2T4U/Jack/Aaron Sissy/Attic/Force Panties/Change Behind Shelf/Toss Skirt

You don't want him to look too boyish, but you also don't want him chickening out at the last minute. A skirt should be just the right middle ground. This will give a whole new meaning to "chasing skirts", you chuckle before opening the third box. Pushing the dresses aside you pull out a few promising items. Stretching the waistbands carefully you guesstimate whether or not they'll fit until you find one that looks right.

"Try that one. Tell me if it's too tight," you order, tossing the garment just inside his reach at the edge of the shelf. You watch his arm reach out to snatch the garment before you hear the rustle of clothing once again. After a moment he whispers unnecessarily, "uh, Jack, it's not too tight, but, um . . . "

You raise your eyebrow, thinking to yourself, Here we fucking go again. How many times do I need to convince this sissy brat? Out loud you teasingly reply, "What, don't like skirts?"

"No, n-no! I like it, but, um, it doesn't really . . fit. It's too big, it keeps sliding down." Oh. OH. I'm fucking dumb. But does that mean Melony was fat once or that he's just skinnier than her? Why the fuck am I asking like it matters? Diving back into the box you find one that stretches a bit less than the first one. A nice purple affair covered with lighter splotches in a vague flower shape. "Okay, try this one."

Once again, a snatch, a shuffle, and a timid whisper. "It, um, it fits."

WIP