Sissy Shoe Shopping

and try to walk in the shop in front of the female attendants. Be sure to force him to buy a pair of reasonably high heels that have a fastening strap around the ankle which you can attach a lock to and lock them on him. When you get home, make him practice walking in them until he can perfect his feminine walk by making pace the room back and forth with books over his head

Another great public humiliation, as he is forced to try on obviously feminine shoes under your watchful wicked eye and the help of some giggling shop attendants.   This will force him to be embarrassed while he gains a whole new respect for how far you will take him to painfully humiliate him. 

Just in front of the female shop attendants you should help him pick out a mid size healed women's shoe.  Tell him that he needs to remember to pick a color that matches well with all his girly outfits.  Have him try several pairs, then get the women working at the shop to judge and recommend the final one he should buy.

He should be in chastity of course, but you should also have him wear some pantyhose or stockings that will be visible when he's trying on shoes.  This is also a good day to make him wear a bra under a blouse, so that he feels really ridiculed in his femininity.

Surprise him when walking buy some cute women's shoe shop where you see some young attractive, but bored female attendants. You'll need to have planned ahead of time in order to make sure he's dressed properly with stockings.  Take your time to get the right pair, and ask him if he wants to wear them home afterwards.  You could even bring along a couple of small locks to snap on while the attendant holds his hands back, so he doesn't have a choice.

Make sure you do this where the ladies working in the shop are attractive and the time and open mind to play with your sissy's mind.

Don't do this in a shop where another man is around or where the woman attending you is not nice, sweet, and attractive… otherwise it will be a turn off.  Make sure you have full control over your sissy (chastity or other method) to force him to obey and endure the humiliating scenario.

Take your sissy on a surprise trip to buy some high heel or feminine shoes.  Make him try on several pairs and stand up