Corporate Stiff By Day & Stiff On Demand By Night

I had the means, the motive, and the opportunity. The crime, as it turned out, was one of the best decisions I'd ever made.

Let me set the stage. I'd recently graduated from a top business school, with the price tag to go with it. I'd moved from New York to Washington, D.C., for a new job, and was totally unprepared for the contrasts between the two cities. New York is salty. We make loud small talk in the elevator, dance with strangers in bars, and live for friend "pile-ons." D.C. is a dry cocktail party, with endless conversation about "Eric's transcendent --and did you hear how expensive!--kitchen tiling... ." Despite my best efforts, after six months, my social life in the District was flimsy. As flimsy as my new paycheck, after I'd slipped a few rungs on the corporate ladder to pursue a new career path.

One night, I bumped into an old college friend, and we got a beer. He told me he was in town visiting one of his benefactors. To fund his career as a musician in Los Angeles, he'd become a rent boy (definition: one who rents himself to others) on the side. We didn't get into the nitty gritty, but it was clear that his male clientele was keeping him in the black.

Doing something off the rails like this had been tucked away in my mind for some time. I'd read Camille Paglia's Sexual Personae in my teens and it changed my world. She writes about the myriad of human sexual desires--and that society's function is to build walls between us and these desires--to make us feel shame in pursuing them. Since then, I've carried the idea that I want to avoid being "tricked" into not exploring sex. You could argue the pendulum swung too far the other way, but I firmly believe that knowing your true sexual self is an ingredient to a life well lived.

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I did my research. The gold standard for those looking to peddle their charms was, not surprisingly, Rentboy.com. I searched on Washington, D.C, scanning through the hundred or so ads. I was shocked to find such slim pickins in our nation's capital. I assumed Republican congressmen alone would sustain a healthy industry. I was wrong.

I was ready to start building a persona, but first I had to decide who I wanted to be, and who I wanted to attract. My mother always told me to accentuate the positive. I was not 25. I didn't have 10 inches. So I played up my education and that I'd lived overseas, hoping to speak to men looking for something more than a transactional hotel-room fuck. My ad stated I was available for massage and role play, and left the door open for more. I invited people to email me their fantasies.

I cropped my head and any other recognizable details from some recent shirtless pics. I created a slutty Gmail address and paid my $49 a month to be listed. And just like that, I became Rentboy.com's newest recruit. Little did I know that in a month's time, I'd be making more in a night than I did in entire week at the office.

I used only email because I was afraid of being found out. Losing the job I'd toiled through business school and left New York for because I was "renting" on the side would be an epic misfire. Or what if someone in my burgeoning circle of friends found out? I was comfortable with what I was doing, but still couldn't imagine how the stigma would sting. Email allowed me to screen people and stay somewhat hidden. But there was always the chance, since clients also use names and emails that hide their identity, that on the other side of the next door was someone I'd met at a party, or even worse, a co-worker.

Photo via Pixebay.

Once, I was at a holiday party at a chic furniture store on 14th Street. I recognized a man I'd had a session with six months earlier. I avoided him, but eventually our paths crossed. He kept saying, "You look so familiar. I can't think where I know you from!" With a girlfriend from work at my side, I did nothing to jog his memory. I could only hope that if he did remember, he wouldn't snap his fingers and shout: "I've got it! I paid you $500 to fuck me in my office over in Georgetown last summer!"

The first few days after posting my ad, I checked my inbox every 10 minutes. I felt a rush with each new message. A lot of guys were interested in role play. There was a flood of questions: What does that mean? What are your specialties? How far will you go...?

I've always been a fan of role play, so it was easy to talk about it--and to deliver. It's all about power; some want to submit, others want to exert. I've played both sides of the flunking student who drops by teach's home for extra credit; the dumb jock who takes care of coach to stay on the football team, the junior executive who desperately needs that contract signed to get promoted. And my personal favorite: the straight masseur (with baseball cap on backward, natch) who talks about his girlfriend while absent-mindedly dangling his cock, straining against his briefs, in front of his client's face. You'll never guess what happens next!

One of the first requests I got was to drive to a guy's house in the suburbs and knock on his door. I told him my car broke down and asked to use his phone. Once I was inside and calling the imaginary local garage, he got down on his knees and sucked my dick until I came. Another man asked me to babysit him. I went to his house, made him Kraft Dinner, got him in the shower, and then tucked him in to bed. That was it--no sex. Before the visit, he asked me to pretend I was a foreign exchange student and put on a French accent. I did my duties and picked up the money he'd left in the front hall on the way out. Driving home, I put the pieces together. A crush from childhood. A real exchange student that, growing up, he could never have. Acting out the fantasy to satisfy--and maybe dislodge--that enduring desire stuck in his mind.

From the beginning, I liked the idea of leading a double life. Corporate stiff by day, stiff on demand by night. Once, I was locked up in an especially deadening work meeting. There was no air in the room. After lunch our boss attempted to breathe life back into the proceedings by asking us to go around the room and say something about ourselves that the team didn't already know. The guy next to me shifted uncomfortably in his seat, raised his hand, and asked, "Does it have to be interesting?" I thought, I'm going to leave these people, have dinner with a married banker, fuck him for a $1,500 overnight engagement, and come back to this. Game on.

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At the end of two years, I was ready to hang up my jock strap. I'd learned a lot about my fellow man and myself, and had paid off my MBA. Not once did I have a bad experience, though occasionally I'd get a bad feeling over email and wouldn't agree to meet the person. I always knew that if I was ever uncomfortable with a situation, I need only walk out the door. However, I met only nice men. Some were randy and just needed their nut busted; some had wives and needed a discreet way to find pleasure; some were lonely and simply wanted to have a good time in the company of a man. I never ran up against any drugs, disrespect, or deadbeats.

I'm not suggesting this is a path for everyone. I am just saying that from experience, good things can come from the world's oldest profession. Sure, it's still a crime, but sometimes crime does pay.