I’m reasonably sure that the feds don’t care about the guys who were checking out the goods on Rentboy, but there’s some things you can do to keep yourself a little safer if you’re worried. Please read through my security page for ways I’m helping keep our correspondence safe, and what you can do to help.
If you’re not worried about that, then it’s probably just details you’re concerned with. I get it. I’m a “measure 50 times, cut once” fellow myself. So let’s start from the ground up. Here’s a handful of questions guys have asked me before:
I don’t like the word “meeting,” and I definitely don’t like the word “appointment.” “Date” seems like a much more agreeable sounding thing, and a more accurate representation of what you’re in for anyway. Let’s call it a date.
And the truth is that the possibilities are endless.
I’m the sort of guy who works just as well between the sheets as I do between Major Gift Donors at the Met. I love theater and opera and I’m reasonably well versed in both. I spent years at the School of Visual Arts studying graphic design and art history, so I’m no slouch at the museum, either.
I’d love to meet you for dinner someplace cozy (I can do fancy, but what I love more than anything is someplace quiet and out of the way where I can really get to know you better) and talk about your life and how you came to know about me.
Afterwards, there’s nothing more exciting than a walk together through city streets, both of us excited to get back to your place. New York has some of the most beautiful hotels and real estate in the world, so I’m forever brimming with excitement when I get to see an impressive suite or apartment with a view.
When the door closes, it’s just the two of us, and nobody needs to know what else we learn about each other (or how many times the hotel has to call to ask that we stop jumping on the bed).
What you should expect is that I will be as clever and present as I’ve promised here. And that your worries about rejection or not being X enough for me will be unfounded and dismissed. I’m excited to get to know you, and that’s what our first date will be about.
It’s sordid, isn’t it? There’s just no good way to talk about it without someone feeling diminished. So I prefer not to. My rates are posted, and fair, and all you should worry about is how much time you’re ready to spend with me.
I only accept cash – it’s cleaner for everyone involved, in the long run – and I expect payment at the time of service (just like the Doctor’s office). Since I don’t like discussing it, be discreet and slid it into my pocket when you kiss me goodbye.
We’ll figure out the total before we meet, so don’t be worried numbers will change from go to whoa.
Many female companions insist on a deposit up front for their time. I’ve never liked to play that way and only require a deposit when I’m traveling to meet you. I like to make my own arrangements, and a portion of my consideration up front allows me to do that and simultaneously be sure you really mean it.
Well, what if you don’t like ME? It happens. Not often, but occasionally, you or I may realize that the chemistry between us just isn’t there, and I will need to politely excuse myself. It goes without saying that I never take my fee if I need to leave early for this reason.
If we meet and you are certain that I’m simply not what you were expecting, it’s important that you let me know as soon as possible, so that I don’t get too attached to you.
We’re all just human, after all. Sometimes it simply isn’t a match.
(If it reassures you any, I’ve only ever had this happen once, and he was a perfect gentleman about it. I think of him fondly to this day and respect his ability to be so forthright.)
I would LOVE that! But no. You absolutely don’t. It always seems a little lopsided at first – me with this enthusiastically detailed site about everything I like and how I like it, and you, about whom I know nothing – so I’m always grateful when a gentleman wants to share what he does or what he looks like with me in advance. I promise that physical appearance won’t ever be a deal-breaker for me. It’s just so I know who to look for the first time we meet.
There’s a good discussion of things like this on this post at my blog. Worth reading if you’ve ever reached out to an escort and been confused by the response (or lack thereof).
Funny enough, this is the thing that guys hiring for the first time are often most worried about. It can be a source of anxiety and embarrassment no matter how experienced (or not) one happens to be. My policy is that I always arrive table ready; there’s never additional prep work required for any fun times that may occur.
I suggest getting yourself as clean as possible in the shower just before we meet up to make sure you look and feel your best. Really get in there and give everything a good scrub so you won’t ever have to make this face 😳 if things get serious.
And you should really feel free to ask any questions you might have, even if they seem embarrassing or silly.
It happens. Not often for me, but my turn offs aren’t very many:
The truth is I can’t say for certain. All I can do is tell you about who I am and what my past experiences have been like. That unpredictability is what I love about this work. Sometimes I get to go to ultra-exclusive group sex engagements as a VIP. Sometimes it’s just about being with someone when they need some kind of intimate connection with another person. Sometimes I get to take part in stuff that’s almost more intimate than fucking: first we ■■■■■■■■■■■■■■■■■■■■■■■REDACTED DUE TO AWESOMENESS■■■■■■■■■■■■■■■■■■■■■■■ and then eating pizza and watching Murder, She Wrote. It’s all gold to me.
If you’re looking for an hour of hardcore, drug-fueled, pornstar sex, I’m not your man.
But a clothing optional evening where you and I trade stories (and I get to tell you about what I got to do on one of the terraces at the Four Seasons, or what it’s like to get a blow job in Central Park in broad daylight), and share some close-up time sounds like an evening well spent to me.
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