Pretty Girl of the Day, August 12, 2016

Today’s pretty girl never expected to be climbing onto a platform stark naked in broad daylight!


Lisa is just a freshman, you see, new to the College, so she’s still not completely used to the idea of being naked in public. Even in high school she was shyer than the other girls. On Health Day, when most of the girls come to school naked, shy Lisa wore a t-shirt. You see, the girls are asked not to dress for one day in the interest of time, but it’s completely voluntary. If a girl is just too shy to come to school naked, it’s totally fine for her to wear a top, but bottoms were discouraged. It was just one day a year that the girls had to come to school naked, so most of the girls just took it in stride.

Unfortunately, Lisa felt like she was picked on by the teachers for her shyness. In sex education class, a girl was needed to volunteer to wear a “cheeky” dress and no panties as part of a harmless demonstration of the male erection. When none of the girls volunteered, the teacher “volunteered” Lisa. And while spanking was no big deal, she wished she didn’t have to pull down her panties for a proper spanking.

So how did Lisa get herself into this pickle? Was it an Inspection gone horribly wrong? Nope. It was just a fellow student who happened to notice she was violating the Dress Code with some minor overlapping of clothing.

prettygirl2016-08-12nHonestly, I’m on Lisa’s side in this case. Her t-shirt only overlaps her shorts a tiny bit. And her jacket, well, that’s a bit much, but lots of girls get away with wearing jackets. On the other hand, the student who challenged her was well within his rights. He wanted to make sure Lisa was following the rules because he didn’t want to be distracted by a girl of her obvious hotness who was violating the Dress Code.


He pinched the bottoms of her cheeks and asked her to start stripping. Lisa was horrified at the prospect of doing a strip tease for the boy, but she had to admit he was right, so as much as she hated to do so, she began stripping.


“Keep going,” said the boy.


“Is this good enough?” Lisa asked.

To me, and the others who had gathered to watch Lisa strip, it seemed plenty good enough. Lisa was obviously very shy, and none of us wanted to see her suffer, so stripping down to just shorts seemed quite fair. Besides, she really looked great!

“I’m a little suspicious,” said the boy. He explained that Lisa’s shorts are zipped and buttoned, which is unusual. Most girls at the College leave their shorts undone, for obvious reasons. It’s important for girls to not only follow the Dress Code but to obviously follow the Dress Code. Girls do it all the time, so maybe it goes without saying, but I’ll say it anyway, for those of you who don’t attend the College…

A girl who’s wearing a dress is following the Dress Code as long as there’s nothing under it. But if her dress is too long, it’s hard to be sure she’s not wearing something under it. An Inspector, or any interested student, for that matter, would be well within their rights to ask her to lift her dress just to check, or just lift it himself. Most girls find it tiresome to be be repeatedly stripped, so, naturally, girls wear dresses short enough to avoid this problem.

Similarly, a girl wearing shorts will typically leave them unzipped, so people can see she’s not wearing anything under it (or at least, it makes it much harder for her to wear underwear). So the boy is right. Lisa’s habit of doing up her shorts is suspicious.


D’oh! And he was right! Bad, bad Lisa!


She hurried out of her shorts, but the damage was done. Her credibility was shot. (Her butt is very cute, though, isn’t it?)


Well, Lisa, you have a very pretty smile, and you look nice wearing nothing but a little black thong. Honestly, if you had dressed this way from the get-go, I don’t think anyone would have faulted you. Sure I understand you’re shy, and going topless in public might be a little much for you, but come on, honey, this is the College. No one is going to look twice at your adorable little tits, because lots of girls dress this way. By College Standards your thong is very decent.


But Lisa, you didn’t dress this way from the get-go, did you? You violated the Dress Code in at least three ways. I sure hope there isn’t a bush hiding under that thong, because we’re about to find out. You see, the boy is completely within his rights to make you strip completely naked, not just to prove you’re finally following the Dress Code, but to make sure you’ll remember this, and to never ever do it again.


So, Lisa, I’m sorry, but the boy is right. And, by the way, you are nicely shaved, which is very nice to see. I think at heart, you’re a good girl, Lisa, but you just went a little wrong when you got dressed this morning.

For this, you need to be punished, don’t you agree? So turn around, and let’s see your pretty butt and then run over to that platform.


Do you notice a pretty pink vibrator on the platform?


