After quite a bit of research I was recently able to pin down the date of the first time I ever saw a Sex Worker. It was September 2, 1999. Her name was “Heather” and she came to me from an Escort service.
I have to admit, I was nervous as hell that day. I had made the appointment earlier in the day, mostly on a whim. I had never been with a Sex Worker of any kind. I hadn’t even been to a strip club yet (though I soon rectified that). Up until this point I had only had any sort of sexual contact with just 3 women, and only had intercourse with two of them. To say that I was sexually inexperienced would have been an understatement.
At the time I was 22 years old. I had only recently moved to Fresno, CA to go to university. I was single, horny, and had a fair amount of money in the bank. I’d already picked up a part-time job and—overall—things were going pretty well for me. Except when it came to the ladies. I’ll be honest, I had no “game”, as they say. I’ve never been good when it comes to flirting and have never once successfully “picked up” a woman. All of my personal, romantic relationships in life have always started out as friendships.
So I was already feeling very lonely. Before moving to Fresno I had never really considered being with a Sex Worker. It was just not something that ever came into my mind. I had never tried, never even thought about trying. But things changed. Maybe it was the act of moving out on my own that created a willingness—truly, a desire—to do new things. I had seen numerous ads for escorts in the Classified section of the newspaper. Yes, back in those days, ladies and agencies used to advertise in the paper!
I saw an ad that day and decided to just do it. I really had no idea what to expect. The ad had been for Heather, but the call went to an agency. I asked for an appointment, got the time scheduled, and that was it. No actual screening process. The agency gave me a description of Heather: 26 years old (though I think she was closer to 36), 5’8”, 115 lbs., blonde, with blue eyes. I asked that she be dressed modestly (I lived in a fairly busy apartment complex).
When she arrived She was not dressed modestly at all. She had on a long black dress with slits that went all the way to her hips and a neckline that went down to her belly. I could see her out the window as she walked up to my door. I was surprised to see a man walking with her. Her driver/security. I didn’t know anything about that yet. A knock on the door and a hello. She asked for her fee right then and there. I’ll admit, I was hesitant to hand it over for a moment. I honestly thought she might just take the money and go. But she didn’t. She just handed it to her driver. He walked away and Heather came into my apartment.
I think she could discern that I was terribly nervous. She worked quickly to put me at easy. She looked through my CD collection and found something she liked. The music helped settle the mood nicely. We talked for a couple of minutes and then she slid onto the floor in front of me. I won’t go into the sexual details (The ValleyScott Blog is not that kind of website), but I will say that we did quite a few sexual things. Looking back, I can say that it wasn’t the best of sessions—fairly average compared to all of my experiences since—but at the time it was quite the sexual exploration for me.
We finished our pleasures just as the hour was ending. She dressed and left. I showered and reflected on what had just happened.
To be totally honest, I was a little freaked out by what had happened. I couldn’t believe what I had done. I guess it was a combination of nerves and adrenaline, but I actually got the shakes afterward. I was shocked by what I had just done. I was shocked at how easily I had been able to have a woman come to my home and have sex with me. I was shocked at how easily it had been for me to have sex with her. I was shocked by how casual the entire experience had been.
Up until this point, my sexual experiences had been linked to intimate relationships. Love, of some level, was involved. The sexual acts had been a culmination of friendship, followed by dating, and a slow progression from kissing to more intimate activities. But this, this had been totally different. A complete stranger had been naked and performing oral sex on me within minutes of meeting her. My mind was having a difficult time assessing the situation. I had just paid a woman to have sex with me.
The ethical and legal questions bothered me for hours, as they collided with the confusion over the event itself, as well as with the morals of my upbringing. Looking back, I can honestly say that as a 22 year old man, I was not fully mature enough to handle what I had done. In some ways, I wish I had waited until I was older to start seeing sex workers.
It took me a few days to calm down. Afterwards I found that I was a bit dissatisfied with the overall encounter. She wasn’t all the pretty up close. Her body type was not really what I liked best. But I also felt happy with it. I felt like I had done well. And I figured that I could do it again, and do it better, if I wanted. I waited about 4 weeks before I tried again. The second time was better than the first. She was more to my liking, in a physical sense. I was not any less nervous. This was the pattern for me for a while. Over the following months I would learn the basic rules of seeing Sex Workers (though they often have their own rules), and I would start to feel comfortable with being a client.
Over the years I have seen many different women. Hundreds I guess. I never counted. But I still remember Heather. She was not my best, but she was my first. I do hope that where ever she is today that she is happy and living the life she wants to. If you happen to read this, Miss Heather: Thank you for being my first and taking me on my first adventure in Consensual Transactional Sex. I’ll never forget you!
[“Before ValleyScott” is a series on my experiences before I became the Hobbyist I am today. I wasn’t always the man I’ve become known as within this community.]