If you have to get a package or something from a friend… send him to get it, as your personal messenger/assistant. In fact, have him go dressed slightly feminine when he's sent to pick up a package from a girlfriend.
The point is to exercise your authority to command him to work for you by being your personal currier or personal assistant, which can be humiliating to him in front of the woman he's being sent to deliver or retrieve a package from. If you have him wearing something slightly feminine, you can play with his mind, making him think that he's vulnerable to being exposed as a sissy to another woman...an exciting element of mind-play, fear, and humiliation.
Tell him you have to pick something up or deliver something, and explain to him that he'll be doing that job for you (as you clutch the key to his CB). Remind him to be respectful and polite to the woman at the other end and comply with anything she says... and not to be late!
Make him wear his Marry Jane girls shoes, or have him wear a bra under a blouse with a sweater or jacket on top. You can tease him by having your girlfriend insist he takes off his jacket when he's at her door or you can make him think will.
Do this if you need to send or receive something from a close girlfriend or just pick something up from a shop for example. Since you can use him as your currior, don't be afraid to send him accross town just to drop off a simple envelope, that may not even contain anything at all (just for your amusement, and to play with his mind). If you need a little time alone at home, its the perfect excuse to send him out fora while.
You don't have to involve the other woman or explain anything to her if you don't want to; However, to maximize the humiliation impact of this treatment you could ask the other woman to play along by requiring him to help with something when he's at her door or simply insisting tha he take off his jacket (which would possibly reveal the outline of his bra unerneath his blouse), or have her call him by his sissy name when she see's him (leaving him to wonder just how much she knows).
Don't over-abuse this, but rather use it as a time to humiliate him and get an errand done at the same time. In order for this to have a stimulating impact, make sure you put something feminine on him before, and be sure to at the very least make him think there is a fair possibility that he's vulnerable to exposure as a sissy.