Was Dan really that shocked I’d be open to it? Daddy/boy roleplay is pretty low on the kink scale.

I wanted to know more about his boyfriend. “So you’ve tried it with him and he’s not into it?”

“No,” he says. “It really upset him. We almost broke up over it.”

Obviously everyone has their limits. But dumping someone over incompatible roleplay interests is pretty extreme in my books.

“But it doesn’t bother you?” he says again.

“Of course not,” I say with a wink. “You can be my daddy anytime you want.”

He smiles and excuses himself to the kitchen to grab another beer. I’m blissfully staring into space when the line of photos above the couch catches my eye; I sit up to take another look. There’s a row of different snaps: some with him, some with a woman and a bunch with two strikingly handsome blonde guys who are probably a few years younger than me. He comes back to see me looking at the pictures and confirms what I was thinking. The woman is his ex-wife. The blonde guys are his sons.

My kink neurons start firing in all directions, but instead of getting turned on I just feel confused. I’ve done plenty of daddy/boy stuff before. But it’s never occurred to me that one of the people I’m calling daddy might literally be someone’s father, or that he might have a son who’s almost my age. How does that change the situation? Is there a cause for concern? Or does he just have a desire for a specific kind of sex that in no way relates to his literal experience as a parent?

He finds his place on the couch, passes me a beer and eases my head back into his lap.

“So you don’t think it’s wrong?” he says. “Guys usually get really uncomfortable when they know I’m into that and I have kids.”

I launch into a long explanation of the boundaries between fantasy and reality; how roleplaying daddy/boy doesn’t in any way relate to my literal father or his literal sons. But as the conversation progresses, it becomes clear that no matter what I say to assuage his discomfort, it’s not going away. The fact I don’t see a connection between his interest in playing the daddy and his experience of being parent doesn’t matter. He sees it, and it disturbs him.

I continue to see Dan after this first visit, and the sexual encounters are the same. But his paranoia and discomfort around the psychological implications of our banter keeps increasing. On my last visit, the discussion over his conflicted feelings nearly brought him to tears. It’s a rare occasion when you have to fire a client, but this turned out to be one of them.

I find him incredibly attractive and I love the sex we have. I’m not at all disturbed by the roleplay or the fact he’s got two sons my age. But what does make me uncomfortable, the reason I have to call it off, is that he’s disturbed by it, and that’s something I don’t know how to deal with.

I have a special combination of skills that make me the sex worker I am. But I also know I’m not capable of dealing with every situation. I don’t think there’s anything wrong with Dan’s desires, or that they’re sick or immoral. But the fact he feels that way means he needs to reconcile them before he can fully enjoy his sexuality. I’ve studied psychology and have been through plenty of therapy. But I’m not a therapist — not in the way he needs me to be. It sucks to cut off a paying customer, even more so when it’s someone you genuinely enjoy having sex with. But passing a client off to someone who can really give them what they need isn’t a gesture of failure. It’s the mark of a true professional.

<Previous: When daddy and son roleplay crosses the line (Part 1)

(Follow Devon on Twitter @devondelacroix. devondelacroix@gmail.com)

(Photo credit: Drasko Bogdanovic)