Conversations with a Rent Boy: Inside the Shutdown

The LGBT community, and its allies at large, were rocked to their core last month upon the federal bust of‘s NYC headquarters., a site that hosted profiles for gay escorts, had been a mainstay of gay culture for 18 years, even hosting floats during the city’s annual Gay Pride Parade.

It came as quite a shock then for the federal government (Homeland Security no less) to arrest the site’s managers and shut down the site altogether on the charges of prostitution. There has been a lingering sentiment that this bust took place specifically to target the gay communities, others still have posited even darker theories behind the unexpected attack. Even the New York Times have addressed that the circumstances behind the raid were shady, to say the least.

Regardless of the reason, it has instilled a community of fear amongst those formerly involved with the site. This fear was most self evident when reaching out to a former Rent Boy in regards to an interview. Our contact, who in this article will remain anonymous, repeatedly denied the option for a conversation due to outright fear of persecution. Luckily for us, he changed his mind. Milk’s Paul Bui met up with the escort to discuss his former experiences, the legality of sex work, and his own theories as to the controversial site shut down.

When did you first start escorting?

I first started escorting about a year after I moved to New York. At that point, it was something that I did on Craigslist. I was a slutty 21 year old and I was on there a lot anyway to hook up with people. Reading through, you would always come across ads saying ‘generous man,’ or ‘generou$’. They would offer whatever to meet young people for some purpose. Curiosity, and being broke, got the best of me and I eventually responded to some of them.

Have you been continually using RentBoy.Com since? Were there points where you had to stop?

At a certain point, I didn’t really need to do it anymore because I was working in more industries and making more money, but I kept finding myself going back to it as a nice supplementary income. There’s also something really fun about it. I enjoy men and meeting them. I enjoy weird experiences and going to apartments I don’t know and having these encounters. You see a world you otherwise wouldn’t see doing it. You hook up with a lot of dudes you otherwise wouldn’t. It’s nice because it’s a very clearly defined thing that’s happening. The terms are very clear so it’s not awkward. Because it’s just sex, it doesn’t have all the baggage associated with other relationships. There’s no awkward emotional stuff.

“I enjoy weird experiences and going to apartments I don’t know and having these encounters. You see a world you otherwise wouldn’t see doing it.”

What was your first time with a client like?

I was pretty nervous walking to their apartment and ringing the doorbell. You see all these movies and episodes of Law and Order about prostitution being some wicked thing where someone dies. That’s how murders happen: you go to a stranger’s home and are never seen again. I was very careful when I first did it. I would always tell a friend exactly where I was going and tell them, ‘If you don’t here from me in a few hours, this is the address. Alert someone!’ Eventually I stopped though because there’s not that need to be paranoid. It’s super easy. If anything the other person is more paranoid, more awkward about the situation than you are. When you go to someone’s house, they’re usually kind of awkward and are calling you for sex for a reason. Even though you’re the person visiting their house, you’re in a position of power and have the ability to move things along. 

Do you think there’s a misconception about prostitution being an unsafe profession?

For some people it’s definitely a lot riskier. For people that are forced to do it on the streets, they are certainly at a greater risk than people that have the luxury of doing it on the internet, and being more selective about clients. That’s harder to do when someone it rolling up in a car, while you’re walking the street. Those people are certainly in a lot more danger. There’s a more privileged form of sex worker by doing Rent Boy, when it was up. 

Tell me more about your relationship with RentBoy.Com.

It’s just a site that hosted your ad. It was a convenient thing where you could post an ad and people could discover you or find you. You could meet some very nice people and make a lot of money with some very fun experiences. I definitely appreciated the site. It provided a good service in that it made it safer for sex work.

Why do you think it was shut down?

