Sissy Humiliation Assignments Series 26 – Pantyhose & Shoe Shame

For this task you will need pantyhose. If you don’t already have some (and I can hardly believe you don’t, sissy), you will go buy a pair of black, sheer 10 denier pantyhose in your size.

Choose a pair with a silky finish so you can truly savour the sensation on your freshly shaved legs — yes, that’s right, if you want extra humiliation, shave your legs beforehand so you feel utterly feminine every step of the way.

This is another shopping humiliation assignment, but the focus isn’t on buying the pantyhose themselves. Your task is to wear your pantyhose under your male clothes and go shopping for shoes. You will not wear socks — your pantyhose will be the only thing between your feet and your shoes.

You will wear your usual male footwear: oxfords, loafers, or trainers. Just knowing that only the merest glint of nylon-covered ankle could peek out with each step will make your heart race. No one may notice, but you will know.

Here’s your mission:

• Go to a shoe store — it can be one selling men’s shoes if you’re too terrified to enter the women’s section. But if you’re brave enough, aim for the women’s shoe section instead.
• Browse slowly. Touch the shoes. Pick some up. Build your courage.
• Choose at least two pairs of shoes to try on.
• Sit down on the fitting bench. Undo your shoes and pause: this is your moment of truth. You know the assistant (ideally a woman) will see your pantyhose as soon as your male shoes come off.
• If the assistant comes to help, let her. Picture her kneeling before you, eyes flicking to your nylon-clad feet. Feel your cheeks flush as you slip off your shoes and expose your pantyhose. Notice her reaction.
• Slide your feet into the new shoes. Enjoy the smooth, effortless glide that only nylon can give. Feel your erection strain as the humiliation and excitement surge inside you.
• If the shoes feel loose, imagine the assistant offering you socks. Or better yet, imagine her teasingly suggesting you try something more appropriate — like women’s shoes — since you’re already halfway there in your pantyhose.
• After trying on both pairs, thank the assistant, smile sweetly, and leave with your head held high. Bonus points if you actually purchase a pair of shoes — imagine telling friends or colleagues about your new shoes while knowing what you were wearing when you tried them on.

Advanced sissy option:

• Before you go, shave your legs to feel the full, silky effect of the pantyhose.
• Paint your toenails a soft pink or bold red so every time you slip off your shoes, you know how utterly feminine you look.