In the infamous carol “The 12 Days of Christmas,” the singer brags about all the bossy gifts their “true love” gave them for the holidays. But since since six geese-a-laying and a bunch of turtle doves seem unsanitary — not to mention a violation of city ordinances — we decided to gift you with 12 of something better: A handful of sex workers you should absolutely know about. Whether they’re becoming literary superstars, breaking the “stunt cock” mold or literally embodying gay Jesus himself, they’re the real gifts we need this Christmas. And no, not one of them is a turtle dove.
“Is it on, honey? Is this thing recording?”
“What’s up YouTube Land, Twitter Land, Instagram Land, Snapchat, Grindr, Scruff, BGC, Jack’d, Facebook, Periscope and, last but not least, every single one of my bitches on Christian Mingle all across the land,” Madison booms, her Floridian drawl drenched in charisma. “It’s your girl TS Madison coming to you loud, live and, always and forever, in color from the marvelous chateau, honey!”
The seven-bedroom, five-bathroom “chateau” is a pet name for her home, but with its plush sofas and ornate, gold picture frames, it’s every bit as regal as the moniker suggests. A back wall is painted the same blood red as Madison’s plunging wrap top, which shows off the impressive cleavage that helped her earn a Lifetime Achievement Award at the 2016 Transgender Erotica Awards.
As she pauses for breath, I sheepishly explain that our interview will be written up, not broadcast live. “Oh,” she says, cracking up. “Well, tell them that I did my iconic entrance!”
It’s not hard to see how Madison has racked up 1.5 million followers on Facebook alone — with her quick wit, no-fucks-given attitude and hilarious soundbites, she’s basically a social media wet dream. Ever since she went viral with her “New Weave, 22 Inches” clip on Vine back in 2013, she’s built an online empire on the strength of her comedy, titty jokes and sexed-up gags. More recently, she branched out into Hollywood with a scene-stealing turn in the 2021 film Zola, based on a real-life Twitter thread by a sex worker. And in March, she grabbed headlines by becoming the first Black trans woman to executive produce and star in her own reality show, The TS Madison Experience. Since then, her phone has been ringing off the hook. For her next trick? “I’ve got to do ABC News or some shit this morning,” she laughs.
If she’s stressed, she doesn’t show it. Before long, she’s describing her “fascination with the English Tudor dynasty” and rubbing her tits lustily as she declares her thirst for actor Henry Cavill. “I watch all the period dramas on Showtime,” she cackles. “That Queen of England, she’s a real high-riding bitch!”
Although the gags come thick and fast in her reality show, Madison pulls no punches when revisiting her childhood as a Black trans woman raised in Miami (“Baby, it wasn’t easy,” she says in the show’s opening monologue). There’s a particularly poignant scene in the fifth episode, where she attempts to build bridges with her “pops,” who struggles to accept her as a trans woman. It’s ultimately heartwarming, but it doesn’t change the fact that Madison was forced to fend for herself as a teenager.
This was the mid-1990s South, after all. There was no “transgender tipping point,” barely any trans media representation and no federal laws to protect trans people from being fired for their identity. “I came out of the womb like, ‘Honey, I know I’m the girl that I am, and I know that I’m the shit,’ but everyone used to look at me like I was weird,” she explains. Still, she started outwardly expressing her femininity around the age of 17. Three years later, in 1997, she started transitioning hormonally.
Madison finished high school but dropped out of college. Throughout her mid-teens, she worked various minimum-wage jobs in care homes and call centers alongside her studies to make ends meet. “I was coming to work in a dress, so I’d have co-workers leaning back in their seats, staring at me,” she recalls. “Then, somebody would whisper: ‘That’s a man.’ It’s crazy — when I worked as a home health aide, people would literally say to me, ‘I don’t want you in here.’ I don’t think people really get it. I’ve been living in my transition for 27 years, and I got used to people staring like, ‘Hey, what are you?’ It’s really not easy.”
Tired of being harassed at her call center gig, she retaliated by flipping the table and cussing out a transphobic colleague. Then, at just 17, she was jobless and facing life on the streets. That’s when she “hit the stroll” — street sex work became not just a form of survival, but a mode of access to other, older trans women who Madison has credited as instrumental to her own journey.
Working the streets also made her realize that not everyone would punish her for being trans. In fact, she tells me, there were plenty of boned-up dudes out there begging to pay and worship her. “Sex work freed me,” she says. “It taught me a lot about the way people work. Lots of women see the filtered versions of men, but I get to see who they really are behind the mask — that dirty, down-low part. I don’t get the opportunity to see that nice man walk through the door. I get the guy saying, ‘Let me pull your pants down, suck your cock and eat your ass. Let me pay you to do all this freaky shit.’”
After a few years of hustling to stay off the streets, Madison got her first taste of the porn industry in 2003. Her on-screen career began with photo sets for websites like BlackTGirls and Grooby Girls (then known as “ShemaleYum”), but she also found a best friend and mentor in the form of the late TS Eve, whose recipes inspired Madison’s hilarious YouTube cooking shows. Before long, Madison racked up a growing fanbase; her combination of charisma and high-femme beauty made her a huge hit in the porn industry.
Sensing an opportunity to ascend the ranks, she began studying famous porn stars like Jenna Jameson and Traci Lords. Their secret? They were more than just beautiful women being fucked on camera — they had charm and personality, and their scenes often had character, a story arc and, of course, a filthy climax. Madison took notes, and in 2009, she launched her own porn company: Raw Dawgg Entertainment.
