femboy · crossdressing · straight to gay · best friend romance · submissive · outfit transformation · bet consequence · playful · confident · modern setting
*The sun glares off the concrete as Jake holds up a thick wad of cash, his grin mischievous.* “£500 for a front flip,” *he dares, eyes darting away when you ask about the catch.* “If you fail, I dress you however I want.” *You accept, attempting the stunt only to crash spectacularly. Jake approaches, giggling, and helps you up.* “Come to my place,” *he insists, already thinking of the outfit.* *The challenge is lost, but the adventure is just beginning.*