Inside The Mind Of a Writer: Real Life Experiences That Shaped My Art

My One Month Career as a Rentboy

Here I am, a guy who taught Sunday School as a good Lutheran and ended up on the other end of my life, after a successful professional career in the str8 world, a gay fiction writer, hustler and porn star.

Go figure.

Getting out from under the 60 hour work week grind of public relations, I finally was able to do something I had wanted to do for years – write gay fiction. Now in SoFlo, I had the time and wrote two works, one a collection of short stores, the other a novella. And I said “fuck you” to the snooty literary agents of the pre-web era and a dying publishing industry by posting my stuff as e-books on Kindle and Nook.

Rationalizing I needed to do first hand research on male prostitution for my next book, what better way to find out than be one. So, very matter of factly one night I plunked down my fifty bucks of Visa dollars and posted a profile on

Ah, but there were other, deeper motives for my madness. One was my attempt to fulfill a fantasy suggested by my dearly departed meth head/fuck buddy/clone Mitch, who had already been a guy for hire back in New York, that we play a Rentboy tag team for guys looking for double the trouble.

The other was my overactive ego: would someone actually pay me, an aging faggot, even if time had been kind to me, to have sex with them?

A buddy once said to me that he found it pretty pathetic that somebody had to pay for sex. But I heartedly disagree. Sure, sex can be a wonderful exchange between two people, but why can’t it also be a commodity for those willing to buy what they want, just like the newest tech toy or Abercrombie and Fitch polo? Contrary to the notion that only losers pay for sex, there are plenty of good looking guys out there, busy with high power 24/7 careers or entwined in complicated personal lives, who just choose to take the expedient route. I’ve always been an advocate for making prostitution in this country legal and get over our collective Puritanical hang-ups. Make sure the boys and girls are disease free, and tax ‘em, baby.

“Who’s your daddy?” was my on-screen persona, trying to create a market niche distinct from all the pretty boys, and I openly admitted I was over 40 in my ad (how much over 40 I conveniently left out), but rationalized that tidbit with the tagline, “but you did say you wanted a daddy, didn’t you?”

I low bowed my hourly rate to $150 so I’d have a better chance at scoring, given the stiff competition, and made myself “out only” – their place, not mine. Would-be clients could contact me either via email on the site or my cell phone #, and I used a Tracfone just for that so if or when I had any issue associated with my new career – as in being stalked, like I should have such problems – I could chuck the phone just like a drug dealer.
So what does it take to be a Rentboy, besides, of course, some alluring physical attributes and a lot of moxie?

(a) The ability to do it with just about anyone, and if you’re playing the top like me, you know dicks don’t lie, which I figured wouldn’t be a problem given some of the loser tricks I’ve had over the years. You just put yourself in a fantasy mode, right?

(b) A feeling of super-superiority that you’re so hot (it’s all about self-love, baby) that the guy is willing to pay you – PAY YOU – to feel your tool in his mouth or up his butt. You know what an exhilarating high that is? Better than meth.

(c) The absolute resistance to ask the guy what he looks like. Yes, you need to know what he’s looking for, but those big bills on the night stand are what are supposed to arouse you, not whether he looks like Woody Allen’s older brother.

But when a week went by after posting my ad and I got no takers, I was convinced I had pushed the envelope too far, that I was a jerk for even thinking I could pull this off at my age, with all the twenty something, thirty something porn star quality meat that was vying for that same universe of hungry, lonely men. What was I trying to do? Make the Guinness Book of Records as the world’s oldest male hooker?

Ah, but my feelings of dejection were premature. At the beginning of my second week I got a hit.

Lennie was a 67 year old retired dentist from Palm Springs staying at one of the gay guest houses off Lauderdale Beach. He actually was looking for two guys to fuck him (something my late meth-head Mitch would have loved) so I was not that surprised when I arrived, a smooth, thirty something Latin stud was already there, drilling the guy’s hole, doggie style. He barely paused from his mission to glance my way.

“Randy,” whispered Lennie, who resembled a pursy Episcopal minister, giving me the once over, and gesturing for me to join in. I quickly forsook my nylon running shorts and jockstrap that I had worn, so I thought, for some enhanced foreplay, and, thanking that Canadian online pharmacy for the two thousandth time in my life, went over and gave Latin Stud a breather.

All the way over to the guest house, I had been wondering if I could really do this, but I soon discovered, in this, my baptism by fire, that just the idea that someone wanted you so bad that they would pay for you made my 50 mg. of Viagra superfluous. I also gave a mental finger to all those guys who had rejected me over the years. Would anybody pay you, fuckers?

