Pay It as It Lays: In the 50 Shades Era, Male Escort Services Are On the Rise

Horny converts join new ‘Christian’ coalition!

DIANA IS A SINGLE WOMAN who uses Cowboys 4 Angels as part of a dieting plan. Each month, if she meets her weight loss goals, she celebrates by paying for sex. She has a few favorite escorts but would like to try them all. “It is safer that way,” she explained. “I don’t want to get emotionally attached to any one guy.” She’s even started a blog to track her journey. Photos of Diana on the blog show a grinning woman with round cheeks and blond hair. Before a date, she likes to smoke a joint and take her time getting ready. “I never repeat my outfits with any of the guys,” she confided. Clothes she’s worn and can’t wear again include a red and white polka-dot rockabilly dress and an array of cute tops that show off cleavage, “my best asset,” she laughed.

The 10 minutes before the escort arrives are “the most exciting” part, she said. “I feel like a kid on Christmas.” Diana greets the cowboy at the door and they sit down with a glass of wine and chat for about 20 minutes before disrobing. “Every single one of my dates has been 100 percent focused on my orgasm” she said. The cowboys all begin the same way—dropping their faces below the sheets and seeing what works. “Some of them ask, ‘Is this good?’ and I’ll be like, ‘Lower, left,’ or whatever.” Diana says one escort brought a giant bag of sex toys and an iPod and speakers—everything you could need. “There have only been two dates where we didn’t end up having intercourse, and also only two dates where the guy did not climax. And what I love is that I don’t have to feel bad about that or analyze it. He doesn’t climax, not my problem!”

It is this paradigm shift that makes sex with the professionals so good, she said. “When I am with someone I am dating, my head is constantly going, ‘Am I getting this right, what does this mean?’” she explained. “But with the pros, that isn’t there. I am mentally clear and I can focus on getting what I need.” Diana says there is a safety in going to professionals—it just feels less complicated that way.

What it takes for things to remain uncomplicated for Casanova Carter is to stay single. “It would feel like a betrayal, being so emotionally intimate with patrons, if I had a long-term partner,” he said. He has been seeing one of his clients for five years, he said, adding, “which is the longest relationship I’ve had—period.”

For him, the job fulfills a certain emotional need. “I wasn’t the popular guy growing up,” he said. “But I always loved getting into women’s minds and figuring them out.”

Clearly, some of the drive to succeed comes from the sexual cachet of being a gigolo in addition to the “fun money,” but I wonder if it also stems from loneliness.

Despite his hunky appearance, Cowboy Darren was a square growing up. This admission came over dinner, when I asked, “Tell me something you’ve never told anyone.” Darren added that he was still a mama’s boy. His mother knows about his side-gig and doesn’t approve. While he has never told a client “I love you,” he admitted there is one patron who gets to him. His demeanor changes from smooth to distant and wistful as remembered how she insisted on going to the same barbecue joint every time, how they would often just sit in Times Square and make fun of people for hours. I feel a heaviness in my chest for him as he talks.

Corrine lives in Vegas—a city where advertisements for escorts are in yellow pages and on the tops of cabs. She had gone recently through a bad break-up when she came across Smith, an escort who offers the boyfriend experience. Corrine booked him for her birthday, at a rate of $2,000. He showed up at her hotel room with red roses. Online photos depicted a man in a suit and a lip ring, with most of his face obscured—it turned out he was handsome. The first time they kissed was a few hours later, out for drinks at the Flamingo. “He asked me, ‘Can I have my kiss now,’ and took me to a secluded area.” After dinner when the two walked down the Strip holding hands and an old couple stopped them and asked if they were newlyweds, Corrine couldn’t stop laughing.

At the hotel reality sunk in. “I realized, I paid this guy. Would he be here if I hadn’t?” Sensing her hesitation, Smith got down on one knee. “He told me I didn’t have to do anything I was uncomfortable with,” Corrine said. Over the next few months, she saw Smith again and they talked on the phone. Corrine wasn’t seeing anyone else, and she knew she was getting attached. One night, she had a fight with her ex-boyfriend. Corrine called Smith crying and asked if he would see her for free. He wouldn’t. It was over.

Casanova Carter says he has fallen in love with clients and doesn’t view it as a problem. The only bad part of being an escort, he says, is when women “treat him like a piece of meat.” The worst part, he added, is being told “You have to do this—you’ve been paid for it.”

COWBOY DARREN is supposed to be splitting a margarita with me, but I’m the only one drinking. Feeling light-headed, I press him for details about his clients. Many of them are beautiful, he says, and a lot are married. Sometimes the husbands actually book the appointments. “These are busy guys, rich guys, who don’t have a lot of time,” he explains. “They want someone to take their wife shopping or to dinner.”
That sounds pretty innocent, I say. He laughs. “The women make the most of the sessions,” he said. “They always go in for the physical.”

Darren is bursting with cowboy adventures. He says the youngest woman he had dated was 24 and wildly gorgeous. Now, inexplicably a little jealous (that would be the tequila) I change the subject. “I heard that you cowboys can do some tricks with your tongues,” I say.

After dinner, we part outside the restaurant. Darren asks if he can put his number in my phone, and I let him. I go to hug him goodbye and my hat falls off. “Whoops,” I say, and then we give each other one of those confusing kisses—one that is supposed to land on the cheek but somehow winds up near the mouth instead.

editorial@observer.com