Tim wasn't the first person to make porn out of his very specific kink, but he was probably the second. "Somebody had started a site a few years earlier with this particular content. But it was still images only; that's pretty much all there was at the time," he says. "Eventually they started publishing videos." But, that site went out of business (after getting sued by a patent troll) and Tim heroically stepped up to fill the void. The fetish is girls playing games where they bet their clothes one item at a time, while the viewer excitedly waits to see who "loses." Pretty straightforward as far as fetishes go.

"I bought a cheapie video camera, got a hotel suite," Tim remembers. He found a number of models on Craigslist and, since this was 2004, he was rightfully concerned that they might be violent serial killers, rather than sexy ladies. He took appropriate precautions: "My friend Jeb came along with me and brought a baseball bat."

PhotoBylove/iStock/Getty Images
Usually, when baseball bats mix with porn, the actors demand a lot more money.

So Tim's Craigslist models showed him the ropes of filming, because, he says, "I didn't know a thing. I had no tripod, I had no lights." He'd planned on using the hotel's lights at first, not knowing "that'd turn everything orange." At this stage, Tim was so nervous he had trouble asking the girls to rub themselves in oil, do jumping jacks -- pretty tame stuff, from the perspective of a pornographer. But thankfully, "They were friendly, smart, and they thought it was adorable the way I blushed when they walked out naked. That was a theme for my early shoots."

Ingram Publishing/Ingram Publishing/Getty Images
Low camera shots are an overexcited rookie porn director's best friend.

So there was some luck involved -- Tim says if he'd gotten less-helpful models that first time, he might have abandoned the whole enterprise instead of turning it into a lucrative living for the next nine years. "Sometimes I wonder if there's some sort of providence out there that likes my site and wants to see it succeed."

"The girls we were hiring were models, not actresses," Tim says. So he decided the best strategy would be to actually have his models play real games of chance, and "what happens, happens." This new strategy, if we're using the most charitable definition of the word "strategy" imaginable, wound up working much better than Tim had predicted. See, his fans weren't interested in sexy scripted videos with professional actresses.

John Howard/DigitalVision/Getty Images
No one wants to hear your 75th variation of a "I got two pair" joke.

The exact appeal of Tim's particular kink is that these are "good girls" and boys awkwardly flirting with one another and very much embarrassed about losing games and stripping off their skivvies. If the models are awkward or aren't quite sure what to do, that just helps sell it. He had invented an art form that he could screw up only by doing it too well.

But early on in his career as an impresario of erotic delights, the otherwise unreasonably lucky Tim took a shot to the chops from Lady Fate: He was diagnosed with multiple sclerosis, a disease that sucks pretty damn hard. MS can cause blindness, tremors, and a whole host of other problems that make it difficult to work a full-time job. Over time, his porn career morphed from "hobby" to something of a retirement fund. He now relies on his website as a source of income and for a sense of purpose. That said, the last few years have been tough for niche porn purveyors.

First, there's the fact that polite society just doesn't approve of porn -- which extends even to the financial institutions where you're trying to deposit huge paychecks. Tim had his bank account with Washington Mutual, which was acquired by Chase during the 2008 recession. And then, four years into his career, his bank decided they were done with him. "I got a letter from Chase informing me they were closing my accounts without explanation, without warning. It could be that they found out how I got my living," he says.

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"Come back when you've found honest work, like drug-dealing or running a cockfighting ring."

Tim's not just being paranoid, nor is he the only porn person that Chase slammed the door on -- apparently receiving a $25 billion bailout makes you into kinda a prude.

CNBC
"Too big to fail" definitely didn't refer to the size of their balls.

Tim's porn operation also ran afoul of Google. "It really hurt us when Google decided to stop accepting ads for adult content. I never understood why. People go to porn on the internet, but they won't take our money. We were kicked off of YouTube and kicked off of Dailymotion and kicked out of Model Mayhem."

Model Mayhem is, essentially, a dedicated Craigslist for modeling work. It seemed like the answer to Tim's filthy dreams. "Their site is set up to do nudity; they allow people to advertise as looking for nudity," he says. But they don't allow anything that falls under the heading of porn.

Model Mayhem
You're only allowed to get naked naturally, not thanks to a bad beat at the roulette wheel.

And that's kind of the general story with being a porn producer. Conventional internet wisdom is that "everybody" consumes porn, at least sometimes. That may be true, but it's also true that a majority of Americans view it as immoral and would be OK with putting more legal restrictions on the industry. We watch the stuff, and then we hate ourselves for it, and then we punish the people who make it. Don't ask why; it's just how polite society works.

But each of those videos will make less money than before. The rest of the world has jumped on board the "girls making naked bets" train, so there's now plenty of competition even for that specific fetish. "Sales have been way down, either from the lack of Google ads or saturation," Tim says. This has created a sort of arms race in which video makers are forced to be more and more explicit. "Every time we push the envelope, people seem to like it," he says. "In the early days it was very tame. You have to do jumping jacks or rub baby oil into your breasts. Since then things have gradually escalated."

This creates an unexpected problem, in that the fetish's fans are "into the whole embarrassment aspect," as Tim puts it. On the other hand, he says, "If you can find a girl willing to take four cocks at once, she's usually not embarrassed about it." Also, it seems like there's a pretty stark line between "I want to see a modest girl giggling because she lost a game of Truth Or Dare!" and "I WANT TO SEE A GIRL FORCED TO PERFORM SEX ACTS SHE IS VISIBLY UNCOMFORTABLE WITH."

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"If it's not double-digit cocks, what's the fucking point?"

Add it all up and you wind up with a man for whom porn has lost its magic. More than 500 videos into his career, Tim is desensitized. "I no longer blush when I see the models come out naked. I used to hesitate when I said things like, 'After this, could you just sort of ... touch yourself there?' These days I'm more comfortable saying, 'You three go over there and take her.'" He added, with some sorrow in his voice, "I rarely get turned on by my own material."

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