Tell him to add another reward for himself

"F-fine then!" you gasp in frustration, both sexual and otherwise. "Just pick another prize to give yourself if you win!"

He hesitates at your entrance. You can feel the tip pulsing against you, and you're so wet that sliding into you would take no effort at all right now.

But he doesn't. Not yet.

"Alright then, here's a GAME. If you win, I'll fuck you with a condom. But if I win, I'll fuck you bare, and..." he pauses for effect, smiling smugly, "you'll have to let me have sex with you however I want at least once a day for the rest of the school year."

You gulp.

"And if you refuse to play, you still have to let me have sex with you once a day, in any way I want, for the rest of the year. But I will use a condom right now."

Your toes curl as your mind races. Frequent sex doesn't sound like a bad deal, but you're not sure you want to be contractually obligated to do it every day.

"As for the CONTEST, well that's simple..."