local yellow pages.

After several such encounters, I was given a hand-me-down VHS-C video camera, so it was obvious to me that I should record my exploits for posterity and for future masturbation sessions - the internet effectively did not exist at that time, so posting my adventures was not a driving force.

After that first six year long period of easy access, I moved to the other side of the country, and much to my chagrin it was MUCH harder to locate these services in my new environment. My rate of paid sexual encounters dropped to about 1 or 2 times per year, being highly dependent on business trips, which I took only occasionally. Starting in about 2000, my out of town trips decreased even more, so I had very few opportunities, and other exigencies of reality clamped down on my ability to hire sex workers. The last time I paid a live person for sexual services was in about 2003, in Albuquerque. I do miss this a lot.

Massage parlors and strip clubs would not allow cameras, so my video sessions were restricted to outcall and streetwalkers. Also, my camera was so bulky that it was problematic to take on airplanes, although I did a couple of times, notably on a trip to Puerto Rico where I hired an ex-porn actress that was then in the "massage" industry, but did outcall as well. These factors, combined with the limited local opportunities after 1992, means that I only have video for ten of these encounters.

A detailed account of my exploits with "pay for play" will appear in my upcoming memoir covering my sexual escapades over a span of more than 60 years now, starting with agreeing with the little girl down the street to watch each other piss when we were 5 years old, but that is a long-term project.

Here, however, I simply intend to give a little context for my "Fun with Pros" series of videos for those who are interested. The pros are numbered in chronological order that I encountered them, but the postings are in a completely different order. I hope this is not confusing.

Pro #6 - Video 169 - about 1991: Posted 2018-07-27.
This was probably the cutest girl I ever hired (sorry I felt obliged to obscure most of her face). I picked her up on the street in the city where I lived and took her to a motel room rented specifically for this purpose. If memory serves, we agreed on $80 to let me watch her masturbate, pee on her tits, and cum on her pussy.

She did a good job of finger-fucking herself, then I gave her a bra I had brought specifically to piss all over. She was a little embarrassed by that, but she was a trooper and I had a fine time pissing on and in the bra while she was wearing it.

After that, I wanted her to pee with a dildo in her pussy, but she was unable to do so, and even without the dildo, no urine was forthcoming. A shame. She said nobody had ever asked her to piss for them before, and I think she was too embarrassed to relax enough to pee.

After that, I had her stick the dildo in her pussy while I jerked off on it. Oh my, that was delightful.

If I had ever seen her on the streets again, I would definitely have reengaged her.

This is essentially all of the footage I have of this encounter. Only minimal editing has been done to obscure her identity and remove a few frames with distortion from the VHS tape. I intend to do a better editing job at some point in the future.

MORE CUMMING SOON...
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i love sex workers, mostly honest and usually better at sex than amateurs 
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Ukwanker57
Really nice bit of writing...
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