I Lost My Virginity to a Prostitute: 6 Terrible Realities

By going to an actual prostitute, that's how. It becomes a rite of passage, like getting your driver's license or flaying your first sabre cat.

Consequently, brothels have a long and squelchy history as a portal into manhood, spanning the globe from Gilead (a fictional place) to the Netherlands (allegedly a real place). Napoleon lost his virginity to a prostitute he found near the Louvre. Mussolini lost his by hiring "an elderly woman who spilled out lard from all parts of her body." Charlie Sheen and JFK might be famous walking sex dispensers, but both paid for their first times. Bryan Cranston's first woman was a Dutch professional; Roger Ebert's was South African. Oliver Stone's dad booked his son's first woman, leading him to say, "My father was a generous man, and I love him to this day for it." This also explains a significant portion of the family relationships in Oliver Stone's movies.

Juan Naharro Gimenez/Getty Images Entertainment/Getty
"She just kept asking for me to move back and to the left. I guess it just sort of stuck."

According to Marcos, in El Salvador, it's generally the Oliver Stone experience -- a father takes his son out to a prostitute for his first time, most often when he's 15. That means ...

All that happened is one day, his tutor said, "... how it would be nice if I were taken to prostitute so that I learned how to be with a woman." Lots of boys Marcos' age were doing it, so he felt he could no longer avoid it. "He told me the girl was good-looking and thin," Marcos says. "She was, but I wasn't terribly attracted to her." They picked her up at a mall. Then they drove off to the nearest dedicated sex hotel. In America, this is any hourly motel that shares a parking lot with a Pizza Hut, but in El Salvador, it's an entire industry (but more on that in a moment).

And even this was two years after the first opportunity. Marcos' father first broached the topic when Marcos was 13, over the phone. He called out of the blue (Marcos' parents are divorced) and told him that a girl had seen him and wanted to desvirgarlo [take his virginity]. "I didn't really go out at that age, so I asked him where she knew me from. He told me he didn't know. Then he asked if I was interested. Since I'm an awkward person, I said no at that time." Another of his friends was asked to go through with it by an uncle (creepy) at age 12 (unspeakably creepy) and agreed.

Valueline/Valueline/Getty Images
"Ideally, our sons would move from one breast directly to another."

Now, by "girl," Marcos assumes his father meant "working girl," but we should note here many prostitutes in El Salvador are literally girls -- reports say that 10 to 25 percent of "visible prostitutes" are under 18, and 40 percent of those contacted privately (and expensively) are children. When an El Salvador boy goes to lose his virginity, his family may be paying someone not much older than he is.

So we're talking about a boy who's pressured by his family to have sex (and, at least some of the time, actively doesn't want to) and a girl who's probably forced by circumstances to become a prostitute (and who may be too young to have made a conscious adult decision to go into sex work either way). You somehow wind up with a sexual encounter in which neither party wants to be there. What's that word, for when a custom is so awful that it's almost impressive?

When you rent an auto hotel, you rent two rooms. The ground floor is a one-car garage where you park your vehicle before entering the second room, a tiny bedroom connected to the garage by private stairs. There's no front desk whatsoever. What they have instead of a concierge is "... a hole in the wall with a wooden box covering it. The wooden box had a small door so you could pay for the room without having to open the [room] door or looking at the person who's charging you." Yep -- your only contact with any hotel employee is a disembodied hand popping out of a wooden hole like fucking Thing from The Addams Family.

Via Mark McMahon
High-fiving it is not forbidden, but it is frowned upon.

And boom. You got your own room, with more privacy and anonymity than Frank Underwood at his most undercover-boningest. There's typically a giant mirror, sometimes on the ceiling. There'll be porn. Some have handlebars and other equipment for those with special requirements and/or very specific fetishes. On one wall of Marcos' hotel room hung a poster on proper condom use. You could even buy drinks via the faceless hand box -- Marcos' prostitute ordered a Gatorade, presumably to stock up on electrolytes before vigorously obliterating his chastity.

If you're not turned on by any of this, we have to say, it doesn't get better ...

Marcos continues, "She checked the time on her phone and put it on the nightstand next to the bed. Then she gave me some oral sex, which my teacher had already told me might happen, and put the condom on with her mouth. It was all very surreal and awkward, and I didn't know what to do."

