The first time he found himself in a skirt, it wasn't too bad. Well, it was mortifying, but at least it wasn't out in public--he was with his girlfriend, and no one else. She was confused when he started sputtering and trying to take the pleated thing off.
"But I thought you wanted to try it out?" She asked. He furiously shook his head, and threw the skirt in the trash the next day, much to the annoyance of his girlfriend.
"I could have worn it, at least..."
The second time he found himself wearing a skirt, he only realized after almost walking out of the house in it, and stopped only because he saw himself in the mirror. The skirt was a different color, this time a ruby red, and still pleated, and for a moment he found himself sucked into the vibrant red color, running his hands down its pleats before he realized what was wrong.
"You told me you wanted to give it another shot. Maybe even thigh-highs. That's what you said, wasn't it?"
He couldn't even remember.
The third time he found himself wearing a skirt, it was when he himself was putting it on. It felt normal, just slipping it over his hips and looking forward to giving those new thigh-highs a try--when he stopped and realized what he was doing.
It took him a full two minutes to remember that he wasn't supposed to be wearing them.
"You look wonderful."
He smiled, a dazed, fogged-over expression on his face, and did a small twirl; this skirt was plaid patterned, and he felt so pretty in his black thigh high socks. He looked at his girlfriend, waiting for something else.
"You can say it," she said.
He jumped excitedly. "I love wearing pretty skirts!" He said, and as if he was receiving a hit of dopamine smiled even more broadly.
"Yes you do," she said, grinning wickedly. "And I'm sure you'll want to show off your skirt to all of your friends, won't you?"
"And I'm sure you won't find anything strange with wearing a skirt. After all, you've always loved them. I bet you don't even remember saying you hated how they looked before."
He covered his mouth in horror. "I would never!"
She smiled. "Wake up then." She snapped her fingers, and he blinked, and looked down.
He smiled. He couldn't wait to show all his friends his new skirt and sock combo.