Yes

"I'm Richard's friend, My bag of clothes got swept down the river while Richard and I were playing in the river. I was soaking wet and Richard offered me your clothes. He told me these were your spares. He also said you already knew that I was going to wear your clothes." You say

"But you don't really have a reason for wearing my bra and skirt, do you?" Kristy asks you. The outline of the bra was prominent under your dress. The bra also caused you to be slightly more busty than a normal guy.

"Kristy, He just found out today that he's developing man boobs." Richard laughed.

Kristy stared at your chest. "You got to be kidding me."

Kristy took out her phone. "Hold him." Richard hold you down by your arms. He was much stronger and bigger than you are and you couldn't move. Kristy took several photos of you in her sleep tee and skorts.

"Listen to my commands now sissy. Or I'll circulate the photos into Twitter, Facebook and Instagram. I'm sure there are bound to have common friends between you and me." Kristy demands

Now with the photos, you are at her mercy. She could ask you to do anything.