Grooby's Transformation: From One Paysite Grew a Community

This article originally ran in the April 2016 issue of AVN magazine. Click here to see the online edition.

When Steven Grooby, founder of and more than a dozen other websites devoted to transgendered people, arrived at our offices for an interview, he’d just come from spending two hours with his marketing and editorial director, Kristel Penn, trying to figure out seating arrangements for the following weekend’s Transgender Erotica Awards, or TEAs.

The TEAs—formerly the Tranny Awards—are in their eighth year and bigger than ever, but that’s overshadowed by the fact that this is the 20th anniversary of, the first transgender paysite on the internet.

British-born Steven Grooby didn’t set out to be “King of All Trans Media.” He began his journey as a film production major at Kent University in the United Kingdom. After graduation he worked for the BBC off and on, but the lack of steady employment led him to investigate other avenues, even as he managed to get his hand on a computer—hardly ubiquitous in the early ’90s—and tried writing film scripts.

“Of course, what happened is, once I was on the internet, I started finding porn, and porn took up a lot of time back then, because you’ve got a 28.8 [modem] connection, and the image, you could see it slowly, slowly loading from the top down,” he explained. “So I started looking around, and Asian women are my thing, and of course, I very quickly saw some few scans of ladyboy stuff and it was in newsgroups; all the porn was really in the newsgroups.

“I was just always kind of fascinated by anything that was different, and when I first saw them, it was in peepshow video booths in New York in Times Square in 1988.”

With the help of HTML for Dummies, Grooby began to learn the fundamentals of programming, and by early ’96 he’d created his first website,

“‘Groovy’ wasn’t available, so I bought ‘Grooby,’ and I could only afford one domain name; they were $80 apiece back then,” he explained. “I could have probably bought back then; I could probably have bought, but I could only afford one, so it was,, and or shemale.”

But in those early days before digital cameras, being a webmaster wasn’t easy. Though his travels through the newsgroups had put him in touch with plenty of amateurs who’d send him scans of their photos just to see their creations on the internet, Grooby yearned for more reliable sources of images.

“Then there were the people who photographed girls in Thailand, the Philippines, places like that,” Grooby noted, “but they were only coming in three or four photographs at a time; they weren’t sets. The next step was being contacted by a guy from Texas who calls himself ‘The Commander,’ who said, ‘I can get photographs of girls in Texas. Would you be interested in putting them up on your website? Can we do a deal?’ So I paid this guy $150 a roll, and after two weeks, I went to the P.O. box; there was an envelope with these rolls of film.”

Grooby scanned them, posted them, “and the stats just went through the roof. That’s why we can say we’re the first company to have shot transsexuals specifically for the internet; there wasn’t anybody before us.”

Before long, Grooby had established his company base in Hawaii, where he met his wife and the couple had their first child, but he yearned to return to England. He moved the offices to Burbank and commuted “across the pond” every six or eight weeks to take care of whatever business couldn’t be handled electronically. Eventually, though, he gave up those offices, and now his entire staff telecommutes. Grooby uses the savings to pay his employees “a little bit extra to take care of themselves at home”—and, he says, “Productivity went through the roof!”

But getting to this point has been something of an education for Grooby, who recalled some of the first trans people he ever met, including Gia Darling, Kimberly Devine (“She just passed. She was huge back in the day, 1999”), Meghan Chavalier, Brandy Scott, and even Dana Douglas from the 1980s. He added that he expects to create a Transgender Hall of Fame in time for the next TEA show.

“The mid ’90s was the first VHS stuff, the stuff John [T. Bone] was doing, that Joey [Silvera] was doing,” he recalled. “His first Rogue Adventures was shot in Brazil, though. We started producing in Brazil in 1999; the first company to produce regular content from there. Gigi Appleton of Androgeny was our first distributor.”

In fact, Grooby was the one who first got Silvera started online.