She then climbed on top of him for some awkward genital fumbling. "I had trouble putting it in, and she helped me with that with her hand. I had trouble finding a comfortable way to position myself ... During the whole thing, she told [me] to touch her on the butt and breast so I would enjoy it more. I didn't want to touch her much because it felt awkward. I had trouble keeping an erection, and when she suggested changing positions, I just went with it. Then, after some time when I felt I could maintain an erection for long, I just [told] her, 'I'm done,' which she took to mean I had orgasmed. Which was a relief, because I hadn't."

So thanks to a bout of uncomfortable, joyless sex, Marcos was now a man, according to everything he'd been told. Yay.

Marcos never wanted to agree to this. When his teacher first brought it up, he says, "I avoided the question, but I also felt pressured to do it ... honestly, I thought the whole thing was kinda dumb. I didn't want to save myself for marriage, but I did want my first time to be with a girlfriend or a girl I liked." Humble desires, really.

Still, he had expectations. "I was always made to feel inadequate at school and kind of thought that maybe I would indeed grow up if I lost my virginity. Once I had resigned myself to the fact it would happen, I sometimes told myself, 'Maybe this would indeed make you a man, you idiot.'" However, his excruciatingly awkward experience in the auto motel made Marcos feel about as grown up as a letter to Santa Claus. There was no sudden explosion into manhood. His maturity switch did not get flipped.

Visual Ideas/Nora Pelaez/Blend Images/Getty Images
It's almost enough to make you wonder if helping a boy become a man might take longer than five minutes.

He's far from the only person to ever have this reaction. Marvin Gaye, whose legendary hit song "Let's Get it On" has seen the end of many virginities, lost his own virginity to an impatient, overworked hooker. He was scared shitless. "I can't even remember if I got hard," Gaye said. "I know I tried to fight my way through her fatty flesh, but then my mind won't remember any more. I felt betrayed. Sex was crude and frightening." Once again, that's Marvin Gaye, the man who would later write one of the most famous songs about genital collision ever produced.

Russell Brand describes losing his virginity to a prostitute as, "not sexual, just giggly and intrusive." Jerry Springer lasted seven seconds. Dennis Rodman paid a woman to take his virginity at 20, despite not being wholly attracted to women. After Tolstoy lost his virginity to a prostitute, he stood by the bed and wept. We're not exactly prudish, but it seems like maybe your first time having sex shouldn't be a session with a hired stranger that winds up as the darkest chapter in your autobiography after you get famous.

Sergey Prokudin-Gorsky
Good rule of thumb: If it's too dark for Leo Goddamn Tolstoy, then it's too dark for a 15-year-old.

Yet when Marcos' friends talked about their own adventures in auto hotels and nightclubs, all of them "seemed to be thrilled at the idea of having sex." So he lied and said that he'd had an amazing experience too, figuring that the revulsion he'd felt had been a symptom of his social anxiety. In other words, he thought that he was the weird one. Not until this interview did it occur to him that some (if not most) of the others were probably lying about it, the same way he did, because that's what was expected.

As his brother took one room, Marcos took another, and had another uncomfortable encounter with a prostitute. "I was afraid of what might have happened if everyone realized I didn't want to do it," he says, although he admits he doesn't truly know what the reaction would have been.

Marcos has checked into auto hotels a few times since then, gaining a little more experience with sex but never really enjoying it. Today, at age 21, he's only had sex with prostitutes. He's dated, but says he's never had a real girlfriend. He even briefly dated his tutor's daughter -- the tutor actually set them up himself, and we'll let you decide what to make of that. ("Hey honey, did I ever tell you about the time ...")

Jupiterimages/Pixland/Getty Images
"So if you guys break up, is it cool if I'm still his wingman?"

It really does seem like a tradition that only benefits the brothel owners. Unless the point is specifically to turn teens off of sex. You know, instead of guilt-tripping them or scaring them about diseases, they show them how sad and degrading it can be if done under the wrong circumstances.

If so, maybe just show them this article, instead?

Ryan Menezes is an interviewer and layout editor here at Cracked. Follow him on Twitter.

For more insider perspectives, check out 5 Ways Being a Legal Prostitute Is Weirder Than You Think and No Fat Tourists: 5 Rules Of Life As A Prostitute In Vietnam.

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