The Honest Courtesan

I’m a virgin who will soon be 40, and I’ve been wanting to engage the services of an escort.  I read your piece on the topic in Reason, but I don’t know if going the sex worker route would make me feel any better.  I realize she wouldn’t be hot for me, but I dread the thought that she’d just not want to be there at all.  Sensing that I’m just a chore to get through would make me feel worse. I don’t want to rent a living sex doll, I want…I don’t know how to articulate what I want out of the experience.  I know I want a woman to have sex with me for free, just because she wants to, but it isn’t happening.

The concept of “free sex” is largely a male fantasy.  As Billy Crystal once humorously expressed it, “Women need a reason to have sex.  Men just need a place.”  Sure, there are exceptions to every rule, but waiting for a woman that you personally find attractive who just wants sex with you because she’s “hot for you” to come along is kinda like refusing to demolish that old barn on your property because you figure that that sooner or later it’ll be struck by lightning and burn down.  The great majority of women are going to want something else other than the mere physical act, partly because we’re wired that way and partly because it’s so easy for most women to get sex from men that the chances of one picking you in particular, without any effort on your part, resemble those of winning the lottery.  For the typical woman, the “something else” is likely to be some kind of romantic relationship; for the more pragmatic sort, it’s likely to be money or some other means of support.  And women who are specifically looking for a husband rather than a mere boyfriend combine the two.  You haven’t given me enough to determine why you’ve never stumbled into a romantic relationship over the past two decades, so I’m going to guess you’re shy and lack the self-confidence to ask girls out on traditional dates.  And I further suspect (unless there’s something you aren’t telling me) that the origin of your fear that an escort would view seeing you as especially laborious is that same lack of self-confidence.  Truly professional escorts, women who view sex work as a career and proceed accordingly, have professional ethics and standards; they are no more “living sex dolls” than boxers are “living punching bags”, and the only reason you believe otherwise is all the anti-sexwork propaganda permeating American culture.  Given that, I think you need to adjust your thinking a bit if you’re to correct your problem.  I suggest you peruse my column “From the Top”, which includes links to a number of columns for newbies; also this essay from a guy in a similar position to yours.  If you don’t find anything to help you there, I suggest buying my book Ask Maggie (both volumes) and reading all the essays whose leading questions speak to you (there are probably more of them than you think).  And once you do stop making up excuses to avoid seeing a professional (because that is what you’re doing, honestly), I think you may find the mystique around sex will start to evaporate, and your problem with it.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)