1 comments/ 26785 views/ 10 favorites An Appropriate Punishment By: Frixmaster I'd just turned 18, and was heading into the final few months of my high school years. Then something happened that year that would change the rest of my life forever. School started like any other Friday: I caught up with the other guys, giving each other a hard time with whatever banter we could come up with, then trying to predict the weekend football results and arguing over who the best players were. Not being one of the real jocks, nor in the typical cool crowd, I just knew who and what I liked, and luckily managed to make a few friends that way. It worked well enough, and I'd got through those high school years mostly unscathed. As far as it went with the girls, that was a bit of a different story. I was friendly enough with some of them, but was basically locked down in the friend zone, still very much a virgin, and well behind on any 'bases' you were supposed to have covered by 18. In my first two years of high school, I'd managed to develop something of a 'creep' reputation with some of the girls. I don't completely know why, but it was probably because I'd get caught staring at breasts or short skirts once too often, or maybe just my lack of confidence talking to any of them. Whatever it was, that reputation was about to take a whole new turn. Every second school Friday started with an assembly of all the students in the hall. Announcements, awards, meetings, notices, and other matters were all done then. Most of us normally just switched off and waited for things to close. We sat around in the back messing around, trying not to get caught. But something was different that day. In between all of our shenanigans, I somehow caught the one announcement that wasn't just a boring drone. Carrying clearly across the assembly hall, Ms. Berkowitz's voice called out: "Would all senior girls please stay behind in the hall, for our regular meeting." That seriously piqued my interest. I'd heard via the grapevine, only recently, that those 'meetings' were a subtle announcement for something else. They weren't even that 'regular'. They were always announced the same or similar way, with no further detail ever being given, and it seemed to happen in no particular pattern or order. My curiosity was starting to grow, so I tried to think about what it could be. The problem was that I only had some theories for what it might be, but I'd never find our or know for sure. Thinking about the upcoming end of year, I didn't know when I'd next have a chance to find out. The idea of that mystery not being solved got the better of me. I gave in to my curiosity knowing somewhere in the back of my mind that it was a risky decision, but too excited to give it much attention. The general crowd filed out of the hall, slowly exiting through the various doors. I was lucky to be the only one of my friends who had a free period straight after assembly, so I said goodbye to my friends, and headed in the opposite direction, saying I was going to go do some work in the library. Instead, I took a back route that led to a little known door around one of the alleys. That door led backstage of the hall's main stage area, and I only knew where it was from working on a few school plays. I was hoping to find a space backstage where I could see back through the side of the curtain to the main hall area. I crept up behind some of the stage equipment, very slowly to the end of the curtain at the side of the stage, and...jackpot! All the senior girls were there with Ms. Berkowitz, and my position was just behind her. I couldn't believe my luck when I realized that they'd only just settled down for her to start this supposed 'meeting'. "Alright girls, quiet down. Let's get this started as quickly as possible so that you're not too late for your classes." She always had a way of standing and speaking that immediately told you who was in control: her. Ms. Berkowitz was in her mid-thirties, about 5'9", with dark auburn hair that was kind of short, but without being masculine in any way. Her figure wasn't skinny, but slim, with curves in all the right places, including her seemingly perfect 36C tits. She was always dressed in tightfitting, neat clothes, and seemed to me like the woman who wears lacy black underwear underneath it all (or maybe that was just me fantasising). I managed to bring myself out of my daydreaming about her in a state of undress, just in time to catch up on what she was saying. "Have we got all the doors and curtains closed? Yes? Good. Now, as you all know" she began, "all of us teachers keep a keen eye on adherence to the school dress code, and it must be said that those of us who are more...observant...have seen a number of you not keeping to the simple school rules on underwear." I could see many of the girls getting nervous, and one or two were shifting uncomfortably in their seats. In the meantime, I was completely transfixed, hypnotized and excited. Could what I thought was going on really be happening? "As per our previous 'meetings'," she mimicked quotation marks here and added extra irony to her emphasis, "we will be inspecting each of your states of dress, after which you can all return to class, immediately! I'll be sitting over here," she indicated a chair a few feet behind her (and about ten feet in front of me!) "and I want each