Sienna Sinclaire is a very naughty girl. And she wouldn’t have it otherwise.

Making her way through an exuberant crowd of porn stars and purveyors at a trendy West Hollywood club, she rocks knee-high Jimmy Choo stiletto boots and a clingy cashmere sheath, beneath which her Yoga-trained flanks undulate appealingly. Behind her trails a cloud of intoxicating scents, the dominant of which seems to be her perfume, Judith Leiber’s Night, “a blend of sexy florals and hot spices made for elegant occasions,” which pretty much describes Sinclaire herself.

It’s nearing 11 p.m. on an unseasonably cold weeknight in Los Angeles. There are 500 people in attendance at Hyde Sunset Kitchen. The occasion is the Second Annual RISE Adult Talent Appreciation Gala. Put on by XBiz, a web publication that covers the sex industry—with co-sponsors including Penthouse and—the party honors the flesh and blood stars of a business which tallied an estimated $97 billion in worldwide sales last year.

Sinclaire is both a performer and a businesswoman, a self-styled “naughty lifestyle entrepreneur.” With her silken blonde hair, Barbie-blue eyes and degree in international business, she has managed to turn her natural assets and abiding pluck into a cottage industry devoted to all things risqué.

Amidst the eclectic, living room-like appointments of the club—a favorite of the moment among Hollywood’s hip hop elite—some of the brightest names in smut have gathered to catch up and party the night away. There’s James Deen, Chanel Preston, Jessica Drake, even veteran temptress Nina Hartley, who at 57 is still doing MILF loops and girl on girl—all of them here to celebrate themselves, their lifestyles and the recent defeat of California’s Proposition 60, which would have required the enforcement of federal occupational health laws calling for the use of condoms in porn films.

Thanks to the prop’s defeat, the penises of porn stars will stay unwrapped on film, at least for the near future—though regular checkups and blood tests are still mandated for adult performers.

Sinclaire follows a male colleague through the fray, staying close like a running back shadowing a pulling guard, zigzagging past a pair of young women playing tongue hockey; past a group photo of starlets with boobies exposed; past a dirty dancer with her dress pulled up over her waist; past knots of schlubby guys from the business side, sipping drinks, eyes agape.

A girl next door of a certain age, Sinclaire is both a performer and a businesswoman, a self-styled “naughty lifestyle entrepreneur.” With her silken blonde hair, Barbie-blue eyes and degree in international business, she has managed to turn her natural assets and abiding pluck into a cottage industry devoted to all things risqué.

She’s got a series of primers for different cities, The Naughty Girl’s Guide; an app is in development. Her website,, features naughty photos and movies but no actual sex. Once nominated by Adult Video News for best website, Sinclaire’s paid portal features images of a classic American blonde—there’s glamour, burlesque and vintage pinup looks . . . and also some fetish stuff that’s a little bawdier. As Sinclaire likes to say, “a woman can be naughty without being a slut.” Therein lies her area of expertise.

Primarily based in Los Angeles is Sinclaire’s Naughty Tours—regular group and private outings to area strip joints, swingers’ clubs, fetish hotels, porn movie sets and dungeons. She also has a line of sex toys and a photo studio for women or couples who want to take a naughty portrait. And she’s certified as a sex and dating coach by the American Association of Sexuality Educators, Counselors and Therapists—couples and women only, please. On her blog, “Naughty: Your Guide to Living a Naughty Lifestyle” she covers her prime verticals—sex, dating, travel, shopping, fitness and living the single life. Her parties—Sienna Sinclaire’s Naughty Circus, Pantiless White Party, Topless 70s Disco Roller Skating Party, etc.—are regularly covered by LA Weekly.


We arrive at last at the bar. Sinclaire’s colleague, a handsome guy named Keith Caggiano, takes care of negotiating the drinks. He runs a company called Rock On Products, which sells a line of supplements said to enhance physical and mental performance in the office, gym, and bedroom. There’s even a syringe shot for hangovers. In 2013, Rock On won XBiz’s award for Best Sexual Enhancement product. This year, with his newly diversified line, he’s hoping to win best crossover product.

Passing over the drinks, Caggiano falls into conversation with the director of Larry Flynt’s classic Barely Legal series of porn films. Sinclaire and I turn around to survey the room. For the first time since our arrival, we catch a clear look at the man speaking on stage.

