50 Kinds of Kink: Crossdressing

He glowered at the stack of clothes in his hands. She loved taking him shopping. His frame was slender for a guy, which MUST have been why she enjoyed doing this. He grumbled as he held up a shirt, her giggles from outside the door tickling his ears.

She never shopped for things in his size; Always hers. She loved it, picking out clothes she'd love to wear and forcing him to try them on. Worst of all, she bought almost everything.

He tugged his own shirt over his head, his masculine form in the mirror seemingly mocking him. He pulled the girl's shirt over his head with some effort, sighing in relief when his head popped through. He jammed the arms in the holes, wincing at the warning creak of the fabric stretching as far as it could.

He looked in the mirror, his face flushed almost to matching the pink of the shirt, decorated as a sports jersey with the number 04. He didn't even know what that meant, or if it was a random number. Not like it mattered anyway, he guessed.

He dropped his pants, and sighed in shame at the reminder of the silk panties he was wearing. "Right..." He forgot every time, the reminder making him flush at how comfortable they were, comfortable enough that he consistently forgot about them.

The last thing he had to put on was a stupid short plaid skirt. It would have been nice if -she'd- tried it on instead, but that wasn't very likely to happen. With a sigh, he resigned himself to stepping into it, chanting all the while in his head 'almost done, just this and you can go and no one will know' as his personal mantra.

The skirt fit over his hips okay, but there was difficulty in zipping it up. He gave it a harsh tug and yelped, causing an explosion of laughter from the girl outside. The muttering grew slightly harsher as he examined the zipper, paling at what he saw:

Not only had it snagged, but it had snagged in the hair on his ass. He -definitely- needed help.

Fuck.