My Sexual Awakening with a Male Escort for Older Women

 & 
July 5, 2024

My Sexual Awakening with a Male Escort for Older Women

 & 
May 29, 2023

(The author “Madelyn” is a long-time, active member of the MEA community. Names and identifying details, including the author’s, have been changed.)

Chip’s Note: I’ve known “Madelyn” for more than a quarter-century and have always appreciated her authenticity. But, with this three-part series of her sexual awakening, she’s taken candor to a whole new level. I hope that many of you can relate or are inspired by her story. Ironically, I’ve known her “Michael” for more than a dozen years as well, but they’ve only recently met.

I’m sixty-nine, and I’m about to have sexual intercourse for the first time since I was fifty-two. The man I’m about to have it with just drove into my driveway… 

Seventeen years ago, my beloved husband David became sick. One form of cancer, then serious heart problems, then another form of cancer. I was by his side as his caretaker through multiple major operations the whole time—and still am. We’ve been married thirty years, and raised a beautiful, happy blended family of my children from a previous marriage, and his. 

When David became ill, our passion and desire was still there. But his ability to have sex was not. We tried everything—from pills to positions to porn. The only form of sex that he had energy for was me going down on him. At first, I was enthusiastic. But over time, it became repetitive and started to feel like one more chore on top of all the other daily caretaking of my sick husband I was doing: after giving hour-long blowjobs without an orgasm in sight, I practically needed chiropractic adjustments for my neck and jaws!

A few years ago, I brought up to David that I felt, in order to be the best caretaker I can be for him, that I needed to get my own sexual needs met from someone other than him; going without any sexual satisfaction for over a decade and a half was no longer tenable for me.

I can’t say David was thrilled at my expression of this need, but he understood. He gave me permission to get my needs met elsewhere; he just didn’t want to hear the details.

And so, I went “cruising” on a cruise… but I’d been out of the dating game for so long. Evidently, flirting is not like riding a bicycle… I learned that you can lose this skill. Anyway, I wasn’t interested in any of men, and they weren’t interested in me. I returned from the cruise unhappily unfucked. 

This March, my friend told me about her friend Michael, age forty-seven, who works in the Bay Area as what he calls a “M.E.O.W.”—a Male Escort for Older Women. She said she’d known him for a long time, and trusted him. I instantly asked for his number. 

I’d seen Good Luck to You, Leo Grande (which Chip mentions in Learning to Love Midlife), so I knew that this sort of thing was possible—at least for Emma Thompson in the movies. But it hadn’t even occurred to me to look for it myself. What was I going to do, Google “hire a male escort”? That seemed tacky, and potentially unsafe.

But now I had the number of a real “cat’s M.E.O.W.” in my hand, trusted by a close friend of mine. I shot him a text and we arranged a Zoom call. Instantly my trust for him went even higher. He was a writer—he shared his real name with me and I saw several of his published books online. He was not some random guy off the Internet. This work was an art for him among many—something he did for fun, for the love of women, and to support his writing. 

And now, Michael the M.E.O.W. is stepping out of his car, in my driveway. I’ve still got several months until my seventieth birthday—but Michael is my present to myself. I needed this present early. 

He doesn’t look like a movie star, like Leo Grande, but he is a solid, good-looking man. In good shape, with a shaved head and sparkling blue eyes, in designer jeans, black leather boots, and a stylish hipster jacket—and a warm smile.

I’m about to pay to have sex for the first time in my life. And I’m about to get fucked for the first time in seventeen years. I can barely wait for Michael to walk into my home—and into my bedroom. 

Coming tomorrow--Part 2: Fireworks.

(Note: I’ve been keeping a diary of my experiences with Michael, and gave him permission to post entries from this diary on his own blog. You can read my diary entries here.)     

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