Bailey's Night Out: Pegged & Humiliated

Bailey Wilde, still buzzed from his night out as a woman, stumbles into his apartment, only to be ambushed by Jake Grand and Cassidy Cream. They've been waiting for him, eager to turn his feminization into a full-blown sissification session. Bailey tries to resist, but Jake quickly secures him with a chastity cage, rendering him powerless. Cassidy lubes up a silicone dildo, pushing it into Bailey's tight ass while Jake holds him down. Bailey squirms and moans, his protests muffled by the panties stuffed in his mouth. Cassidy and Jake take turns pegging him, their laughter echoing through the room as Bailey's makeup runs down his face, a picture of feminine distress and humiliation.

• anal
• sexy
• ass
• amateur
• homemade
• tranny
• transsexual
• sissy
• sissification
• feminization
• femboy
• anal-masturbation

• shemale