I was waiting in the Hilton restaurant for Christine, my date for the day, to arrive. She'd agreed to pay me my usual escort fee - 150 dollars per hour. I was at her disposal for that fee; we could just talk or go up to a room and have sex. From our phone conversation, I expected her choice to be sex.
When I started in the escort racket as a student over four years ago the money was very important to me. But nowadays the different types of women that I get to meet, and the sex that I have with some of them, are more important to me than the money.
I'm obsessed with women: I love how women taste and how they smell. I love how their legs look when enclosed in nylons and how the swell of a woman's ass and tits starts my juices flowing.
The people who I work with down in Wall Street would be shocked to learn that I lead a double life. I'm a financial analyst for a hedge fund forty hours per week and an escort on nights and weekends. When I graduated from the Business School at NYU I stopped working for the Midtown Escort Service but placed my own personal escort ads when I realized that I missed the escort life.
I don't have sex with every woman that I escort. In fact, I've been with over 200 women since getting into the escort business and have had sex with only about 20 percent of them. And, even if an escort job involves sex, it almost never happens on a first meeting - these things tend to evolve over time. At least that's the way I like to play it. Some guys in the business are more anxious to get pussy as soon and as often as possible.
Christine arrived at the time we'd agreed upon. I chose a booth for privacy so that we could get acquainted and discuss exactly what she wanted.
In that first meeting in the Hilton restaurant with Christine it became obvious that she was interested in getting serviced sexually; at that point I decided to get explicit and describe the range of sexual services that I could provide for her, in clinical detail. If the other people in the restaurant could have heard our conversation they would have been shocked. She blushed when the conversation became explicit but I have enough experience in these matters to get her to openly admit that she wanted to get oral sex from me and to get fucked.
She paid the check and we went up to the room I'd reserved for the afternoon.
When we got into the room I told Christine that it was time to disrobe. I turned away from her so that she could remove her things without having a stranger watching her strip. I took off my clothes at the same time, folding them neatly on the dresser. I gave her plenty of time to get naked before turning to face her. That sort of thing is usually difficult for new clients.
After slowly removing my clothes, I turned and found Christine naked and sitting on the bed. I sensed her nervousness but I also felt her desire. Sitting down next to her, I held her hand. With this show of tenderness on my part, she relaxed. I cupped her chin and turned her face away so that I could gently kiss the soft spot under her ear. Her hand clenched my fingers as she turned her face toward me. Her free hand touched my shoulder in a tentative embrace as I kissed her mouth. When she let my tongue touch hers, I was as caught up in the moment as she was. I released her hand and moved mine to the heated center of her thighs. Her legs spread open and I moved a finger gently up and down her slickened lips. Her moans took my breath away.
"Lie back for me, Christine. Spread yourself wide for me."
She did as I asked. "Richard, I'm so hot. You have to eat me, you have to fuck me!"
I complied. I've found throughout my 'career' that women appreciate a man who takes his time. I wanted this experience to an incredible one for her - after all, that's how I built my client list - so I moved my head to her pussy and started slowly licking down the length of her. It's so beautiful to watch a woman respond. As her excitement grew, her outer lips drew apart. I wanted to touch the tip of her clit but it was hidden. This aroused me because there is nothing more sensual than slowly bringing a woman to the brink of an explosion. I drew circles on the soft pink folds with my tongue, coaxing her clit into exposure. When it finally appeared, I touched the top of it, felt it quiver under the little flicks. Her moans became music to my ears as I drew this little pearl into my mouth. I held it between my lips as I lightly sucked it, letting my tongue move across the tight bud. She gave me an experience to remember when she came. I gripped her hips to hold her down as her orgasm took control.
After the oral sex I had her lie back with her legs spread and fucked her slowly and thoroughly. Before I screwed her I put on two condoms, standard for guys in the sex business. You can't feel much that way, but you need real protection when fucking strangers - God knows who's been there before you! Protection works both ways; the woman has protection from pregnancy and disease when I use a double condom.
