Confessions of a Real-Life Madame

Real-life Madame
Daniel Fishel/Thrillist

When you think "madame," you probably imagine the caring, tough matriarch with a wild streak type from various Westerns. Or maybe Suzette in Cathouse. Either way, you're thinking of a woman in charge of a house full of prostitutes, who runs her girls with a firm but loving hand. It's true that some madames are exactly like that. Others, like "Jenny," have much more interesting stories.

I interviewed Jenny over the course of several weeks in order to prepare for ghostwriting her memoir. Jenny is a slight woman with a calculating stare and a bubbly personality. In those meetings, she shared many insights into her history before becoming -- and her experiences as -- a madame.

Her background is incredibly dark

A safe and happy childhood eluded Jenny; who only managed to escape her sexually abusive stepfather by running away from home as a teenager. Things didn't get any easier, though -- from the time she was 16 well into her 30s, she managed to date assholes: guys who hit her, scammed her, abused her, and robbed her.

In a darkly ironic twist, Jenny took the burden of this pain and manipulated her way into the hearts and wallets of other men later on. She took up exotic dancing, and after a few hundred times of being asked to do a little more than dance for a lot more than dollar bills, she forayed into prostitution. The first time it happened, she'd been asked by a regular client to join him for a weekend trip… and to invite along some additional female guests to be his traveling companions. She said at the time, it didn't feel surprising. These asks were just natural progressions of what she was already doing. Plus, they were opportunities to make more money -- opportunities she took.

Jenny has hundreds of stories about milking regular clients for thousands of dollars in the club, for investment money out of the club, and for gifts and favors that would make a senator blush. She was happy taking the power in a work relationship. But as soon as that relationship became an affair, she relinquished control instantly; voluntarily. I personally saw that in action while negotiating the contract to write for her. She wasn't an unreasonable bargainer, but took control of the conversation instantly and was completely frank about what she needed financially and professionally.

Madames rarely consider themselves as such

Jenny hired me to do a stripper memoir with a stronger angle toward her more legitimate business ventures than the part with the T&A. She was proud of some real estate and event management she'd made decent money from, and considered herself a businesswoman. When she began telling me stories about convincing, coercing, and even threatening women in order to get them to have sex for money, she was honestly surprised when I called her a madame.

"Jenny thought of what she did as conducting business… one arm of which just so happened to involve the facilitation of escort services."

According to Jenny, most of the madames and pimps she knows don't really consider themselves as such -- they like to think of themselves as businesspeople. Jenny thought of what she did as conducting business… one arm of which just so happened to involve the facilitation of escort services. Pimps thought of themselves as men whose girlfriends would occasionally (or frequently) shag somebody for money.

Jenny's obviously seasoned by the details of the business. You'd have to be, to keep on doing it. Today, Jenny can discuss renting women out to paying customers without so much as a blush or squint. When it all started to feel normal for her, she can't really say.

There's a lot less sex than you'd think

Once upon a time, Jenny arranged for three women to accompany three ridiculously wealthy men for a three-day weekend in the Caribbean. That's two overnight stays in the same hotel room. No sex happened that she knows of (though she half-suspects one of the girls did make a deal, but didn't tell Jenny so she wouldn't have to split the fee). Each girl collected $2,000 a night, plus made extensive use of the resort's room service and spa to ring up a five-figure bill.

"You probably already know this, but most stripping and hooking isn't really about sex," Jenny said. "It's about companionship, being made to feel important. For the worst clients, it's about enforcing power. You can do a lot of those things with your clothes on. For some things, it's easier without the sex." Over the course of her time as a madame, Jenny guesses only about 75% of her paying clients actually had actual sex… and that number would go to about half if you only counted penetration to orgasm as "actual sex."

Famous people are part of the package

Madames like Jenny aren't overseeing the stereotypical group of women frequenting street corners -- they're arranging nights, weekends, or vacations with companionship to the tune of four and five figures a night. That means money, and money means celebrities.

One of Jenny's straight jobs was as a promoter for a Vegas nightclub. During that time, she gave VIP treatment to visiting bigwigs -- including sports stars, politicians, musicians, and the head coach of a college basketball team.

Jenny claimed she wasn't particularly starstruck by most of these encounters: they were just more chances to make big money. But one time, as a madame, Jenny set up an encounter for a lead player on her favorite basketball team. She found out he was coming to town through a handler, made arrangements through that intermediary, found a "partner" for him, and arranged "delivery." She was excited to meet the athlete during the hand-off; but admitted to ultimately feeling a little disappointed in him for his proclivities.

Violence is just another tool

Over drinks one night, Jenny told a story about how she knew the aforementioned head coach was coming into town. She knew he liked a variety of, let's say, "surprising" behaviors with convincing male-to-female transvestites. Jenny reached out to a boy the coach knew danced at a trans-friendly club, and found a petite and friendly candidate. Arrangements were made. Half got paid upfront.

"Jenny, who weighed all of 95lbs, pushed him into a corner and slapped him until he agreed to go out and have sex with the coach."

But when it came time to do the deed, the candidate -- for whom this was his first gig of the kind -- got cold feet. He fled into the bathroom, saying he couldn't do it. So Jenny, who weighed all of 95lbs, pushed him into a corner and slapped him until he agreed to go out and have sex with the coach.

"Most of the time people come through," Jenny said nonchalantly. "It's a lot of money." To Jenny, the violence she unleashed was just part of sealing a big deal.

"Weird" is just another workday

And, actually, violence plays a role in the fantasy element of escort services as well. Jenny told a story about a man who stopped her at random at a gas station and offered her $100 to slap him in the face. She talked him up to $200, then hauled off and hit him. Jenny told me she'd see him from time to time on the Strip and he would always make the same offer. Each time, she hit him, he thanked her, and he disappeared into the night. Jenny knew a variety of "specialists" who were happy to indulge in any fantasy you can imagine -- plus a bunch of fantasies you can't imagine.

The weird didn't stop at fetishes, sex acts, or inserting every imaginable kind of Tab A into every standard-issue Slot B found on the human body. Jenny's girls role-played with clients and assumed names of those clients' daughters. They accompanied clients to events while posing as wives or sisters. And a surprising number of Jenny's workers simply gave back rubs and basic spa treatments.

Once you cross over into this world, Jenny explained, it becomes easier to break right through any taboos that present themselves. If you have someone willing to pay for sex, the kind of sex -- and the behaviors surrounding it -- is pretty wide open.

The madame's name, along with a couple locations, were changed to protect the guilty.

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Jake Simons is a Thrillist contributor who has never paid anyone to slap him in the face (though some people have done it for free).