of you to come forward, lift you skirt first at the front, then the back, so that I can check that you're complying completely with school rules". This was too good to be true! Here I was, with a perfect view of a panty inspection! Truth be told, I had a bit of a thing for lingerie, and panties especially. They were just so intriguing to me; so many different kinds, colours, and fabrics, coyly hidden like a naughty secret, yet often seen by accident if you just happened to be in the right place at the right time. For me, this was definitely the right place at the perfect time. "Allow me to remind you that, any of you found not to be wearing the regulation white or black panties with lace trim, will have your current underwear confiscated and replaced appropriately". I could see a few faces of displeasure at this. It seems some girls had had it happen to them before and, judging from the conversation and the gestures, the replacement panties were pretty small and tight. Ms. Berkowitz looked down a list and said "Tracy Ascott, let's start with you." I could barely contain my breathing. Tracy got up on her long, slender legs and walked nervously over to the teacher. She was quite pretty, though a bit thin and not really my type. She stopped, stood in front of Ms. Berkowitz, and lifted her skirt just a little, barely showing anything and let it back down again. "Come on now Tracey, you don't have to show the whole group but I need you to lift that skirt right up, until I tell you to drop it and turn around for the other side. That goes for all of you by the way!" she said, addressing the other girls. Tracy looked down, crestfallen, and lifted her skirt high and held it there. She revealed a pair of very skimpy light blue panties, with a thicker than normal lace waistband, and only a small triangle of nylon covering her vagina. "Well now, not off to a good start are we? Turn around and show me the back" The back turned out to be a thin thong, and showed off a nice, tight ass. Even though I did feel somewhat guilty for spying, I could barely concentrate on anything but the scene before me, and of course: my growing erection. "Right, Tracey, take those off, give them to me, and grab a replacement pair from the box in the corner by the door. Then you're free to go." Tracey reached up under her skirt, and skillfully slid the tiny, sexy underwear down her legs. She then stepped out of them, crouched down with her legs together and picked them up. She held them out with one hand to Ms. Berkowitz, who took them and swung them round playfully, looking out at the other girls almost threateningly before continuing down her list of names. "Katie Atwell?" she called. Katie stood up and walked forward, quite confidently. She was definitely one of the girls I had a crush on. She had a slightly Mediterranean look about her, and a happy, gorgeous smile. She was just so fun and friendly to just about everyone. Once she was in front of the inspecting teacher, she stood and lifted her skirt, almost proudly. Her underwear was indeed white, with a subtle lace trim, but they certainly weren't cotton. At a guess, they were silk, or silk/satin. She gave Ms. Berkowitz a cheeky grin. "Wipe that smile of your face Ms. Atwell. You've complied with the rules so far. Show me the back." Firm but fair as always, it seemed the teacher was annoyed with Katie's attitude. "Of course, Ms. Berkowitz" said Katie with a smile. She turned around and flicked her skirt up, bending over just slightly and looked back at Ms. Berkowitz with a look of faked innocence on her face. The panties were full backed, and nice and tight against her beautiful bum, spread smoothly with not a stitch of lace out of place. They seemed to fit with regulations, as Ms. Berkowitz just seemed to nod slightly, before saying: "Very well Katie, you may go. However, in future, if I find you trying to bend the rules with anything but cotton again, there will be consequences." Katie virtually skipped off, seeming to just happily enjoy getting away with what she wanted to do. After that, Ms. Berkowitz continued with her inspections. After Katie, the next girl was in line with regulation, cotton black panties with a slight lace trim. In her checking, Ms. Berkowitz even adjusted the waistband here and there, adamant that the underwear was being worn correctly. However, after that, it seems that hardly any of the girls had complied with the regulations. The next couple of girls were all wearing either lacey g-strings, or had tried to get away with more expressive colours. Each of their pairs of panties was taken and added to the collection next to Ms. Berkowitz. "What seems to have gotten into all of you?" she said, "do you think that with just a few months left to the end of the year you can start sexing up your underwear at school?". I was thoroughly enjoying myself, there I was getting a full and perfect few of all the girls, lifting their skirts to show their panties. I knew I was going to go round all day knowing exactly who was wearing the standard underwear, and who wasn't. This was definitely worth the risk. At least, that's what I thought, but then it all went wrong. "Excuse me Ms. Berkowitz," said our head girl, Megan "but I think there's someone behind the curtain!" I looked and realized I had leant forward just enough that my shoulder had pushed against the curtain, and