She is litterally sucking his dick and this guy still wonders whether it's a punishment game? Damn, he's dense 😑. This will hopefully and probably stay vanilla, but normally you would find dense MCs like these in netorare manga as the ones who miss out on the action due to their own hesitation.
I fully get the guy is traumatized but literally what else could she do to make him understand she's being serious? She confessed, came onto him, made a bet with him, and then blew him. And he's still whining about it when he's obviously attracted to her. He knows she's a kind person who helps people despite being seen as an "idol" of the school. And given her reaction when she sees his penis she doesn't seem all that experienced either.
If he has a phobia about women then I get that but he doesn't seem to. He's just afraid of getting attached to one. But everything he knows about her and all of her actions say she's not messing around with him.
@DarkTemplarXIII There's an incorrect translation right off the first page. Little redrawing, or just outright disastrous editing. Many pages are blurry for some reason?