A Challenge for Today’s Pretty Girl

Hi, I’m Deardra, but people call me Dearie for short. I really love Donna’s CP class. I’ve been learning so much about the College, and how to dress, it’s been so much fun! I’ve been using my newfound knowledge even outside of school to impress my friends, especially my boyfriend.

I’m still just in my second month of CP class, so I know there’s a whole lot I still need to learn, but it’s really been fun so far. I like the way Donna eased us into it, by not insisting we follow the Dress Code for the first couple weeks. And she gave us plenty of warning before the first girl would be forced to strip, and spend the whole day naked. None of us were sure which girl would be have to go naked, so we all made sure to shave really well. The assignment for that day was to wear a top and bottom that showed off our belly buttons. Also, the bottom was supposed to be as little as possible. It could be a pair of Daisy Dukes, or a miniskirt.

None of us knew which girl would be stripped naked, so it was really exciting. As the stripping time drew near, Donna asked for a show of hands of girls who might be willing to take off either their top or their bottom to avoid being stripped. Think of it as a kind of insurance policy, she said. I raised my hand, and so did a bunch of other girls. If Donna called on me, I would have offered to take off my top to avoid having to go naked, but luckily, she didn’t call on me. She called on a girl wearing a thin white top and some sexy jeans. When she stood up, her nipples were hard. She offered to take off her top, but Donna told her to wait a minute and calm down. The girl was really nervous.

“Unzip your pants,” Donna said.

So she did. They were tight enough that they opened up, and I could see she was nicely shaved, but still pretty decent, with most of her pussy still covered.

Then Donna took out a pair of pliers and crimped the girl’s fly so she couldn’t zip it up again. Ever. “There,” she said. “Do you still want to take off your top?”

I stifled a laugh. Oh, the poor girl! Now she’s faced with a choice of going topless with her pants wide open, or bottomless (but with a decent top). In the end, she opted to take off her top. I didn’t blame her, because it was still pretty early in the year, and none of us had gone totally bottomless yet.

But I digress. The point is, Donna is a great teacher, and she really helped us feel comfortable with our new knowledge, even though once in a while, one of us had to go naked to our other classes. It’s all just part of the learning experience. Oh, by the way, a girl did have to get naked that day. Donna picked a girl who hadn’t raised her hand to volunteer to take off an item of clothing as “insurance”. See? It pays to volunteer!

So now that you understand what’s been happening — once every few days, one girl has to strip naked, and every day girls are encouraged to volunteer to strip partially. Plus all the usual Dress Code stuff, you know, like having to bend over, or letting classmates feel me up to check for underwear, that sort of thing. It’s good practice for when we get to College.

So on this coming Friday we have an interesting assignment, which is to wear stockings to school. My first thought was that’ll be fun! But then I remembered that stockings count as a bottom. In fact, any socks that come up past your knee count as a bottom. And it’s true that they’re kind of like a bottom in the ordinary sense. They cover your legs like a pair of pants, for example. But, unfortunately, they leave a girl’s pussy completely exposed, which is a bit of a bummer, don’t you think?

A bunch of us girls got to talking about the assignment, and they seemed to think you could wear a top long enough to feel decent. But I would be afraid a top that long would count as a dress, and the Dress Code is pretty specific about not wearing both a bottom and a dress. I was pretty sure we were expected to be naked from our belly buttons down to the tops of our stockings. That was the challenge, I told them.

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I knew one of us would be stripped naked, and knowing Donna, it would be a girl who didn’t quite measure up to the Dress Code. And Friday is a special day. When a girl gets stripped on a Friday, she’s supposed to stay naked all weekend. And not like a hermit, either. She’s supposed to go out with her friends, and try to have a normal weekend.

Trust me when I tell you this actually happens. How do I know? Because all the other girls — the ones who aren’t naked — make sure to invite the naked girl out for some fun. And it is fun to go out with a naked girl. All the heads turn looking at how naked she is, so it gives me some freedom to dress a little sexier than I would otherwise. You know, like a t-shirt that’s maybe a little shorter than I would ordinarily wear. Or something backless, like an apron or a loin cloth.

So this Friday, I’m already thinking ahead to what I’ll be wearing when a bunch of us girls go out with the naked girl. And you know what? I think it’ll just be a cute top and a pair of stockings… That’s right, exactly what I wear to school that day. No special outfit required!

Oh, who am I kidding? How could I possibly wear something like that to school? I need professional help.

“Mom!” I called, as I set down my books.

“Hi, honey,” she said. “It’s a shame what they do to you girls,” she added, glancing at my bare bottom.

