Pretty GIrl of the Day, May 1, 2017

Hi, again, it’s Donna. Sorry I haven’t written much lately, I’ve been really busy with my girls, you know, getting them ready for College. Not only that, we have a new vice-principal now, and he’s really tough. That’s partly a good thing, because he likes the College Dress Code that I’ve been teaching. He even implemented it for the female teachers under 35, which is nice. There are eight of us, now — “the girls”, we call ourselves. Of course I never wear underwear, and a few of the girls didn’t either. But now that the vice principal comes into our classrooms, and inspects us in front of our students, you can be sure none of the girls wear underwear any more.

Jack Jackson is his name. He’s kind of like a cowboy. “If you wear jeans,” he told us girls, “you can be pretty sure I’ll come into your classroom and make you take them off.” We all giggled, but it turned out he was serious. He wanted to use the girl teachers as examples for the students. He always noticed what we were wearing, and encouraged us to dress, well, “comfortably”. That’s what he called it. To be honest, he wanted us to dress a little sexier than even I thought was appropriate for teaching high school. No jeans, sure, that’s standard. But no pants of any kind, not even shorts. That’s a little extreme, especially since we weren’t allowed to wear underwear, don’t you think?

As it happens, around the time Jack came to the school, I was teaching the girls in my CP class to wear just a top, and to wear it proudly, like a dress. That’s not an easy lesson for a girl just in high school, because a top long enough to cover her pussy often leaves her butt only partly covered. Many girls feel “bottomless”, even if their top is plenty long enough to serve as a dress. So what I like to do with my young girls is let them come to school wearing a top and a bottom, and dare them to take off their bottoms in class. I would call on the girls one by one to stand up, and describe for the class what they’re wearing, whether pants or a skirt. If they’re wearing a bra or panties, they should mention it, and if they’re not wearing any underwear, they should mention that, too. When describing her top, I would ask the girl to say whether she feels her top covers her breasts nicely, and if it might be even long enough to cover her belly, or even more.

Then, after all the girls have spoken, I look for one girl who is wearing a top I feel might be long enough for her to wear by itself. Naturally, the girl is shy, and maybe a little embarrassed, but hopefully, she has expressed some degree of confidence that her top covers some of the most vulnerable parts of her pretty little body. It’s rare for any of my girls to be wearing any underwear, but some of the shyest girls often come to school wearing a bra or panties, in which case I ask her to please take them off, and just drop them in the trash can. In the rare cases that a girl asks for privacy to remove her underwear, I let her step out into the hallway to disrobe.

Now comes the moment of truth. I point out to the girl that her top is very pretty, and it’s long enough to serve as a dress. If she doesn’t get the hint right away, I ask her to please take off her bottom. Some girls do it right away. Others beg me not to make them take off their bottom. Some cover their face in embarrassment. Eventually, most girls shed their bottoms, but once in a while, a girl will be simply unable to comply with my request.

In cases like that, I try to work with the girl. I ask her if she would rather be topless for two days than bottomless just today. Or maybe she would be willing to come to school naked on a future day. Sometimes a girl feels shy being the only one taking off her clothes, so I let her pick out one or two other girls in the class, and force them to strip, too.

Today’s pretty girl is one of my best students. She’s happy to wear a thin top without any bottom, and of course no underwear, not even a bra.

At first, as you can imagine, she was a little embarrassed that her nipples show through the thin fabric. But as she went from class to class wearing nothing but this adorable little top, she got lots of nice compliments. “Such a cute dress!” one girl said. “It’s a perfect length,” said a boy in one of her classes.

It was nice to hear these compliments because she was honestly a little afraid about the length. It seemed short to her at first.

It was such a perfect length that her pussy was covered most of the time, but still, she kept tugging at the bottom of it, imagining that maybe some people could still see it. Of course, this was silly for a number of reasons, but who looks for reasons when feeling self conscious?

First of all, none of her classmates really expected her to keep her pussy covered all the time. Her top was just too short for that. Lots of girls were wearing tops just as short, and you could see their underwear, but they weren’t embarrassed by that. What made this girl different? Just her lack of underwear? Really, it was no big deal to anyone except the girl herself.

As the day wore on, the girl became more comfortable wearing her short dress. She relaxed, and spread her legs a little. What’s the worst that could happen? Someone might realize she’s not wearing any underwear. But who would even see? It’s not like people are always looking up a girl’s dress to see if she’s wearing underwear. Some girls wear underwear, and others don’t. That’s all.

In her sixth period Health class, the day’s subject was all about proper hygiene for girls. This is something important for both boys and girls to learn about, so the teacher asked all the girls to please strip down to their underwear — bras and panties only! He was quite firm. Most of the girls did as they were told, but a few girls hesitated. It seems they weren’t wearing a bra, but the teacher said that was fine, they could just wear their panties for today’s class. He didn’t mind if they were topless this once. After all the girls had stripped down to their underwear, the teacher’s eyes fixed on today’s pretty girl.

“Any reason you haven’t taken off your pretty dress, young lady?” he asked.

So she lifted it, and showed him she wasn’t wearing any panties.

“Oh! I’m so sorry, honey,” he said, blushing. “You can wear your… your…” waving dismissively at her pretty top.

He really hadn’t known she wasn’t wearing panties. That made her feel good.

After that experience, today’s pretty girl felt comfortable and secure in the knowledge that her top was long enough to feel just barely decent, and short enough to relax and have a good time.

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