Say you were to actually really get beneath Doflamingo's mask in such a way, he wouldn't be quite what you would have expected initially. Doflamingo is a cruel, cruel man and he's proud of that. He is because he was born a god. He could do whatever he wanted! Well, until someone ruined it. But alas.
But now, he has you. Not just as entertainment, not just as something to temporarily show off. No. He has you in a way that he refuses to go to sleep without you in his arms.
You came to learn that for as cruel as he was, he was starved of attention painfully so. It started when he began seeking you out more, not even for his fun, but your touch. The way he leaned into your touch as if he had never felt something this soft he didn't. The way he stayed there, head unconsciously settling on your lap for a long time if it mean a gentle caress to his face or hair.
That's when you realised. This guy longs for the touch of care. More specifically, a mother.
It made sense. He told you how he saw her die and you saw how his face had become grim before his masked slipped back on. And yet, when you hold him so gently, it's like he crumbles bit by bit. And so what I'm trying to say is that, Doflamingo maybe be all roughhousing and sadism, but deep down, really deep down beyond that, he's a man starved from every bit of affection he deserved to have as a child. And as compensation, as a misguided attempt to heal that, he takes and takes from others. However, he doesn't take from you. Not what you expected him to take. He just gets it eventually and that's honestly sad.
Sometimes, when he thinks he wants something rough, it's the longing for something he never had acting up. Due to his warped understanding of those needs, it translates as something rough, when it are your hands he simply wants cradling his face. He's half-aware of this. He hates how weak it makes him seem.
