The First Time

Minor things can become moments of great revelation when encountered for the first time. –  Margot Fonteyn

A week ago Friday (March 11^th), I received the following email from a young man who asked to be called “Joseph”:

First, allow me to say that I greatly admire your blog.  I stumbled across it while trying to find out more about that recent CNN special about ‘selling the girl next door’ and found it very enlightening, intriguing and engrossing.  And a bit frustrating, since I am in my mid-20’s, still a virgin, never even had a girlfriend (one high school crush notwithstanding) and can’t envision getting laid unless I found someone like yourself (in your previous job of course).  That’s impossible because of my job (military stationed overseas).

Since I can’t ask you to help me break regulations and find a professional in my area, I have another question.  You’ve mentioned that occasionally parents would hire you to take their son’s virginity.  Would you ever talk more about that?  I’m not looking for lurid details, mind you, but what were those jobs like?  Did the parents tell you why they went to such lengths?  Did the son know about what the parents were going to do?

Anyway, thank you for your time and keep up the fine work.  I read your blog every day.

As I’ve written before I’m especially fond of military men, so I told Joseph that I would be happy to oblige.  Joseph, if I don’t answer your questions adequately please let me know and I’ll try to elaborate in a response!

At the time I received my first such request, my personal policy was not to see men under 21; any younger than that just didn’t feel right.  Not that we exactly had a large volume of requests from men that young, mind you; it’s pretty rare that any man below about 25 has the money to hire an escort.  Once in a while there’s the frat boy type, but that’s about it.  Well one night, I went on what I expected to be a normal call; the gentleman sounded middle-aged, was polite, from another state, staying in a nice hotel, that sort of thing.  And when I got there he was much as I had expected, but before he paid me he told me that he had actually called me for his son, who had just turned 18.  Now, I knew that at one time it was not at all uncommon for fathers to hire prostitutes to take their sons’ virginity, but it’s not exactly usual nowadays and in any event I had never done it.  Still, I’ve never been one to turn down new experiences so I agreed.

The young man was, understandably, very nervous; it didn’t seem to bother him that I was 10 years older than he was (actually 15, but I claimed 28 in those days), but he had never been alone with a naked woman in a well-lit room before.  I asked him what sort of experience he had and it was the usual fumbling through clothes in dark cars with high-school girls, so I invited him to look me over and touch me as he pleased. Like many virgins he was almost too gentle for fear of hurting me, but I assured him he needn’t be so tentative and that if he accidentally hurt me I would let him know.  We didn’t do anything really unusual; I gave him the typical activities most men like, and even though I didn’t usually kiss clients I was happy to show him how most girls like to be kissed.  I kept the pace relaxed and interspersed with bits of casual conversation so he could see I wasn’t all that different from any other women he had known.  Inexperienced men often find experienced women quite intimidating, so I was careful to make everything seem as natural and comfortable as I could.

From my high school and university days I knew that virgins and near-virgins tend either to climax very quickly or to take an extremely long time due to nerves and performance anxiety; he was one of the latter sort, so I kissed and verbally encouraged him until nature took its course.  We then lay together for a long time while I caressed his chest and reassured him; like many young men he was very concerned that he had performed adequately.  I said he had done just great and that if he always strove to pay attention in bed, to give his partners more of whatever they seemed to like and to avoid whatever they seemed not to like, I was pretty sure most of his future girlfriends would be very happy with him.  All in all, I really made an effort to make the experience as special and memorable to him as possible; after all, to me he was only one customer, but to him I was and always would be his first.  And I must have succeeded, because later that evening I got a call from the father thanking me for making his son so happy; apparently the young man was singing my praises after I left!

He was the first young man whom I initiated, but he wasn’t the last; sometimes they paid for themselves, one was paid for by his friends (they took up a collection!) and another was actually arranged by his mother.  The latter was a very cool lady; we talked on the phone for quite a while so she could feel me out, and when she was satisfied that I was the right woman for the job she tasked me to show her son how to make love because she wanted him to know the right way before he inflicted himself on coeds.  What made the date even more interesting, however, was that the boy wasn’t a virgin after all; he just didn’t want to hurt his mother’s feelings by telling her after she had gone through all the trouble to carefully select and interview an escort!  It turned out Mama had nothing to worry about; he did at least as well as the average man, which was really my experience with most virgins.  It was certainly the case with a young Indian man in his late twenties who had come to America to make his fortune and was about to send for his bride; he wanted to be sure he knew what he was doing so he could make her happy in bed.  And though he asked me to critique his performance, I could find nothing to complain about.

Indeed, this sort of thing happened so consistently with virgins I sometimes wondered if most men don’t start out with good instincts and then tend to lose them over time.  Perhaps as some men gain experience and confidence they start taking for granted that they know what they’re doing, or perhaps they fall into bad habits that none of their lovers bother to correct.  Some men may just be so selfish that once the initial novelty wears off, they just don’t care about what women (especially not paid women) might like, and others may be so mired in the masculine “never ask for directions” thing that they try to teach themselves (by reading books or watching porn or whatever) and end up firmly convinced of their own expertise no matter how wrong they are.  I’ll bet a lot of them even learn from other virgins, and when the blind lead the blind the outcome is not likely to be a good one.  Maybe the parents who hired me for their sons understood that; in the absence of an older girlfriend to learn from, perhaps for a young man to enjoy his first time with a caring and patient harlot isn’t at all a bad idea.