Topless Challenge

Hi, it’s Donna again. Thanks so much to my good friend Dick Hertz for letting me take over his space so I can share this article. This is my third year (I think? So hard to keep track) teaching at the high school, and it’s such a rewarding job. My expertise is, of course, College Prep – or CP as we say – a class mostly for the high school seniors who will be going on to the College, which, as you know if you’ve been following my story, has a rather unusual Dress Code. It’s so unusual, in fact, that we need to prepare girls while they’re still in High School for the rigors of College life.

For those of you who are new to my story, and unfamiliar with the Dress Code (DC) and the overarching College Code of Conduct (CCC), let me start off with a brief introduction to it. The Dress Code is the first of four pillars. (The other three pillars of the CCC being “Inspection”, “Modesty”, and “Punishment”) The CCC is a truly wonderful methodology for bringing out the most wholesome character of the sweet, adorable girls in my class.

I definitely want to tell you the story of today’s lesson, which is the “Topless Challenge” I’ve laid before the girls in my class… but first, especially for new readers, I would be remiss if I didn’t explain the CCC, which forms the basis for the entire curriculum of propriety and Decency which is defined a little counterintuitively as adherence to the Dress Code. I say “counterintuitively” because a girl can be half naked and still follow the Dress Code and thus be considered “Decent” according to the letter of the regulations.

So let me back up a little, and explain: In a nutshell, the College has found a clever way to give its female students complete freedom to dress however they like, but at the same time offer inducements to encourage girls to cover their most intimate areas. The first thing to know – and it’s been widely publicized, so you most likely already know it – is that girls at the college aren’t allowed to wear underwear — bras, panties, and the like. Panties, in particular, are completely forbidden, as are anything that might resemble panties, including thongs, shorts, and even pants. To keep it simple, just remember: nothing between your legs. At first, you might think this would be counterproductive. You would think a girl wearing a short dress would be less decent if she isn’t wearing anything under it. But then you would miss the point: a girl not wearing panties would be careful to pick out a decent dress. Not only would she ensure it is long enough, but at the same time she would avoid overly thin or transparent fabric, or any number of other attributes that might make a dress less decent. And that’s the beauty of the College Dress Code – by simply outlawing underwear, girls are motivated to choose clothing with all the attributes needed for decency without the need to spell them out individually.

Naturally, some girls will cheat, and wear underwear, so Inspections are necessary. For simplicity and transparency, Inspections are carried out in public. A girl wearing a top and a skirt, for example, may be asked to prove she is Decent. To prove it, she just needs to remove her skirt, and she will usually spread her legs a bit and raise her arms so her lack of underwear is manifestly evident. It is usually not necessary for the girl to remove her top, but she will gladly do so if asked, because the most important thing for the girl is to prove her innocence. Once the girl’s Decency has been fully verified by the Inspector (and by the students who have gathered to observe) the girl is allowed to put her skirt back on, and go about her business.

On the other hand, if a girl isn’t following the Dress Code – i.e. she’s Indecent – then she’s immediately stripped naked and then severely Punished. Being stripped naked in public is bad enough. But the punishment she will face later is much worse. I don’t like to talk about it, because the details are sexual in nature, and they might come as a shock to some young, innocent girls.

Girls are encouraged to cover themselves decently by the Dress Code as enforced by Inspections and Punishment. For most girls, these rules are sufficient to encourage them to keep their pussies nicely covered. For those girls who need additional encouragement, there’s one more pillar of the CCC that helps girls be more decent: Modesty. The Modesty pillar of the CCC forbids boys (or other girls, for that matter) from touching a girl through or under her clothing. This is a great protection for girls at the College, and at the same time encourages them to cover themselves as fully as possible. The flip side of the Modesty provision is that a girl’s bare skin may be freely touched by other students, and in fact girls are required to make themselves fully accessible for touching by fellow students. By allowing boys and other girls to freely touch a girl’s bare skin, a girl is encouraged to cover herself even more decently than she otherwise would.

I promise I’ll get on with today’s story of the Topless Challenge, but I don’t feel the short introduction so far has done justice to the College Code of Conduct, so let me first paraphrase it so everyone can clearly read and understand its provisions. Then I’ll get on with the story. I promise.

The Four Pillars of the College Code of Conduct

The College Code of Conduct, CCC for short, is a set of rules and concepts to help students – girls and boys – adapt to College life while maintaining their dignity and youthful innocence. For girls, the CCC guides them toward the proper choices in attire and conduct to focus them (and their male counterparts) on the important job of learning and preparing for the future. The CCC includes a simple Dress Code, which allows girls express themselves through their choices of attire while encouraging decency by limiting some clothing options while gently guiding them toward more decent clothing styles.

