“Luke Jackson,” 32, makes around $30,000 a year as a part-time, New York-based male escort — a side business he started eight years ago. See his business story below:

I never would’ve guessed that being a male escort would be my calling. I mean, I was a late bloomer growing up in rural Virginia. I didn’t even lose my virginity until I was 19, with someone I met on vacation in Puerto Rico.

I started to explore sex in my mid-20s, around 2007, after I moved to D.C. I didn’t have any specific fetishes or interests: I just knew that there was more out there than what I’d experienced with my college girlfriend, who was pretty vanilla. I was curious about group sex, anal, BDSM … things like that.

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. A woman named Claire* replied; she said she was a PhD student in literature. From her emails, she seemed sexy and smart. She was also a high-end escort, she said: Her clients were politicians, CEOs, and a few TV news personalities she couldn’t name.

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.

“You might want to think about becoming an escort,” Claire said casually, after we were done. “You could do it on the side while you focus on your journalism career. There aren’t a lot of straight, open-minded, and well-endowed men in this line of work.”

Maybe I should say here that I’m 9 1/2 inches long and as wide as a beer can.

Really.

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 mid-20s, 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!” to “That looks painful.” Some women call me “Horse.” You have to learn different techniques when you’re my size. Patience and focusing on foreplay becomes really important, because you can hurt someone.

I couldn’t believe an escort like Claire — someone who charged $5,000 a night and was just sleeping with me because she wanted to — thought I was good enough in bed to make a business out of it! 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.

“Are you serious?” I asked.

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. 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: “Luke Jackson,” a nod to Paul Newman’s character in one of my favorite films, Cool Hand Luke. 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. 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.

In early 2008, about a month after I put up my site and listed my services on Concierge du Monde, an email from a Swiss banker named Veronica* popped up in my “Luke Jackson” account. 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. (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. She wired me half the money — $5,000 plus hotel and airfare — and I remember staring at the computer screen for a good five minutes, unable to believe this was really happening. 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. 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. 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. 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. My baseline price is $1,500 for an evening, and $2,500 for a full day or overnight. 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. 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: someone who helps women figure out how to voice their desires, needs, and fantasies. A lot of my clients have been involved with men who aren’t interested in what turns women on. The advantage of hiring an escort is that I’m up for whatever you want to try. I’ve never really had an awkward moment with a client — [at most,] there have been uncomfortable silences when we don’t have anything pressing to talk about — but when you’re playing with a new person, it’s part of the job to understand what they want, to ascertain their boundaries and desires. You can feel that out before you meet just by asking, but you also have to pay attention to their reactions — what they enjoy, what they don’t.

This job is not simply about being “good in bed.” It’s about enjoying sex and sexuality. I’ve been to sex parties and sex clubs, but I’m not a big fan. They tend to be trashy and forced, and I prefer to let things unfold more organically. (Well … as organic as it can be when someone has hired you.)

I often meet clients with their partners too. Usually, the guy hires me to fuck his girlfriend or wife, or we’ll have a threesome. (I don’t have sex with the guy though. I’m just not sexually attracted to men.) Size is a big thing with couples — often, the guy wants to see his wife with a bigger man. I assume it has to do with a generation that’s been watching porn and seeing well-hung guys having sex.

Once a guy hired me to have sex with his girlfriend in a hotel for her birthday. She was blindfolded the whole time; she wouldn’t recognize me if I bumped into her on the street. And then two weekends ago, another man asked me to sleep with his wife and her best friend while he watched. It was the wife’s first time with another man. Everyone had taken molly, so they were raring to go. It was one of the more intense sexual experiences of my life: two days in a row, five hours of foreplay, fucking both women and watching them fuck each other.

At this point, I know I’m pretty damn good. I’ve made a lot of women squirt for the first time. There’s definitely a technique to that. But in general, I think there’s too much focus on “technique.” I’m good with my hands and tongue, but I’m not claiming to make you come no matter what. Still, so much of my business is word of mouth, so to speak. I wouldn’t be able to keep busy if I didn’t satisfy the clients.

This probably isn’t the best way to make a living. Being physically and emotionally on top of your game can be exhausting. I mean, it is a service industry. Last year, I started an ad agency with a friend, and now that’s my day job. My night gig is a great supplement; on average, I make a couple grand a month from escorting — enough to pay my monthly rent and to travel. I don’t have great savings though. I’ve had a risky career and started new ventures, and it takes a long time to pay off loans.

The few friends who know about my part-time job always ask if I’ve ever had a client I absolutely wasn’t attracted to. Not everyone is someone I’d sleep with under traditional circumstances, but that’s not really the point: In most instances, I would never have met them, so that dynamic doesn’t bother me.

And I’m always worried about telling people the truth about what I do. You don’t know how they’re going to react. About six months after I started this, I called my best friend, a woman I’d briefly dated years earlier. “So there’s this thing I’ve been doing, and it’s kinda crazy, but I wanted to tell you,” I blurted out. She didn’t exactly salute me — “Well, as long as you’re being safe and careful,” she said — but she didn’t condemn me to hell either.

My parents still don’t know, but I told my brother and sister five years ago on a visit home to Virginia, about a year after I told my friend. My brother and I were at a bar and it seemed like a good time. “I’ve been moonlighting doing some other stuff,” I said. “Drinks are on me!” He was speechless for a few seconds. Then he started barraging me with questions:

“Do you worry about STDs?” he asked.
“Of course. But I get tested every two months at different clinics in New York, and I always wear condoms,” I said.
“Aren’t you worried about getting busted?”
“I was at first,” I admitted.
“Do you ever date clients?”
“No!” I said. “I’ve become friends with some, but I wouldn’t even consider dating them. No one wants to get their feelings hurt and have the wrong expectations.”
He didn’t say much else. I think he was just absorbing it.

About two years into escorting, I got into a serious relationship. She knew about my work — if I start dating someone, I’m always honest about what I do — and she didn’t mind until two months into our relationship, when we were lying in bed one morning before I was supposed to go meet a couple for a session. “Don’t go,” she said. It wasn’t a moral thing; she was into kink too, and we went to sex parties together. But she wanted me for herself, I think. So I emailed the couple and told them I couldn’t make it. I made up some excuse; I don’t remember what exactly.

Then I sent out emails and texts to my regular clients, telling them I was grateful for the experience but I was moving on in life. I also took down my Concierge du Monde profile. Everyone wished me well, and every so often, I’d get a note from a client, just checking in to let me know they were thinking of me, but I didn’t go out with them. I didn’t really want to. I was in love, and my girlfriend and I were having plenty of sex. I missed the money and the travel, but I didn’t miss the physical connections.

We broke up two years later. A few weeks after that, I reposted my profile on Concierge du Monde and created a new website. Partly it was financial: I’d launched my own company; I needed money. But I’d also missed the ego boost and the adventure. So I emailed or texted my old clients to let them know I was back in business, and most were very happy to hear from me. These days, I don’t have any plans to quit. I truly like my clients and feel I provide a service. It’s a break from their real life … and it’s a break from mine too.

By Cosmopolitan