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I Was a Gay-for-Pay Craigslist Prostitute

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By HVculture on March 12, 2012

A Redditor who has since deleted his account posted an Ask Me Anything on the two years he spent offering “sensual massages” and “companionship” on Craigslist. We found it absolutely fascinating: He says he auctioned off his anal virginity to the highest bidder, had a client who wanted him to fart on him, and once caught ringworm from a guy’s dirty bed — all the while telling his girlfriend he was a non-sexual masseuse. He never even considered selling his services to women — he didn’t want to “cheat.”

We reached out to the anonymous user before he deleted his account, but we doubt he’ll respond now. Still, his story is worth sharing. Here are some (obviously NSFW) highlights from his Q&A:

How old were you when you started? How old where you when you stopped and what made you decide to stop?

Was 19, I think it was 8 months to a year I was doing it (as in actively advertising), and I think I actually saw a few clients over a period of up to 2 years total — not with terrible regularity though. And I would flake on them if I were depressed at the time.

I am bipolar and was in a manic phase, which leads to grandiose thinking, risk-taking, and generally bad decisions. I was convinced that I would get super rich, retire early, and pimp out a bunch of other guys to do the job I used to do. Completely delusional.

I came out of my mania and entered depression. Had to go check how old I was at the time — looks like I started when I was 19 based on the timestamps on my e-mails. Though it looks like I also lied about my age +/- 1 year … I think out of fear of someone recognizing me than anything else. (Yea, how stupid is that? OH THIS GUY LOOKS LIKE [xxxx], BUT HE SAYS HE’S A YEAR OLDER. CAN’T BE HIM!).

Did you receive anal sex? Did anyone in your life know about it? Have you subsequently told partners about this?

Have received anal sex — it’s actually pretty pleasurable once you get used to it. The getting used to it wasn’t terribly fun. I’d actually recommend that any straight man try that kind of stimulation with your female partner.

Did you like some clients more than others? What made you like/dislike them?

I tended to like clients based on how they treated me as a person. Some of them I was nothing more than meat to, others actually engaged me intellectually. My favorite client was sweet, genuinely caring, asked me about my life, recommended theaters and shows to me, and had philosophical discussions with me. He was the closest I came to actually liking a man romantically.

What’s a typical gig like?

I would make postings advertising sensual massage, nothing explicitly stated, paying me for my time and companionship etc. Get a ton of e-mail responses from typically middle aged, sort of weird men … I would then sort through them and exchange replies to see who seemed normal enough to have as a client. We’d sort out the specifics in person. We’d either meet at their home / hotel or bath houses — many wanted a massage w/ happy ending, oral… what surprised me at first is how common a request it was for a guy to want to pay me so he could give me a blowjob. Those were the easiest jobs.

What was it like being paid to receive oral? How much did you enjoy it? Did it depend on the physical attractiveness/attributes of the John/client? What was that like compared with in your regular/personal sex life/with women? Did you have to put on a performance/act as if you were enjoying the sex/oral? How did that feel?

It was a really weird experience. The idea that someone would pay me to suck my cock was just so foreign to me at the time, but I wasn’t going to turn down that kind of easy money. My enjoyment was less than it would have been receiving it from a woman of comparable skill, but some of those guys were REALLY, REALLY good at giving head and made up for it. I guess that kind of skill is what happens when you have 35 years of experience sucking dick though! I never had to put on an act about enjoying it — what feels good tends to just feel good. There wasn’t the psychological excitement that one gets in an encounter with their gender of preference, but that’s the only reason it was any worse than with a female.

I will ask the standard money question: How much did you charge for hand jobs, bj’s anal etc? How much would you make in a week, how long were you doing it for, and did you come out the other end (pun intended) with a bunch of savings?

The really sad part is I spent all that money on designer clothes, expensive hotels for stay-cations, expensive restaurants and leaving $200 tips on $50 meals… mania makes you spend like crazy and impulse buy as well. So I truly ended up with more or less nothing at the end of it. None of those clothes fit me anymore (I was really skinny, since started working out). My Versace sunglasses are the only thing I really still have from that time in my life.

$200 for an hour massage with happy ending, I may have lowered the rate a few times to attract new clients too. I think I added 25% to that or so for oral finish, I recall about $350 for anal (though I auctioned off my anal virginity geisha style for $1000 with a guy at a nice hotel). I’d get around $75-$100 to let a guy blow me, and I’d show up for a quick plain handjob/blowjob for I think $50/$75. Most wanted whatever with the massage though.

Have you ever gone to a gig and been completely disgusted by the client’s hygiene?

One word: dingleberries.

See the full conversation here. Credit to tabledresser for collecting all responses.

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