To support and enforce the Dress Code, the CCC includes Inspections, which require a girl to disrobe upon request, giving her an opportunity to demonstrate publicly that she is indeed following the Dress Code. Inspections are necessary to prevent girls from cheating, and although they are carried out several times each day, all across the College campus, each individual girl is rarely subjected to an Inspection. It is much more likely that a girl will see another girl undergo Inspection than be Inspected herself, which makes Inspections less a personal fear, and more an enjoyable spectator event for boys and girls alike.

Modesty is the third pillar of the CCC, which works hand in hand with the Dress Code and Inspections by strongly encouraging girls to dress as decently as possible by first requiring girls to wear at least some clothing, prohibiting other students from “fondling” a girl beneath her clothing without her consent, and prohibiting the public display of sexual excitement. To be clear, the Modestly provisions don’t outright prohibit girls from experiencing sexual excitement. A properly dressed girl may be excited, and even achieve orgasm in public, either by masturbation or during sex with another student, as long as her clothing is sufficiently decent.

Finally, we get to Punishment, the fourth pillar of the CCC. Although the rules are simple, and easy to follow, there can be no question that girls who violate the rules need to be punished. If a girl is suspected of violating the Dress Code or resisting Inspection, her clothes can be confiscated, by force if necessary, and taken as evidence against her. If she violates the Modesty provision by refusing to allow proper touching of her bare skin, then she may also forfeit her privilege to wear clothing. Although depriving a girl of clothing is a rather mild punishment in itself, a naked girl loses all the helpful protections of Modesty. She is no longer protected from fondling by other students, and she isn’t permitted to run away, use her hands to fend off would-be fondlers, or even cross her legs. Quite the contrary, she must submit to fondling by relaxing her body, and even raising her arms and spreading her legs in order to give full access to her naked body. This intensifies the punishment of depriving a girl of clothing, reminding her of the value of clothing, and serving as an example to other girls so they will follow the rules.

The most serious punishment goes to a girl who allows her sexual excitement to be seen in public by other students. For this situation, the punishment fits the crime, you could say. The girl is required to accept vaginal or anal penetration by another student, faculty member, or other authorized person. The penetration can be either by a finger or other body part, or by an object such as a vibrator, any of which may cause the girl to reach orgasm. Although the student handbook never refers to the vaginal or anal insertion punishment as “Consensual Rape”, as it is called by the students, forcing a sexually excited girl to accept penetration and cum in public is a serious punishment, expected to occur only very rarely at the College.

Taken together, the four pillars of the College Code of Conduct encourage girls to dress and behave Decently, and punish any girls who step out of line. The Dress Code, backed by Inspections, encourages girls to wear sufficient clothing to cover their bodies. The Modesty pillar, backed by Punishment, encourages girls to cover their most intimate areas.

The next few sections of this paper will go into the details of each of the four pillars of the CCC, showing how they reinforce one another to ensure modesty and decency. Feel free to skip these sections if you are already familiar with the Dress Code and the other pillars of the CCC, so you can get on with reading about today’s story of the Topless Challenge

Dress Code

Unlike high school dress codes which require skirts and dresses to be of a certain length, or tops to be opaque and fully cover a girl’s breasts, the Dress Code at the College provides a small number of very simple rules for all girls to follow to dress decently.

The first and simplest rule is “no underwear”. If you’re new to the College Dress Code, you might think that prohibiting underwear would be less decent, but in fact, a girl who is not wearing underwear will choose her outer clothing more carefully to avoid accidentally exposing herself. To avoid quibbles over what, exactly, constitutes underwear, the term is defined broadly to cover any kind of shorts or pants; in short: any article of clothing that wraps around the body and also goes between the legs.

In addition, underwear includes any item of clothing (or pubic hair – more about that later) that is worn under another item of clothing, just as the word’s components “under” and “wear” suggest. Essentially, this means a girl is limited to one layer of clothing; no overlapping clothing is allowed.

Finally, the Dress Code requires that girls wear at least some clothing; they are not permitted to parade around the College completely naked. In short, no nudity. The reason for this rule is partly to encourage girls to dress decently, although we really expect them to do that on their own. More importantly, the requirement to wear clothing serves to identify and stigmatize girls who have been forced to remove their clothing as a punishment or as a result of a suspected Dress Code Violation.

That’s it. Three rules. No underwear, no overlapping clothing, and no nudity. The beauty of the Dress Code is its simplicity. Absent from the Dress code are quibbles over what constitutes a top vs. a dress. A top and a dress are essentially the same thing, differing only in their length. If she wants to, a girl can wear a t-shirt as a dress; nothing in the Dress Code prevents it. She can wear a skirt with any kind of top, as long as her top is short enough to show some skin above the skirt’s waistband.

