Timber Spruce thought that him going to a Halloween party in a dress wouldn't be weird. After all, Twilight said she'd go in a boy's costume, and it would be funny! But now she's wearing a different costume, and Timber is left dressed like a girl. How could this night get any weirder? Well, a certain older boy who's been admiring Timber's lacy costume is about to strike up a conversation and answer that very question.

WARNING: Contains Crossdressing, Petticoats, Bisexual, Skeezy Older Brother, Femboy Fetish, Femmecon, Very suggestive conversations and actions but no sex

Done as a commission for shortskirtsandexplosions, and thus contains short skirts, but no "explosions."