Elena Lincoln (Kim Basinger) and Christian Grey (Jamie Dornan) in “Fifty Shades Darker.” (Doane Gregory/Universal Pictures)
“Fifty Shades Darker,” the latest installment in the big screen adaptation of E.L. James’s erotic trilogy, touches heavily upon the topic of sexual mentorship. In the series, Christian Grey plays the S&M-loving benefactor and sexual mentor to his love, sweet Anastasia Steele. Kim Basinger, no stranger to steamy roles (ahem, “9½ Weeks”), appears as Grey’s former sexual mentor, Elena Lincoln, a.k.a. Mrs. Robinson. Like many members of the kink and sex communities, I find the “Fifty Shades” series woefully flawed. The books did, however, push a few taboo topics into mainstream conversation, including BDSM and sexual mentorship.
Intrigued by the verboten topic of older women showing younger men new paths to pleasure and curious about the economic concept of sexual supply and demand — but not necessarily to acquire an enthusiastic new lover — I placed an ad on Craigslist in December:
Are you looking for a sexual mentor?
If you’re a younger male looking to connect and safely explore mutual sexual interests with an older, experienced woman, let’s chat. I’m smart, sensitive, open minded and thoroughly enjoy sex and its many permutations. Instead of masturbating between the sheets at every opportunity, why not spend some time with a skilled lover who will teach you how to please a woman?
Me: 40-something, sex-positive woman with a high sex drive, practices safer sex, STD/STI-free.
You: 18+ with an insatiable sex drive, practices safer sex, STD/STI-free.
Just imagine the possibilities.
Within 10 minutes, my inbox was flooded with more than 120 replies. The ad was quickly flagged.
“I am 28 years old and very much a ‘late bloomer.’ If what you’re offering is true, then I would very much like to say that I am interested,” wrote one potential mentee.
Another emailed, “What you offer is precisely what I’ve been seeking for quite some time. I’m tall, attractive, playful, and well-versed if not well-spoken, but I’ve never really embraced my sexual desires nor had much guidance in that domain. I would love to have an experienced woman teach me the secrets to pleasing her.”
The large volume of “Is this for real?” reactions was to be expected. There was also a substantial number of unsolicited pictures of men’s private parts. (Groan.) My takeaway? There are a lot of young and hungry men out there who want to step up their sex skills with an older woman.
For most women I know, exploring sexual pleasure was not something we were ever taught or encouraged to do. I’m a sex-positive woman who understands consent, practices safer sex and brings vast and varied experience to the bedroom. Sex should be fun and playful. Every interaction, sexual or otherwise, is an opportunity to learn — if you’re curious. I encourage exploration and advocate for pleasure.
Yet, the erotic frisson between an older woman and a younger man is alive and well, as Christian’s much-older mentor Elena demonstrates in the book “Fifty Shades Darker.” The concept of a woman striking out as a sexual pioneer is still very much taboo, but the sexual appetites of younger men and older women are closely matched in terms of stamina and spontaneity. Older women bring confidence and years of practice to the bedroom. A woman who knows what she wants and communicates that knowledge can be a huge turn-on. Combine that with a young man’s short refractory period, and you have the makings of mind-blowing sex.
In my experience, the big difference between an educational experience and robbing the cradle is the erotic know-how a skilled woman offers. Imagine sexual mentorship as a rite of passage, where partners discuss what turns them on and which boundaries they are willing to push. With time and practice, they develop greater cognizance and connection.
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Over the years, I’ve repeatedly found myself in this role organically. Most recently, I doled out practical advice about how to please a woman orally and use sex toys to a local couple two-plus decades my junior. In my early-20s, I schooled a first-year law school student on the ins and outs of anal play. I’ve given menopausal women who’d experienced decades of male pleasure their first-ever orgasm from a female partner. I had a behind-closed-doors arrangement with a 30-something fella who’d come to my apartment on demand to play out a “Secret Mommy” fantasy. He presented the role play; I was willing to explore.
There’s no shortage of friends with benefits options in the world, but I find it far more satisfying to share a deeper — maybe not committed, but connected — sexual prowess with others. My casual relationships often outlast their committed counterparts. When I’ve dated openly, these dynamics have allowed for sexual diversity beyond a primary partner.
As much as I disagree with many aspects of the “Fifty Shades” franchise, it has helped redefine what is normal sex — whether it’s a kink, fetish or tendency.