After a couple of years of living in a small city I had got into the habit of picking up the local free paper – every town has at least one. It has concert listings, usually has some indie band on the cover, or else some one of local interest and the articles and editorials delve into the minutia of local politics and local zoning squabbles. Every North American city I've ever visited seems to have these, and in most, the back few pages are always the same, some sex advice columnist and adds for escorts, phone sex chat lines and other "adult" services.
I'd been leafing through these for a long time, and over time had noticed that the escort ads really boiled down to two types. The short little text ads that really didn't say much, and the more elaborate ads for agencies. The agencies always have names like Sultry Rose and Secret Escape or what have you, and they always featured some stock model, or occasionally a pretty girl with an obscured face and the words, "Real Photo!" There was one ad that caught my eye more than the others, I don't know what it was, if it was nicer, or maybe it had run longer so I noticed it through repeated exposure – whatever the reason, one day I got curious and decided to call.
A girl answered, I asked how much and she said $80 for a half hour and $120 for an hour. I told her I'd never called before and wasn't sure what to ask next and she told me that I could chose a girl from the descriptions she had and then come in. It hadn't occurred to me that I would go there, I assumed that this was an escort agency and that they would send the girl to me. I asked about that and she said that they did do that, but that there was an additional charge. I told her not to worry and that I could come to them.
She started reading from a list of girls with descriptions like:
"On tonight is Amber who is a beautiful and sultry blonde, she's busty with long curly hair and blue eyes. Also available is Melissa, a slim and perky brunette, she's 21 years old and has a playful attitude."
It was a little weird, like choosing from a menu, and I couldn't stop wondering who wrote the little descriptions, if the girls had to do them themselves or if the agency did it for them. I let her prattle on for a bit and then said, "Listen, I'm 22, if possible, I just want a pretty girl my age." She laughed and suggested a girl, gave me an address and instructions on where to park and then told me to be there in 45 minutes.
The address was a little bit of a surprise, I had a couple of friends that lived near there and it seemed like a normal white bread neighborhood. I drank a beer, then drove over. The house was basically a normal house, set a little further back from the street than the others on the block, and surrounded by high hedges on both sides. Because it was near the corner of the street and because of all the trees and hedges in the neighborhood, it occurred to me that the neighbors wouldn't see men coming and going at weird hours.
I walked up to the front door, rang the bell and was let in.
The inside looked like a normal house, if not a little darker than normal since all the curtains were drawn. The woman who let me in was a really pretty, tall slim with Italian looks; long straight black hair, dark eyes and a nice smile. She wasn't wearing anything special, just jeans and a black sweater, and she wasn't wearing any make up. She asked my name and who I was here to see. I had forgotten the name of the girl they had suggested so she went into the other room to ask. When she came back out, she had a bit of an embarrassed smile. She said that the girl I had requested was running very late, and if I wanted, I could choose from one of the other girls that were there.
"What about you?" She seemed genuinely surprised and oddly enough, a little flattered, at the suggestion and said that she didn't usually do that kind of work, that she was really mostly an exotic dancer. After a second's hesitation, she smiled and asked if I was sure I didn't want to see any of the other girls. I was sure, this girl was hot, and she seemed really nice.
She sort of smiled and shrugged and led me into a bedroom. She seemed to suddenly be seized with a bought of self-consciousness and started apologizing for not being properly shaved "down there", not having any make up on, and generally looking like a mess. I laughed at her, told her I thought she was really beautiful, and that I was really excited. She asked if I had done anything like this before, and in a quick bout of forgetfulness, I told her that this was my first time. I gave her the money, $80 for a half hour, and she left the room for a minute.
Before leaving she told me to take off my clothes and to try to relax. I was nervous at first, but there was something just so genuine about this girl that I did start to relax. I stripped down to my boxers and sat on the bed, wondering what to do next. She must have decided that I would have at least asked to see the other girls if I didn't think she was attractive, because her little bout of self-consciousness seemed to disappear when she came back. She started to wiggle out of her clothes in a sort of hurried strip tease, not really dancing, but clearly putting on a show.
Now, this woman was probably at least 5 or 6 years older than me, maybe even more, but she was smoking hot. She had a dancer's tight body with great abs and an awesome ass and legs. I couldn't tell if her boobs were real, but they seemed big for such a trim figure, definitely C-cups, and perky. When she dropped her bra and panties, I was incredibly turned on. She told me to lie on my stomach and she'd start me with a back rub.
I was a little annoyed actually, because I just wanted to look and touch, but I did what I was told and let her rub my back. In retrospect, it was really great. It helped me relax, it was intimate without being too intimate. We made small talk as she rubbed my back, and she asked why a young, good looking guy was hiring a pro. (That's the word she used, "a pro".) I told her the truth, that it was curiosity mostly, that I'd been noticing the ads in the newspaper for a long time and I just got horny. University was great for getting laid, but a little unpredictable, it always seemed to be feast or famine when it came to girls on campus. She laughed and asked me about what I was studying, where I was from and told me a little about herself.
Eventually I turned over and things got really fun. I kissed her almost all over, she did the same to me and then, after pausing to add a little lube and put on a condom, we got down to the actual sex.
It was awesome! It didn't last nearly as long as I would have liked, maybe 10 minutes total, but it was a great 10 minutes. She seemed to be genuinely trying to enjoy herself, which really turned me on. Since then, I've really enjoyed sex with a pro where it was all about me, but that time, I really liked that she was trying to get off too (or did a convincing acting job). She was even telling me where to rub or what positions were working for her. She obviously didn't get off, but she really turned up the heat when it became obvious that I was getting close. Between coaxing, talking dirty and generally encouraging me to increase tempo and depth of the thrust… man, great orgasm. I've had a lot of mediocre sex with pros, and a lot of good sex with pros… but that time still stands out as one of the best.
Afterwards she lay there with me for a few minutes before getting up to get me a hot towel to clean up. She put on a little kimono and came back with stuff for me to clean up. I was still pretty young, and by the time she came back, the sight of her in her half open kimono was enough to get me hard again. I didn't ask for another go however, because I didn't have any more money. I cleaned up, got dressed and left in a pretty good mood.
This was the start of a pretty good little working relationship with this agency, even as it changed and continually re-invented itself over the years. One thing, I did try to make another appointment to see the same girl, but they told me I must have been mistaken since she only did shows and bachelor parties, and she didn't sleep with clients. I tried to explain that "it was me" but I never managed to book another appointment. I considered hiring her as a stripper just to get her to my house, but they charged so much more for that that in the end, I just experimented with the other girls there.