“I’m in Hawaii, very early on—this was my first year there—when I get a phone call, ‘Hey, Steven, it’s Joey.’ ‘Joey who?’ ‘Joey Silvera.’ He’s so unassuming. And I’m like, ‘Wow! Is this really Joey?’ And I’m whispering to the others, ‘This is Joey Silvera on the phone!’ … I was on a plane the next day to L.A. to meet him, and we set up a website together that was quite successful for a number of years,”

At present, Grooby Productions has over a dozen full-time employees as well as 10 content producers, 15 paysites, perhaps the most prominent of which is, and multiple solo sites under

“We’re constantly trying new ones, but unlike a lot of companies where they’ll do these [sites] that all go into one section, a number of front doors all going into one, we don’t do that,” Grooby said. “Each of our sites stand as a solo entity, and it has to fail or win on its own content. If it doesn’t work, it doesn’t work. We’ve just done, which is girl on girl, tranny on tranny, or tranny on [cis]girl, and the content is great.

“Mona Wales just shot five scenes for us in San Francisco, and she’s agreed to a whole series for us,” he added. “I’d been hanging out with Kink, and Mona turned up, and we knew each other because she’d worked for us before but I’d never met her, and within an hour, we’d done the deal for her to come on as a producer of a series for us.

“As far as the producers who are actually on staff, right now we’re working with River Stark, who’s done some modeling, done some shoots. We’ve just done a deal with Krista Michaels, whose model name was Bird Mountain. She decided to get out of modeling and work on the East Coast; she’s good. Jamie French has been shooting stuff for us. She’s shot for us here and there over the years. She’s a very unique individual. ... She performs, writes music, plays in a band; she’s a fabulous editor. She’s got a really, really amazing creative mind.”

We asked Grooby about what he thought were some of the trends in transgender porn over the time he’s been in the business.

“The first shoots of the girls in the ’90s, Bob [of Bob’s T-girls] was shooting for us in L.A., and they were mainly Latin girls, Mexican girls actually, but we used to get them from the donut shop on Santa Monica Boulevard, which was the transsexual hangout. They looked like transsexuals: The boobs, the ass, the nails, the hair—they looked like the stereotype you could see in a movie of a shemale: over-feminine, over the top.”

Over his company’s 20-year history, Grooby has seen a rise of diversity in performers. More non-Latino models started working in the early to mid 2000s, he recalled, and “the white girls came hand in hand with a lot of the alternative girls and the girls next door as well.” And in 1998, when Grooby started, “we only had three weeks’ worth of content” and it was a struggle to find models. Now, he said, “BlackTgirls is one of our best sites; it’s still very, very popular. Ethnicity is very popular. Blacktgirls works; SheMaleJapan is one of our most successful sites as well. Just to be able to shoot in Japan is amazing, and we sell it back to Japan without the mosaic.”

Also in the mid-2000s, Grooby began to see regional diversity, including “a lot of New York Bronx girls. … They were great. And we started to get a lot of different girls coming through who were skater types, gamer chicks, alternative, tats—Remember the whole Joanna Angel thing, when tats became so popular? Morgan Bailey’s been in it for about eight years, but she wasn’t that tatted when she started. But the alternatives, Pacific Northwest crowd, they started coming through, and that was a sort of milestone.”

Another trend on the rise, according to Grooby: educated, tech-savvy T-girls who don’t focus as much on makeup and have a more androgynous look.

“A lot of them are into other girls, other transsexuals,” he continued. “I’ve never seen so many who are into other transsexuals.”

He noted, “There’s much more fluidity, and you’ve also got trans people who are into trans, so there’s a lot of trans relationships going on now genuinely. I wouldn’t shoot it in the past, because when you put two trans porn star types, the old school ones, together, they weren’t into each other; they’d just fake it. You could see it; it was just like lesbians who weren’t into each other. Now, these girls are into each other, so that was a milestone, getting real girls who were into each other, probably within the past five years.”

One interesting facet of the Grooby empire is how he’s decided to handle trans models who may not be sure if they want a career in adult.