A special note about pubic hair: A “bush” normally counts as a bottom, but it gets special treatment under the Dress Code as well as the other pillars of the CCC. While most girls have either permanently removed their pubic hair or shave regularly, some girls prefer to sport a bush. The College, being open and inclusive, allows these girls to express their individuality, but with some restrictions. For consideration of overlapping clothing, a girl with pubic hair longer than an eighth of an inch is considered fully clothed from the waist down, so her top can’t be longer than waist length or “belly button” length. But to judge a girl’s nudity, her bush doesn’t count as an item of clothing; to avoid being considered naked, a girl must wear one item of clothing in addition to her bush.

Taken together, it is perhaps counterintuitive that the prohibitions of the Dress Code tend to encourage girls to dress decently. But put yourself in the place of these girls, and imagine the embarrassment you would feel if you accidentally flash your tits or pussy. As you can imagine, the College girls take great care to ensure these intimate areas are properly covered.


It goes without saying that most girls follow the Dress Code. But it’s possible that a girl may cheat. To guard against cheating, and to keep the girls honest and Decent, the CCC provides for Inspections, which require a girl to disrobe upon request. A very young girl who is new to the College may be shy, and reluctant to strip completely naked in public, and this is understandable. But every girl should understand the importance of being able to prove she is following the Dress Code, and as embarrassing as it may be, she must be willing to remove her clothes as part of the College’s strong effort to keep all the girls as decent as possible.

The way a girl dresses can affect her chance of being Inspected. A girl wearing a dress long enough to cover her butt is much more likely to be Inspected than one wearing a shorter dress, or even just a top. The trick is to find a short dress or top that’s long enough for a girl to feel comfortable without being so long as to hide her lack of underwear from public view. Each girl must strike that delicate balance between the probability of being Inspected vs. the discomfort of going bottomless.

At first, only trained Inspectors were allowed to force girls to strip naked in public. But in the past few years, the College has allowed boys to Inspect their classmates as well, if they have a reasonable suspicion the girl may be violating the Dress Code. A girl wearing a dress or skirt long enough to cover her bottom is suspicious, for example, because she might also be wearing panties under it. A girl who hesitates before removing her skirt is also suspicious, because her hesitation might be due to a Dress Code Violation.

The ubiquity of boys has been a real boon to the Inspection process. Now it is possible for a girl to be Inspected at any time or place, as long as it is done in public. Even during class, a boy may turn to the girl next to him, and ask her to remove an item of clothing, and she is required to comply. This is an awesome power that boys have, so they are asked to please use it wisely. A boy should not ask a girl to remove her clothing just to see her naked. Instead, he should use his gift to help girls dress more decently.


Modesty is the third pillar of the CCC, which works hand in hand with the Dress Code and Inspections, which gently guide girls toward decency by carefully limiting their options while at the same time leaving girls completely free to make their own choices. Modesty requires girls to wear some clothing while in public, with some exceptions: Nudity is permitted in designated areas such as the College pool, and while walking from the dorm to the pool. Nudity may be required during an Inspection. Nudity is permitted in classrooms if it results from sanctioned activity such as a stripping game which is played by a group of girls, or if a girl is required by her professor or instructor to remove her clothing in class as part of the learning process. Even if the rules of the game allow a girl to permanently forfeit her clothing, it is the girl’s responsibility to ensure she doesn’t forfeit her last item of clothing so she is not completely naked when the class ends. This is true even if the rules are written in such a way that one girl will be required to forfeit her clothing. It is each girl’s responsibility to avoid being that one girl who will leave the classroom naked.

Modesty protects girls from unwanted touching by other students. Students are prohibited from touching girls’ clothing or reaching beneath her clothing to touch her bare skin. Conversely, bare skin may be touched by other students, and a girl is not allowed to prevent unwanted touching. The purpose of this rule is to protect the girl who makes good choices, and to gently discourage improper choices. If she is wearing a short skirt, for example, her inner thighs may be freely touched by other students; She may not press her legs together to prevent such touching, and in fact she must spread her legs apart to freely allow such touching of the areas of bare skin which are not covered by clothing. If a girl’s skirt is too short, it is possible that by spreading her legs as required to give access to her bare skin, she may fully expose her vulva, her perineum, and even her anus as well. Continued unwanted touching of these areas would be a good lesson for the girl to wear a longer skirt in future, even if doing so would increase her risk of being Inspected.

Modesty forbids girls from public display of sexual excitement, such as vaginal secretions, vulva lips that are engorged, separated, or reddish in complexion. To be clear, the Modestly doesn’t prohibit sexual excitement. A properly dressed girl may experience sexual excitement, and even masturbate any time she likes, as long as her clothing is sufficiently decent. And even a naked girl should try to refrain from displaying sexual excitement.

