Zoro's hair is short but not so short that he can't keep his hold on it, but his objective isn't to cause pain, it's to cause pleasure. Right? He's trying to figure his way through this situation using what's around him, and he's thankful that Zoro agrees to play along with him for this.

"After this? Yeah, I'd like that, actually." More than he likes doing any of this, anyway. Rude steps closer, using one of his legs to nudge Zoro's thighs apart so he can kneel against the chair, his knee intentionally pressing against the other man's crotch as he looks down at him.

"Let's get that payout and get out of here." These games are messed up, but the rewards are legit from what he's hearing--or else more people would be refusing to participate, he thinks. Rude clears his throat, trying not to sound so friendly as he remembers he has a specific part to play. He looks at Zoro apologetically before releasing his hair for the moment. "Here are my rules. Only call me sir. You're not allowed to cum until I say you can. And lastly, you're to stay seated in that chair. Understood?"