That’s right. You’ll be putting on a little show for us, Lisa. But before you sit down, do you might pausing for a minute? That’s right. Right there, with one knee on the platform. Just relax while I slip my fingertips between your cheeks, and slide them down between your legs. Up and down, that’s right. Mmmm, so wet! Thanks. Now, have a seat, and spread your legs wide.


Poor Lisa knew what she would have to do. As uncomfortable as it was to do it in public, she spread her legs and began masturbating. She knew the boy wouldn’t let her down until she came, so she tried to make the best of it. She closed her eyes, and tried to ignore the cheering crowd while she thought sexy thoughts. Like when she was in high school, and wore her first really sexy dress… It went sort of like this…


She cast her mind back to high school, when she “volunteered” to participate in a demonstration of male erections. She was scared to death that Monday morning as she put on her sexiest minidress, with nothing under it. It was a white billowy thing that flared out from her chest, and sort of flowed in the breeze as she walked. It was scary enough with panties on, but today she was going commando for the first time ever in this dress.

So she makes it through all her classes — and up and down the stairway! — and finally arrives in Health class. The demonstration time arrived, and so Lisa, her heart beating a mile a minute, got up from her seat and came to the front of the room. She faced the class, her legs tight together to minimize the amount of her pussy showing at eye-level to the whole class.

The teacher said, “Lisa, it was a good try, but your dress needed to so some cheek. Do you have a shorter one?”

Lisa was indignant! “I’m showing plenty of cheek,” she said, turning around to show the class her pretty cheeks.

The teacher cleared his throat.

Lisa bent over and spread her legs. Her dress went up over her head, and every single boy got an erection. But it wasn’t good enough for the teacher. “Try harder tomorrow, okay, honey?”


So Lisa went home, and found a stash of dresses she had outgrown over the years. One of them was a “little black dress” she had worn when she first started to sprout boobs. She remembered wearing it without anything under it so as to avoid panty lines. She remembered being excited at the time, because even as a little girl, she felt sexy in it. It was tight enough that she was able to fine-tune its length, and it more or less stayed in place. So, to get out of the house, she would pull it down over her butt, and her mother would approve. Then, when she got to the party, she would pull it up to show a little cheek, but not enough to show any pussy, at least not while she was standing. If someone decided to look up her dress while she was sitting, well, that wasn’t her problem. (She kept her legs together, though, just in case.)

Now, she tried on the dress again, and boy oh boy, did it ever fit! This time, even when she tugged on it, it failed to cover enough of her butt to be decent. Her mother would not approve! She looked at herself in the full length mirror. (The mirror was tilted up so she could gauge the whether the dress was long enough when viewed at crotch level… It wasn’t!) But it was close enough. It was so scary for her to come to school this way, but  she really wanted to get the Health class “erection demonstration” over with.

She knew she had made a big mistake when she stepped onto the school bus, and everyone cheered. She sat next to a boy she knew, because she was scared of what the girls would think. He was really sweet. He rested his hand in Lisa’s lap to cover her pussy from all the kids in the front of the bus craning their necks to see up her dress. Lisa relaxed her legs, and let the boy gently stroke her inner thighs. He was a perfect gentleman, never once touching her pussy, even though his fingers were within inches of it the whole way. When the bus arrived at the school, everyone stayed in their seats so they could watch Lisa leave. The poor girl was so self-conscious!

Fast forward to Health class. Lisa stood in front of the class as before, but this time her dress barely covered her pussy. The teacher asked Lisa to sit on his desk, and face the class. Lisa understood somehow that she was expected to leave her legs apart. She was glad she had shaved! “It’s still not good enough, honey,” said the teacher. “You’re sitting on your dress, do you see that?”

What the fuck are you talking about? Lisa wondered, but she didn’t say anything.

“Tomorrow, I want you to come to school wearing a dress so short that when you sit down, the back of your dress just barely touches your butt crack, okay?”

Lisa was flabbergasted. “You mean you want me to come to school bottomless?”

The teacher laughed. “Sure, Lisa, if you want. But you don’t have to go to that extreme. All I want is for you to wear a dress short enough that when you sit down, your dress doesn’t quite touch the chair.”

“So my naked butt will be on the chair. Is that it?”

“Yes,” said the teacher. “And the boy sitting behind you will see the top of your butt crack between the chair and the bottom of your dress.”

Oh, my God! Thought Lisa. He wants me to be bottomless! For the rest of the day, and on the bus ride home, Lisa was in a full-blown panic, not like this morning, when she was worried about her little black dress. Something far worse! She was so worried about the next day that her dress actually felt decent!

