This one is for the working man...

“Shannon, remember, it is just as easy to marry a rich boy as it is a poor one.”

But my hyper-enthusiastic extended family forgot to mention the flipside of that shiny coin, it sure as hell ain’t as much fun to fuck him.

Growing up on the North Shore of LI, like many young pretty intelligent women, marrying a nice rich Jewish boy became an idealized prize. As soon as I shed the ripped jeans, the blue hair and Muppets lunch boxes that plagued my awkward adolescent years, my mother got in touch with the LI gossip brigade and the blind dates of friends’ of friends’ sons began. All of them rich, all of them came from “good” families and all of them were assholes.

My life has been filled with these “catches”, moneyed boys who only had to worry about disappointing mom and dad as opposed to paying for their rent. There was the heir to the automotive throne whom I was practically betrothed to at birth. Mark came from oodles of money, from a good respective family and also asked me point blank to suck his dick after he took me out to dinner at a very chic NYC restaurant.

“Hey, so, uhm…Shannon,” as he is kissing me in my living room, “Could you please suck my dick?” he whispered.

“Excuse me? What the fuck did you ask me?”

He has no game. Boys who ask, shall not receive.
I pushed him off of me.

“Who the fuck do you think I am? I am not one of the prep school sluts that is going to suck your dick because you took her out to a nice dinner! Do you kiss your mom with that mouth?”

“I..uh..” He stammers.

“Is that what you expected? How the hell would you treat me if we weren’t family friends? Throw money onto the table and skip dinner altogether?”

“Please don’t tell your mom..”

“Tell my mom?!” I interrupt, “Why would I tell her that you asked me to suck you off?”

Then there was the London fag who couldn’t find my clitoris even if I handed him a map. Evidently, he never found it important in love-making before. We have the MBA from the University of Arizona who I dated when I was 19 and he was 36. He thought it was cute that I used a fake ID and it reminded him of his summers he spent on the Vineyard. He also kissed like a lizard, pressing both of his lips tightly together as his tongue slithered between his pursed mouth.

No matter how expensive the dinners nor enticing the conversation about their parents’ wealth, their sexual ineptitude left me feinding for my vibrator by the nights end.

The white collar guy is a “great catch” by NYC standards. He makes a lot of money, his family’s connections will get your engagement announcement published in the Times, and after he sowed his wild oats by fucking half of Manhattan and having his herpes scares he will make a great father, devoted to the children that he was brought up to want. But since everything came easily to him, either via SAT prep tutors, daddy’s nepotism, or even the band new car he “earned”, these boys have never had to experience what hard work is all about. If a boy never had to get his hands dirty, how the hell does he know how in the bedroom?

Wouldn’t Karl Marx be proud. Although the blue collar man is a slave to the bourgeoisie he can still fuck better than the white collars who exploit his labor power.

My date with the CL dude brought my sweeping generalization to life. A school teacher who had none of the hand outs that my pampered ex’s had. He sat across the table from me at one of my favorite wine bars recanting stories from his childhood in the city. He told me about the fist fights. The odd jobs he worked. How he got what he had because of his charm and his confidence. As we broke every rule of the first date, talking about dating and mating and post modern feminism, I found myself inching closer to his side of the table.

His self-assurance was engaging. He grabbed the top of my thigh without the usual tentative apology for being a man who found a woman attractive. Unlike my white collar sweeties, who are too afraid to reach out and touch my leg, too afraid that their desire for sexual gratification could be construed as sexual harassment that could end in a potential lawsuit.

I mean, that is the only way I could rationalize why a boy would politely ask for a dick suck.

However none of them could be as bad as the worst case scenario. A rich kid acquaintance I know with so little game and a body that shows how he’s lived amongst excess that he’s spent the last seven years of his life paying for sex because he can’t snag a woman. Including the fat and not so attractive ones with no self-esteem. I mean, that is pretty bad. He can’t even get them to his room to disappoint them.