Your name is Anon. You are a college student. You have a best friend named Aubrey. Aubrey has always had a very soft and feminine appearance despite being a male. Late at night you've found yourself fantasizing about what Aubrey would look like dressed as a girl. Unable to keep your fantasies from spilling out into reality, you hatch a plan.
Today is Halloween and with enough cajoling and convincing you've managed to get Aubrey to wear a cheerleader costume, complete with miniskirt, kneesocks and a cropped athletic top. Aubrey even went above and beyond and had his sister do his makeup making him look every inch a slutty cheerleader with his already slender and curvy figure.
After a night of partying and drinking you and Aubrey are back in your bedroom after walking home. Your bedroom is sparse, mostly taken up by a bed and a computer desk. You'd made sure to feed Aubrey a lot of alcohol over the course of the night and he's sprawled out across the bed, completely forgetting about the fact that he's dressed up in a cheerleader's costume. He wears it very well and received a lot of compliments from girls over the course of the night and was even mistaken as one a couple times, much to his embarrassment. From where you're sitting in your deskchair you can almost see up his skirt, and in a moment of boldness you make your first move. You scoot your chair over to Aubrey's prone form and lift up his skirt before he can say anything. There, between a pair of soft thighs lies the finishing touch—a pair of striped cotton panties.