Exclusive Interview With NYC Escort Cub Sailor

Sailor’s been escorting his way around New York City for years, and more recently, he’s been writing about his experiences. He’s one of the seven LGBTQ sex workers featured in Red Umbrella Diaries, a documentary currently in production. Last week was the film’s big finale, a live show in which all seven performers told intimate stories about their lives in front of a sold-out audience.

(Visit the Red Umbrella Project if you’d like to know more about them. Their work is pretty awesome.)

Sailor is the kind of daddy cub type I tend to fall for hard—I know not everyone likes a forty-something guy with hairy shoulders, but personally, I’d love a chance a romp around with this seaman. Luckily, I can ogle his fuzzy naked body on screen, and sometimes on his Tumblr. He’s recently begun dipping into porn, shooting with Ray Dragon in films like Joe Gage Sex Files Vol. #14 Lunchtime Milking Club 2.0 (the title of which really deserves some kind of award).

– Lawrence

Photo credit: Krys Fox

Find out what he had to say when we spoke yesterday:

Hey Sailor. How’s it going?

Good. I’m listening to my upstairs neighbors. They’re both very lovely people, but they’re fighting right now. I like them, but there’s blood curdling screaming. It’s crazy. And their little dog keeps running back and forth.

So, tell us a little bit about your performance last week.

I’ve read with Red Umbrella Diaries before, but this time we had to be there the entire day. Dominick [one of the other performers] and I went to the baths first to relax. I can’t believe how stressed out I was, before and during. There was no reading this time. We had to either memorize our stories or ad lib as we went along. And I think everybody but me was able to do that. This thing was really a show! We actually had rehearsals. And I’m not really a performer. I read a piece about having a nervous breakdown, but when I got on stage, I didn’t remember anything. My ears were ringing.

But I’ve never felt that much crazy energy in my life. And I was really exhilarated until Friday, and then I plummeted. And then Saturday, I really enjoyed the experience again. I really got a kick from being up there.

Speaking of performing, you recently made the jump into porn. How’s that going?

I’ve done about a half-dozen porn scenes now. I’m getting more comfortable. I like being naked. When people are all weird about nudity, it’s like,x what’s your big deal? And I do the go-go thing, too, for the Piggy Bear parties.

I did three or four scenes for Ray Dragon, and he’s a sweetheart. He’s upstate, and he rented out an old mechanic’s garage. With him, your audition actually is your jerk-off scene, and it was just him, and I was jerking off. I kept saying I was nervous, but he told me I wasn’t nervous, and I just kept saying I was. I don’t know, my socks were wet. I wrote a cheat sheet on my hands, and I forgot my glasses, so I couldn’t actually read them.

And then I worked with New York Straight Men. They actually shoot every scene in an hour and forty-five minutes. They have the same bottom there all day, and the tops are in and out on a tight schedule. But my nerves actually work in my favor in those cases. Sometimes, if I’m not into a dude, I’ll get like a nervous raging boner.

When you’re shooting everybody keeps saying there’s no pressure, but as they’re saying it, they’ve got tense foreheads and their eyebrows are arched up. That’s actually pressure! And then you feel strangely validated by their pats on the head when you’re done. Which are basically really physical things. The way porn works, the directors don’t really do anything to make it seem like we’re actually into each other. I did my first hardcore scene a few weeks ago, just to see if I could. The guy who was shooting basically left us alone to do whatever we wanted, which helped. That was better.

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Is shooting porn enjoyable, overall?

One of my friends told me she’s worried about me ruining my life with porn. And I said, you know, all of your gay friends are doing what I’m doing. They’re just not doing it on camera. And how secure is your future? Or anybody’s?

On the one hand, I feel like I don’t have a lot of confidence. But it takes a certain level of confidence to walk into a hotel room with a stranger and have sex with them. It seems fake to pretend that I’m not confident.

I have to remember to add things, and to say things. If the bottom is telling me what to do, it’s hard. It’s kind of like a performance in a way. I like listening to breathing and heartbeats, but sometimes the guys want me to be really verbal. So they’re saying things that they’ve heard in porn movies or whatever, and I’m repeating things that I’ve heard.

Any other major plans in the works?

I’m doing a new photo shoot next week. I’m trying to find photographers that want to do something more interesting.

I’m trying to write a book and sell it. I think maybe I can. And then maybe I’ll leave New York. Or else I’ll take my act on the road and do a farewell whore tour. I moved here in 1991, and I want to really write an honest account of my finances at the time and the promises I assumed I could keep to myself. About New York and money and living.

Now it seems like everybody in New York has money. I don’t remember anybody having money when I first moved there. But I was looking for an apartment six months ago and the only one-bedrooms I could find were between $2500 and $3000. I know escorts that live between Hell’s Kitchen and Chelsea, and they can’t say no to anything. How could they, with the rent they’re paying?

And tell me about where your name came from.

I always thought the names guys used in porn were so cheesy. I hate porn names. My first job in New York was working at Limelight. I did go-go there. I would wear a sailor outfit. Nobody told me to, I just did. With cutoff shorts. I was so young that I couldn’t even drink. Nobody cared then. That was the Michael Alig period. But that’s what I decided to name myself. Plus, I like to sail, and I like boats and all that kind of stuff.

Sometimes people will say, “Please have a name.” And I realize the reason they’re asking is because they probably hire escorts all the time and don’t want judgment.

A lot of the young guys in porn are just clones. Even if they’re great, interesting people in real life, they’re packaged in this way where it doesn’t even matter whether it’s one guy or the next one that looks like him. That’s the great thing that comes with being a little bit older. If I tried to package myself as anything but myself, it wouldn’t work.

And I won’t do anything that I don’t want to do. I don’t want to find out what I’m willing to do. Once someone asked me to [do this really gross and unsanitary thing], and I said I wouldn’t like it. And he said I don’t want you to like it, I want you to think I’m gross. And you know, I just don’t want that vision in my head when I’m in bed at night.

That’s fair. Can we forget [gross and unsanitary thing] and talk about how hot you are? Let’s end on a positive note.

It’s my dream to be a Penthouse centerfold so I can answer the questions the way they do, with my own handwriting. Do you know what I mean? Nobody ever knows what I’m talking about when I say that. But I love all the answers. “What’s your biggest flaw? My inability to ever say no to a nice guy. What’s your pet peeve? Men that come on too strong.”

Okay then. Biggest turn offs?

When somebody bites too hard. I hate that. Sometimes people bite my beard.

And turn ons?

People who look you in the eye. And kissing. Sharing someone’s air.

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