He started out being submissive to his tennis coach, an obviously alpha male who would order him to get into matching bra-and-panty sets for his twice-weekly lessons and apparently enjoyed watching him stumble around the tennis court in a pair of high-wedge espadrilles, followed by some cock worshipping and ball-licking in the changing room.
Since then, this caller's sissy-boy saga has gone on to include his wife, his stepdaughter, his golfing buddies, other middle-aged men taking tennis lessons, a would-have-been female fling in San Diego, the Middle Eastern convenience store owners down the street, and the tennis coach's Latino head gardener.
In addition to a standard cock-sucking framework, my sissy has a strong preference for humiliation. This is not an unusual fantasy combination, in my experience. What is unusual is how nuanced his hierarchy of privilege is, in terms of where the humiliation is coming from. I confess, I'm a little curious about how much of this is conscious in his non-sissy-boy life, but mostly when I talk to him, I am paying attention to where the humiliation dynamic is located in whatever interactions we are discussing.
Yesterday when we talked, it seemed like he was going somewhere entirely different in the fantasy. He was hanging around his house, fully sissified, when there was a knock on the door. A middle-aged white man in a suit was there, and handed him a note from the Latino head gardener. In the note, the gardener said that the man had paid him $200 so that he could be turned into a sissy-boy cocksucker. It was now my caller's turn to enforce the sissy dress code and humiliate and get his dick sucked.
Wow, that's a change, I said. How did that feel to be on the powerful side for once?
"Good. It felt good." But the tone of his voice told me that wasn't all. ...
Two hundred dollars, huh? Are you getting a cut of that?
"A little bit."
I mean, that's a lot of work, to turn someone as thoroughly as you were turned.
"I liked it, it felt..." but I interrupted.
You like being the Latino gardener's whore, you mean.
"Yes." This was very quiet.
Tell me again, in a complete sentence.
"I like being the Latino gardener's whore."
You'll do any fucking thing he tells you, won't you? I mean, you'd do it for free. But he's got you making money for him, selling your services. You're the Latino gardener's whore. SAY IT.
"I'm his whore."
"I'M HIS WHORE." And then he came.
See what I mean? I hate that all that stuff—sex work, a brown-skinned master, sissy play—carries the baggage that it does, but if the humiliation is the hot button, then I have to find the best way, in 10 minutes, to push it.