Losing Your Virginity to a Sex Worker Can Be Therapeutic

"Buddy" was back in Maryland for a birthday party, spending the week in a camper parked outside the house he grew up in. He was 29 years old and was determined to enter his third decade without his virginity. "It was something I really tried to keep private, a reason to keep me out of relationships," he says. "The 'main' reason I did it was that I was staring down the cold end of 30-year-old virgin territory. I didn't want that to be my legacy."

He spent the evening at a bar with some old buddies from work, grinding down any lingering apprehension with the infinite powers of alcohol and peer pressure. He handed his phone over to one of the guys who picked out a girl in his price-range from Backpage. Buddy gave her a call, told her his address, and articulated his particular situation. "I needed her to know I was a virgin," he says. "She needed to be able to react to that on the phone and not in the bedroom."

There was an ATM trip and a pep talk, and suddenly Buddy was sitting in his parent's camper, smoking weed, awaiting his reckoning.

"We both knew what was happening here. That was comforting, there wasn't anything that I could have done or said that wouldn't result in sex. The anxiety of stressing over every word was gone," he says. "I told her that I was a virgin and super nervous, and she did what she could to be reassuring. I finally had 'some' experience, instead of 'none.' So, I knew what to look for next time."

Male virginity shouldn't be a tragedy. There is ostensibly nothing wrong with having limited sexual experience into your 20s. But a millennium's worth of teasing and fragile masculinity has turned it into a genuine phobia. As such, it's easy for a young man to regard his virginity as an albatross. When it feels too heavy a burden to carry, sex workers can offer a mutually understood place where chasteness can be quietly removed.

"[Virginity] is a failure in their minds," says Maggie McNeill, a long-time sex worker and writer who's taken a number of virgin clients over the course of her career. "The pressure to lose their virginity becomes an animal, it becomes this goal. When they're talking to a girl in a social sense, that desperation shows. If [a client] goes to a professional, once it's over and done, he can go into other relationships like 'I can do this.'"

McNeill does her best to be gentle when she's working with someone with limited experience. Her usual clientele generally have a good idea of what they want. But virgins don't have the benefit of foresight. She describes it as "turning her patience switch to high." "I'm not gonna get exasperated, I try to be more verbal. 'Oh yeah that feels good, do that some more, most ladies will like that," she says. "With virgins, I'm very aware to say 'I like that, but some ladies might not.' I try to repeat that several times. 'When you're with a lady, pay attention to how she reacts, and if she reacts badly, stop doing that thing.'"

For men who have let intimacy grow into a monster, getting it over with can be a way to start banking some confidence. "It opened my eyes to what I've been missing out on. To me, it was a fantastic form of therapy; it really helped ease my depression," says Nathan, a sales rep who lost his virginity to an independent escort at 20.

The four men I spoke to who lost their virginity to sex workers are all in the stages of developing more consistent sex lives. Buddy started seeing men on Grindr and is currently courting a girl he met offline. Nathan tells me his new goal is to establish a longterm relationship with someone. A 25-year-old Verizon employee named Arthur tells me he's been less anxious and more confident since losing his virginity in a massage parlor. All of them still occasionally see escorts. "Toby," 29, says he thinks that will be his only option for life.

"By the time I saw this escort I had more or less given up on ever realistically entering into an actual relationship with another girl mostly because I just can't bring myself to put forth the effort to go meet one and start that process," he says. "Also because even if I did want to put in the effort, I don't even really know how to." Toby says he tried dating apps and websites like Tinder and OKCupid, but came up empty. "They were mostly full of bots from my experience."

Casting off the imposed shackles of virginity was "semi-rehabilitating, but not overly so," says Toby. He had very high expectations, one the experience ultimately failed to meet.

Losing your virginity is complicated no matter the circumstances. It's never been a magic bullet; you don't perceive the world in a radically different way afterward. One of McNeill's most memorable clients was a young Indian man who was about to be married in an arranged ceremony. He came to her so he could know how to please his bride-to-be. "I told him to proceed in the way he thought was right, that seemed sensible to him, and that I would gently correct him," she says. When it comes to taking a clients virginity, McNeill says she always takes the responsibility very, very seriously.

"I try to make it a special experience," she says. "This guy is one of many, many, many customers to me. But to him, I will always be his first time. It's a big honor in a way. I will be in his memory. I try to make it as nice as possible."

Follow Luke Winkie on Twitter.