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The Lasting Legacy of Cyd St. Vincent and His Bonus Hole Boys

For a few good years, Bonus Hole Boys was a much-needed epicenter for trans male porn that catered to trans guys’ sexuality in a way few sites do — even today

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.

It’s 10:30 a.m. in New York City and Cyd St. Vincent — the most famous trans male porn star who isn’t Buck Angel — has just returned to his apartment after a few days of traveling. Now in his late 30s, he’s well beyond his porn heydey, but his boyish appearance hasn’t changed — his cheekbones are still rosy and sculpted; his brown hair remains slicked carefully into place. It’s been a while since he gave any interviews — he now lives a low-key existence and works at a consultancy firm — but he’s eager to talk about Bonus Hole Boys, the groundbreaking porn site that marked a landmark step forward for “men built with an extra hole.”

Though it’s no longer active, the site’s landing page still comes with a telling disclaimer: “You will see authentic sex on this website, some of which has rarely been depicted in video before.” Underneath this message is the naked, tatted-up body of St. Vincent, making out with some hunk under what appears to be a shower. The site’s mission was simple and direct: Depict cis guys fucking trans guys in a plethora of kinky, hardcore situations. 

When St. Vincent launched the site in 2011, this wasn’t a common thing to see. While there was some trans representation in the mid-2000s, it was rare — if not impossible — to find videos of trans men having real, authentic sex. Thus, for the years it was active, Bonus Hole Boys became an epicenter of trans male porn, catering to trans guys in a way that few others do, even today. To wit, its catalog can be found on the queer porn site PinkLabel.TV — according to site representative Jiz Lee, it holds “just as much cultural significance as plenty of porn classics” and “serves to expand the expressions of queer masculinity and desire.”

But click “enter” on the Bonus Hole Boys’ homepage, and you’ll find the site is dead. St. Vincent’s OnlyFans page is dead as well, and there are almost no studios that produce trans male porn of that caliber today. So what happened? Did the wave of trans male porn the industry desperately needs live and die with Bonus Hole Boys? 

The story of Bonus Hole Boys begins in early 2000s San Francisco. St. Vincent spent his teenage years shuttling between New Mexico and Australia, and they were fraught with confusion. At the time, all he understood about himself was that he was “definitely not heterosexual,” he says with a laugh, but soon he began slotting pieces of his puzzle together. In his late teens, he came out as bisexual; a few years later, he came out as a trans man and moved to San Francisco. 

Particularly around the mid-aughts, San Francisco was developing a reputation as a queer porn powerhouse thanks to the work of Shine Louise Houston, who founded Pink & White Productions in 2005 (though it’s now expanded into a streaming site, PinkLabel.TV). Unlike mainstream porn studios, she shot hardcore porn scenes filled with gender non-conforming bodies. It was the promise of a sexy, queer mecca that lured St. Vincent. “I saw that porn had a lot of power,” he tells me. “San Francisco has this really special, unique sexual culture. I saw sex workers creating the porn they wanted to see, and the world of possibilities that arose because of that.”

St. Vincent had been a sex worker before moving to San Francisco, but transitioning opened up a new set of challenges. “The transition from escorting as a woman to escorting as a trans guy was harsh,” he tells me. Pre-transition, he had more clients and less expectation to engage in draining conversations around gender and identity. When he started presenting as male, he did find some clients — “but they were pretty rare and very, very fetishistic,” he explains. “People didn’t really know who I was and what to do with me.”

In St. Vincent’s eyes, making a name for himself as a porn star could lure in new clients and help guys understand exactly how to fuck people like him, so he started trying to connect with studios. At the time, it was a tough sell. The porn industry was still being rocked by the presence of Buck Angel — the self-proclaimed “Man With a Pussy” — and the stigma was intense. “No one would talk to me in the porn industry,” Angel has said of his earliest years making porn. “Nobody. Everybody hated me. They thought I was a freak.”

