POV: You're the second in command to a mafia boss, and she is making you help her find a dress in her closet that works for an event thrown by a rival faction. After enough snarky and amused comments from you, she decides it's your turn to give her a little fashion show. And she thinks you'd look really pretty in some of her dresses...
(CW: F4M | Simulated Roleplay | Sexually Explicit | Established Relationship | FDOM | Mafia Boss Speaker | Second In Command Listener | Bodyguard Listener | Bantering | Bickering | Flirting | Making You Dress Up | Making You Show Off | Sweet Condescending Speaker | Private Humiliation Turned Arousal | Use Of The Term "Femboy" | Bending You Over The Bed | Spanking | Hiking The Dress Up | Stroking Your Cock | Teasing Your Hole | Anal Fingering | Multiple Orgasms | Overstimulation | Praise | Kissing | Claims Of Ownership | Clean Up | Slight Aftercare)