“We launched FemOut for the early transitioning ones—the girls who are not quite ready for SheMaleYum—and that’s been successful as well,” Grooby noted. “Most of them have just started hormones and it’s just started to come through, and they want to get on the first stepping stone. … If someone shoots for FemOut, the idea is if they’re good enough, they go on to SheMaleYum and But if they shoot for FemOut, after two years if they want the photographs removed, I’ll take them back down if they decide it’s not for them, and they want to go and get a real job and all that stuff. I can’t do that for the other shoots—it’s crazy the amount of money that we put out there—but for these ones, I’m prepared to eat that after two years and say, ‘Let’s take it off.’ That’s the deal I make with them on that. I think it’s kind of a cool way to go, to give somebody an idea of what the industry is like, and them maybe realize it’s not for them.”

But simply giving transgendered people a friendly place on the internet wasn’t enough for Grooby. Through his award show, he provided a place for the community to celebrate itself.

There were only six awards given out online in the original Tranny Awards, but it drew a lot of people to Grooby’s website. Soon, Grooby was discussing the awards concept with prominent director Buddy Wood, and between the two, they came up with the idea for a live show with sponsors.

“We held it at a club called Blue Moon Nights, which Buddy was promoting, and it was great,” he recalled. “Michelle Austin was hostess of that. There was just a little stage, and they had an outside area—but everybody wanted to come out to this shitty little club for this one night, so the next year, we said, ‘Let’s try something big; put a little money into this,’ and we went out to Glendale, the Palace of the Stars; we did that for two years and that brought it up, and we had proper sponsors. … Now we’re at the Avalon, and that’s fantastic. So the step up to the Avalon was good.

“I think the success of the TEA Awards has been, first of all, the sponsors,” he added. “We could afford to do it without any sponsorship money, and it’s a big chunk of money, but it’s never been about being Grooby, Grooby, Grooby; it’s always been about the trans community, and the thing is, where else can these girls go as a community and have that night out where they are the focus? … When they come to this, they’re dressed and beautiful and they get honored and get respected.”

Although the award show’s first after-party was run by Tranny Strip’s John Ed, Grooby quickly decided to bring the event “in-house” in part because “we were grown to the size where people were coming in from all over, from the U.K., from Japan, and I said, okay, we need to take over the second night and do the after party properly, not only for the financial stuff, but because it was our brand.”

And then, almost inevitably, there was TEAcon, the world’s first convention devoted exclusively to the transgendered.

“It was all Kristel’s idea, but lots of girls came down, and it was nice for them to be able to get together and talk before the show, and Kristel took care of them,” Grooby explained. “Anybody who had a ticket for the show got in for free. Otherwise, it was $5, and the idea was, they come in, and the girls promote themselves, sign autographs and sell things. It’s not about making money; it’s about giving back to the fans. We had people coming in this year from Japan, Chile, U.K., Germany—two from Japan, actually—and all across the states, Canada—people book this weeks in advance, months in advance.

“Kristel’s amazing; she’s my stealth weapon,” he added. “I send her to places where I can’t show up, really, because I’m too big a target; I’m a cis white male. So she goes to all the feminist porn stuff and what is somebody going to say to her? They can’t even plunk what her gender or sexuality is, and she’s just five foot of girl, and everybody just wants to hug her.”

We asked Grooby about current top performers, and he named Aubrey Kate (“I just think she looks amazing”), Jessy Dubai (“a great performer”), Foxxy (“She’s been around for 13 or 14 years, and I think she’s just getting better “), and Kylie Maria (“Look at that face! Wow! And the body and everything, and she’s cool, she’s fun.”) As for current “up-and-comers,” he mentioned Chanel Santini, Aspen Winters, Mia Maffia, Miran (“She’s at the top of her game. She’s like the Japanese version of Foxxy. She speaks perfect English; she’s lovely, she’s tiny, she’s got boobs, great little face; a really cool cat.”) and Natalie Mars, the winner of this year’s Best Newcomer trophy.

And what of the future of transgender porn? Grooby has a few ideas on that score as well.

