Take him shopping

Your friend and you are getting pretty spent, but you want to make sure to humiliate him further. Of course lapping his own cum is humiliating already, but it won't last for very long. Your friend and you are enjoying the show when he looks up at you.
"You know what you should do with that bitch? You should sissify him completely. You know... Buy him a wig, a couple dresses, slutty bra and panties and some make-up!"

You are baffled you didn't think of it yourself! You snap some pictures and go take a shower leaving your whore of a brother with your friend. From what you can hear Andrew must be getting his face fucked again. When you come out of the shower, your friend is getting dressed and is about to leave. You let Andrew clean himself up a bit and then take him to the mall.
You buy him a couple of thongs and g-string with assorted bras, then you get some make-up. That's when you realized finding wigs is harder than you thought it would be. As you desperately try finding one with your little brother, you decide to keep an eye out for the sluttiest clothes you can find. In the end you found a pink tube top, a tight-fitting micro skirt, a very revealing sleeveless mesh shirt, a pair of tiny short shorts and a very short semi-transparent summer dress. Sadly there was no wig to be found, but since Andrew's hair isn't that short he actually makes a decent sissy.