The jock is probably the best bet.

"Hey there. Aren't you one of those guys on the swim team?" Talking to people isn't a issue for you. He does look up from his phone, so you've got his attention at least. "Yeah. Are you fan? I don't remember seeing you around practice. I know, I would have remembered you." He has a confident smile and it's clear that you are probably not the first to approach him like this.

"Nope. But if I was, I'd remember you. I bet you really stand out to all the other guys there." Is that too much? It feels like it is, but he doesn't seem to mind. "If you stopped by to see me in action, I'd make sure that I did." This all seems to be going easily enough. "Nanako. Nana's better though."

"Shiro. If it's you, then just call me whatever." There is something to be said about how self assured he is but on another slight level something about it is ever so slightly annoying. Still, he doesn't really seem like a bad person. "Ro-ro. That's your name for forever from now on."

"My theory is right. Anything sounds cute coming from you." It's not the first time that someone's called you that, but you can feel the blush forming on your cheeks which only adds to feeling of embarrassment making it even worse. "I'm going to shove a big spiky dildo up your ass?"

"Mmm...yeah...that's still way more adorable than it should be. If you look at me with those eyes? It actually would be pretty dam hard to tell you not to." His smile shifts into something of a worried look. "But you're not being serious, right? I'm not going to wake up in the middle of the night with you suddenly yelling "Surprise!"

"Wait. Why are we in the same room, sleeping together?" Inquiring about it just causes him to grin. "Well, you can give me a chance to see where that leads. Do you got anything to do after school?"

Well, that was easy enough. He's not bad looking at least. But there's another slight issue. How much time is there? Should you really wait until the end of the day without your doll or power it as soon as possible. It's hard to imagine, he's going to say no if you suggest something sooner but there's no doubt it would have to get really physical.