Despite this stigma, trans people were slowly but surely trickling into industry — but the variety of bodies on display, as well the depictions of how they wanted to be fucked, were still relatively limited. In particular, there was a dearth of what St. Vincent calls “gay men who just happened to have a vagina,” which is how he defines himself. As a result, the cis gay guys who paid to fuck him as an escort often left their sessions feeling confused. “Guys would have sex with me, and afterwards they’d say, ‘Okay, so does this make me straight?’” he tells me. 

St. Vincent starred in a few scenes for Pink & White’s pioneering Crash Pad Series throughout the late 2000s — as well as trans porn star James Darling’s website FTM Fucker — but a change of address toward the end of the decade introduced him a new neighbor, a director named Ex Libris. The two started talking about the kind of porn they wished they could see, and St. Vincent told Libris about his desire to watch trans guys and cis guys fucking on-screen. Soon after, they co-founded Bonus Hole Boys.

The word “authentic” gets thrown around a lot in the porn industry, but St. Vincent turned out to be a real exhibitionist who reveled in the opportunity to script and film his wildest fantasies. Forget the fake moans and staged cum shots of mainstream porn — on Bonus Hole Boys, the pleasure was real. “I’m not a sex worker anymore, but sex work was always such a huge turn-on for me,” he says. “The fetish of being considered so hot that someone pays to have sex with me is really embedded, plus I’m a huge show-off — I loved shooting scenes with these guys.”

In fact, for St. Vincent, the site was more of a vehicle for his own fantasy fulfillment than anything else. “One of our first shoots was with [gay performer] Mickey Mod, and I definitely wrote that scene around my fantasy with him,” St. Vincent laughs. “I get to have sex with this guy and do it exactly how I want? Great! I think he fisted me while fucking me in the ass, and that was a new experience for me.”

Casting wasn’t easy though. Transphobia was as rife in the gay community then as it is today, and St. Vincent was met with his fair share of it. Even in 2018, when he was cast in a cis gay porn scene, he was scorned by Twitter trolls, who couldn’t wrap their head around the fact that some men have pussies. Thankfully, Libris’ performer connections at were largely happy to take part in the scene instead. “We were really lucky to have the site’s young, gay male actors work with us, because it was a huge risk for them,“ St. Vincent explains. “They were willing to work with us despite the stigma and backlash.”

Plenty of this stigma came from the idea that shooting with trans guys made you a “crossover performer” — in other words, someone who fucks both men and women. “I know a lot of cis guys that worked with us got feedback like, ‘Oh, are you straight now?’” he explains. There were the fans to consider, too. “I don’t really give a fuck about gender from a personal level, and it’s not really interesting to me to think about the parameters of what classifies as gay porn and what doesn’t,” St. Vincent continues. “But we were also trying to anticipate what our mostly cisgender audience would be able to hold on to, understand and respond positively to.” 

He says there were some transphobic comments — it’s pretty much a given — but the trickiest minefield was to anticipate how far would be too far for their audiences. “We were trying to cast guys who hadn’t had top surgery, and we did flip-fuck scenes with trans guys topping,” he says, referring to scenes were the trans guy would be fucked, and then fuck their cis partner with a strap-on. “Those felt like risks at the time, because we were already selling content that pushed the boundaries of gay porn.” 

Because of all this, St. Vincent also wanted to raise awareness of how to treat trans guys, how to talk to them and how to fuck them. Post-scene interviews — which had been done before on sites like but were still a relatively new idea — became a good way to have these important but lighthearted conversations. In one chat with performers Viktor Belmont and Ruckus, Ruckus advises cis gay guys like himself not to let “dated-ass bigotry” get in the way of fucking trans men. “If you like fucking guys, you’re going to like fucking any guys,” he shrugs nonchalantly as he eats a slice of pizza. “If you connect with someone, what does it matter if their dick is a different size or shape to yours?”

