When the Hired Hire

Guys will occasionally ask me if escorts ever hire other escorts. The simple answer is, yes. Then the next question is, “do you tell him?” In other words, does the escort doing the hiring tell the escort being hired that he also escorts?

Well first of all, escorts hire other escorts for the same reason any other guy does: you want what you want when you want it. Rather than rolling the dice on Grindr or going to a bar, just find the guy you want to meet and make it happen.

The first time I hired a guy (as I wrote about a while back) I didn’t tell him I was also in the trade, partly to see how he handled an appointment and maybe to learn from him. Part secret shopper, part mentorship. That was nearly a decade ago, and other than massage appointments I didn’t hire any guys.

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Then a year or so ago there was a Coverboy on Daddy’s Reviews who caught my eye.  His picture seemed too good to be true, like one of those phony ads where they post photos of a model or porn star.  But the review, ad and photos all seemed to add up.  His ad was a massage ad, and though I would have preferred an escort session I put a massage with the guy on my “wish list.” He was located in Southern California so meeting him would have to be on the longer-term side of things.

Fast forward a few months, and a new review appears with the guy running a full-fledged rentboy ad.  Now we’re talking!  But when would I be in Southern California? I’d been corresponding with a photographer in San Diego to get new pics taken so had already been looking for an opportunity to head south, so I hatched a plan to make a trip to do both. I gotta admit it all felt indulgent.

But tell the escort I was also in the trade, or go incognito? I opted for incognito. And as it turns out, it was a useful to go this route since he was really good, and provided a great example of how to make someone feel at ease. Communication was easy and productive.  He responded promptly to emails, with a fun and witty banter.  I gave him a few possible dates and he chose one, agreeing to host at his place.  The morning of the visit I had planned to give him a call to confirm, but he beat me to it with his own confirmation and request to phone to go over details.  We talked briefly and I really enjoyed how he came across on the phone. I felt nervous, as I’m sure most every client feels setting these things up, but the guy’s skills at communication gave me a good feeling.

None of this prepared me for what I would encounter when I arrived at his place that evening: he opened the door standing in sexy boxer briefs and a big smile, looking exactly like his photos (if not better).  I’d been afraid a guy who looked this model-perfect would be full of attitude, but quite the opposite, he was friendly and welcoming.  He gave me a kiss as he closed the door.

He offered me a drink and we chatted for a bit.  No pressure, no weirdness, just very relaxed and friendly. Do I tell him? No. What I really wanted to do was just grab him but figured that would come soon enough.  It was fun to just get to know each other.

And soon enough it was time to go to the bedroom.  “Am I the only one who’s gonna be in my underwear?” he teased.  I find sex fun so appreciated a sense of humor and playfulness.  So off to the races, starting with a long make-out session.  I love kissing, and this guy was really good at it.

Funny thing is, in setting up the appointment I did not discuss anything about what I wanted to do sexually.  Somehow I just figured things would just evolve, and in fact I was curious to see how it would go given it would be improvised.  I didn’t even know whether I’d be topping or bottoming or both – being versatile I was prepared for either, and would have welcomed either.  Not really knowing ahead of time gave a sort of sense of adventure to the whole thing.

In this instance, I ended up topping. When it came time to come, he held his load until I was ready to come, and we came together. This guy was the total package – great looks, great personality, and a knockout in bed.

Then some friendly chatting before heading out. But before leaving, an awkward moment: he asked me if I was familiar with the Daddy’s Reviews site, and encouraged me to submit a review if I’d enjoyed the experience. He mentioned that reviews are really helpful for developing business, which I know to be true. So now do I tell him? How could I stand there and not say anything? I felt deceitful, not because I was lying but because I was omitting relevant information. But if I said something now, would it seem weird that I hadn’t said anything before? Given how nice this guy was, I felt like a heel for not disclosing I knew more than I was letting on.

When it came to coordinate the review, I decided this was the time to come clean. I mentioned it in an email, and his response was characteristically gracious – he said he was flattered. So all good in the end, but would I handle things differently another time?

Another time came a few weeks ago. I’d logged into Rentmen, the usual parade of ad pics flashed by, and a sexy guy I hadn’t seen before caught my eye. He was strikingly handsome, and mentioned that he’d be in town for the month ahead. I read through his interview questions and liked the vibe I got from him, so got in touch.

His communication was prompt, professional and friendly – definitely a good sign. He responded by text and we exchanged some messages back and forth. I asked if he could do an incall, and he responded that we could meet at the hot tubs. Initially I was taken aback by this suggestion, but the more I thought about it I got more intrigued with the idea. I’d only been to the tubs once (with a client), and found they were as clean as any hotel room and satisfactory for the purpose.  The idea of meeting this hunky guy at the hot tubs felt sort of tawdry, and I liked that. We made a date for the next evening.

I’d contacted him through my Rentmen account, so this time that side of me was shared up front. We didn’t discuss it when arranging the appointment, but when we finally got into the room he was curious. The story was simple enough – I made the appointment because I thought he was sexy, same as anyone else.

With the disclosure out of the way, we engaged in an hour that was part play, part shop talk. It was a fun back-and-forth. I asked him to strip, and he dutifully complied. We kissed, explored each others’ bodies, took turns fucking, and came together. We took a few minutes in the hot tub to talk about how long we’d each been in the biz, what our travel plans were, plans for the future.

It felt better being able to talk and be open about things. And yet I also felt a bit nervous, a mix of giddiness and wanting to be liked. It was a feeling I hadn’t felt in many years, like a school-aged crush. I was smitten.

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One escort I’ve talked to about this tells me he goes incognito. He doesn’t show his face in his ads, so when he hires another working guy, that guy won’t recognize him. He told me he likes to preserve his anonymity.

I can see the point in that, but having tried both approaches I think I prefer disclosure. It’s great to not only experience getting you want what you want when you want it, and seeing things from the client’s perspective, but also meeting some truly great guys along the way.