First Time With a Prostitute
My first time was with a prostitute. I was eighteen, and I had just moved to the big city. I came from a conservative, sexually-repressed family, and I was still very shy around girls and had no idea how to approach them sexually. I discovered these magical ads in the back of the local free paper. They were for "escort" or "massage." When you called them, a sexy-voiced woman would answer, and she would quote you a price for "full service." It doesn't get much less ambiguous than that.
After calling around to these services for a few weeks to figure out how they worked, I got up the guts, and the money, to schedule an appointment. I remember my hands trembling while I pulled the $200 from the ATM, realizing that this was the money that was going to get me laid. I went home and called one of the services. The husky-voiced madame told me to go to a coffee shop out in some suburb. I told her it would take me like two hours to get there . . . I had to take a subway and bus. She said that was fine, I should just call her from the pay phone in the coffee shop when I arrived.
That suburb was a magical place. It had a bunch of seedy little motels, all with their blinds drawn. You could tell this place was full of sex. I wandered around there a while, and actually stopped in a drug store to buy condoms, because I didn't know if the girl would have any! Shows how green I was back then. Finally, I found this coffee shop and went in and called the madame. She said, "The girl is on her way. Sit down and have a cup of coffee and then call me back." I drank a cup of coffee, my hands still trembling, and then I called the madame back. She gave me a room number at the seedy motel across the street.
I crossed the street to that motel. I was so excited and almost drunk with desire, I'm lucky I didn't get run over in the traffic. I went up and knocked on the door, and open sesame, a woman was standing there in a short nightie. She invited me in. She wasn't a knock out, but she was pretty enough and very friendly. She could tell I was nervous, and she said, "Don't worry, I'm a very nice person." And was she ever! She asked me a couple of times if I was a cop, and I told her I wasn't. Then she reminded me that "full service" was $200.00, and she said we could do "other things for less money." I told her I definitely wanted "full service," and I gave her the money. She counted it and put it away in her bag. Then she told me to take off my clothes and lie down on the bed. I lay face down, and she massaged my back with oil. Then she told me to turn over, and she massaged my part with her hand until I was ready. She had her own condoms, and she put one on me. Then she slipped off her nightie and lay down beside me. I told her I'd never done this before, but she was nice and explained it. I got on top of her, and she guided me in with her hand. Once I got the rhythm, it was the best sensation I'd ever felt in my life, and I was so happy and grateful she was willing to do this with me. I finished really fast, like in maybe two minutes, which would have been embarrassing if I'd been with a girlfriend or something, but didn't matter since I was with a pro. She just held me then and said, "There, baby, do you feel better now?" I did. It was a wonderful first time, and she was a wonderful person. And prostitutes have been some of my favorite people in the world ever since.