Turned On and Freaked Out

Friday, October 17, 2008

Question

After we finished a huge project at work, my office mate suggested we go out and celebrate. He called a girl he knows and we went out to dinner together. There were too many cocktails and too much wine, and before I knew it we were back at his apartment, having sex with her. I was boozed up and brave, and definitely got to blow off all of my tension. But at the end of the evening I was shocked to see my friend hand her three hundred-dollar bills before they hugged goodbye.

I'm not sure how I feel about sleeping with a prostitute. But I have been fantasizing about her a lot since that night, and I think I want to see her again. If I ask my friend for her phone number, will he be jealous? I guess I feel uncomfortable, too, having him know this big secret about me. We're pals, but you never know when a chance to ruin somebody else's reputation will be a way to get yourself ahead, do you?

I wish I could tell you how hot this girl was and how good it felt to have uninhibited, no-holds-barred sex with her. So how do I hook up with her again? Do you think there is any chance I could just take her on a regular date and get to know her like any other woman I was attracted to?

Answer

I want to answer your last question first. The answer is no. Suggesting this is the fastest way to alienate a sex worker and guarantee you don't get a second appointment. I think you ought to read Paying for It: A Guide by Sex Workers for their Clients, an anthology edited by Greta Christina. Greenery Press, 3403 Piedmont Ave., No. 301, Oakland, CA 94611, www.greenerypress.com, is the publisher. Christina's authors come from every part of the industry—peep show booths, strip clubs, massage parlors, phone sex services, a corner in the red-light district, etc. They all have amusing stories to tell about the bad guys and moving anecdotes about the clients they treasured.

Let me outline the basics. Buying sex is a contract. You are expected to be on time, be clean, have the money on hand, and fork it over without complaint. Telling the truth about what kind of sex you want is also a big plus. But getting romantic with a sex worker violates her boundaries and will only make her uncomfortable. And let's be real here: The only reason you are so excited about seeing her again is that you think it's dangerous and forbidden to fuck a prostitute. Don't screw up the fantasy by trying to turn her into the Girl Next Door.

Asking for the phone number is no big deal. I doubt your friend will be jealous. He already knows you did the Big Naughty Thing, so don't worry about additional blackmail. He was there too so I doubt he could make himself look like a pure little angel at your expense.

Call her up and find out how she prefers to handle her appointments. She might work for an agency that books clients on her behalf or she might be an independent. Either way, be a decent guy, respect her limits, and follow the rules. Let her entertain you, enjoy it as a very special treat for yourself, and don't hassle her for showing you a good time.

In conclusion, please be aware of your local laws regarding the sex industry. None of what I've said above should be construed as encouraging readers to engage in illegal activity.