As we have mentioned, it is a violation of the Dress Code for a girl to be completely naked except while being Inspected or in a designated area. Even so stripping games are permitted in the classroom which force one girl to end up completely naked. One very popular stripping game requires all of the girls to wear two items of clothing to class – a “belly button” top and a bottom. The boys and girls take turns answering questions from the class material. If a girl gets the question wrong, she has to take off an item of clothing – either her top or bottom, her choice, and she sits down. If a boy misses a question, he also sits down. The last student left standing wins for his or her team. If the girls win, their reward is to keep all their discarded items of clothing. If the boys win, then the girls forfeit all the items of clothing they removed, and in addition, if any of the girls are still wearing their bottom, the winning boy picks one, and she has to forfeit her bottom as well, leaving her completely naked. It’s a fun game for both the girls and the boys, not just because it involves stripping, but because of the element of strategy. You see, when a girl misses a question, it would be easier for her to take off her top, but then if the girls end up losing it will be one of the topless girls who will have to strip completely naked. So many girls choose to take off their bottoms, which is quite a bit more embarrassing, but avoids risking complete nudity. This choice makes the game lots of fun for both the girls and the boys.

After losing a hard-fought game, this girl was picked by the winning boy. Here she is, spreading her legs to demonstrate her lack of excitement, as required by the Modesty provision of the CCC:

Although girls are permitted to masturbate freely, a girl whose pussy is not covered by clothing should try to keep her vagina closed, and refrain from exhibiting redness or vaginal secretions.


Finally, we get to Punishment. There’s can be no question that girls who violate the rules need to be punished. If a girl is suspected of violating the Dress Code, her clothes can be confiscated and taken as evidence against her. If she refuses or even hesitates to be Inspected, it is reasonable to infer a Dress Code violation, and her clothes can be taken from her, by force if necessary. If she violates the Modesty provision by refusing to allow proper touching of her bare skin, then she may forfeit her right to wear clothing. While being deprived of clothing is, in itself, a rather mild punishment, there may be additional consequences for the poor girl who finds herself in this situation. Being naked means she is no longer protected from unwanted fondling by other students, and she isn’t permitted to run away, use her hands to fend off would-be fondlers, or even cross her legs. Quite the contrary, once she is deprived of her clothing, she must submit to fondling by relaxing her body, and even spreading her legs in order to give full access to her would-be fondlers. So nudity – even partial nudity – can be unpleasant for a girl at the College. But nudity isn’t actually a punishment. At worst it’s an infraction, which needs to be punished.

The most serious Punishment goes to the girl who allows her sexual excitement to be seen in public by other students. For this situation, the punishment fits the crime, you could say. The girl is required to accept vaginal penetration by another student, faculty member, or other authorized person, either by a finger or other appendage, or by an object such as a vibrator, which may cause the girl to reach orgasm in public in full view of dozens or even hundreds of her classmates. This most serious punishment is expected to occur only very rarely on the College campus. Although the student handbook never refers to the vaginal insertion punishment as “Consensual Rape”, this is the term given by the students, and quite frankly, it’s not far off the mark. A girl’s unclothed body betrays her by implicitly giving consent under the rules of the CCC to be raped. Her rape is the inevitable result of allowing herself to become sexually excited, and by failing to cover herself with adequate clothing to prevent her excitement from being seen by all. This provision is clearly spelled out in the student handbook, and upon enrolling in the College, all girls (and boys, too) sign a legal document agreeing to abide by these terms.


Although the Dress Code and the other pillars of the CCC are designed to encourage girls to dress modestly and decently, I would be remiss if I didn’t address the fairness concerns that have been raised by some girls. Accusations have been leveled against the College since our first major revision of the Dress Code. We at the College have taken your concerns seriously, and we have made many improvements over the years. Our first Dress Code was needlessly complicated and hard to enforce. A lot of girls cheated. Especially the freshmen girls who had been used to wearing a t-shirt and panties to their high schools, which was popular at the time, and permitted by most schools. Although it would have been simple for them to wear the t-shirt and simply lose the panties when they came to the College, many of the girls “forgot” and wore panties to their classes at the College.

The problem of compliance was solved by having public Inspections, but these Inspections brought their own problems, including accusations of unfairness. Some girls felt the whole idea of inspections was unfair. Why should we have to strip and be ogled by our fellow students just to prove we’re Decent? The College agreed to reduce the number of Inspections by requiring “probable cause” for all Inspections. Girls with VPL (visible panty lines) were Inspected and punished. But soon, girls started avoiding such outward signs. So which girls might still be cheating? The criteria for probable cause gradually shifted. A girl whose dress was longer than necessary, for example, might be wearing panties. A girl whose top was completely opaque might be wearing a bra. So these girls were Inspected. It was a shame, too, because almost all of them were good girls who just happened to be dressed a little more decently than their peers. Well, as you can imagine, it didn’t take girls long to realize that showing a little cheek and a little nip slip now and then was all it took to avoid being Inspected.