Some time that evening, after her panic subsided, and she realized she would have to be bottomless, despite the teacher’s poo-pooing of that idea, she knew what she would have to do. She went into her little brother’s room, and swiped one of his singlets. You know what that is? It’s sometimes called a “wife-beater”. She put it on without anything under it, and pulled it down as far as it would go, and looked down. It covered most of her pussy. Good, she thought. She looked over her shoulder at her butt in the mirror. Full moon! Oh, well, I knew it would have to be “cheeky”, she thought, and it doesn’t much matter how cheeky. In for a penny, in for a pound.

Her heart still racing, she went downstairs into the family room, where her little brother and her mom were watching TV. She tried to act normal. Her singlet was pulled down so tight, it barely covered her nipples. She kept her legs together. “Hi honey, how was school?” asked her mom. Her brother ignored her.

She sat on the reclining chair, and leaned back. With a start, she noticed her pussy was fully exposed! Her top barely even covered her belly button! As casually as she could, she covered her pussy with her hand. It felt good, so warm, so moist. She began stroking herself, gently spreading her legs just a little so her mother wouldn’t notice.

Ding dong! Her dad answered the door. “Honey, it’s Brad!”

Oh, shit! My boyfriend! He can’t see me like this! Lisa got up and was about to run into her room and put on something decent when…

“Hi, Lisa,” said Brad.

Lisa stammered and stuttered, “I’m so sorry, let me, I’ll just–” then she tried to dash out of the room.

Brad caught her by the shoulders. “What’s the matter, Lisa,” he asked.

“It’s my–” Lisa gestured to her chest, and waved them frantically at her belly. “It’s the way I’m– It’s what I’m wearing, I’m so sorry!”

“It’s cute,” Brad said calmly. “I really like it.”

“You do?” Lisa’s heart was still beating fast. She tried to tug on the bottom of it, but she was too frazzled to make much headway.

“It’s a really cute dress.”

“It’s not too short?”

“Too short?” Brad looked uneasily at Lisa’s mom and dad, who were both studiously avoiding eye contact. “No, not at all. It’s just right, I think. We’d better get going, Lisa. Get your skates.”

Oh, shit! It’s Christian Skate Night at the roller rink! “Maybe I should put on some pants or something.”

“You don’t have to. Lots of girls wear dresses to Skate Night.”

“Just don’t fall,” said Lisa’s dad.

Lisa and her mom rolled their eyes. “Okay, then, I’ll just get my skates, and we can go.”

Once they were alone in the car, Brad grabbed Lisa and kissed her with unexpected passion. “That dress is SOOOO sexy! I can’t believe your parents let you out of the house like that!”

“You think maybe it’s too much? I mean, you know, for roller skating?”

“No! It’s perfect! You’ll be the envy of all the girls. They’ll wish they had your courage.”


Lisa felt a lot better to hear Brad say that. And then, when they arrived at the skating rink, a lot of people complimented her on her dress. Apparently it was just long enough that people thought maybe she was wearing a thong under it, so she felt much better. The skating went great; Lisa didn’t fall even once! And on the way home, Brad kissed her again, and she came.


The next day, Lisa put on the wifebeater, and went to school. The kids cheered as she got on the bus. She blushed, and thanked them for their outpouring of support. As she sat, she looked down to make sure her pussy was covered. When she got up, she knew her butt was mostly bare, but hey, she thought, when I wear a thong, you see most of my butt then, too, so it’s really no different.

She felt confident each time she sat down that her dress was finally short enough, but when she finally got to Health class, she had misgivings, so she stretched her arms up, and this time she didn’t tug on her little micro-mini-wifebeater-dress, so it didn’t quite cover her pussy this time. Letting my classmates see my pussy is a small price to pay for finally being done with this exercise, she thought.


Very nice dress, said the teacher. Your part of this exercise is now completed.

3 thoughts on “Pretty Girl of the Day, August 12, 2016

  1. Ben

    I remember that day, she was such a pretty little thing with such an amazing ass. I remember when she finally finished with the vibrator she hopped off the box to the cheering of the crowd and was let go. We all watched her perfect little ass wiggling off into the distance when she bumped into a group of boys. Completely naked with a soking wet pussie, she would have known she had no choice. We saw her get down on all 4’s and the boys started to tease her. I felt bad for the girl as did most of the Crown but the boys where in the right. I think most of us just turned away and walked off, at least she wouldn’t have an audience for this bit.


Leave a Reply

Your email address will not be published.