“People want to be excited, they want to see a climax honey,” she laughs. “I was the creator of my own adult films, and I was always a comedy girl.” The clips are paywalled, but they’re packed full of gloriously camp, over-the-top acting. In one scene, Madison, dressed in all-black lingerie with her tits exposed, uses a hollowed-out waste basket to “shoot” a criminal and force him to become her sex slave. “I got this, sis,” she says to her scene partner, Sasha Strokes, as she flicks her long, black weave. It’s all totally ridiculous, in the best way possible.
This knack for bringing humor to even the filthiest sex scenes has made it easy for Madison to thrive online. “That’s why it was easy for me to cross over into reality TV,” she explains. “With everything I’ve ever made, I want it to be fun, and I want it to make you laugh.” Don’t get her started on OnlyFans, though. “I feel disrespected,” she says. “Now, the girls on Love & Hip Hop are busting it open on OnlyFans, but when the network contacted me [to potentially appear on the show], everyone was saying: ‘It’s kind of risky, because you have adult films attached to you.’ Then the pandemic came through, and OnlyFans blew up. For me, as a trans person, I feel like I’ve been living through a pandemic for a long time; society has always created a jobless pandemic for us.”
Sites like OnlyFans might be gradually mainstreaming sex work, but street sex workers get comparatively little airtime. When they do, they’re often framed as victims. Madison, however, doesn’t see it this way. “Child, society created the job!” she says. In her eyes, trans women are over-represented in sex work because “if you go through the process of transition at work, you cause a stir. It falls on you to conceal who you are, and then your job is trying to fire you. What are you going to do? You still need to pay bills, eat and find shelter, but how can you do that if nowhere gives you a job?”
In her eyes, sex work is one of the few options available to trans women — and it gives them a sense of agency in a world that often bars them from it. “When I went to [vanilla jobs] in a dress and makeup, bosses would tell me, ‘Take that shit off, you’re confusing people,’” she says. “But I don’t have anything to do with those people over there. I just came to do a fucking job.”
The TS Madison Experience touches on these stories and advocates for trans rights, but always with a sense of humor. In one scene, she confronts her brothers about “deadnaming” (using a trans person’s “old” name), and then about them using the wrong pronouns when referring to her. “I fight for the equality of trans people, so how can I advocate for respect for others when I’m not receiving it in my own home?” she asks. After this, one of her brothers slips up again — she corrects her pronoun again, then turns to the camera. “Now wait a minute, bitch,” she says, as her brothers crack up. “Y’all see me trying to educate, and he still jumped over there into that foolishness. I’m gonna kick me some ass before I leave here!”
It’s a tricky balance to nail, but Madison manages it within her online presence more broadly — one minute she’s cracking anal jokes about Thanksgiving (“The trade got to really know, if you hit it on Thanksgiving, you’re gonna get a little dressing!”), the next she’s cussing out transphobic, online commenters.
Recently, she pissed people off with an appearance on the reality show I Am Jazz. In the scene, Madison has a video call with the mother of Jazz, a trans woman who came out as trans at just four years old, and was met with the whole-hearted approval of her parents. As a result, she started taking hormone blockers, which delay the onset of puberty, at 11 years old. In the scene, Jazz’s mom speaks about her daughter struggling with clinical depression. At this point, Madison asks a few questions: “What about the hormones doing that to the body, or what about blocking her from receiving the male hormones? I was really worried when the story about Jazz first came out; I was like, ‘Are they really trying to turn her into a girl this fast?’”
But as the conversation progressed, Madison changed her mind. “People are different,” she explains. “We’re both trans, but I was raised in a home where that wasn’t accepted. I had to fight for it down the line. We got to a place where my mother loves and respects who I am, but she still loves God — that’s still in her. I’m 44 years old, and I’m looking at this young girl [Jazz], who’s been on hormones since she was 11. Of course I’m like, ‘Wow, she’s so feminine,’ but there’s also the struggle within myself because I wish I had access to that at a young age. Maybe then I wouldn’t have had to have laser [treatment] to remove my stubble.”
She pauses mid-thought as a realization hits her. “I guess though, for me, it’s important that I got to know — for lack of a better term — the ‘male’ side of me,” she continues. “The hyphen, the in-between. I got to access pre-TS Madison and post, but Jazz hasn’t. It’s interesting for me to watch her transition, just like I’m sure it’s interesting for her to see mine. Both stories are important.”
Conversations like these can be messy and controversial, but Madison has always leaned into baring it all, no matter the consequences. In porn, entertainment and pop culture more generally, she’s credited as a trailblazer — and, as she says with a sigh, it’s “fucking exhausting.” “People talk about me being the first Black trans woman to do this and that, but when you’re the first, you really get thrown into this sea of loneliness,” she tells me. “You’re the prototype, and people forget that you went through hell and high water to figure out what works and what doesn’t.”
Still, after years of hustling, she’s finally getting the spotlight she deserves — and now, she’s eager to keep going. “You put five to 10 years of your life into an idea like a reality show, and then it’s wrapped up in six weeks,” she laughs. “What the fuck? I know fans want to see more, so I need [television network] WeTV to keep it up.”
As we wrap up the interview, she lives up to her gloriously vulgar reputation by pretending to deep-throat her mic as she talks the perfect dick size. “I’m gonna say seven inches, but I do love a good 10,” she jokes. “That’s gonna tear up your booty hole, though! I had a little rendezvous with a gentleman who looked around seven inches in his photos. I’m a vers bottom and thought I could handle it, but when he showed up in person, I was like, ‘Oh no, sweetheart, we’re only doing oral tonight!’”
These truly are the words of a woman living “loud, live and in color.” “I don’t subscribe to any norm, I’m just not doing it,” she says. “I don’t have to act like a lady to be attractive, I don’t need sex reassignment surgery to be a trans woman and I never wanted to get married, have kids and be a doctor. If I want to be brash, bold and vulgar… well shit, I’m just gonna do it!”