Confessions Of A Really Bad Hooker

I had the most interesting conversation with Cindy the other day on how she got into the whole escort service thing. I forget what brought it up, but it's something I've always been curious about. I mean giving strange men handjobs in the comfort of my session room is one thing, but meeting strange men in hotel rooms for sex is a whole other league (at least in my humble opinion). According to her, she just kinda fell into it. So how exactly do you "fall into" hooking?, I asked. I have to admit she had a pretty good answer.

This was back a number of years ago now, when she had left The Business and was pretty deep in her drug problem. She was living with another girl at the time who was "dating" (as she called it) as a sort of night job. Gidget (as we will call her) placed ads on the internet and then met guys in local hotels.

Well when you're a jobless drug addict, the life of an escort starts to look glamorous. So Cindy said she took the plunge like this... one day she was home and heard the answering machine pick up. It was a new guy asking to see Gidget for the first time. It turns out Cindy recognized the guys voice - so she picked up the phone and pretended to be Gidget!

Luckily the guy was pleasantly surprised that they knew each other already. So they arranged a price and a meeting. However, since Cindy basically stole the customer right out from under her roommate, she really had no idea how to get new ones. So for a couple of weeks, she basically just continued to intercept messages during the day, and then delete them before anyone got home.

She also had the foresight to pick the guys brains on how they found "Gidget" so eventually Cindy learned enough about the internet to start placing her own ads. Now I've mentioned before that Cindy isn't the brightest of bulbs. And a woman who thinks Mount Rushmore is a natural phenomenon is bound to make a few mistakes.

Cindy placed her first ad in the "Dating" personals.

She met a nice guy named "Tom" and exchanged a few messages with him before deciding to meet at a local sports bar. They exchanged a few pleasantries over a drink. Tom was being very chatty and asked her about her family and what she did for a living, etc. So when Tom spit out his drink after she asked him if he wanted a blowjob in the car or the full hour session at his place, she started to suspect that there might be a slight misunderstanding here.

Tom was on a date. Cindy was at a business meeting. Fortunately, Tom quickly recovered his composure and then considered this his lucky day since he realized he was going to get lucky - guaranteed.

They worked out the details and decided they couldn't go back to his place since his mom was home (I mentioned how this was his lucky day, didn't I?). Instead they went to hers with the understanding that he was not to talk to Gidget if she was home since she didn't know of Cindy's new occupation.

Now the way Cindy described it, her room wasn't clean. Ever been in the home of a drug addict? It's never something out of Martha Stewart magazine. It smelled of cigarettes, and probably had drug paraphenelia lying around. Tom didn't care, so they started going at it right there. Cindy said the whole thing was over so quickly that she almost felt bad for the guy. Tom didn't care though - he was just glad to have had the most successful first date of his entire life.

But now that they were done with business, they realized that they never actually ate anything at the bar. So They ended up going back out to grab a bite to eat. They went to a local diner where Tom opened his wallet for what was now the 3rd time. Ironically, by the end of the evening, Cindy was on a date and Tom was at a business meeting.

Eventually, Tom became her first Regular, and she became his "rental girlfriend." She said there were times they'd actually do dinner, a movie and sex just like real couples (except for the cash on the nightstand afterwards of course). They saw each other for several months before she went off the deep end with the drugs. She hasn't spoken to him since.

Let me tell ya, there have been days when I've thought that would be a sweet arrangement. Especially if the guy looked like Brad Pitt.

CJ