I've learned quite a bit about Christine since our first meeting. She didn't tell me much about herself but I was intrigued and did a little research. She was divorced about nine months earlier from a wealthy older man. Christine runs her own consulting business in the Internet marketing area and has been written up more than once as an example of how women are getting into positions of power in the new world of the Internet. That may be why she intimidates most of the men she meets; they are bothered by a woman who projects self confidence and power. Also, she is pretty picky about who she chooses to go with to social functions. Whatever the reason, she was getting very lonely and sexually unfulfilled. Then she spotted my personal ad for escort service and decided to call me.
Over time the relationship evolved. On one occasion she was pissed off when she called me and I said that I already had a date to escort another woman at the time that Christine wanted to see me. I thought that she was so pissed and jealous that she might terminate our arrangement, but she finally agreed to a session at a different time.
When I next saw her she started asking questions about the other woman and what had happened. "Tell me about that woman you were with last Sunday. Is she good looking? How old is she? Did you screw her?"
"Christine, I will not answer such questions about other clients. But remember that I will never tell another soul about what we do together. Can you accept the fact that I see other women? If not, we can't continue."
She pouted a bit but accepted the situation. She was especially loving that time, giving me a really great blow job.
Yes, a blow job. That wasn't part of our original deal but over time she has decided to pleasure me in return for my taking care of her needs. In fact, she now tells me that fellatio is one of her favorite activities.
Our sessions have settled into a basic pattern (with a few surprises from time to time.) We start out by kissing and fondling each other. I use my hands, mouth and tongue on every part of her body to get her aroused. At this point I usually perform oral sex on her. That's a skill on which I pride myself; I know from the reaction of my clients that most have never had their pussies eaten, or that the guys involved didn't really enjoy oral sex.
The next step for me is usually to fuck Christine. Luckily, for a guy who is into servicing women, I can have many orgasms within a short period of time. It's a valuable skill if you're going to do the sort of thing I do for women. I'm sure that one reason clients tend to continue with me is that I'm a much better lover than the other men that they know. That's due to good stamina, excellent technique, and real desire on my part. You cannot fake desire!
More recently Christine has taken to sucking my cock before or after I fuck her. I remove the condoms from my dick so that I can enjoy getting sucked off. That way there's still a slight risk of catching something, but with condoms there's no fun at all for me when she goes down on me, and not much fun for her.
She loves to lick my cock from my balls to the glans, slowly and with passion. Christine is one of the best cocksuckers that I've ever had the pleasure of knowing. She enjoys the taste of my semen, saying that it has a distinctive salty flavor - and she swallows it with relish. I get great pleasure from seeing her expression of lust and fulfillment as she gives me oral sex.
I told her, "Chris, you're a very deceptive person. You come across almost as an unapproachable 'ice maiden' type to strangers. But when it comes to sex you have real lowdown slutty instincts, which I appreciate."
The relationship with Christine has gotten much more intense (and complicated) recently. One day she questioned me about the sort of tasks that I normally perform as an escort for other women. I reminded her that, for most clients, I simply acted as an escort to various events, and that sex wasn't usually included. I hastened to add that sex with her was great.
"Am I unusual in being so needy for sex?", she asked.
"No, no, Chrissie - you're not unusual. Many women have strong sex drives but don't quite know how to get what they want. I like to see the expression on your face when I make love to you. I do this sort of thing for money but what I really get is satisfaction if I can satisfy a woman like you. And, of course, I have my own strong need for sex."
After a pause, she said, "This coming weekend would you please take me to a new play that I want to see? I'm sure that I can get tickets. Let's make a real date of it. You know, pick me up at my place and then we'll have dinner, followed by the play. I'll make all the arrangements. And....I'd like you to spend the night with me - none of this quick fuck thing at the hotel. Naturally I'll pay for all expenses and whatever money you want for your time. Please do this for me, and I think you'll have a good time."
I hesitated for a few moments and then agreed to see her on the following Saturday and spend the evening with her.
When I showed up her apartment house on the Upper East Side that Saturday I felt very strange; it was like picking up a date many years ago when I was a high school kid. I was nervous as hell and wondered if she would like the evening with me.