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Men Who Lose Their Virginity to Sex Workers

To get entirely too personal: I lost my virginity at 18, shortly after graduating high school, which I do recall thinking was just in the nick of time. Strange that I should have seen it this way, considering it was my girlfriend who lobbied for the milestone (this was her first time as well) and that previous crushes had scared me off with their eagerness to go all the way. By almost every non-anatomical measure, I was not ready to have sex until more or less the exact moment I finally did — and I count myself immensely lucky for that, a privilege too many are denied. But why all the mounting pressure behind it?

It’s possible I had some preternatural awareness of the statistics for heteros — that the mean age at which both men and women swipe the V-card hovers around 17 — and could sense myself “falling behind.” I definitely had male friends who got to college still desperate to do the deed before a suitable window of opportunity had passed. Most likely, though, all of us had absorbed a wealth of pop-cultural riffs on the fateful transition from virgin to sex-haver, the kind of movies that created a social expectation over and above one’s ordinary interest in genital pleasure. For my age cohort it was American Pie, Cruel Intentions, and Can’t Hardly Wait, though this is a genre dating back to The Graduate. Even newer self-aware stuff like 40-Year-Old Virgin trades on the anxiety of inexperience. And people ask the internet every day: How late is too late to jump this sexual hurdle?

A burgeoning literary nerd, I became most fixated on a scene from a novel that many suffering privileged white teens read and reread with religious fervor: At one point in his New York odyssey, The Catcher in the Rye’s Holden Caufield comes close to losing his virginity with a prostitute. As self-deceiving and unreliable as Holden’s narration is, his stated motivations betray the very conformity he despises: “Anyway, while I was putting on another clean shirt, I sort of figured this was my big chance, in a way,” he explains, waiting nervously in his hotel room. “I figured if she was a prostitute and all, I could get in some practice on her, in case I ever get married or anything. I worry about that stuff sometimes.” Then the other shoe drops: “I kept hoping she’d be good-looking. I didn’t care too much, though. I sort of just wanted to get it over with,” he confesses.

“Just get it over with” was advice I heard men give each other a lot in my generation’s era of have-you-or-haven’t-you. The idea is to give up on waiting for love, or even emotional intimacy, when on the quest toward one’s first PIV (or Penis-in-Vagina). This follows naturally from the dubious proposal that having sex is not as important as having had it already. There’s the assumption, too, that losing one’s virginity will always be awkward and potentially humiliating; taken together with the purely transactional approach to punching one’s ticket.

Hiring a sex worker can appear to be the ideal solution: discreet yet unambiguous, a “practice” run to alleviate the mental block that obscures our future sexual identity and romantic prospects.

Over on Reddit’s r/relationships this week, people were questioning that logic. In a since-deleted post, a mother asked for advice on how to handle the revelation that her husband had arranged, without her knowledge, for their 18-year-old virgin son to sleep with a prostitute — because “male virgins have less of a chance of getting laid as they grow older without having sex.” The dad thought it would “boost” the boy’s romantic life as well as motivate him “to lose weight and take care of himself to attract girls.”

Beyond the troubling lies and illegality of the situation, commenters worried about the lingering consequences of introducing a young man to sex this way: “What if he finally meets the woman of his dreams, she finds out he paid for sex, she’s staunchly against it, and he loses her?” someone asked. Another lamented that he has now “had direct experience of how women can be paid for sex, how sex can be divorced from love and affection, how easy it is for a husband to lie to his wife, that an old boys’ network exists…”

While the son said he enjoyed the encounter apart from the familial angst around it, any long-term impact remains to be seen. Other young men who lost their virginity to sex workers have have written that they feel “ashamed” by the “underwhelming” and “mechanical” procedure, or both “glad and disappointed” at how “meaningless” it was, or lovesick at the illusion of a deeper connection with a stranger whose job it is to create that emotional atmosphere.

Then there are the guys with no regrets: “I did it about 4 months ago,” wrote a bro on a bodybuilding forum. “Dropped a lot of anxiety about sex and managed to have sex without paying for it as well after losing it.” Another echoed that sentiment — “I did and would recommend it. Being a virgin fucks with your head” — but one commenter replied that “losing your V card to a pro is cheating,” the shortcut through a rite of passage that means more than mere intercourse.

Overall, when it comes to the question of whether to take the plunge, men seem evenly split. As Luke Winkie wrote for Vice, “it’s easy for a young man to regard his virginity as an albatross,” and a sex worker is uniquely equipped to lift that weight, but they cannot do it alone. At any rate, the stigma of hiring one should be no obstacle — by some estimates, 1 in 5 American men have done so.

Perhaps it’s silly to expect a one-size-fits-all solution to the stresses of male virginity; as with the broader spectrum of erotic delights, everyone has to find their true fit. And to hear it from my veteran sex worker friend — I’ll call her “B.” — you could do a lot worse than book an escort, if that’s what you really want. Based out of Las Vegas, B. has seen two virgin clients in the past few weeks, she tells me, though such appointments are “not super common.” Both, she says, “were shy, socially awkward but sweet dudes in the 24 to 26 age range.” One was upfront about his inexperience, while the other didn’t tell her until she arrived. “They were both super anxious and nervous and self-conscious. Took a while for them to finish,” she adds, along with a good-natured laughing emoji.

In these scenarios, B. says, men usually just feel like they want their first time to happen already — to stop missing out on the fun. One of the recent clients “seemed to be a victim of circumstance,” very quiet “but relatively cute.” The other was an avid online gamer “who had self-esteem issues because ‘every time I talk to a girl and show her a pic of my face she ghosts me.’ He was a big teddy-bear, very smart and gregarious. But online dating isn’t really great for dudes like that. (Or anyone, really).” B. felt for him: “I don’t think he understood that people are mostly shit and this kinda thing happens to all of us.” This guy, moreover, was keen to learn the standard physical interplay, or the “right” methodology of sex, treating his session like a naked tutorial. He’d never so much as kissed before, and B. guided him from this innocent art through the rest of it, noting how well he took suggestions. With any luck, he left a more confident man.

“I can’t speak for their mental states, but I know I did my job and left them both feeling pretty damn good,” B. says. “I don’t think the self-esteem issue is something that can be ‘fixed” by sex with anyone (let alone a pro), but I think [the gamer] appreciated hearing that it’s tough out here for everyone, that these feelings he was having weren’t just him.”

B. is adamantly opposed, meanwhile, to the sort of set-up described in that r/relationships thread, and would never participate in one which her presence is a “surprise” to anyone involved. “I think dads bringing their sons to brothels/strip clubs is a super awkward rite of passage,” she says. “I see where the motivation comes from and don’t see a problem with it as long as the kid is of age and wants to do it.” As a counterexample, she cites dads who do this in an attempt to “convert” their gay sons to a life of heterosexuality: “That is not okay.” Unsurprisingly, then, the ethics that guide any form of sex are crucial to a successful devirginization by a professional: consent, maturity, safety, candor, respect, and, preferably, keeping your parents the fuck out of it.

Does this mean every 20-something virgin should start scouring Craigslist personals? Not before some basic soul-searching. They say it’s never really too late to lose it, and nobody should just because their friends tease them. Sleeping with a sex worker to get the ball rolling is no less a leap than a drunken one-night stand or consummation with a loving partner. It’s not a magical cheat code for masculinity. But sex also isn’t a sacred pact. It’s messy, imperfect, and often rather weird. As B. says, you’re bound to get your feelings hurt sooner or later. The value in doing it for the first time is to remove it from the airy realm of abstraction. The real challenges come after.