I remember this because I was at the College when many of these changes were taking place. Like the other girls, I knew there was nothing wrong with being Inspected. My pussy was clean shaven, and I didn’t even own any underwear, so I wasn’t worried. Sure, like most girls, I was a little shy about taking off my clothes in public. But I knew the importance of the Inspections, and I was proud to be a Decent girl, at the College where almost all the girls were clean-shaven and completely decent under their cute little dresses and skirts. And that was the problem. Inspections were too effective. The Inspectors had a quota to fill; they needed to find girls wearing panties, or they would lose their jobs. So any girl wearing a top or bottom that could possibly hide her underwear was Inspected. And the Inspections were getting less and less fun. It used to be that a girl would strip naked, and then stand around for a few minutes. Maybe she would have to bend over or spread her legs, and she was done. She got her clothes back, and went about her business.

But then it happened to me. I was wearing a cute little skirt and a tank top. My skirt was a little cheeky, so I really didn’t expect to be Inspected. But then it happened. I was late to my calculus class, but it didn’t matter. I had to strip and show him I was a good girl. I got naked as quick as I could, but he wasn’t satisfied. He made me spread my legs as wide as I could, and bend over, with my bare ass facing the gathering crowd. I begged him to let me go, and he finally agreed, provided he could keep my skirt. My first thought was “no way” because being bottomless feels just like being naked to me. Maybe worse. But he let me put my tank top back on, and it was better than nothing. It covered my tits, and I felt like it came down almost to my crotch. I felt relieved to be wearing something after being naked for so long. One of my classmates said I looked cute in just my top, so off I went to my calculus class. Listen, I knew my pussy wasn’t covered. I’m not naïve. But it was almost covered. And my butt… same thing. Part of my butt crack was covered. Sure, if I spread my legs you can see my asshole (and my pussy, too, from behind). So I just don’t spread my legs. Still, even though I chose to end the Inspection early, and I chose to wear just my top, I felt like it was a little unfair that I lost my skirt through no fault of my own.

But here’s the thing: I was at fault. I wore a skirt that was longer than necessary. It left an Inspector wondering if I was a Decent girl. And he was right to wonder. He had no way of knowing I wasn’t wearing underwear, and so he Inspected me because it was his job. If I had worn a shorter skirt, my lack of underwear would have been evident, and so I wouldn’t have been Inspected. I realize now that girls bring Inspections on themselves, and if they end up half naked as a result, it’s their fault.

No Dress Code or Code of Conduct can be completely fair in all situations, but the College has made its best attempt to be fair to all the students in preparing these rules and in their implementation. Girls must take responsibility for their choices and behavior. If a girl chooses to wear clothes that cover her pussy, she risks being Inspected, stripped naked, and she might find it unpleasant. But it was her choice in the first place to wear a skirt long enough to cover her pussy. On the other hand, a girl whose skirt is too short takes a risk, too. A boy might place his hand between her thighs while she is waiting in line at the cafeteria. As required, the girl will spread her legs, allowing the boy to freely feel her bare skin. If her dress is very short, it’s possible that the lower part of her cheek might also be exposed, allowing the boy to not only touch her cheeks, but also gently place his fingers between them. Modesty requires the girl to relax her cheeks, and allow the boy complete access while refraining from becoming sexually excited. If the girl loses the battle, and allows her vagina to become wet and open on its own, the boy is within his rights to remove the girl’s clothing and even consensually rape her. I can see how a girl can become frustrated with the Dress Code because of these risks of a skirt being both too long and too short at the same time. To a girl who views it as unfair to be raped after experiencing vaginal wetness she can neither control nor cover up with clothing, I would her to think back to the situation that brought about her nudity in the first place. If her nudity was the result of an Inspection, could she have been more cooperative, and thereby kept at least some of her clothing? And what brought on the Inspection in the first place? Perhaps she should think twice about dressing in a way that could conceal a Dress Code Violation. By following not just the letter of the rules, but the spirit as well, a girl has the best chance to avoid the most severe punishments.

Sorry for the digression, now back to today’s CP class

Let me set the stage. It’s early in the school year. It’s my third year teaching CP, so I know the importance of patience. Some of my cutest little girls are also the shyest, and many of them don’t yet have the experience going bottomless, or even wearing skimpy clothing without any underwear. So I need to ease them into it. I start simple, and I never ask my girls to do something I’m not willing to do myself. Which is why I taught the class wearing just a top on the first day of the school year. I know it sounds risqué, but trust me, it was a pretty decent top. It came down a good inch or two below crotch level, and covered almost all of my butt.

There are two schools of thought about whether to tell the girls in advance what they’ll have to do, whether it’s going topless, or bottomless, or even naked – or just make them do it. If you tell them in advance, they have time to get used to the idea, to plan for it. But they might also dread it, and brood over it. So I split the difference, and warn them the day before, giving them an idea what they’ll have to do the next day without telling them the whole story. So yesterday, just before I dismissed them, I told them what to wear to school the next day, which is today. I told them to wear a skirt, the shorter the better, and a cute top, and nothing else. What I didn’t tell them (because I didn’t want them to worry) was the lesson for today: the topless challenge.