Who knows what the real reasons were. It’s definitely strange that we have these over funded agencies like Homeland Security getting involved in prostitution cases and shutting down these sites. It just shows that they have such a bloated budget. If this is one of their priorities and somehow tied to terrorism, which is what they were originally created for, that’s spooky. You have to wonder why it is that they were pursuing this. I think it also had to do with the Ashley Madison hack recently. There was a lot of worry about what might have been disclosed if Rent Boy was ever breached in that way. There was the risk of a lot of people of power being exposed, as there was a few months ago with that Gawker story about Timothy Geithner’s brother. I have to question if that didn’t play a role in it as well. The Obama administration is very close to the Geithner family, so this may have been a form of payback for them. It’s a very weird scenario. New York police and prosecutors were taking part in it as well which is all sorts of fucked up. Mayor De Blasio was involved in the crack down too, even though he’s supposed to be a great liberal hope. This isn’t the first instance of De Blasio being somewhat anti-gay, or his police force and the people in his employment at least. They’ve been targeting gay men cruising in Prospect Park. There’s been stepped up police presence and harassment at the gay section of Jacob Riis Beach. It’s part of a broader creep of the city policing gay sexuality. 

“I think it also had to do with the Ashley Madison hack recently. There was a lot of worry about what might have been disclosed if Rent Boy was ever breached in that way.”

So there’s been a lot of passionate debate recently about legalizing sex work, and the UN came forward recently in support of it, what are your thoughts on the issue?

I think it’s going to happen anyways and to make it the safest it can be for all parties involved it needs to be legalized. It’s when its something that’s forced underground, that people have to put themselves in situations that are less safe and put themselves at more risk. When it’s above board and a legal thing, then the options become a lot safer for people.

Do you feel like you’ve made genuine connections through escorting?

I’ve definitely made friendships; I’ve gone and visited some people in the hospital when they’ve been ill. There are definitely some people that I’ve become super close to that I originally met through Rent Boy, people that I’m still in contact with and that I care about a great deal. 

And how have they taken the website shutting down? 

People are definitely spooked. I think a lot of people are scared about what’s going to happen to all these records that the FBI courted off. Are they going to start looking through those? Are they going to start going after people who have used the service? People who have advertised on the service? I think there’s a lot of fear in a lot of people’s minds right now. It’s just a very bizarre weird time right now.

“Are they going to start going after people who have used the service? People who have advertised on the service?”

Do you have a typical clientele? 

No, there’s no typical type of client. There’s definitely a share of older guys on there, as you would expect, but an equal share of younger guys on there, middle aged guys, hot 40 something’s. There’s been times when I’ve gone to somebody’s apartment and been totally shocked when they open the door because its someone that’s fucking gorgeous and sexy as hell. I’m like what’s happening? Am I really getting paid right now to do this? This is awesome, okay cool. And then there’s definitely times where I open the door and it’s the exact opposite.

What’s been the most unexpected kink, or the most memorable or strangest fetish you’ve encountered?

I’m trying to think of what I want to say. One that comes to mind right now, its definitely not the strangest, but I used to see a guy who was very into super hero role play. He liked to pretend I was the good super hero and he was the bad super hero and punch my stomach. He was really into punching stomachs – that turns him on a lot.  

What about dating when you’re escorting? Is that harder?

No, it’s not harder. Not that I date much anyways, but when I was living with a boyfriend he didn’t mind. He did it too. I sort of got him into it, but I feel like most people don’t mind. If anything I think most people are kind of turned on by it. There are definitely some people that do mind and its sort of like a litmus test – it lets me know who I should and should not be investing time in. If someone has a really prudish reaction to it, its very clear we are never going to be a perfect match and it just makes it a lot easier for me to know that right away rather than several months down the line.

Are you spooked by all that’s happened?

Less so now. The day off, when this news story first broke and my friends started texting me who also did it, freaking out – I mean there was definitely this giant panic that was going around the Brooklyn, queer, gay scene that day.  


Just because so many people do it. Half my friends that are gay men in their 20’s are either doing it or have done it at some point. It’s a really common thing. The repercussions of this could affect a great many people I know, and it’s a scary thing because no one knows what’s going to happen. Hopefully nothing will happen because of the blow back that’s already been coming about like the New York Times editorial calling us out as well as lots of other voices out there. Hopefully things will fizzle and die out. Hopefully they wont start going through the records that they have trying to go after people that advertised on the site or that used the site – but there is that fear of what might happen. So there’s a huge fear, and its not so much prostitution that’s the fear but tax issues, that’s a fear too – if they start sending those files to the IRS about who uses the site. There’s all sorts of potential issues that are terrifying for people that have used that site, myself included.

Stay tuned to Milk for more updates.

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