Sex worker who has slept with over 10,000 men answers the questions women never dare to ask

If you had the chance to ask an experienced sex worker any question, what would you want to know? In her latest post, Calico takes exception to the mundane things a certain UK tabloid considered questions “women wouldn’t dare to ask” and comes up with some queries of her own. For instance, when a client has a thing for walking around with a butt plug inserted, does the client supply the plug, or is this part of the sex worker’s services rendered? If so, does she get to write off the plug on her taxes? In this modern age when everybody reviews *everything*, what recourse does an escort have when someone posts a false negative review? Does she just mock the guy’s penis size in the comments section, or do lawyers need to get involved?
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For more of Calico’s incisive, thought-provoking lines of inquiry feast your eyes on her post “She Sure Didn’t Address The Questions I’d Dare To Ask” Read on…

By Calico Rudasill,

Whenever I see an article with a title like “Twitter Tips: Everything You Wanted To Know But Were Afraid To Ask” or “Everything you wanted to know about US elections but were afraid to ask,” what strikes me is how not-scared to ask any of the questions addressed therein I would be, if they happened to occur to me.

I don’t know if it says more about how obnoxious and shameless I am, or how easily frightened or embarrassed the headline-writers are, but I have yet to run across such a piece which poses a question I’d hesitate to ask, were it to cross my mind.

The latest example of an article like this I stumbled upon is no different. In fact, it’s even more disappointing in context, because the subject is one on which I do have many questions, some of which I maybe should be afraid (or at least too polite) to ask.

The Best You Can Come Up With Is “What Do Guys Really Want?”

In this case, the article in question has a slightly different spin on the “but were afraid to ask” construction, but the gist is the same. “Sex worker who has slept with over 10,000 men answers the questions women never dare to ask,” reads the headline.

Oddly enough, the first paragraph of the story suggests far from being unable to bring themselves to ask her daring questions, former sex worker Gwyneth Montenegro answers in her book “the golden questions that many women ask,” including “what do men REALLY want from sex?”

See? We’re one freaking line into this dumb story and already the questions have changed from allegedly unaskable to entirely mundane.

Seriously, this woman has had sex with over 10,000 men and the best you can come up with is “what do guys really want from sex?”

I’ve only had sex with a small fraction of the number Montenegro claims, and I still think I’ve got the answer to that one. Offhand, I’d say men want to (a) get their rocks off and (b) come away believing they’re God’s gift to feminine sexual desire.

Sure enough, Montenegro says among her legion of former clients, what they desired most was the “feeling of being needed and wanted.”

“Wanted badly by a horny woman,” she added. “It is their ultimate fantasy.”

I’m stunned. No really; who could have guessed guys paying for sex would want to feel like it was more than a mere transaction, but rather a mutually awesome experience which would leave their fragile egos stoked?

Seems to me like even those of us who have never sold sex should have been able to work this one out before our tenth encounter, let alone our ten-thousandth.

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Practical, Business-Related Questions

Presented with the opportunity to discuss her former line of work with someone experienced and successful, there’s no way I’m settling for mushy, pop-psychology questions about what her clients wanted from their paid sessions. No, I’m going to take the opportunity to garner some advice which has the potential to be useful.

For instance, I would want to know how many times she had a client ask her to put a butt plug up his ass, then call him at his work every hour to make sure he still had it inserted?

Also, in such a circumstance, does the client supply the butt plug, or does she keep some plugs handy to field what I assume is a common request? If Montenegro must supply the plug, does she get to write it off on her taxes as a business expense? If so, do the plugs get categorized as “office supplies,” or do they go under some other heading?

Important Questions Of Recourse

If I had the opportunity to directly pick the brain of someone like Montenegro, one of the most important areas of inquiry for me would involve how (or maybe if) she went about getting satisfaction at those sadly inevitable times when her clients did her wrong.

For instance, in an age when everybody fancies themselves great and necessary critics, how did she respond to negative reviews of your services posted online? (See item #5 on this page, btw.) Did she lawyer up and threaten to sue for tortious interference with sexual contract? Did she respond to the review in the comments section by mocking the man’s penis size?

How about if the client was just so sexually inept it made it impossible to reasonably perform her end of the bargain? I mean, never shot a client for being bad at oral sex, right?

Hmmm. After that last query, maybe it’s best people with more fear than I have (or at least a more effective filter) ask these questions, after all.


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