I know, to you it seems easy. Come to school wearing a top and bottom. Then, during the homeroom period, each girl just takes off her top, lays it on my desk, and spends the rest of the day wearing just her skirt. It seems easy to me, too. But now imagine that for many of these girls, this will be the first time in their entire high school life that they’ll be showing their boobs to their classmates in all their other classes, apart from the occasional punishment for infractions like talking in class.

I could tell they were nervous as they chatted amongst themselves before class. There as an extra level of excitement in the air. The girls’ skirts were extra-cute, and I was happy to see they were short, like I asked. Their tops were cute, too, including “belly shirts”, tank tops and halter tops.

The bell rang, and the kids settled down. Time to take inventory of the girls’ attire. “I asked you to wear a short skirt and a cute top, did everyone do that?” I sensed some uneasy stirring. This happens early in the school year when one of the girls misunderstood the assignment. Sometimes one of the girls wears panties by mistake, for example. If this happens, I usually let the girl strip down to just her panties, and come up to the front of the class. Then I ask her to choose: panties or clothes. Sometimes the girl chooses panties, which is fine. I get it. Wearing just panties to her classes helps her feel comfortable, and it feels to her almost like being fully dressed. But most of the time, the girl chooses to remove her panties and hand them to me. Then, if she is able to spread her legs slightly and leave her hands at her sides for a minute or two, I let her go back to her seat.

But this time, there wasn’t anyone wearing panties. The commotion was caused by something else – something I don’t usually expect until well into the school year. One girl stood up. It was Doreen, regarded by many students as the prettiest girl in the whole class. I mean not just my class, but the whole Junior class of the high school. She was also, in my view, one of the shyer girls in the class, but that could be just because she was a Junior, and most of the other girls were Seniors. Doreen’s top was what I call the “perfect length” – loosely covering her cute little breasts, and long enough to cover her belly button, with the bottom resting gently on her hips, partly covering the creases at the top of her long legs, and also partly covering the tops of her adorable cheeks.

“Did you forget to wear a skirt?” I asked. I tried to be as kind and understanding as possible. There would be a time, later in the year, for me to turn into an unreasonable shrew. But today, I would try to show some compassion.

“No, Donna, I didn’t forget.” Then she started to tell me some cockamamie story about how she had gotten dressed in a micro-mini-skirt and this top she was still wearing, and tried to sneak out the door past her mom, hoping the bus would come before the neighborhood kids made some sort of comment about her short skirt…

“Let me stop you there, Doreen” I said. “The fact is you’re wearing a top and no bottom, so you failed today’s assignment.”

The look of shock and outrage on Donna’s face was priceless.

“Listen, honey,” I said. I tried not to laugh, because Doreen was clearly in a state of great anguish. “I can see that you’re embarrassed, and I’m sure you feel it wasn’t your fault that you came to school dressed in only a top, even after I told everyone clearly that today’s assignment will require both a top and a bottom.”

Doreen’s lower lip quivered, but she kept herself from crying. “I still want to participate in the lesson, Donna. Please don’t give me an ‘F'”

“Do you even know what the lesson is?” Doreen shook her head. “Okay, I’ll tell you, along with the whole class. We’re going to practice taking off our clothes in class. Many of you girls are shy, and it’s understandable that you aren’t used to taking off your clothes in front of your classmates, especially the boys. And it will be uncomfortable for the boys, too, don’t forget. The boys are not accustomed to seeing the girls disrobe in class, either. So today’s challenge will be for the girls to see if they’re able to remove their tops in class, and then after as many girls as possible have removed their tops, we’ll continue the class as normal. The girls will try to behave just as they would if they were fully dressed, and the boys, too, will behave as if nothing unusual were happening.” I paused to take in the mood of the room. I sensed the excitement, especially from the boys, but also from some of the girls.

But there were some girls who were not happy. I dare say they were filled with dread. This is understandable. I picked on one of them, and asked her to stand up. She had on an adorable little miniskirt and a tank top that showed her belly button. “Can you take off your top, honey?” I asked. Some of the students gasped. It’s understandable. They knew if the girl refused to take off her top, she would fail the lesson for the day, so there was a lot of pressure on her. She hugged her small breasts, but seemed unable to remove her top.

“I’ll do it.” It was Doreen. All heads swiveled in her direction. Her hands were crossed in front of her, grabbing the bottom of her top, ready to pull it off. She seemed to be waiting. Was she gathering her courage? Was she hoping I would stop her from removing her top just because she wasn’t wearing a bottom?