“I think trans movies with storylines are a coming thing,” he opined. “Last year, Buddy Wood did The Tranny Chaser; that was hilarious; then Tranny Chaser 2: Adventures of a Pool Boy, that was great, and then there was Morgan Bailey’s Bad Day, which was funny. This year was Shemale Shenanigans, and there was another one involving the president and First Lady and the secret service agents, SheMale Secret Service.“Then we have the parodies we’ve seen this year, like Kaitlyn Gender. I loved The Tranny Bunch from Devil’s, because Aubrey was in it and it was hilarious, and Delia [DeLions], I thought it was brilliant; I loved it. I’ve never seen so many features as those that came out in 2015, and the stuff Nica Noelle is doing is stunning; I’m a big fan of hers. She won an award a couple of years ago for her first trans one. I love her work. It’s not what we want to produce, but some of the stuff River Stark will do will be along those lines, but I think it’s just beautiful.

“There’s going to be a lot more trans-for-trans porn, I believe, where there are more trans girls buying it, and that’s a market Grooby is aiming for, is trans-for-trans, which appeals to a lot of those girls I talked about earlier, who are trans but they’re really into girls.

“I think VR is going to be massive; we’re investing a lot of money into getting VR going,” he concluded. “We’ve already PR’d the site, GroobyVR, but we haven’t shot anything for it yet. Can you imagine, most guys who are into transsexuals will never, ever meet one, but I tried some VR with some of the girls we’ve been shooting and I couldn’t believe it. … I think that’s going to be huge in the industry.”

Grooby is also doing his part to help producers who are just trying to break into the adult industry, but who have no way to get in.

“One of the things we’re doing with David [Peskin] at Exquisite, we have a Grooby Spotlight, so if any producer comes to me, like a one-off producer, says, ‘I want to produce five scenes or four scenes,’ we’ll say, ‘Well, do it through us; we’ll distribute it; we’ll keep a percentage but we’ll do all the marketing for it; Exquisite will distribute it, and you don’t have to go and find a distributor and all that.’ Because a distributor isn’t going to take somebody with one or two scenes a year; it’s too much work. It’s a great way for somebody to get their stuff out there, and make their money back and they can sell it online, and it allows them to take a risk with something as well.”

Finally, Grooby not only wants to give newcomers a chance, he actually wants to make the entire transgender community better—and to do it, he’s one of the founders and main supporters of the Trans Adult Industry Foundation, or TAIF.

“It started with Buck Angel; he and Kristel are the directors,” Grooby explained. “When we start bringing in money, we’ll get other sponsors. It came from when we tried to donate money to some of the stuff in San Francisco, the homeless shelters and other things, the Transgender Law Center and the suicide hotline for trans people. We sent them money; they returned the check; said they don’t want it from a company—not an adult company; a company that uses the word ‘shemale’ in their name. So I wrote a big article about why a shemale is not a shemale; that’s just a porn word. So they turned their backs on us, and Buck Angel was just furious about it, so we sat down and said, ‘You know what we’ll do? We’ll start our own foundation, and five percent of our photo shoots, the money from it, goes into this foundation.’ Some of the money from the Tranny Awards is going into it, and we’re taking all this money in and we’re also going to reach out to some trans companies, and the idea is to take that money and give it out to trans homeless organizations, not individuals, and AIDS research, different ones, and transgender youth organizations. Nothing to do with porn, but it’s a way for the adult industry to give some money back into the community that we’re working with.”

So even though, by his own estimate, Grooby travels more than 130,000 miles per year tending to business and attending conventions and trade shows, he’s a lifer in the adult transgender community.

So it’s exciting times,” he reflected. “I still enjoy getting up every day, going to work. When it gets boring, you stop, right? When you begin to hate it, you stop. Frankly, I don’t see myself ever stopping; I’m enjoying myself way too much!”

Who can blame him?

Pictured above, Steven Grooby (far left) with some of his staff at the after party for the 2016 Transgender Erotica Awards. Photo by Chris King/