Memory Lane

I have a book shelf that has old notebooks from school, day planners and such. I recently decided that it’s time for a major purge so I’m sorting through all of it and throwing out what I don’t need.

Going through the pages of one of the day planners I came across one of my first web-based sex work experiences. Scribbled on the back of a printed email is the name of a store and cross streets in San Francisco. That was where I met him at- across the street from his apartment. And his phone number, just seven digits, because everybody in SF has a 415 area code.

He had posted an ad on craigslist.org seeking a student who’d be interested in mutual masturbation. I was about 20 or 21 years old. At the time I lived outside of San Francisco. I had been a dancer, but there weren’t many dancing opportunities in the town I’d moved to. So I sought out sex work opportunities in the Bay Area because it was the nearest city where the sex industry was easily accessible, but it certainly is not the only city where the sex industry is easily accessible.

So I replied to his ad. Sincerely able to say “I’ve never done this sort of thing before.”

The idea of going to a man’s house and letting him watch me masturbate really turned me on. Getting paid for it was even better. But obviously, I had safety concerns. Was he really going to respect my boundaries and not touch me? What if he was psycho? I didn’t really know what to expect, but how would I know if I didn’t just drive into the city and find out?

He asked me what sort of porn I like to watch. I told him girl-girl porn because I was mostly into girls around that time. I took all of the safety measures that I could think of. I gave the address and his phone number to a friend and promised to call her when I left his house and when I got back to my place. I did call her when I left, but I forgot to call her when I got home. I was so tired I just fell asleep. A mistake that I will never make again. It’s not fair to leave people who care about you to worry. Especially when they’re being supportive of your choices and helping you be safe.

So after many emails and phone calls I finally felt safe about going to SF for the meeting. I was excited all the way there. It was one of the most outrageous decisions I’d ever made. But I felt prepared and equipped to make that decision. I felt very safe after some investigation and planning with friends. If I had been driving into the city with nobody looking out for me I may not have been so confident. Having a friend who knows what you’re doing is so valuable.

I didn’t even have a cell phone at the time. When I arrived at the store he was there to show me where to park. He was in his mid-30’s, balding a little bit, about 5’10”. A little over-weight, but not obese. I could tell he was nervous, which somehow made me feel relieved because I wasn’t nervous at all. I think in that moment I understood that I was the one with the power, even if I couldn’t articulate that feeling at the time.

So we went up to his apartment. It was a typical one-bedroom in San Francisco: wood floors, tiny kitchen with tiny bathroom that hadn’t been updated in at least ten years, a decent sized bedroom and a living room. He was a bachelor working for some tech company that was probably later bought out by Microsoft or Oracle.

When we got into his apartment $200 was sitting on the counter. He just sort of waved toward it then offered me a drink. I asked for water and slipped the cash into my purse. Then I used his phone quickly to check in with my friend.

I was happy and enthusiastic. It was obvious that nothing was going to happen if I didn’t initiate it. So I jumped right in.

“Let me check out the movies you got!”

“Oh, they’re in the bedroom,” he said in a mumble. Now I was starting to have sympathy for him. He was so nervous! I wondered how long it had been since he’d had a girl in his apartment.

I went into the bedroom and chose from three videos. I opted for a dvd with a three-girl scene. Why not? He put in the video and then said, “Uh, I got you some toys too.”

“Yay!” I was genuinely pleased about that.

He handed me a package that had a little mini-vibe plus additional attachments. Perfect.

I didn’t see any reason for making conversation. It would have just put more stress on this socially awkward guy. He wanted to hang out for a while with an adventurous woman who would show him a good time. So I did.

The girls in the movie were hot and it had some elements of kink with boots and riding crops. I liked having the movie there for both of us to look at in order to avoid awkward interactions with each other. But what I really got off on was being watched, and knowing that he was getting off on watching.

So we masturbated for each other while watching porn. Nothing too kinky or unusual. He was very respectful. He didn’t make any unwelcome advances. He seemed to understand that if I felt comfortable that I would take the experience to a fun place that was pleasing to both of us.

As we watched the movie and played with ourselves I got more and more excited. I took one of his hands and placed it on my right breast. I turned so that he was directly in front of me and placed one foot on each side of his body so that I was straddling him, spread eagle with a clear view of my pussy while I massaged my clit with the mini-vibe and fingered myself to climax. I felt him squeeze my tit harder as he moaned and came into his own hand.

“Wow! That was fun!” I wanted us both to feel good about the experience. I knew that his pleasure was reflected in my pleasure. And I genuinely enjoyed myself.

He was shy, but clearly happy. He offered me a clean towel if I’d like to have a shower. I accepted and quickly rinsed off, sure to take my purse and all of my clothes into the bathroom with me. He seemed nice, but I was still protective of myself and the money I’d just earned.

When I came out he had a bottle of water for me and smile. He thanked me for coming with a shy giggle. He was sweet and I was happy to have shared the experience with him. I used his phone quickly to say I was heading out the door. And I left.

On the way home I stopped for gas and realized that I was standing at the pump with a huge grin on my face the entire time. It was kinky and fun, and I’d just made in one evening what I was used to making in a week. Suddenly, so many options were available to me that I’d never had access to before…

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