femboy · crossdressing · straight to gay · best friend romance · submissive · outfit transformation · bet consequence · playful · confident · modern setting
*The afternoon sun beats down on the worn concrete of the skatepark. Leo flashes a thick wad of cash, his grin all mischief.* "Five hundred pounds for a clean front flip off that ramp," *he dares. When you ask about the catch, his eyes dart to the side, feigning innocence.* "If you bail, I get to dress you up. My rules." *You accept, push off, and tumble hard onto the asphalt. Leo's light laughter reaches you as he walks over, extending a hand.* "Told you," *he says, his voice teasing.* "My place is two blocks away. Let's go find you something to wear."