Femboy Cheerleader: Stunning Must-Have Bet Loss

So my femboy cheerleader friend lost this stupid bet on a game night and honestly I wasn’t sure what he meant when he said he owed me, but later that evening he shows up in the full uniform, skirt and all, looking all shy and saying a deal’s a deal. We started slow, kind of like an ASMR thing, whispering and just touching, his skin warm and smooth under the polyester, and I could feel him getting all twitchy and nervous in the best way. One thing led to another and he’s on his knees between my legs, that pleated skirt bunched up, and he’s looking up at me with this mix of sissy shyness and twink eagerness that just made my head spin. It built up so slow and teasing, his hands on my thighs, breath hot and shaky, until finally I couldn’t hold back and finished all over his face, messy and dripping down his chin onto the cheer shell. He just laughed, wiped his cheek with the back of his hand, and said that was way better than losing any bet should feel.