had obviously caused a ripple. Either that, or Megan had looked directly where I was hiding and saw my silhouette in the shadows. As I tried to back away, I bumped into a chair stored backstage, which fell over and completely gave up my secret hiding spot. Before I could react, Ms. Berkowitz was already on me. She'd made it up on to the stage, and was round the back of the curtain before I knew what was going on. She grabbed the collar of my shirt, while I tried to fight her off and run off in a blind panic. She said "Stop fighting! You're already caught and it's going to be far worse if you run! I'll let you go if you come quietly, but you're going straight to a meeting with the headmaster and your parents if you keep fighting me off." For some reason, what she said made sense to me and I gave in. She motioned me to step in front of her, heading back onto the stage. As I walked out she called out to the girls from behind the curtain. "It seems, ladies, that we have a late arrival to our meeting". The girls all gasped as I came out of the shadows, and started chatting furiously in their close-knit circles. A few 'Oh my God' comments were audible, while other girls seemed just shocked at first... but then livid with rage. "Thank you for joining us Michael. Given that you seem to not care for punctuality, maybe we can bring you up the queue to see if you care to conform with dress code." It took me a few seconds to work out what she was implying. "P-pardon Ms. Berkowitz?" I stammered out, barely able to think from the adrenaline and the insanely rapid beating of my heart. "I'm saying we'll skip ahead down the list and see if you are wearing the appropriate underwear." she explained, taking the whole situation in stride and talking to me like I was being entirely silly. "Uh, no, no that's...that's ok Ms. Berkowitz," I began, trying to find a smooth way to exit, "I'd just like to say I'm sorry, really sorry and..." " Now listen here, boy! There is no way, at all, that I'm going to let you walk out of here without these girls getting to see as much of you as you saw of them!" Having finally shown her genuine intentions around what had happened, her voice was like thunder and ice at the same time. It was cold, threatening, and terrifying all at once. Some of the girls sat back and looked expectant, like justice was about to be served, though none of them seemed keen to speak up when Ms. Berkowitz was worked up to an anger. Ms Berkowitz then continued, though in a tone more like she had to coax a shy person into speaking in class. "Now stop you're nonsense and come over here, to the middle, and let's see if you're a good model student" Accepting my fate, I walked forward and stood in front of her, while the girls all looked on. She then knelt down, unbuckled my trousers, and pulled them down in one swift motion to my ankles, then held my shoes and told me to step out of them. The girls all laughed, as my blue briefs came into view, with my now semi-erect penis jutting out about ninety degrees. To make matters worse, Ms. Berkowitz lifted my shirt for them all to get a better view. "Well... they're almost the right type, but completely the wrong colour, and absolutely no lace. How disappointing..." Some of the girls couldn't help giggling, especially when Ms. Berkowitz grabbed me by the shoulders and firmly turned me around, showing my backside. One of the girls let out a wolf whistle, which got a few more laughs. I wasn't heavily built, and a little on the skinny side, but I had a decent enough body. There were definitely nerves, and a lot of adrenaline, but being pantsless in front of the girls wasn't as bad as I'd imagined it might be. I even started thinking to myself; this isn't too bad, I might actually get out of here just fine". Then Ms. Berkowitz said something that sent shivers down my spine. "Well, you clearly haven't followed the rules you were so happy to join in checking earlier. You'll have to find the appropriate replacement." As she walked over to pick up the box of replacement underwear, the entire hall was completely silent. Surely she wasn't going to take things this far was she? She dropped the open box at my feet. Inside were a bunch of panties, but they weren't at all regulation. They were all pink, all satin, and all with plenty of equally pink lace trim around the waist and leg openings. They also seemed to have something printed on them in black, but I couldn't see what it was. Ms. Berkowitz picked a pair from the box, and held them up in front of me at eye level, looking first down at my now almost flaccid penis, then back at the panties. She shrugged her shoulders, seeming to have come to a decision. "I think these should fit you nicely", she said as if she was out shopping with a friend. She held them with just her thumb and index finger, extending them to me to take them. I couldn't believe what was happening. Surely she didn't expect me to put a pair of pink satin panties on, in front of all the girls in my year? Having subconsciously admitted defeat, I slowly took them from her, and held them up in front of me. I could now read the text printed on the front: I must wear proper panties. I looked back at her, pleading in my expression for her not to make me do this. Instead she did quite the opposite. Apparently losing patience, she said: "Oh hurry up, get on with it!" Without