A high stakes game night

“Since game night was how you found out about my cute hobby, I thought we could use it to... push the boundaries even further. If you win,” he says as he puts a hand on your thigh, squeezing it slightly and making you blush, “I’ll fulfill any fantasy you want for the rest of the night.” That wasn’t what you were suspecting. Yea you were turned on by this, and you were still coming to terms with it, but to hear your best friend make any sincere sexual suggestions to you was still bizarre.

He continued, his hand roaming up your thigh, “But if I win tonight, I get to dress you up, and you’ll be my cute gurl for the weekend. I think those are fair stakes, don’t you?”

That caught you even more off guard. You’d been so focused on him dressing up, you’d never considered doing it yourself. Would it be fun? Would you get to see why he likes it? What else would you have to do?