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This is a female dom male sub, femdom sissy, crossdressing feminization, exhibitionism/voyeurism erotica.
Jeff loses a wager to his girlfriend, Kate, and has to be the chauffeur for her and her girlfriends on a girl's night out. They go from bar to bar, getting a little rowdier each time they return to the limo. Jeff is getting tired of this and looks to redeem himself.
Short on his luck, he loses another wager to Kate, and finds himself wearing panties and a dress as he joins Kate and her friends at the bar. Jeff is humiliated and resigns himself to feeling like a loser. Yet, he gets hit on by a guy who's been watching him, and Kate gets a little jealous.
After leaving the bar, seated in the back of the limo, Kate gets Jeff to prove his loyalty to her in a way that seals him into the role of a sissy. Kate has her way with him while her friends watch in awe.
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