Stealing my pants.

One morning in late September, I woke up late for school. I rushed to my closet to grab some clothes, hoping I wouldn’t get into too much trouble for being late--I’m a really good kid, and I never ever get in trouble for anything, especially being late. Except that when I looked inside my closet, I discovered a bunch of skirts hanging there--all my pants were gone. Nowhere to be seen. I ran around the whole house looking for them, but I couldn’t find them anywhere. Even in my panic, I recognized the skirts as Jessica’s, and I knew then what had happened.

I was furious at first. What the hell kind of practical joke was this? Did she seriously think I’d go to school wearing one of her skirts? That was insane! Better to ditch school and get in trouble than get made fun of for the rest of my life.

But then I started to calm down. I’m never much good at making decisions or coming up with ideas when I’m emotional, but if I have a little time to think…

I bet Jessica giggled when she put the jean skirt in my closet. It was so short, I couldn’t even imagine her wearing it, let alone me! It would barely cover my ass. That’s when I decided I was going to show Jessica how to pull a real practical joke. I grabbed a pair of shorts--it was too cold already for shorts, but I knew my desire for **** would keep me warm. Over the shorts, I put on the little jean skirt. It looked ridiculous, but it was going to be worth it.

The first person I saw when I got to school (just on time for the first bell, thankfully) was Mandy. I suppose she’s cute enough, with her short, curly brown hair and nice pert tits, but she was one of the most annoying people I have ever met. Loud, rude, and the biggest gossip in the school. I’d never been so happy to see her in my life.

“Oh my god, Mike! Like, what are you wearing?” she screeched. Every sound she made grated on my ears.

“Oh, this?” I replied, for once not doing everything possible to avoid talking with her. “Just a bet I have with my step-sister Jessica. She dared me to wear the skirt and shorts to school today, and said if I did it, then she’d wear the skirt without the shorts to school tomorrow.”

Mandy burst into obnoxious laughter as I tried to shush her, and eventually I gave up. “But listen, Mandy, don’t spread this around. Part of the bet was that I wasn’t allowed to tell anyone, so you’ve gotta keep this between you and me.” I knew telling Mandy not to gossip about something was the quickest way to ensure the entire school would hear about it in record time.

Mandy did her job better than I could have imagined. People pointed and laughed at me less and less as the day went by, and by the end of it, there was something like gratitude in the eyes of many of the guys. I didn’t blame them--the miniskirt would definitely show off Jessica’s firm tanned thighs, and there wasn’t a straight guy in the school who didn’t drool over that image. But the best **** of all was the fury on Jessica’s face when she saw me at the end of the day. If she backed out of this “dare,” the entire school would think she was a liar or a coward.

When Jessica came down to breakfast the next morning dressed in a typical school outfit, I whispered to her that her fan club was going to be very disappointed. She just gave me an unreadable look in return, and at school I found out why. After getting to school, she changed into that miniskirt. It was everything that I’d dreamed of--her legs were beautiful, her caramel skin flawless. And the super-short skirt made it very clear that she’d picked out bright red panties to wear that day. I tried to guess what percentage of guys in the school would masturbate while thinking about her that night. 50%? 60%? 75%? I knew I definitely would.

For one day of my life, I was a hero. Guys I didn’t know high-fived me in the hallways. Ryan O’Connell, the quarterback of the school football team and far too cool a guy to be seen talking to me, came over to my table at lunch and thanked me for “taking one for the team.” At the end of the day, Jessica brushed past me. I was so worried about her noticing my boner and getting mad at me that I almost missed her whispered threat, “oh, it’s on now, Mike.”

Oddly enough, our ongoing feud became the basis for a real friendship. Jessie appreciated having another practical joker in the house, and she thrived on the competition I offered her. My relationship with Marisa, though, started off very differently….