Crossdressed for a prize

A boyfriend helps his girlfriend win a contest
"Are you sure this is really necessary?", Derek asked as he pulled on the miniskirt. The satin skirt didn't even come down far enough to cover the top of his stockings.
"Yes, you look adorable, now stop making such a fuss," Shelby replied. "I intend to win this costume party first prize."
When Shelby had come home and told Derek that there was a costume party at work and first prize was a weekend away he was all for supporting her in winning. It was only after he had committed himself to her cause and suggested she go as a tart that Shelby told him of her plan to win the contest by dressing him instead...
When Derek tried to offer alternative costume ideas Shelby wouldn't back down.
"If it was good enough for me, it'll be good enough for you," she said. "Besides, a crossdressed boy is always good for a bit of fun."
Now he was fully made-up and dressed a sexy street walker.
"Do you know, I quite like you like that," giggled Shelby as she took another picture of him. "You should do it more often..."