An Appropriate Punishment Ch 02 1

If you have not read the first story ‘An Appropriate Punishment’, it is recommended that you do, otherwise the full context of this installment may be missed.

Having now left the hall, I made my way in the direction of the library, barely able to put one foot in front of the other from the distraction inside my pants. To hide my now rock hard boner, I pulled my school jersey down as far as I could, and tried to tuck the tip of my cock under my belt. It seems to work well enough.

I kept wondering how I was going to get through the day, worrying all the time whether anyone would see or otherwise find out about my predicament. Before I knew it, the first period of the day had ended and I went off to my next class, thinking that if I just kept quiet, and didn’t attract any attention, then I would be ok.

As I stood outside the classroom, more and more of my peers began to arrive. Some of the girls of our year, who I’d only seen a short while before, were giving me sneaky looks and giggling almost childishly. I tried my best not to blush, and thankfully had managed to keep my boner in check. The problem was that I never received even this type of attention from the girls, which my friends were quick to notice.

“What’s all that about?” my friend Karl asked.

I could only reply with a shrug and a simple “No idea” even though my heart was racing at a hundred miles an hour.

Luckily, the teacher let us in for our chemistry class at that point. We walked into the room, and then took our seats. As soon as I sat down, the satin panties I had been forced to wear tightened even further on my balls, wrapping them tightly in that maddeningly soft, smooth fabric. That whole class passed like a complete blur, and I was unable to focus on anything at all.

The rest of the day went much the same, though for me each hour passed with ever increasing dread, as I imagined what Ms. Berkowitz had in mind for later in the day. The girls would chatter to each other in between, giving me the same furtive looks, and clearly laughing at my expense. I was just lucky that they didn’t see me semi-hard penis straining against the satin of the underwear I was now wearing.

Then finally, the end of the day came, and I managed to sneak away to Ms. Berkowitz’s classroom.

Her classroom was on the third floor of one of the blocks, and pretty standard. She had a large desk in the corner, facing the class at a diagonal angle. The white board stretched almost to the top of the classroom ceiling, and Ms. Berkowitz had a small step that she often moved around and stood on to reach the top of the board. I was glad of the fact that the classroom windows faced either to the open air, three stories high, or were high windows above the eyeline of anyone walking on the adjacent corridor. I didn’t want anyone knowing I was here.

I knocked on the door, and heard Ms. Berkowitz say, “Yes, come in”.

I walked in, and saw her sitting at her desk marking a mountain of papers. She looked up at me, and her whole face brightened to a look of excitement and expectation.

“Well, if it isn’t my little sneaky panty pervert” she said loudly. I quickly shut the door behind me, hoping no one outside would have heard.

She giggled softly at that. “I suppose you’re wondering what I’ve called you in after school for?”

I was completely speechless, I couldn’t even work out if I should somehow respond or not.

“Hmmm, not so talkative are we? Come sit here,” she indicated the desk and chair right in front of her desk. I made to sit in the chair, but she stopped me.

“Uh uh uh, sit on the table, or better still… stay standing. You may lean on the table if you wish.” I did as I was told.

“Now… tell me, are you still wearing those pretty pink panties I had you put on earlier today?”

“Yes, Ms. Berkowitz” I replied, hanging my head in shame.

“Why? I didn’t say you had to wear them for the rest of the day. You could have taken them off at any time. You could have, what do they call it? ‘Gone commando’.” She looked at me with a grin on her face and an inquisitive kind of stare.

As she said it, I realized she had a great point. I wasn’t particularly a fan of not wearing underwear, but it would have been better than having to wear panties!

“I just assumed m’am, that that’s what you meant.” I managed to reply.

“Hmmm,” she said, looking thoughtful “I suppose that’s something that may have seemed implied, but I’m starting to think you must actually like wearing panties!”

Given the way my cock was stiffening, I didn’t really have a rebuttal to her comment.

“Anyway, no matter” she continued, “we’re not here to discuss what you’re wearing now, but what you will be wearing until the next meeting.”

My heart dropped completely. Surely she wouldn’t extend this out for that long? Apparently, I was wrong.

