Crossdress Dare Task 27

Everyday Women’s Outfits in the Car

You put on that everyday office-lady outfit — white blouse, tight pencil skirt, black stockings and high heels — and sit in the passenger seat while the other man, dressed in ordinary men’s clothes, drives. The two of you pretend to be a normal guy taking his girl to a fast-food drive-through.

On the way there you have to sit properly, letting the short skirt ride up so your stockinged legs are fully on display. When you reach the window to order and wait for the food, he pulls your skirt straight up right in front of the cashier, rests his hand on your inner thigh, and slowly strokes and squeezes, working higher until he’s almost touching your panties.

You’re not allowed to close your legs or pull away. You can only sit there blushing and let him play with you in public, feeling the eyes of the staff and any passers-by treating you like the dirty little OL femboy slut you are. Stay quiet the whole time and enjoy the shame of being treated like a real woman.

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