A Post-Menopausal Prostitute

A Post-Menopausal Prostitute

Published April 30, 2023

This is an excerpt from Sex by Design, Betty’s memoir.

It was early afternoon when Scarlet called sounding desperate. A girlfriend who was to join her for a paid threesome had just canceled. Although she’d asked me to do a double with her several times in the past, this time I surprised both of us by saying I’d fill in. Besides being curious, I could think of no better way to defy the image of aging than by turning my first trick as a post-menopausal fifty year-old woman. Later on, I’d realize the other factor was the psychological freedom I probably felt now that Mother was gone.

Scarlet’s client paid $200 an hour for each woman. Because she’d made the date, she kept $50 out of my fee, which was only fair. After running so many workshops, I was fully aware of the work that went into signing up someone. That afternoon at four, I arrived at her apartment and was introduced to Marvin, who was wearing a black negligee, sheer black panty hose, and size eleven silver slippers. His wig was very much like Scarlet’s real hairdo, tons of red hair cascading over their shoulders. In his late sixties, Marvin was a sight to behold while Scarlet looked gorgeous in her blue satin negligee and matching pumps. Both of them were wearing tons of makeup, while I wore my own face. Under my ankle length coat, I had my silver studded belt with the big cunt buckle, boots, and nothing else. With short hair and no make-up, I felt like a little macho dude with two drag queens to entertain. I was up to my ears in tits— one set was foam rubber while the other pair was real.

Marvin always had to get stoned before sex, which annoyed Scarlet because he had to sleep off his high for at least an hour, and she didn’t get paid for his nap- time. They always did sex the same way. I’d been instructed to play with myself while she took care of him— an easy gig for a professional masturbator like me. Marvin lay down on the bed and she straddled him with her long slender legs folded on either side of his scrawny old body. Handling his small penis daintily with jeweled fingers and long painted nails, she inserted it inside her neatly trimmed pussy. Lying next to Marvin, I was ready to get off with my electric vibrator, but within mere moments after I’d started buzzing, it was all over. Scarlet pumped up and down a dozen times until Marvin emptied his nuts with hardly a groan— then promptly fell asleep.

I participated in doubles with Scarlet a few more times, until one of the men said that he’d really enjoyed reading my book Liberating Masturbation, and wanted me to autograph his copy. That’s when I discovered she’d been describing my workshops to sexually amuse and arouse her clients. This loss of anonymity took the fun out of it. Not that I was afraid of ruining my reputation— after all, I’d already gone public with my nude masturbation workshops for women. However, once these men knew my identity, I no longer felt like an undercover agent.

Around this time, I was asked to be part of a think tank for Xandria, the second largest sex toy company in America. Throughout the 80’s, they paid my expenses to San Francisco every August. After our afternoon meeting and one dinner out, I’d remain an extra week to run a Bodysex workshop and to celebrate my birthday as an anonymous sex worker with one of my prostitute girlfriends. They never gave up my identity. Once again, I was an anonymous masturbating voyeur who did hot talk while the younger women provided their clients with manual or oralsex, and sometimes penetration sex. However, most of their male clients preferred blow jobs.

I’ll never forget one of Sharon’s regular clients. He was a big, good-natured black dude named Gus. She dressed me up in white lace lingerie including bra, panties, and thigh-high hose with high heels. Talk about being in drag. I felt like a straight man cross dressing for the first time. At that point, I owned one dress that seldom got worn except to weddings, and one pair of women’s shoes. The rest of my closet was filled with sweat pants, jeans, tops, jackets, and boots.

As I watched Sharon and Gus fucking: he was laying on some smooth moves, as he slid his big black glistening dick in and out of her pretty pink pussy. I was commenting on his excellent technique when all of a sudden, Gus stood up and faced the mirror at the head of her bed. I was standing a bit behind him, off to one side, and could see his reflection perfectly. With a few strokes on his dick, he shot a load that traveled a good five feet and splattered against the mirror.

That’s when I dropped my vibrator and broke into a round of enthusiastic applause. I’d enjoyed it so much that I felt like paying him.

The following year, another client of Sharon’s came over during his lunch hour carrying a shopping bag filled with gourmet food. This quiet unassuming business executive in his early fifties took great delight in cooking us a delicious meal. Again, we were dressed in lingerie while we ate lunch talking about sex, and acting bawdy.

Finally Mr. John stood up, unzipped his fly, and presented his erection. Sharon removed her bra and oiled his penis. Standing in front of her, he put his erection between her full breasts and when she squeezed her titties together, he fucked her cleavage. Positioning myself to the side of her chair, I watched and played with myself. This time I didn’t have a vibrator because he liked to see a woman use her fingers. It was such a sweet scene, and he was such a nice man— I was happy to accommodate him. After he left, Sharon said he’d been married for twenty-some years, had four daughters, and still enjoyed sex with his wife twice a month.

Throughout the 80’s, I continued to have dinners with Sharon and her girlfriends every August in San Francisco. These young prostitutes didn’t fit any of the stereotypes of fallen women who were drug-addicted victims. They were very independent and none of them had pimps. A few were investing their money wisely, and several carried pepper spray in their handbags, although they admitted they never had an occasion to use it. I loved hanging out with these smart intelligent women who were as sexually experienced as I was; we always had great conversations about sex. When I spent time with more traditional women, I fell into the role of a sex teacher. Hanging out with professional sex workers allowed me to learn about the buying and selling of sex in America.

My favorite part about a man paying for sex was how it balanced out the fact that women didn’t get equal pay for equal work. Men wanted sex and women needed money, so that made prostitution a fair business deal. The sexual exchange was negotiated, agreed upon, and everyone was satisfied. From my few experiences, I observed that when a man paid for sex, he was extremely polite and very appreciative of the attention he received. In many ways, the dozen or so clients I’d met had better manners than some of the men I’d dated in the past. The one big drawback to prostitution, besides its illegal status, was being on call. When a man wanted sex, it was always “in the moment.” Steady clients were preferable; most were middle and upper-class married men, with a sprinkling of single and divorced men. At the time, there was one wealthy playboy who made the rounds of the prostitutes; his steady live-in girlfriend sometimes joined him during a trick for a threesome.

It became clear why monogamy didn’t pose a serious problem for that many men. The double standard allowed them to pick a virginal type of woman for marriage and children, while they enjoyed sex with the “bad girls,” beautiful mistresses, and prostitutes who’d learned how to be good at sex. These men got to maintain respectable images of being faithful husbands and fathers, admired by the community. Meanwhile, sex workers were socially ostracized and forced to live outside the law, without any legal protection or social status, as they continued to provide the only sexual joy in the lives of billions of good old boys.

Ain’t love grand?

Post Categories: Article | Menopause

Post Tags: prostitution | sex work

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