“What you did today, spying on the girls during their underwear inspection, cannot simply be dealt with in one day. I don’t think you’ll learn the respect that you should in such a short space of time. I think instead, that you should spend a week in a girl’s shoes, or I should say: in girls’ panties! So that’s exactly what you are going to do. Otherwise, we could take this further up, and get the headmaster and your parents in to discuss your future at this school. Word would probably get out quite quickly about what happened today, and everything that happened today at that.”

I weighed the options up. There was a lot to lose for the sake of a week.

“So which way do you want to go?” she asked, pressuring me for an answer.

“I’ll do what you said,” I mumbled.

“Sorry, what was that? I was hoping you’d say ‘M’am, I’d like to wear girl’s panties for the next week as my punishment for this morning.”

Taking the hint, I repeated what she said. “Louder!” she demanded.

“M’am, I’d like to wear girl’s panties for the next week as my punishment for this morning!” I said, quite loudly. I was glad the windows were closed, but was paranoid that the sound would still travel.

“Good!” she said, “I think that would be a very fitting punishment.”

Just then there was a knock at the door. My heart froze. Had someone heard me?

Ms. Berkotwitz seemed to be expecting this. Looking at her watch, she just said “Oh, right on time”.

She got up, and opened the door, letting Katie walk right in. Oh god, I thought, what is she doing here.

“Come in Katie, and take a seat. I trust you’ve heard about Michael’s current situation by now?”

“Is it really true, Ms. Berkowitz? Ashleigh told me about this morning, but I couldn’t believe her!” Katie said.

“It certainly is, in fact he’s wearing them right now” answered Ms. Berkowitz, looking at me as she finished her sentence.

Katie then finally looked in my direction, also with a look of excitement and surprise similar to Ms. Berkowitz’s earlier. Then it changed to disappointment, though I wasn’t sure if it was put on or not.

“Aaaw, now I’m sad I didn’t get to see any of it” she said, then looked at me.

What she said next was neither said in anger, nor disgust, nor any of the emotions I’d have thought to be on the receiving end of. Rather, it was something said in a way that suggested she was surprised I could be so bold, so cheeky.

“I can’t believe you were actually lurking behind the curtain watching me and staring at my panties!” she said. “I’m so embarrassed!”.

“Well, now that I think of it” Ms. Berkowitz said, “you left early and weren’t there when we caught Michael in his hiding spot. He got a good long look of your… barely acceptable… underwear under your skirt. Seems only fair that you shouldn’t miss out.”

What?! I thought, she can’t mean….

“Michael, please stand up on the step in front of the board and pull down your pants. Then lift your shirt to your chest.”

I really did not want to do that right then. Between the talk of having to wear panties all week, thinking again about Katie lifting her skirt, and the ever-present feeling of the panties I was wearing, I had a full erection!

I tried to get something out. “Ms. Berkowitz, I don’t think that – “

“Quiet! Pull those pants down now or I will open the door, call every possible person in, and do it for you!” she threatened.

I had no choice. I walked up to the step, which was directly in front of Katie sitting in the front row. Ms. Berkowitz was now standing behind her, looking at me with eyebrows raised and an expectant look on her face.

I slowly unbuckled my belt, and undid the hook in the waistband of my trousers. Katie was leaning forward, looking like Christmas had come early.

I pulled down my fly, and before I could draw it out any longer, I took a silent deep breath, and pushed my pants down in one quick motion. Then, I lifted my shirt, closing my eyes and waited for the inevitably humiliating response.

Katie gasped loudly, then put her hands over her mouth. Ms. Berkowitz looked completely surprised, mouth open and eyes wide. She held back her laughter, just about, and said “Wow, Michael. Now, I really understand why you didn’t take them off all day! They seem to be having quite the effect on you!”

Katie just looked, jaw on the desk, occasionally saying “Oh my god” in little more than a whisper.

“It’s not like that Ms. Berkowitz, it’s just… well…” I couldn’t find any words to explain what was happening.

“There’s no need to explain” she said, walking towards me “but these clearly do not fit you right in your current state.”

This was true. My erection had pushed the panties out, creating a gap at the groin through which you could see just about everything. Only the lacy waistband was preventing the tip of my cock from popping out.

Ms. Berkowitz, acting like it was the most normal thing in the world, tugged at the leg openings gently, pulling out here and adjusting there, not really making much difference other then giving my balls slightly more coverage in the satin.

Then she surprised me, cupping my balls and giving them a gentle stroke through the satin, the heel of her hand rubbing firmly against the base of my penis. Katie said, “Ms. Berkowitz!” completely shocked by what was in front of her.

