Forced feminization tip – Panty challenge

Slip a small package with him when he goes to work (in his lunch, briefcase, toolbox,etc...) Mark it private, so he opens it in a secluded place. Contents: panties and a note telling him to wear these the rest of the day and to immediately send a picture of him in them. Wait for your picture. Know that he will be thinking of you more than normal that day.

Bra

At first, I thought forcing him into bras might be to sissifying, but it makes an awesome punishment if he messes up. Force him to put a bra on and sleep in it [in chastity, of course]. In case he might actually enjoy that... Threaten to make him sunbathe in it. That would be a hard tan line to explain away in the gym lockeroom!