The Fashion Towne Chronicles

Little Sister, Big Sister - Ch9

Weeks went by without me wearing anymore girl's clothes. It wasn't easy though. Whenever I saw girls in my class all dressed up, I thought about dressing up myself. Every time I saw a dress or skirt hanging in the closet I thought about how much fun I'd had and how exciting it was when I wore them.

I asked mom to take them out of there but she said she wanted to leave them there for when Rich grew into them.

No one ever did mention that store to me nor did I notice anyone looking at me in a funny sort of way. For a long time though, every time I heard a couple of girls giggling I wondered if it was because of me but like I said, no one ever said anything so I just forgot about it.

Then finally one day, as I was hanging around with a bunch of the guys, something happened. We were playing a game of baseball and I was in center field when the batter hit a ground ball towards second base.

Jack, the kid who was playing second base, got set to catch it and I moved in behind him in case he missed. Jack didn't need my help though, as he quickly bent over, scooped up the ball and threw the runner out at first.

What got my attention, was when he bent over. His pants rode down a little on his butt exposing the top of his underwear, pink, nylon, girl's underwear.

I didn't know what to do or say but I thought it would be better if I waited until the game was over and we were alone if I did say anything. No point in embarrassing Jack and since I'd be the only one in back of him no one else would be likely to see what he was wearing.

Jack and I had known each other for years and lived fairly close to each other, so, just as we always did, we walked home from the game together. Once we were far enough away from everyone else I decided it would be a good idea to warn him about his underwear showing.

At first, Jack said I was nuts thinking he was wearing girl's underwear but once I described what I had seen he became really quiet. When he finally did speak, his voice came out sounding scared.

"I guess you're going to tell all the other guys about me now, huh?" He asked quietly. "I don't suppose I could ask you not to?"

"If I was going to say anything I wouldn't have told you first," I explained. "I could've told everyone back at the field."

"Why didn't you?" He asked in a soft voice. "I really owe you big time you know."

"What? Tell everyone and lose the best second baseman we ever had? And a friend?" I laughed. "I'm not crazy you know."

"I guess you think I'm gay or something, right?"

"I know you're a nice guy and a great second baseman," I replied. "What else do I need to know?"

"You don't want to know why I'm wearing girls underwear?"

I shrugged my shoulders and replied, "That's your business, man. If you don't want to tell me, then I don't want to know." But, in reality, of course, I wanted to know. I wanted to know so badly that I was ready to burst, but I had to play it cool. "That's up to you, I was just trying to help."

We walked the length of the next block in silence before Jack took a deep breath and let it out. He slowed his pace and began to nervously explain. "Well, it was Halloween, when I was seven. My mom thought it would be cute to take me to a costume party dressed as a girl. There was going to be this costume contest and she told me that when she was done with the costume she had in mind for me, there's no way I wouldn't win."

"Did you win?"

"Hang on. Let me tell the whole story."

"Oh, sorry. Go on."