“What can I say” she replied nonchalantly, “he has a nice hard cock, though it looks somewhat below the kind of length I usually expect.” This stung my ego, but I guess I had bigger things to worry about.

“He seems to be enjoying it anyway,” Ms. Berkowitz continued. It was true, from all of her rubbing, my breathing had become faster, and I’d even let out a little moan.

“Turn around, and keep that shirt up” Ms. Berkowitz instructed, getting back to business.

I did as I was told, my heartbeat pounding in my ears.

“He’s got a nice bum!” Katie said.

“Yes, he does” replied Ms. Berkowitz, “and doesn’t it look so nice and tight in his pretty, pink, silky girls’ panties”. She emphasized the last couple of words looking me dead in the eye, then moved around behind me and gave me a sharp slap on the backside.

“Turn back around please, Michael,” said Ms. Berkowitz. “Katie, are you satisfied with what you’ve seen? I daresay it’s more than even I was expecting to see!”

“I think so Ms. Berkowitz. Fair’s fair, I guess. He couldn’t have stared at me for this long” Katie replied.

“Right Michael, “ continued Ms. Berkowitz “you can pull up your pants now. Now I want you both to sit directly in front of me,”

I was glad of this, as by now I could feel the pre-cum at the tip of my cock, and really didn’t want either of them seeing that. Another minute of all this and I may have shot my load on the spot!

When we were both seated in front of Ms. Berkowitz at her desk, she began to explain what we were both doing there.

“Now Katie, I have called you in here as I will need your help, in several ways, with Michael’s punishment here. You’re the only girl, I think, with the maturity to handle the task I have for you. Even though I disapprove of your rule bending, I have to admit that you have a classier, feminine, taste in panties compared to your classmates”.

Katie just said, “Um, er….thanks Ms. Berkotwitz.”

The teacher just continued. “Now you do not have to help me with what I ask, as it is somewhat out of the ordinary, but I thought you may be more willing than others. The choice is entirely up to you.”

Katie just nodded her head, waiting for what was going to come next.

“I have made it clear to our sneaky little perv here” she said, indicating me “that he will need to be punished beyond today to atone for his offenses this morning.

He has agreed, almost too readily” she said, taking another dig at me “that wearing girls’ panties until our meeting next week is an appropriate punishment”.

Katie had to hold up her hand to her mouth, either to hold back her laughter or her surprise, but either way I could tell she was smiling naughtily behind her subtlety. She looked briefly at me, and then briefly again at my crotch, clearly remembering about the girly underwear beneath.

Ms. Berkowitz carried on as if we were discussing an assignment. “Now we can’t have Michael wearing the same pair of panties every day, although I must admit that pink suits him”. Katie gave a little laugh at this point. “I also don’t want to use any more pairs from my replacement box, as I seem to be needing several of those pairs for the other girls.”

Katie indicated her understanding, saying “Of course” with something of a facetious air, as if she was taking it very seriously.

“So what I’d like you to do is help him shop for some of his own panties this weekend.”

I was completely speechless, and I think my face must have shown it. I could feel my jaw dropping somewhere near my chest. How could she get someone else involved like this? And why did it have to be Katie, of all girls?

Katie, rather than being shocked or disgruntled, seemed to have taken this all in stride, clapping her hands together and looking at me with a big smile.

“I’d love to!” she said, almost squealing with joy. “I love underwear shopping anyway, but buying panties for a boy will just be even better!”.

“Good, I was hoping you’d be up to it” said our teacher. “I’d like you both to complete the shopping tomorrow morning, and you will then visit me back here at school, meeting again in this classroom so that I can review his purchases.”

“Sure Ms. Berkowitz, not a problem. Michael,” she said, looking at me, “I’ll meet you at The City shopping centre at around nine, outside the toy store by Rivett Street? Then we can go get you some gorgeous panties!”.

I just nodded my head, not able to get any words out due to feeling completely helpless, nervous, and wildly aroused at the same time. Ms. Berkowitz then turned towards me.

“Now Michael, even though you’re wearing girl’s undies right now, you aren’t actually a girl. Given that this school, with its double standards, doesn’t enforce a dress code on underwear for boys, you are able to wear any kind of panties.”

