It happened a few years ago – way back in the days when Friendster ruled the world of social networking sites.
One day when I was dicking around on the internet, I noticed this Friendster profile picture located in the section called people you might know.
It was a picture of this beautiful gypsy-like woman with dark hair and brown eyes named Vanessa. And when I read her profile, I noticed these shared similarities:
-She was stoner friendly, which was good because I’m a stoner.
-She was a graphic artist, which is interesting because I like doodling.
-And if those two weren’t good enough, she also graduated from Syracuse University – the very same college I graduated from – and not only that, but she graduated from Syracuse the year after I did.
I sent Vanessa an e-mail asking what her favorite pizza place at Syracuse was – Cosmos or Acropolis? She responded later that day with Pizza Jerks. We exchanged a few more e-mails, talked on the phone a couple times, and then finally went out on a date.
I took her to the Velvet Margarita, a trendy Mexican restaurant located on Cahuenga blvd between Hollywood and Sunset. The date started off very well. She was laughing at my jokes, the conversation was very easy, and the funny thing was that we kinda already knew each other at Syracuse…
My work study job in college was driving a community service van. It was my responsibility to drive the students back and forth between the university and the local grade schools where they volunteered their time – and Vanessa was one of the students that I used to drive around. It was an amazing coincident.
Needless to say, we had a great time and really hit it off. And although there was no sex on the first date, Vanessa suggested that we go to a strip club after dinner. I thought it was a little strange that she wanted to go to a strip club, but I was kinda hoping to see some boobies that night, and if it wasn’t going to be Vanessa’s boobies, a random stripper’s would suffice.
We walked to a C-Rated strip club on Sunset called the Cave. The only thing I remember about the strip club was that I kept feeding Vanessa dollar bill singles so she could lay them on the floor for a pregnant stripper to pick up with her pussy.
Watching that pot-bellied stripper pick up dollar bills with her pussy was a beautiful and romantic moment -- and that’s when Vanessa and I had our first kiss.
So after that, me and Vanessa went out a few more times. Although we stayed away from strip clubs, we saw a movie, we went to Disneyland, and for our third date I took her to one of my work wrap parties. That night, I took Vanessa home and we consummated our relationship – which is a fancy way of saying we finally boned.
The next morning when we were cuddling in bed, Vanessa said she had a few things she needed to tell me. She took this time to inform me about three personal facts about herself, which she told me in this order:
1) While living in NYC after college, Vanessa told me that she briefly worked as a dominatrix. Naturally, I was a little taken back but she assured me that she never did any kind of sexual acts with these people and no one ever touched her – it’s just that she would do things like whip people or pee on them.
Okay, maybe being a dominatrix is a little weird but it’s not the worse thing in the world. It wasn’t that bad.
2) Next she told me that she also joined an escort service as a call girl while living in New York. That one was a little hard to swallow but she quickly explained that she only worked at the escort service for a week and never went out on any calls because she could never force herself to have sex for money. I was starting to get a little worried at this point but I was still listening.
3) Finally, she told me about “Carl” – some “sugar daddy” that she took like over $4,000 from. It was a nonsexual thing, but Carl was this fat, middle-aged guy in New York and apparently he would take Vanessa out to dinner a couple times a week and give her a couple hundred bucks for her time.
The funny thing is, I didn’t mind the dominatrix or call girl stuff nearly as much as the sugar daddy stuff. I don’t know, I think what bothered me is that she basically used this poor guy for money. Maybe Carl was a little delusional for thinking he could get a gorgeous girl like Vanessa, but it didn’t mean she had to take advantage of him.
Vanessa also told me about the one real relationship she had in New York with an MTV director named Derek. She even moved to Los Angles with Derek, but they broke up shortly after that – probably because she told him about being a dominatrix and call girl.
But I gotta be honest, I was really bummed out when Vanessa told me all those things. I never really connected with anyone like the way I was connecting with Vanessa and I was really starting to think that she could be the one.
I was torn because something was telling me that this girl could be trouble and yet I was so attracted to her because she was gorgeous and funny – and actually very sweet, despite having taken a guy for four grand. And I assume she was starting to like me too, because there’s no other reason for being so honest.
I did the only thing I could do -- I kept dating her because she was soooooooo fucking hot and I wanted to have sex with her a bunch more! And although we kept seeing each other for another month or so, I guess I stopped talking the relationship seriously.
And like an idiot, I even attempted to date another woman while I was still dating Vanessa. At the same time, a young blond in my building was visiting my apartment wearing only a robe. I eventually puked on that girl and you can read about it here:
But on the night I puked on the girl in my building, Vanessa had called me earlier because she was upset. Her grandfather passed away a month earlier and his last voicemail message had just erased from her cell phone. Vanessa was looking to me for support and unfortunately, I was out drinking with some friends. And on top of that, I was hammered and already scheming to call the blond in my building as soon as I got home.
I made a dumb joke to Vanessa and hung up the phone. After that, Vanessa started pulling away from me and I let her -- which sucks because I totally fucked things up with the blond after I puked on her.
Anyway, I get bittersweet whenever I think about Vanessa because at the end of the day, she was technically my first girlfriend. I never had any real relationships in high school or college and she was the first girl that I dated for more than one date.
Over the past few years, Vanessa and I hung out a few more times but nothing ever happened. The relationship that could have been was long over.
On a side note, a couple years after the whole Vanessa thing, I got stuck in an elevator with a bunch of crew guys while filming an MTV reality show. And one of the crew guys was a director named Derek.
We were stuck in the elevator for a few hours and at one point, I turned to Derek and asked, “hey, have you ever dated a dominatrix named Vanessa?”
The look of pain on his face told me he knew Vanessa all too well.
Vanessa never caused me any pain – or at least pain any worse than any other woman I've ever been in love with has – which is ironic because she is a dominatrix.