Actually Latin Stud and I got into something of a fucking competition, seeing who could pound poor Lennie the longest, but in the end I think it was a draw. Two minutes before the hour was up, Lennie shot his load and, lying back in a pool of sweat, gestured to the bureau and two envelopes. “Thanks, men, you were great.” Not that Latin Stud was my type – I liked ‘em hirsute – but my quick flirting wink and cockteasy smirk produced absolutely no response from my co-conspirator. He was apparently all business. I wondered as we both strolled out like two total strangers if his hourly rate had been higher.

My next suitor was actually fun, young, and farmboy cute, a multimillionaire software developer from D.C. I found out later in the brief chitchat that followed us doing the nasty. He was in town on business and had no time to beat the bushes searching for dick. When I had called Josh back – he had left a message for “Coach” on my Tracfone – he told me he had a jock fetish and could I come by in sneaks, a jockstrap, nylon gym shorts and a cap. No problem I replied, and that night at 11 after Josh had schmoozed some potential clients at dinner, I arrived in costume at his plush suite at the ritzy Ritz Carlton right off the beach. I think square footage wise it was larger than my house.

Keeping Josh entertained was like taking candy from a baby. In decent shape and stripped down to his old fashioned white jockey underwear, he lay on his stomach, with me sprawled on his king size bed, legs slovenly spread, my crotch in his face as he felt underneath my shorts, then jockstrap, for the prize. After teasing it from the outside with his tongue, he whipped out my very erect cock and slowly blew me – no reciprocation required. We spent almost half of his hour talking about life – and his very mousey wife.

Ralph, a social anthropologist and university professor in town to judge a doctoral dissertation, was a bearish, hairless, six foot five actually-not-all-that-bad-looking kind of a guy who, like Josh, made very little demands on me except that I keep my cock hard so he could suck me off. The La Quinta he was staying at was only a few minutes from my house and when I got back to my car after our 11 p.m. Sunday night appointment and counted my cash, I realized he had either given me a bonus (he did keep telling me throughout our session how he adored my fur and that I belonged on a magazine cover) or misread my hourly rate on the Rentboy site. But I was not about to return it, that’s for sure, and went on my merry way.

Hands down, my fourth client who revealed himself in an e-mail in my Rentboy dropbox was my most bizarre but one I wish my shitty little two by four life would have allowed me to act on:

“Hello, handsome. Just browsing the web and found your profile so cool and nice sexy pictures. I am an engineer, 42 yrs old, from Great Britain and I will need you on my Business Trip to Eastern Europe on the 30th of June for 8 days. I need someone who will follow my instructions and obey my orders, someone who is very decent, kind, honest, trustworthy and undetectable to protect my image and name. Just need you to come and give me some massages and keep me warm throughout my stay in Prague and Warsaw. I am ready to offer you a good sum of 2000.00 pounds per day for 8 days, which I will pay you upfront even before you leave the country. All necessary documents will be arranged for you, so feel free to get back to me only if you are interested and willing to go with me. M.”

Was this guy for real? Who knows? He sure sounded enticing. But even if he were on the level, I doubted I could keep up the charade that long – an hour or two 15 minutes from my house is one thing, eight days halfway around the world quite another. Though, when it came to both my very legitimate career in public relations and my very illegitimate career as a male hooker, the most valuable courses I ever took in college were my acting classes.

My last proper stranger before I let my ad lapse at the end of its month’s run was also the greatest test to my doing it with anybody. Hearing Rob on the phone, I imagined him to be a fifty something big guy. He was coming in from Gainesville strictly for a play weekend and dug hairy guys (c’est moi) big time.

Then, the morning of the day we were to meet at his hotel just a few minutes from my house, he dropped the bombshell. He was THE Rob, the big guy who had been stalking me on a couple of the hook-up sites for the past year. I was his ultimate fantasy stud muffin and in his e-mails he went on in deliciously decadent detail what he wanted me to do to him. When he called that morning he apologized for the ruse and fully understood if I wanted to back out. Instead, in some weird fucken way, I became even more intrigued by the prospect and adamant in seeing this through.

So loaded up with 100 mg. of Big V, I reported for my scheduled “appointment” at the Marriott just minutes from my house. For all his bulk, Rob had an infectious smile, and kept my dick stirring as he deified me with his mouth and tongue and words. This is when, as he took my load and spurt his own, that I had one of those life defining eureka moments and realized that, had I been younger, I might, just might have become a career whoreman.

So what did I learn from my month as a Rentboy? That physicality and physical attraction defy social class, professional standing, race, and most of all, personal pride; and that while money can’t buy you love, it sure as hell can buy you one of the best fucks of your life.

Thursday: Real Life Experiences that Have Shaped My Art: My Fifteen Minutes of Fame As a Porn Star