Crossdress Dare Task 30

Sexy Outfits at Vending Machine

Put on an ultra-short sexy dress or miniskirt (nothing underneath, or crotchless pantyhose), apply light makeup and lipstick, and style your hair as femininely as possible.

In the evening when there aren’t many people around, go to a nearby vending machine and buy a drink or a snack. Walk with a deliberate sway in your hips and take small, quick steps so the skirt flutters with every movement. When you stand in front of the machine choosing what to get, lean forward a little so the hem rides up naturally, feeling the cool air on your inner thighs and between your legs — that sharp little rush of shame.

If anyone walks past, immediately lower your head and act like an ordinary girl, but keep silently repeating to yourself: “I’m a dirty little sissy out in a tiny skirt with nothing on underneath…” After you finish buying, don’t leave right away. Stand there for a few seconds, pretend to adjust your skirt, then sway your hips all the way home.

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