I gave her a few seconds to think about it, and then I said quietly, “Go ahead, Doreen.” I wasn’t sure she would go through with it, but she did. One of the boys started to say something, but I shushed him. When she was naked, I addressed the class. “Give her the space she needs. Treat her the same as you would if she were wearing clothes. Today’s class will be hard for Doreen, especially because I won’t treat her any differently just because she’s naked. For example, I expect her to raise her hand and participate in class, just like anyone else.”

I gave the class a moment to think about what had just happened. This was a real learning experience for both the boys and the girls. “Doreen, I want to congratulate you for your courage. I want you and the whole class to know that for removing your top, you’ll be receiving a passing grade for today’s lesson.” Then, looking around the class, I said, “I would like at least four other girls to remove their tops.” I walked up and down the rows of desks. “I want to see your belly buttons, girls, as you try to muster the same level of courage as Doreen.” One by one, the girls removed their tops, and placed them on their desks.” Soon, I was greeted by fourteen pairs of adorable little breasts. In that moment, I felt so proud of my students! Not just the girls who took off their tops, but the boys, too, for being proud of their classmates for their courage.

“Now, which of you is up to the Topless Challenge?”

One of the boys said, “Wait, what? Didn’t they just do the challenge?”

I caught myself laughing. Oh, crap, I hope it didn’t sound like an “evil” laugh. I need to work on that. “No, kids. That was just a warm-up. The challenge is to see which of the girls can hand their tops over to me, leave this classroom topless, and spend the rest of the school day topless. And not only that… I want you to try to get on the bus topless, and go home to your mom and dad, and convince them nothing is wrong. For those girls who normally wear a nightie to bed, I want you to leave off your nightie for tonight, even if you normally wear your nightie without anything under it. When you get up tomorrow morning, I want you to wear the absolutely shortest skirt you can possibly wear, and nothing else. No panties, no top. Just the tiniest skirt you can imagine. That’s the Topless Challenge.” Some of the girls just gaped at me. Some of the boys adjusted their pants. I continued, “If you meet the challenge, you get your top back, and you can wear it proudly tomorrow, knowing you made the grade. I recognize that not all of you girls will be able to meet the challenge. I’ve set a high bar, I know. Some of you won’t succeed, and I know that for a fact.”

One of the boys asked, “How can you know for sure that some of the girls won’t succeed?”

“I’m glad you asked,” I said. And I was glad, because it gave me a chance to explain the hardest part of the Challenge. “In order to meet the Topless Challenge, each girl will need to wear a skirt that is sufficiently short. And the way I’ll judge if a girl’s skirt is sufficiently short is very simple: It must be short enough so anyone can see at a glance she’s not wearing any underwear, not even a thong. And — and this is the most important part, so listen up — each girl’s skirt must be shorter than at least one other girl’s skirt. That requires you to imagine what the other girls will wear, and then wear something just a little shorter. It’s a challenge for a reason. It will challenge you to go outside your comfort zone, and then just a little further.”

One of the girls asked, “How can I make sure my skirt is short enough for people to see I’m not wearing any underwear?”

“Another great question! You don’t want to wear a skirt that’s so short you’re embarrassed to go out in public, but on the other hand, it should be clear to anyone who looks at you from behind that you’re not wearing any underwear. Take a look at these pictures, and see if you think their skirts are short enough:”

I walked up and down the rows of desks explaining the perfect length skirt and showing the pictures to the students. They were so focused on the subject matter that not one girl objected as I gathered all of the girls’ tops. “The secret to wearing a skirt that’s the perfect length is when you spread your legs slightly, your asshole should be clearly visible just below the hem of the skirt. Here’s another picture. This girl is wearing a short skirt, which will help people see she’s not wearing any underwear, while at the same time affording her sufficient modesty to feel comfortable in public.

Although this skirt is long enough for her to feel decent, it’s still short enough to show her asshole when she spreads her legs while playing tennis.

And yet, from the front, she is completely decent, as you can see:

“Now, listen, girls, — and boys, too — I get it. These skirts are shorter than the ones you’re used to wearing without underwear, and in fact they may even be shorter than any of the skirts you currently own. So when you get home this afternoon, get your mom to help you hem a skirt that’s a good length for you — short enough to show your asshole when you spread your legs, but long enough for you to feel somewhat decent at home. If you feel adventurous tonight, why don’t you see if you feel comfortable going on a date with your boyfriend, or hanging out at the mall wearing nothing but your new extra-short skirt. You’ll be surprised how supportive your friends will be, and this will give you the confidence you need to meet the Topless Challenge tomorrow. Remember the rules for the Topless Challenge when you dress for school tomorrow — your skirt needs to be short enough to show your asshole when you spread your legs, and it also has to be shorter than at least one other girl’s skirt. Got it? Great! Oh, what is it, Billy?”

“Me? Oh, well, it’s just that, well, I guess it’s okay. Never mind.”

