[Older Virgin Week] Should a woman hire a sex worker to lose her virginity?

Cable has Shark Week, we have Older Virgin Week! In honor of V-Day, by which we mean Virgin Day, all this week we’re reposting some of our favorite older-virginity-related stories. This post originally ran in January 2011. Share your biggest older virgin myths here.

“I have never met a woman who raved about the experience of losing her virginity. Perhaps that’s partly reticence, but from the stories that I have been told, for most women, losing their virginity was awkward, painful, a total non-event, ruined by their partner’s excitement and inexperience, or some combination of those things. Which, to me as an escort (whose job is making sex and sexuality fun and enjoyable) is a shame.”

That’s John, an Australia-based escort, talking about why women might seek out a male sex worker  for first-time intercourse.

Young men losing their virginity with female sex workers is a standard narrative trope, and in some cultures a celebrated rite of passage. Nevada’s Moonlight Bunny Ranch, a brothel which calls itself the ‘devirginizing capital of the world’ isn’t talking about virgin women (except for Natalie Dylan, the one notorious, if unconsummated, exception). And aside from the rom-com The Wedding Date, where the escort isn’t even hired for sex, women hiring male sex workers remains a very taboo subject.

Given all that, we wanted to know more about why John, whose clients are usually sexually experienced women and couples, started reaching out to a new potential group:

First, we’d love to know how you define ‘losing your virginity,’ since it’s sort of a hazy thing.

I will admit to being a bit “conventional” there. For me, losing your virginity (for a heterosexual couple) means penis-in-vagina sex. Why? Probably mostly because that is what I learned as I grew up. But also because to me it is the most intimate act possible between two people.

Everything else – while just as or even more enjoyable – is “foreplay”, or an extension of sex to me, but when you get right down to it, penetrating, or being penetrated by another person (especially-face-to face) is as intimate a connection as you can make with another person. That may be one reason why rape is so devastating, because it perverts and abuses that intimacy and connection.

Why do you think women might need or choose to go this route, sexually?

I don’t know if this is something that is “needed” as such (like food, or water are “needed”), but it fills a gap caused by the nature of our society.

No woman should feel that hiring an escort is the only option for them. But because of the problems caused by things like religion and the emotional immaturity of most of our society this is unfortunately how some women do end up feeling. I would be happier if that wasn’t the case and men and women were able to treat each other with respect. Because this isn’t always the case, there is an opportunity for me to help these women.

Do you think demand is growing?

Yes I think so. It is a result of two things: 1. our generally more relaxed social attitudes to sexuality, and 2. our ability to communicate with more people more easily.

Women who are virgins can hear about the idea of employing a male escort more easily, they can find and participate in positive discussions on the issue more easily, and ultimately they can connect with male escorts like myself more easily (and with complete anonymity).

That wasn’t possible prior to the Internet and given that people are more open minded about sexuality, it leads to more interest and perhaps more demand. You could also view this issue as a consequence of women taking more control over their sexuality. As a result some are choosing to employ a male escort for their first-time sex.

How do you think women differ from men in terms of the experience they’re looking for?

Since I am a straight (heterosexual) male escort, I can only speculate on that question. Being male though and knowing other men I would say that the difference is significant. Most men (I think) don’t see any inherent value in being virgins, we are just interested in having sex. So losing my virginity was a milestone, but I didn’t see it as a “gift” or something that a woman would actually value.

As mentioned on my website though, I was lucky enough to meet a woman who made losing my virginity a very memorable experience. It could have been much less enjoyable for me, but that wouldn’t have made me any less eager to actually do it.

By contrast, my experience with women considering losing their virginity with me is that there tends to be more emotion invested in this experience than there was for me when I lost mine. However every woman that I talk to about losing their virginity is different in what they think and feel. Some don’t care much about it and want to lose it and get on with life. Others are worried about having a bad experience, so are looking for someone who understands and will put their needs first. Then there are the women (often older) who find it hard to establish relationships with men (let alone have sex). For them virginity, emotions, self image, and doubt all seem to get tangled up together, which makes things very hard for them. The second and third groups are the ones I have most experience with personally.

The third group are the women who seem to get the least support in our societies. That is why I like the work that people like you and The Accidental Virgin are doing. I try to support that effort by being available for women to talk to about losing their virginity (be it with an escort like me, or any other man). So the difference, in my opinion, mostly comes down to the emotional content of the experience of first-time penetrative sex. It “matters more” emotionally to women than to men. So it’s not surprising that the majority of women don’t have the glowing memories of losing their virginity that I do.

How about the differences between men and women in terms of social taboos?

The social taboos are probably too numerous to list here, but women seeking a male escort to lose their virginity with just adds one more opportunity for narrow minded and manipulative people to stigmatise women. Which is ironic perhaps, given that the service that I offer is meant to help these women to overcome the shortcomings of our society in the first place. Thankfully though many women seem to be supportive of a friend who is considering employing a male escort.

A surprising twist on this issue is that I have been told by a father once that he would much rather his daughter lost her virginity to me (an escort who will actually try to make it a good first experience of sex), than to some random man (with all of the uncertainty that implies). Fathers may have (rightly, or wrongly) even more emotion invested in their daughter’s welfare and virginity than their daughters do, so maybe that shouldn’t be surprising.

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