“Look who it is!” says Sinclaire. Her eyes widen with mock suprise, as if she’s just seen a UFO.

Dressed all in black, speaking into a cordless microphone, is the MC for the evening: Ron Jeremy, a.k.a. “the Hedgehog,” no. 1 on AVN’s list of the “50 Top Porn Stars of All Time.”

A former teacher and failed Broadway actor, Jeremy is short and homely guy with long thinning hair and a furry moustache; hence the nickname. Talk of his moneymaker often includes comparisons to a curved scimitar or a bent tree limb. A four-decade porn vet who has enjoyed some mainstream fame, Jeremy is an icon—a star who actually grew old in the business… and continues to live the dream.

“Viagra is the new thirty,” Sinclaire laughs.


Sinclaire and I first meet for lunch at Villa Blanca, the Beverly Hills eatery formerly owned by reality TV’s Lisa Vanderpump. At 2 p.m., the place is beginning to empty. Most of the servers have made themselves scarce. Sinclaire is resplendent in an all-white outfit.

“Obviously, my real name is not Sienna Sinclaire,” she says with what seems to be a slight Southern twang. “I keep that very private. You give too many details and the next thing you know, people are looking you up on the internet.”

Early on, Sinclaire says, she discovered her talent for enterprise. “My mom was one of those people who would give me whatever I wanted, but my dad wasn’t like that. He was like, ‘You want new clothes? Work for it.’ ”

Sinclaire’s father owned a hair salon. “When I was five, I set up a nail station and offered to do manicures. So of course, nobody could say no. I charged one dollar, but people were always giving me like fives and tens. My dad was really proud of me for making money. Even then I had the makings of an independent woman. I really got it from him.”

After several moves between her divorced parents, Sinclaire went on to college, earning a degree in International business with a French minor. Sometime later, after a stint in London working at a magazine, she moved to Washington, D.C., her sights set on grad school. To make ends meet, she worked as a bartender and as a waitress. Eventually, with bills piling up, she took a waitressing job at the Camelot Showbar, a D.C. institution not far from the White House, known for its intelligent and beautiful lineup of strippers and its all-you-can-eat buffet lunch.

“I wasn’t going to dance, I was just going to wait tables,” she says. “But then I saw how much the dancers were making. In those days there were no back rooms or lap dances. You just would sit with a guy and he would buy drinks and then he’d tip you like one hundred dollars. And when you were dancing, of course, you made hundreds in tips, all in one dollar bills.”

“I never wanted to be a porn star. It’s not for me. Though I do give them a lot of credit. To be able to get banged all day in all three orifices and to take these massive cocks, it’s a talent.”

In time, Sinclaire was drawn to the more lucrative market in Manhattan. She auditioned at Scores, the strip club where the rich and famous played. “I did ten days on and ten off. I’d go up there and stay in this hotel that kind of catered to the girls. It would take like three days to pay off your costs—your gas, parking, food and hotel, the money for the house mom, and also the money for the DJ and the tip for the staff. So if you stayed for ten days, the last seven days were all profit.”

Soon Las Vegas beckoned. Interestingly, Sinclaire says, the earning potential was about the same as New York. “You’d have big crowds in Vegas but the guys in New York were higher rollers. So you made the same money. I’d alternate when I got bored. I always kept my apartment in D.C.”

At some point Sinclaire began to branch out and create an internet presence, which allowed her to give up the dance life. “You might make $3,000 to 5,000 on an average night dancing, but you’re on your feet from like 9 ’til 1 in the morning—it’s grueling. It’s like being an athlete. It’s tough on the body,” she says.

Tempted by warmer climes, Sinclaire moved west, and so it was that LA’s naughtiest girl was born—one woman’s attempt to capitalize on her natural assets, both physical and intellectual. As the industrialist Andrew Carnegie used to preach at the turn of the 20th Century, she has achieved what she has conceived.

“I’ve been a dancer, I have an adult website, I specialize in knowing everything naughty that is available. If I was a journalist, you could say that naughty is my beat,” she says, taking a fork ravenously to the lightly breaded whole fish that has only just been delivered, nearly an hour after we sat down.

“But I’ve never done what people consider porn,” she insists. “I never wanted to be a porn star. It’s not for me. Though I do give them a lot of credit. To be able to get banged all day in all three orifices and to take these massive cocks, it’s a talent. A talent I do not have. And I’m not interested in being portrayed on camera that way—with my makeup messed up and someone doing things that I don’t want someone to do to me. I don’t mind people doing that in the bedroom to me, I just don’t want it on camera.”


