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At the time, I was dating a bunch of different women. One wanted to have a threesome, so we put up a Craigslist ad to find our third. From her emails, she seemed sexy and smart. She was also a high-end escort, she said: I'd never known anyone who did sex work, but she was totally open about it. We never did get around to having that threesome — my original partner and I stopped seeing each other — but Claire and I kept in touch, emailing about life, literature, and sex. We eventually met in person for drinks and had incredibly intense sex that night, thanks to the tension and buildup from our exchanges.

There aren't a lot of straight, open-minded, and well-endowed men in this line of work. I didn't realize that my size was so unusual until I started getting into the kink world. I'd shown off during high school, playing around on web cams, but it wasn't until my mids, when I started having a lot of sex, that I fully realized what a selling point it can be.

I've heard everything from "That's the biggest thing I've ever seen! Patience and focusing on foreplay becomes really important, because you can hurt someone. She was mysterious, glamorous and sophisticated; I was fascinated by her world. It was so far outside my daily life — like a window into something that happens only in movies. She told me about an online forum called Concierge du Monde, advertising "the finest male companions, for ladies only" since most male escorts are meant for gay men. Over the next few days, I did lots of research. Clearly, it was lucrative; Claire made high six figures annually, and I had major school loans to pay off.

Plus, the idea of getting women off got me off. I loved sex. I didn't have a girlfriend at the time. Why not get paid to do something I enjoyed? Of course I worried about the fact that it's, you know, illegal. But that was part of the allure.

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And I think prostitution should be legal. It's no one's business what anyone does with his or her body. I know sex work is a very complicated area, with feminists standing on both sides of it, but I don't have a lot of sympathy for people who consider all sex work to be trafficking. That creates a lot of stigma for people making an independent living. Human trafficking and exploitation of women is abhorrent and should be stopped, but I think often, real issues like trafficking are used as an excuse for broad repression of sex workers.

So I came up with a pseudonym: I'm a huge Newman fan, and I relate to his character's boyish Southern charm. I built a website, and a woman I was sleeping with took photos. She knew about my plan, and thought it was both crazy and cool; it didn't bother her at all. My photos pointedly hid my face, of course: I didn't want the cops to come knocking.

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But I don't outright offer sex for money on my site — just companionship and conversation. I wanted to hint at sex without being over the top, so I didn't pose much; I just walked around and tried to be relaxed while she shot. My stomach lurched: Holy shit, this is real! We emailed a few times, then moved to the phone. Oddly, I wasn't nervous: We talked about what I was studying and the books we were reading. I was relieved to find I felt comfortable with her.

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I'd start to learn that this is important; if the conversation doesn't click, then I don't get together with people. Veronica offered to fly me to London for a long weekend. I began thinking of all the things I could do with that money, and the stories I could tell If I were ever to come clean. I was definitely nervous when I boarded the plane. Physical safety wasn't a concern; you always want to be conscious of it, but I'm 6-foot-3 and strong. Still, I called a good friend to tell her where I was heading. When I arrived in London the following morning, I went to the hotel and cleaned up, then met Veronica in the hotel lobby.

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She was blonde, blue-eyed, in her early 50s, and looked just like her photos. Someone who knew what she wanted and had the means to afford it. She was married, but both she and her husband explored other things on the side. Veronica had made dinner reservations for us at a nice restaurant in Mayfair. At the end of the night, she gave me a quick kiss on the cheek but nothing more.

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  8. For the rest of the weekend, we strolled the city, but that was it. She wasn't looking for sex, actually. It sounds nuts, I know.

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    I felt like I was supposed to have sex with her: Why else was I there? On the other hand, you have to do what the client wants. I just followed her lead. This was her trip and at the end of the day, it was a job. And as I've continued this work, I realized that Veronica wasn't that much of an outlier. I'd always thought that the idea that men seek out prostitutes just for companionship was bullshit. But now I think a part of it is true.

    Two or three of my clients this last year mostly wanted companionship. The sex was secondary. Within the course of the following year, I probably saw one client a month. Most are in New York, where I live, but I'll fly anywhere.

    These rates are on the higher end for a guy, but they're lower than prices for most female escorts. Some of my clients are married, and I'm their secret.

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    I have one client who's around my age and gorgeous. She's been married for most of her adult life; her husband doesn't know about me. For her, it's a mix of the need for intensity and a safe space to explore new things that her husband won't do, like bondage, spanking, anal play.

    I think our interactions have helped their marriage, actually. She's become honest about what she wants; they've started having sex with other couples. In fact, I often feel like a kind of sex therapist: Very cute, around 5-foot, with dirty blond hair—definitely not someone who looked like he was an escort. Before I knew it, we were inside the party, sitting at a booth beside a dancing Alexa Chung and Lydia Hearst.

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    As for how much he actually works as a rental date? He said it varies anywhere from one to four times a week. He then went through an extensive interview, and screening process, he said. The date struck the perfect balance of companionship, without that feeling of having to babysit someone. He made sure all the people we were talking to had a drink at all times, did the small-talk game happily with my acquaintances at the party, and regularly told me he was having a good time. He told me he lets his dates decide if they want to disclose any more information.

    The only hint I got that he might be a tad uncomfortable getting paid for companionship was when I asked if he had told his parents what he did. And as for the more controversial aspects of being an escort, he did admit to stripping, but that was about it. The whole experience did give me at least a little bit more insight into why so many men seem to enjoy the company of women escorts. Will I make a habit of hiring dates to escort me to fashion parties?