Pretty Girl of the Day, November 11, 2013


“Not now!” giggled today’s pretty girl as we snapped her picture. “I’m not dressed yet!”

But we couldn’t resist, she was so adorable slipping into her navy blue sweater.

As she dressed, she told us a story about a day that was her most fun, scariest, and most exciting day ever in high school. It was near the beginning of my Junior year. The class was called “College Prep”, or CP for short. This class was optional for girls, but I’m glad I took it because it really prepared me for College, especially the Dress Code. It was fun to be in the class because it meant we didn’t have to obey the high school dress code any more, but we did have to start obeying the College Dress Code.

We were supposed to change over to the new dress code at our own pace, but the teacher helped the girls along by doing “mock inspections” every few days, which meant she would pick a girl, and make her strip, and then if she wasn’t following the College Dress Code, she would have to name her own punishment, which had to be worse than just not wearing panties for the rest of the day, but the teacher never said how much worse it had to be. If a girl had been wearing a t-shirt and shorts that overlapped, then she would usually agree to wear just the shorts for the rest of the day. I think some girls secretly wanted to be forced to go topless, just so they could pretend it wasn’t their idea.

It didn’t take long for us to realize that the girls with the longest dresses were the ones our CP teacher stripped, and forced to name a punishment for themselves, so I started wearing t-shirts with nothing underneath, so I wouldn’t ever get picked to strip. Although a few of the other girls were also dressing this way, it still felt really strange to come to school with nothing covering my bottom.

And gym class was a little embarrassing for me, too. You see, our gym uniforms were really just t-shirts. We were supposed to wear a bra and panties under our uniforms, but the underwear was optional. Most girls didn’t wear bras, and every now and then, a girl would forget to wear panties for some reason, but the girls in the CP class were consistently naked under their gym uniforms because we never wore underwear to school after the first week.

But I digress… So I was sitting on my bare butt in CP class, because the t-shirt I wore that day wasn’t long enough to sit on, and the teacher announced that Monday would be “Pajama Day”. There was a lot of hooting and general commotion. Apparently, the boys knew all about Pajama Day, but it was new to me, so I listened intently as our teacher explained the rules. All the girls would wear a pair of baggy pajamas to school, a top and bottom. (Obviously, nothing underneath!) Then here’s the fun part: The girls would walk around the classroom, up and down the rows of seats so the boys could decide how baggy each girl’s pajamas were. Then all the girls would sit down, and the eight girls with the least baggy pajamas would have to strip stark naked in front of the whole class! But wait, it gets better! Each of the naked girls gets to pick a partner—a girl still wearing her pajamas—and the girls switch bottoms.

So you can see the strategy, right? You need to wear the baggiest possible pajamas, not only so you win the competition and don’t get stripped naked in front of all the boys, but also so you can keep that baggy top on for the rest of the day. So I went home, and found a pair of my dad’s pajamas. Did I tell you he’s a portly guy? Well, it was hilarious! I went to school holding my pants up, because they wouldn’t stay up on their own. Not that it mattered if I “dropped trou” in front of everyone, because my top came down to my knees!

So, all laughing and giggling, the girls sat down in their baggy PJs waiting for the festivities to begin. “Take off your tops, now, girls,” said the teacher.

[Sound of record skipping] Wait, what?

She smirked. “Oh, did I forget to tell you that part? We won’t be able to judge how baggy your pants are unless you take off your tops first. Didn’t you realize that? Chop chop, girls!”

Well, we all looked at each other for a while, and then some of the girls took off their tops, so I finally gave in, and took off my top. Even though I was just topless, my pants were so loose that I felt completely naked, as if I was wearing nothing but a towel draped over my lap.

“Fold them neatly, and place them on your desk. Now, stand up, and begin walking up and down the aisles.”

We all got up, most of us holding our PJ bottoms so they wouldn’t fall down, but one or two girls realized that gravity would identify the baggiest bottoms, and let them slowly slip down as they shuffled around the room. One of the boys “pantsed” me as I walked past him, which he thought was very funny. I immediately bent over to pull up my pants, which gave the boy an opportunity to whack me on the butt! How embarrassing!

“Okay, girls, I think we’ve seen enough. Everyone return to your seats, now.”

I was glad to get back to my seat. The teacher called the eight girls with the baggiest pants. Each girl was made to stand next to her desk without holding onto her pants. The class laughed as each girl’s pants fell about her ankles. The laughing subsided after the eighth name, however, as the remaining eight girls had to strip naked, and turn in all their clothes. Each of the naked girls found a partner, and my partner was a cute blonde with small breasts. She sat on my lap and spread her legs in case I wanted to stroke her pussy as we negotiated the splitting up of my pajamas, which I thought was sweet, although it was her soft, supple breasts that I most wanted to touch. She rested her head gently on my neck as I stroked her sexy body, then hugged her tight, and kissed her first sweetly, then passionately.

As the teacher started wrapping up the class, an idea came to me. Why lose the intimacy of this sweet little girl? We can share the bottom and the top. I took off my pajamas, and then with her sitting on my lap, I put them back on again, around both of us! One of each of our legs was in each leg of my dad’s pajama bottoms. And the same with our arms in the top! We went around to our classes—some of mine, some of hers—and had a really fun day!




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