Our next stop: Hamburger Mary’s in West Hollywood, famous for Drag Queen Bingo. They pack the place for two different seatings every Wednesday night, at 7 and 9. After making a bunch of phone calls, Sinclaire has secured a long, high table in a prime spot near the front. With her tonight are eight members of her group, Naughty Los Angeles.

Altogether, Sinclaire says, there are more than 200 people in the group. She hosts these free gatherings once a month. While there’s no money for her in tonight’s activity, she knows that maintaining the group is another way of cultivating an audience for her various tours and parties, for which she does collect fees.

Tonight’s group joins a raucous, sold-out crowd at the LGBTQ-friendly, upscale hamburger franchise. The optional $20 cover buys you a pad full of bingo cards and the use of a large bingo marker. A portion of this money benefits a number of LGBTQ-friendly charities, according to the organizers.

The reining bingo caller is the saucy trans actress and spokesperson known as Calpernia Addams. A large woman in a black evening gown with a plunging neckline, Addams has extravagant blond tresses, oversize white glasses and bodacious ta-tas. Joining her on stage tonight, is the actress Elizabeth Keener, from the cable show The L Word. Together at the podium, they bring to mind Jack Sprat and his wife.

As the numbers are called, the naughty tablemates eat burgers and drink extra-large cocktails; naughty jokes and innuendos fly back and forth through the disco-infused air like so many ironic shuttlecocks. Upon calling out “Bingo!,” each winner must stroll up to the front of the room for a light interview and upbraiding by the fabulous Ms. Addams herself; before the prize can be claimed the winner is forced to run around the room to a shower of jeers and losing bingo cards. The spectacle brings to mind a queer sendup of evening activities on a cruise ship or an outpost of Club Med.

Across the table from Sinclaire is one of her Meetup regulars, who asks to be identified as Lexy. She works as a chef, lives in the San Fernando Valley and considers herself a swinger.

“Sienna accentuates how the women should get the utmost respect. You get to spend time with like-minded people and not feel crazy or like a slut. You can just be who you are. There’s no judgment.”

Lexy first encountered Sinclaire’s group on “I was looking for something to do, and I see this event called Topless Drive-in Movie, and I’m like, ‘That sounds interesting,’ so I went, and I met so many like-minded people that I started going to all her events. There are burlesque shows, sex parties, seminars on different techniques, blowjobs or cunnilingus or whatnot. It’s our way of having fun: We’re just people for whom sex is at the forefront. Like, if you gave us a choice of going to a regular club or a sex club, the sex club is always going to win out. Sexy bingo or real bingo, you know? It’s the same with vacations. Now that I’ve been to Hedonism, I will never ever go to Cancun again.”

Since her first Meetup gathering, Lexy has gotten her boyfriend interested. He in turn has gotten several friends involved. And thus the legion of the naughty continues to grow.

“Sienna accentuates how the women should get the utmost respect. She doesn’t tolerate men who talk shit or act out. She wants everybody to be a family,” Lexy says. “You get to spend time with like-minded people and not feel crazy or like a slut. You can just be who you are. There’s no judgment.”

“What I’m really doing is trying to create atmospheres that are sexy and safe for women,” Sinclaire explains. “Because, let’s face it, when it comes to sex, it’s all about what women want and need. Men don’t really care about all the sexy stuff. They don’t need roses or champagne or a perfect hotel suite. If a woman is willing to have sex with them in an alley, they’ll go in the alley and have sex.”

Just then, up on stage, Keener cranks the classic black metal bingo-ball cage, and Addams calls out the number… “B 17”

Sinclair looks at her bingo card. She has it! B 17. She lets out a little whoop. “Bingo!” she declares. Everyone from the Naughty Los Angeles group cheers.

Only it turns out it’s a tie. A man also has Bingo. He seems a bit reluctant, somebody’s dad. Both winners come to the front, not quite sure what’s next.

To break the tie, Addams explains, she will insert into her ample cleavage two yellow bingo balls. Whoever plucks the ball with the highest number will be the winner.

And then there’s this: The person willing to retrieve it with his or her mouth can go first.

You can guess who wins.


For more naughty stories by Mike Sager please see The Devil and John Holmes and Other True Stories.