For years I've taught msm/gay/sgl relationship workshops in NYC. It often comes up about men asking for help, money, etc so I designed a workshop on boundaries which naturally lead to hiring escorts....one of my participants was a pro so he could answer questions.
Afterwards, I was curious and felt sexually narrow especially after the reasoning some men gave for hiring escorts, centering on being sexually pleased without having the consciousness/demand of giving. It struck me how often and much I'd given sexually in my own history and only intermittently gotten back. I decided to hire someone,to receive pleasure without feeding my habit of giving too much. I should've also bought a house because it took as long in searching.
It took about a year.
It helped and hurt that I was an expert because I was able to accurately ask myself what I wanted but my work radar let me see the undercurrents in online profiles. No drugs, I've never done them; no smokers, no unsafe sex, no abhorrent behaviors or mentalities. Lots of ideas around domination and control, humiliation, thug personas, non-intimacy, desperate youth, dangerous hustlers, cross referencing thru review sites and eventually using porn movie appearances as "auditions".
It felt like I was half serial killer seeking a target and yet truly indulgently, shopping for myself. Self interest when it's healthy feels clean, honest, from a clear place. It also pushed me to not simply sexualize someone else but examine my own sexual energy and desires. I found that normally in sex we accept the person so we go along with the sex, but in hiring someone I was in charge of the situation and also my own pleasure. A true pro would show up ready to please, was I ready to be made happy?
I ended up learning how to discern healthy sex workers and respecting them and their work. I also really had to breakdown what I found attractive.
Price controls quality.
Anything under $200 an hour was amateur, desperate, low end.
But too high, say over $300 was almost a form of abuse from an escort and egotism. There's no guarantee that charging a high price means greater value. If they charged $500 or more an hour then were they really worth it? Without a desire for fetish/kink scene I just needed a "normal" sex professional. Multiple hours or an overnight (generally 12 hours---I go into much deeper detail in my book) may be worth more and isn't out of the question because what I've learned in teaching MSM, is I'm a black unicorn. I'm out, I'm very out, like walking down the street out; I have a dollar or two extra; I'm reasonably attractive and I'm clear about my sexuality, boundaries and pleasure. Trust me. I've been in hundreds of workshops with men of color throughout New York and beyond, men of color struggle with a combination of the above, even the sexually active ones.
I learned that pros aren't greedy because they're so good, business will return.
I narrowed it down to a handful, checked times, intuited HIV status from safety or not in films, considered personality from what they would and wouldn't do. Interestingly men who kiss as pros are more intimate, nicer. Non kissers were potential hustlers.
Finally I settled on Carlos. As a second choice when the first choice was out town. Interestingly enough I was often dating and found it comforting to have the resources for sexual play before I did it. It was like owning a car but taking the subway, I didn't need to hunger for dates because I knew I might hire Carlos. I became more confident and sexy. The secret plan to hire made dates spicier and more engaged because it took off the sexual pressure and it also gave me options; I didn't feel like I'd never have sex again or that I had to settle for not being present, giving too much, not being completely attracted to my partner. It literally upped the ante in my own life because the possibility demanded I be fully present in my own sexuality.
It also took time to not be in a dating relationship to hire him but finally I did. Our first meeting got cancelled due to a work emergency but he was so gracious that he moved into the first slot. I found him to be warm and direct, lacking coyness or mixed signals.
The byproduct of hiring an escort are all of these new perceptions.
Finally we set an early morning date. He came over and honestly, I was nervous. Weirdly. I wanted him to almost like me or at least find me attractive "enough". We chatted a bit, on the couch and then I actually felt chemistry and we had a great time. Earlier on the phone (very important to have this conversation first, not just texts and if necessary beforehand write down ten things you enjoy, want to happen---but be ready for the escort to not be "into" doing everything you list. Don't barter, don't bargain, simply accept that car isn't built for that speed and either enjoy as much of that car as possible or move on to another model. Don't waste an escorts time nor pressure them with your grand Disney sex fantasy.), he'd asked what I liked so he showed up geared towards my pleasure. The anxiety of pleasing another went away as did self consciousness. His work was to make me feel attractive and accepted. It worked.
I had a great time.
So much so that I hired him two more times...pros make bucks on the come back.
I also petitioned for a workshop retreat that would include escorts for the 20-40 men we took out of state. So many gay men are sexually frustrated because of stigma and this rush to sex because the acceptance can feel so fleeting you want to gobble it up.
With Carlos, I felt the sex positive messaging I'd been teaching. I understood why a wealthy person would pay tens of thousands to one say, Governors like Spitzer. Its like a therapist, paying deep intimate, sexual attention to just you. Queuing in to your needs. He spontaneously offered me a massage and I suddenly had to relax and let someone take care of me.
The massage was like his bonus toss on to make me feel happy.
I'd had a less positive picture of pay for sex but suddenly I found myself with a professional sex worker. Not a desperate street walker. I want to make that distinction, Carlos actually worked full time.
Safely, with some forethought, self examination, I've often wondered what a sex positive retreat, or on a regular basis in times of being single as a man, would garner. So many men debase themselves for sex and yet to experience a good, healthy time transformed my own appreciation of not simply sex but my own desires and fantasies.
I highly recommend it though I want to stress I mean from a pro sex worker, someone who enjoys it as much as you can and has pro boundaries and ethics.
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