Three Dresses for Charlie

Skirt Shocked

When Charles woke up the next day everything seemed surreal. He had slept in his boy underwear, and he still felt like a boy, but he saw a black and white maid's dress in the corner that everyone expected him to wear today. He thought it might have just been a strange dream, but his room was different; he walked into the bathroom and found Lilly's things. He spent a long time staring at the dress, wondering if he was really going to put it on.

Lilly knocked through the bathroom door, cracked it open, and carefully peeked out, "How's it going in there Charlie?"

"I don't know, I'm just kind of skirt shocked. Does everyone expect me to come out in the dress?"

"We were kind of wondering that ourselves. Kate bet Ms. Hughes twenty dollars against it."

"Is Ms. Hughes going to be mad if I don't?" he asked.

"I don't think so. She's been more quiet than usual. How do you feel about it?"

"I keep thinking about all the kids at my old school laughing at me."

"You see any of them in town?"

"No, but... it still feels that way. Do you think I should put it on?"

"If you want to, yes" Lilly said, "But I'm with you either way."

"It is kind of embarrassing... I mean I don't know about being a girl, but I liked wearing those dresses. It made me feel like I fit in. But then doing something like crossdressing makes me feel like a freak..."

"If it wasn't crossdressing would you do it?"

"What do you mean?"

"It's totally socially acceptable for girls to wear pants, and no one calls them crossdressers. If boys could wear dresses without anyone batting an eye, would you do it?"

"Well... yeah. But that'd be different," he said.

"If boys could wear makeup, and be named Charlotte without worrying about it, would you give it a try?"

"I guess so..."

"What if a boy could be called a girl? Being called 'she' and 'Charlotte' is lot like trying on a new set of clothes. Look, I like you, we all do, and that won't change, no matter what you are wearing. The best case I can make for it is, that it's always good to try new things, and this is a pretty safe place to do it, if you want to. When you leave, you can leave it behind if you like. I'll still be your friend no matter what."

"Thanks, but it still feels like I'd be doing something really wrong."

"Is that the biggest reason for not doing it?" she asked.

"That, and I don't want to start dating boys or anything."

"Hey, you don't see us trying to set Georgia up with any guys do you?"

"No, I guess not."

"Well, I'm not going to make up your mind for you. If you go down there as a guy and Ms. Hughes gets mad, I'll chew her out for you, I swear I will. But I don't think she's going to do that. I think she just wants you to have fun this summer."

"Thanks. I do think the dresses are kind of neat. It was fun to wear."

"Yeah, that's one of the reasons I came here. I like playing dress up a lot. There's just something about wearing a uniform." Lilly smiled. "It's kind of dumb but I like being my own dress up doll. Sometimes I'll look at myself and think I look totally ridiculous, but it's fun."

"That's how it felt. I looked at myself and I looked like another person. It was really odd to see that, like an out of body experience. I enjoyed it, but I'm afraid of taking it too seriously."