A Gay Man's Journey from Boy to Daddy

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Kristofer Weston has a boy, two sirs, a pup, and a pig, and he likes to push them to their limits. "Once your hand is inside," he said, "you can feel their heartbeat."

The pup is not literally a pup, and the pig is not literally a pig—they're men, whose kinks range from playful to filthy. And they're certainly not the typical friend group of a man enjoying his middle age, but Weston's life is anything but typical. He's been a fixture of the gay porn and BDSM community for decades, and these days he's reflecting on his comfortable transition from a "boy" to a "daddy," terms that mean different things to different people. It's a popular arrangement in the gay community, one that plays out much as it sounds: younger gay men paired with more mature partners. It can refer to anything from a romantic relationship that bridges decades to formally recognized community leaders to a hybridized mentor-and-student arrangement.

When Weston entered the kink community, he was decidedly a boy.

"It kind of was by accident," he said. "I was a horny exhibitionist teenager, and answered an ad in LA for wrestling porn." It was 1988, and he was blond, thin, and hairless. He was billed as a water polo player and made $150 for his first gig, to be followed by many more. "It paid for college," he said.

But he was after more than just money. He found kinky sex cathartic and sought out a mentor who could show him the ropes, discovering an eager daddy in legendary porn director Mikal Bales. Also known as Daddy Zeus, Bales brought young Weston to a cabin outside San Francisco with whipmaster Fred Katz and a handsome leather titleholder named Henry Romanowski for an early BDSM experience.

"They tied the three of us with our elbows together in a circle," Weston recalled, "and Fred went around and flogged us. And just being with our three faces right there next to each other—I was 22 with these two big, beefy daddies, taking it as hard as them, and they're blowing their energy into my face, and I'm feeling the energy from the whip and blowing it back into theirs. When it was done, the high that I felt was like, Holy shit. Oh my God. It just made me want more."

"I think lots of people don't have the opportunity to experience the things they want to," he said, sighing contentedly. Instead of merely watching or reading about something like that flogging fantasy—an experience many would love to take part in—he went out and did it.

Daddy Zeus tutored Weston from 1992 to 1995. "It was comforting to have a male figure in my life, especially in my early 20s," he said. "He was very protective. Especially when you're leaving college, going out into the big world and there's a lot of fear and self doubt, it was nice to have someone older and wiser."

Whether it's called daddy/boy today, or philetor/parastates in ancient Crete, it's an arrangement that's been a mainstay of same-sex-attracted men for centuries. In Weston's case, the daddies in his life discovered that he had an aptitude for the business side of porn, and he was soon managing an adult store before founding a porn-distribution company in the mid 90s. He moved to directing porn full-time at gay porn studio Colt studios in the late 90s and stayed until earlier this year; now he runs social media for San Francisco adult store Mr. S Leather and still regularly directs porn.

Being a successful businessman over the past several decades has come at a cost—that is, the passage of those decades.

Just as his beard was turning gray, Kristofer left an unfulfilling decade-long relationship that had kept him monogamous. He was ready to explore again and worried that his age would be a barrier.

But then: "There was this pup," Weston said—an increasingly popular queer identity involving canine roleplay—and for a moment he flashed the shy grin of a boy. "Amp. We hit it off, and I told him flat out: 'I can't do a relationship right now, I just got out of a bad one…' And he said, 'That's OK, I'm a puppy. I'm just here to make you happy.'"

After they'd been playing together for a few months, Amp asked, "What do I call you? Sir doesn't sound right… can I call you daddy?"

"NO! What do you mean, 'daddy?'" Weston had responded, aghast. Then he realized that he was two years older than Amp's biological father, and tentatively adopted the title. Before long, every pup in San Francisco was calling him Daddy, and he found that the title lent him an air of authority and command. He now wears it with pride.

"It just kind of crept up on me when I wasn't looking," he said. "I'd always been the Boy. And then I looked in the mirror and was like, OK—I'm the Daddy… I'm bigger now, I've got more of a beer belly. Growing a beard put me over the top on that one."

Being a daddy, Weston learned, comes with perks and responsibilities—chief among them training younger boys to appreciate classic culture. Early on, Weston discovered that Amp had never seen the 1987 movie Moonstruck. "I didn't know what to say. 'What? How could you not? That's impossible.'" Working with another mentor in Atlanta, he developed a list of 97 films he insists his charges watch, from 1950's All About Eve to 1983's Yentl. They span a wide range of genres, but in general, the films are touchstones that he feels are necessary for having grown-up conversations.

Besides Pup Amp, today Weston also has his boy, two sirs, and a pig who likes humiliation (during one recent escapade, Weston staked him out in the sun, pissed on him, and inserted his fist into the man's ass). So are they boyfriends? Not exactly.

"That's one I'm still trying to figure out," he said, haltingly, as he thought through his feelings. "What I like about this is—when I get into relationships, that two-year-in mark where everything gets mundane… I don't have that with any of these people. I get to have these fun sexually intimate experiences for a weekend, and I get to move on to the next one. I never get tired of any of them."

When I wondered if any of those relationships could become more serious, Weston looked down. "Maybe I've been so hurt by my last relationship that I'm not allowing that right now," he said.

He may be a Daddy, but that doesn't mean he's above learning something new about himself.

Follow Matt Baume on Twitter.