Both St. Vincent and Libris were working on Bonus Hole Boys as a side project, but their collective experience and access to resources made the site a hit. sold the content, helped with casting and offered up equipment, whereas St. Vincent’s experience in the porn industry helped him understand how to navigate days on set. In particular, Pink & White is known for letting performers lead the way — scenes are deliberately written to hit as many of their real-life turn-ons as possible. When it came to directing porn for Bonus Hole Boys, St. Vincent took a similar approach. “I’d definitely have conversations with models ahead of time to ask what they were comfortable with, if they had a preferred scene partner in mind,” he says.

Details like these are important to the story of Bonus Hole Boys. “I think that, a lot of the time, porn directors are like: ‘I’m going to give you money, so you’re going to do what I want.’ But that doesn’t work for a lot of trans guys,” St. Vincent explains. Dysphoria — basically, the feeling that your body doesn’t line up with your gender identity — can be a bitch, and it can color trans sex lives in a big way. Some trans guys might feel triggered by being asked to film in certain positions, while others may not vibe with the way directors or crew refer to their genitals. “Really, a lot of what I did was on the back end of things,” continues St. Vincent. “I’d be present with these guys on-set so they could talk through any fears, and tell us exactly what their boundaries were.” 

Word soon got out that Bonus Hole Boys was breaking new ground (and treating their performers well), and amateur trans guys were lining up to work with them. Being progressive wasn’t always easy, though, especially when it came to diverse casting. “We worked very hard to make it not a mostly-white website, but that was really hard because a lot of trans guys doing porn weren’t able to make a living from it,” St. Vincent says. “At that time especially, nobody was going to be able to make a career from just doing trans guy porn, and only a small handful could survive by doing escorting on top of it. The risks are higher, and I do think there were more white trans guys who were willing to take the risk of shooting porn.” (Stats consistently show trans people of color are the hardest-hit members of the community when it comes to abuse and poverty — basically, many of them couldn’t afford to lose out on vanilla work due to being outed as a porn star.)

When St. Vincent left San Francisco for New York in 2015, maintaining Bonus Hole Boys became a lot harder. The time and cost of creating independent content started to weigh on him, and his shooting schedule dwindled. He briefly dipped his toes into OnlyFans, but he found it just as time-consuming — if not more so — than making his own studio porn. “It really is a full-time job,” he says. “If you really want to do OnlyFans, you have to be constantly online, whether that’s creating content or making connections with people on Twitter. I prefer a world where I can just have sex with somebody for money, you know? That whole idea of having to be constantly on just meant that OnlyFans really wasn’t for me.” To this day, PinkLabel.TV remains the best place to see St. Vincent and Bonus Hole Boys in all their glory. 

Because content featuring gay trans men is still thin on the ground, these depictions of trans dudes living their best sex lives continues to fill a vital hole (pun unavoidable) in porn’s queer representation. “There’s a running joke between trans guys in porn: ‘When will there be enough of us that we fill more than the first couple of pages of Pornhub?’” St. Vincent says. “When we stopped releasing monthly content, we really thought some other studio would come in right away and take our audience. I’m actually really surprised that that really hasn’t happened.” He still doesn’t understand why, either. “I honestly don’t know, I think someone should get on that,” he laughs.

Bonus Hole Boys might not have sparked a tidal wave of trans guy porn stars, but it has left a valuable impact — St. Vincent says he gets text messages from friends who see self-proclaimed “bonus hole boys” popping up on dating apps all the time. He’s also noticed an improvement in the way cis dudes fuck and treat him in his everyday life — now, he can hook up with someone in the back of a bar with less fear that a guy will freak out that he’s trans. 

“I’m not pretending that porn is activism, but Bonus Hole Boys is the one thing I’ve done in my life where I’ve actually seen change happen because of it,” he concludes. “When it comes to activism, there is this constant feeling of: Is this going anywhere? You don’t get many straight-up wins. When it comes to Bonus Hole Boys, that’s not the case. I really do feel like we’ve been part of changing a sexual landscape, and that’s something I’m very proud of.”