I laughed, covering my butt with my hands in a show of false modesty. “No one did anything to me, Mom. Today I was just practicing wearing a top as a dress.” I stood up straight, and tugged on it a little, so it covered about half my butt crack. “See? Completely decent.”

“Okay,” she said, unconvinced. “But you wanted to go shopping, remember? Do you want to put on some clothes, and come with me?”

“I’m already wearing clothes.”

“What’s wrong, honey? Why don’t you want to wear something, you know–”

“A little more decent? Mom, that’s the thing. We’re learning about what counts as decent at the College. You know what’s decent there? Not wearing underwear. None of the girls wear any. And they’re proud of it. Do you think boys don’t see up their skirts? Of course they do. But it’s nothing special. Why? Because none of the girls wear any underwear. And no matter how long a girl’s skirt is, or if she’s not even wearing one, the boys can always see her pussy. And so what? All girls have pussies. So it’s nothing to worry about.”

“Okay, honey, calm down. Tell me what’s wrong.”

That’s when the waterworks started. I couldn’t help it. I told my mom everything. About Friday, how I was going to have to be naked from the belly button to my thighs, all because of a stupid Dress Code rule. My mom held me close as I sobbed, and stroked my hair. It felt good to cry, and afterwards, I felt much better.

“I understand, honey, and I can help,” she said. “Let’s go to the mall, and pick out some nice stockings for you to wear on Friday. Why don’t you change into something cute — a top and a bottom, okay?”

“A top and bottom,” I repeated as I walked to my room, my mom eyeing my bare butt the whole way. I’ll show her. I put on a sports bra as my top, and for my bottom, I put on the tiniest little skirt I could find. I’m pretty proud of it, actually. It’s lime green, and nearly sheer. It started its life as some frilly stuff on a pair of panties. But then I carefully cut away the panties, leaving just the skirt. It’s about 3 inches from waistband to bottom, and very frilly. I’ll admit to you now that I take a perverse pleasure in wearing something so sexy it leaves me nearly naked. On one hand, I’m not naked, so you can’t go accusing me of being a cock teaser. But on the other hand, if I were to take off this little skirt, I wouldn’t be a whole lot more naked, so I’m not really bluffing when I flaunt myself this way, right?

My mom laughed when she saw me. “Okay, honey, if that’s what you want to wear, it’ll be good practice for you.”

“Thanks, mom.” I refused to acknowledge her sarcasm.

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Mom drove in silence until we were nearly at the mall. Then, just before we got there, she asked me if I would mind taking off my skirt.

I was shocked! I covered my pussy in a show of mock decency.

But my mom insisted. She said it would be good for me to get some experience being half-naked in public.

“Maybe I could take off my top, then,” I suggested. What? Go topless in the mall?! What was I saying?

“No, honey, you need to lose that skirt. Then you can wear your new stockings with the top you have on.”

“A top and stockings?”

“Sure, honey,” my mom said. “Isn’t that what you’re planning to wear on Friday?”

I mulled it over.

“Well, think about it, honey. If you’re not ready to take off your skirt right now, then maybe you can ease into it. Why don’t we sit down at the food court, and then while we’re eating, you can just slide out of the skirt. We’ll stay in the food court area until you feel comfortable, then maybe do a little window shopping before buying your stockings. Then, when you have the stockings on, you’ll feel a lot less naked, because, after all, stockings are a kind of bottom. I think after being really bottomless for a while, the stockings will really help you feel much more decent, don’t you think?”

“You know, Mom, I never thought of it that way. It’s a kind of exposure therapy.”

“Exactly.”

So we walked into the mall, and that’s when I noticed it. “You’re not wearing any underwear!”

She laughed. “You noticed.”

“What did you do? Slip off your skirt in the car?” My mom was wearing nothing but a blouse!

Still laughing, she said, “I slipped it off at home, dear. You were so wrapped up in yourself you didn’t even notice! And then, one by one, I’ve been unbuttoning it.”

“And throwing away the buttons, I see!”

“That’s right, sweetie, If a mall cop gives me trouble, I don’t want to be tempted to button it up again.”

“Wow, Mom, you really like to live dangerously!”

By the time my mom had gotten her food, she had thrown away all her buttons, and her blouse was perilously close to revealing her excellent mammaries.

“I see you’re nicely shaved,” I said, and then instantly regretted saying it. I felt my face redden.

Once we were seated, she carried on normal conversation, and sipped her coffee, apparently oblivious to the fact her top was wide open. I couldn’t take it any more. I took off my skirt. “I’m ready,” I announced, as I stood up.

“Let’s go, then,” she said.

I really felt like I was emotionally ready to wear a pair of stockings as a bottom on Friday, thanks to my mom.

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