Random Crossdressing Dare

For you sissy boys.

Roll a die:

1. Bra and Panties: Stuff them slightly so that if someone were to look at you they would know you have little breasts.
2. Small touch of makeup: Light foundation, very light mascara, lip gloss.
3. Paint your nails with a very light shade of pink.
4. Purple or Pink shirt (this can be a man’s or woman’s shirt).
5. High heels of at least 3 inches.

Roll twice more: Once you roll the die and the result is cast, you must wear those items. Then head to Target and buy something feminine:

1. Woman’s earrings.
2. Woman’s ring.
3. Woman’s shirt.
4. Woman’s jeans.
5. High heels (if not already worn).
6. Purple Lipstick.

Make sure it is the only item you buy, that way the cashier will know what a sissy you really are.

Hugs, Trisha