I like the idea of the hyper-masculine man finding out that he is, in fact, a sissy. Maybe it's my belief that many of these men act like they do because, deep down, in a place they don't even permit themselves to look, lay the seed of a sissy. Sometimes it's a curiosity about what it's like to be with a man. Other times, it's a long-buried desire to be pretty. Still other times, it's jealousy of women. But it's there. They want to be sissies; our culture has simply made it impossible for them to admit it.
But what happens when those men are forced to confront those feelings? That's where this caption came from. Did I do a good job of conveying it? I don't know. But I think that turning a gangster into a sissy sex slave is hot, so there's that. Hope you do too.