She made it sound as if I was getting away with a treat, and that she didn’t approve of my freedom of choice in girl’s underwear, even though she was calling the shots.

“However,” she said, “I have developed a shopping list for Katie to use as a guide, just to make sure you don’t stray too far from what should be an acceptable standard of underwear.” She handed the list over to Katie, saying, “You can change some of these selections, but I expect you to ensure that Michael buys some good girly knickers!”

Katie laughed, taking the list and putting it into her shirt pocket. “Don’t worry Ms. Berkowitz, I’ll make sure he gets a collection of really nice panties, of all different kinds and colours!”

“Good” said Ms. Berkowitz. “Michael, this will all of course come out of your own pocket, given that it is your transgression we are addressing here”.

At this point it all seemed to be way too much, and I started to protest. “Ms. Berkotwitz that’s completely unfair! I - “

“M’am, I’d like to wear girl’s panties for the next week as my punishment for this morning”

Ms. Berkowitz touched the screen on her smartphone again, pausing the recording of what I had said earlier. Damn! How did she get that recording so sneakily?

“There is no discussion here, Michael, because I hold all the cards. This recording could go anywhere I choose it to.”

I slumped back in my chair knowing I was defeated. Ms. Berkowitz then decided to make it worse.

“Actually, Michael, I noticed earlier that you were looking a little... untidy… down there” she said in a vindictive tone, nodding at my crotch area. “In addition to the change in your underwear, I expect you to shave your penis and balls completely bare. You will also shave a ‘landing strip’ above the base of your penis, and I expect this to be done before your shopping trip tomorrow.”

Katie was giggling hard, trying to hold back her laughter. All I could say was “Yes Ms. Berkowitz” with my head hung in shame, really regretting my decision to sneak into the girl’s ‘secret meeting’ that morning.

Ms. Berkowitz then turned to Katie, returning to that cool calm and collected tone that always had a hidden sense of danger behind it.

“Katie, I’m afraid that I will also be requiring one more thing of you.”

“Sure Ms. Berkowitz, what is it?” asked Katie.

“As we’ve discussed, Michael will be wearing panties every day from now until our meeting next Friday. I believe it’s only right that he should wear a different pair every day until then, would you agree?” asked the teacher.

“Of course Ms. Berkowitz! I agree completely,” said Katie.

“Good. Now that means that Michael will need a new pair of panties for your little shopping trip tomorrow. The ones from the box clearly don’t fit Michael’s ‘equipment’ very well, so we shouldn’t take a pair from there. I’m afraid also that, having double checked the full school rules, your panties from this morning are actually outside of regulation as they are neither cotton, nor are they laced only at the trim. I wanted to let you pass with the pair you have on, but I’m afraid that I just can’t, and I will have to confiscate your panties.”

Katie looked a little disappointed, but said, “That’s alright m’am, I understand, but how does that fit in with… oooooh...” It seemed Katie had worked out what Ms. Berkowitz was getting at, and it was just dawning on me too.

“Katie, you’re the only girl whose permission I can ask from the many panties I’ve confiscated today. Would you be comfortable with Michael wearing your panties tomorrow, with the condition of course that he cleans them tonight?”

Katie, instead of being appalled or upset, responded by saying “Sure Ms. Berkowitz, that would be fine, here…” With that she stood up, reached under her skirt, and slid the silky white panties down her legs. She then stepped out of them, picked them up, folded them neatly and put them on the desk.

Ms. Berkowitz picked them up, and slid them into the side pocket of the school bag I’d brought with me. Ms. Berkowitz then stood up, went over to the now familiar box in the corner cupboard, opened it and brought out a pink satin pair that was identical to mine.

“Thank you, Katie, here is a replacement pair,” said Ms. Berkowitz, tossing a pair to the now panty-less schoolgirl.

“That’s alright, Ms. Berkowitz, I’ll go without” Katie said confidently.

“Not walking around this school you won’t. Put them on!” Ms. Berkowitz was now far less understanding, and back to her assertive ways. Katie put one leg, then the other into the pair that was given to her, and expertly slid them up. I had looked away, trying to be the gentleman.

“Good, Michael!” said Ms. Berkowitz, noticing, “You’re learning a little respect already. Right, that is all you two, I’ll see you tomorrow here at around 1pm.” She sat at her desk, and returned to her work.