“No, Billy, it’s okay. What’s on your mind?”

“Well, it’s that I’m worried there will be a girl who will fail to meet the Challenge, and, well, what will happen to her?

“Why do you think one of the girls will fail to meet the Challenge, Billy?”

“Um, well, okay, so her asshole will show when she spreads her legs. Maybe this will be hard for her.”

“Don’t worry, Billy. It will be embarrassing enough for the girls to come to school topless, so I won’t them spread their legs, too. Each girl just needs to wear a skirt short enough so that if she did spread her legs, you would see her asshole. Do you feel better now, Billy?”

“A little… but there’s the other thing… You know, each girl’s skirt needs to be shorter than at least one other girl.”

“That’s right, Billy. And you’re right to be worried about it. This rule requires each girl to think about the other girls, and imagine how long their skirts will be, and then she needs to make sure her skirt is just a little shorter. The idea is for the girls to expose as much cheek as they can, without feeling too uncomfortable. Some girls might even show a little of their pussy, but only if they’re not too uncomfortable doing so.”

“But won’t there be one girl whose skirt isn’t shorter than at least one other girl’s skirt?”

“What do you mean, Billy?”

“The girl with the longest skirt. Or tied for longest. Won’t there always be at least one girl who fails to meet the Challenge?”

“Relax, Billy, I’ve been teaching this course for three years. There are always some girls who are shyer than others. Some girls are embarrassed to show their assholes or pussies to their classmates. When this happens, we help the girls feel comfortable by forcing them to strip naked in front of the class, so they will understand there’s nothing to be afraid of. I like to think of it as immersion therapy for shy girls. And, as you suggested, Billy, there will be one girl in this class who will be shyer than the others, and we’ll encourage that girl to strip naked to help her feel comfortable being nude in front of her classmates. I don’t like to think of it as a punishment, although perhaps the girl will see it that way. Sometimes the shy girl prefers not to remove her clothing for various reasons. She may have become sexually excited, for example. I want you to imagine, if you will, Billy, how that girl would feel, wearing just a tiny skirt, knowing her pussy is bright pink, her labia engorged, her vagina moist and open. Imagine if that girl were asked to turn her back to the class, spread her legs, and bend over. Can you picture it? She would be overcome with embarrassment. She might even become terrified, and for some girls, this can even cause her to reach orgasm. A girl in this position might be reluctant to remove her little skirt, so I might have to give her a gentle spanking to help her make up her mind. Not all teachers do this, but I like to plan ahead, and wear a two-piece outfit to school, so I can remove my bottom before making the girl kneel with her back to the class, and lay her breasts and head in my lap. Then, if the girl is wearing a bottom, I gently help her lower it so her bottom is as bare as mine. Then, when the girl is comfortable, I will sharply slap her buttocks, making her cheeks red. Most girls become sexually excited by this, which is embarrassing for them, thus increasing the sense of shame and humiliation that comes with being spanked. To help sooth their anguish, I gently stroke the girl between her cheeks, letting my fingers circle her anus, tickling her perineum, softly dipping a finger into her vagina before continuing along her labia to her clitoris. I stroke the girl, back and forth, once or twice, before giving her another sharp slap. If I sense the girl is about to cum, I stop stroking her wettest areas, and instead rub her breasts, lower back, and buttocks. Then, if I’m able to stroke her inner thighs without bringing her to climax, I give her another quick slap before dipping my finger once more into her vagina. In this way, I am able to keep the girl right at the edge of orgasm for ten minutes or more, while the class watches with rapt attention. By this time, the girl begins moving her pelvis each time I stroke her clitoris, inner labia, and vagina, and then it’s not long before she begs me to let her cum. Of course I tell her no, as it would be inappropriate for a teacher to help one of her students cum, no matter how hard she begs. But I’m a softie. If the girl agrees to some conditions, I’ll let her cum. I know the poor girl will agree to anything, so I don’t make the conditions too bad — let’s just say they involve nudity for a period of time, and perhaps that she make herself available for some light sexual activity while she’s naked, nothing too extreme.”

“Good, I can’t wait,” said Billy.

4 thoughts on “Topless Challenge

    1. Dick Hertz Post author

      Hi, Anonymous, let me say, I totally agree with you. I love the way Donna prepares herself before spanking an unruly girl, and I think she should say more about that. When she knows she’ll have to spank one of her girls, she removes her own bottom at the very beginning of the class period as a signal to her students that it’s okay for girls to wear just a top, as long as they feel comfortable. She encourages the boys in her class to dress comfortably or even to remove their own bottoms in class, if that makes them feel more comfortable. While she’s alternately spanking and arousing a girl in class, Donna likes to spread her own legs to show she’s not embarrassed to have a positive reaction to the girl’s alternating discomfort and arousal, and she takes comfort in knowing many of the boys feel the same way.

      Love, Dick


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