warning, she then hooked her fingers into the sides of my briefs and pulled them down all the way! A few of the girls gasped, but luckily I still had my back to them and quickly covered up my cock and balls modestly, while Ms. Berkowitz pulled the underwear from under my feet. "Now," she said, "unless you want to run around naked, put those panties on and put your pants back on. You may go to class, but I would like to see you this afternoon after school to chat further about your punishment." While Ms. Berkowitz was clearly checking out my cock, I quickly put one leg then the other into the panties. They were tight! Before I'd got them up to my balls I could feel the openings constrict on my upper legs. However, I kept pulling until I got the waistband up and over my dick, creating quite a tightly packed bulge in the little pink panties. I was glad of my long shirt at the back, and the fact that I could put my pants on straight after, but the girls still got sight of my pink pantied ass as I bent over. Some of them were in fits of laughter. However, Ms. Berkowitz then did something I didn't expect. While I was getting my pants on she said: "Now girls, I realise that many of you are still quite angry about our peeping tom over here. However, you are not to talk about this to anyone outside of those that were at the meeting today. Feel free to tell those who left earlier, but if I find out that anyone outside of this group knows the colour of Michael's panties" (the girls laughed quite loudly here) "I will have to share a few stories about people myself". It wasn't an empty threat. Ms. Berkowitz had eyes and ears everywhere, and had strong sway over the other teachers - not really worth the risk for any of the girls this close to the end of their school years. I thought she'd done me a kindness. However, she continued: "Don't worry though, his punishment is far from over. I can't keep any of you any longer today, but we will all resume the rest of the inspection same time next week, including our panty peeping princess over here." Again, a few laughs. "Use your second chance at this inspection wisely, and for god's sake - wear the right undies. Now, get to class". She then turned, picked up the box and her other things, and walked out the other side of the hall. The girls also gathered their things, and none of them so much as said a word to me. They all just gave me knowing looks, with smirking smiles and a few giggles as they left. Meanwhile, I was struggling to register what was going on. The satin rubbing against my penis and balls had given me an insanely hard erection. What the hell? I looked down, tucked in my shirt, and tightened my belt as tight as I could. I did not want anyone to see any pink peeking out from anywhere. I left the hall, struggling to think of anything but the tight panties and the fabric on my cock, balls, and ass. Then I remembered that I had to see Ms. Berkowitz in private that afternoon. What more did she want from me? To be continued... An Appropriate Punishment Ch. 02 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. An Appropriate Punishment Ch. 02 Katie and I both said “Yes, Ms. Berkowitz” and left the room. As we walked out, we initially both said nothing, but walked side by side. Then Katie started giggling. I couldn’t help saying “Ah come on, it’s bad enough without you giggling all the time”. She looked at me, still smiling, and said apologetically “I’m sorry, I just never thought that I’d be walking next to a guy knowing that he and I had the exact same pair of panties on!” I looked around, and luckily no one was there. It was weirdly funny, so we both laughed a little, and I just said, “Yeah, I guess that is a little funny.” We got to the school date, and were about to head our separate ways. “See you tomorrow” she said, with a cheeky smile that gave me butterflies in a different kind of way. She turned and started walking, as did I. She quickly turned around, calling my name. “Oh wait, Michael”. I turned, seeing her quickly walking in my direction. She came up quite close and said quietly, “Make sure you wash those panties tonight, I was absolutely soaking wet in Ms. Berkowitz’s class earlier.” To be continued. An Appropriate Punishment Ch. 03 Firstly, thank you to everyone for your comments and encouraging messages! If you have not read the first two stories in the 'Appropriate Punishment' series, it is recommended that you do, otherwise the full context of this installment may be missed. ***** Showering that morning, my cock was standing straight up at attention. Despite being super horny and almost perpetually hard for nearly twenty-four hours, I was also strangely so exhausted that I just went straight to sleep that night. Then, when I got up in the morning I had no time to do anything but get ready, as I had been instructed. I spent a longer time in the shower than usual that morning, for no other reason than following instruction. Ms. Berkowitz had very clearly laid out her expectations. Almost as an echo in my ears, her instructions rang out as I replayed them in my head: "I expect you to shave your penis and balls completely bare. You will also shave a 'landing strip' on your lower belly, and I expect this to be done before your shopping trip tomorrow." Carefully, gently, and meticulously, I complied with her decree. It felt strange as I was drying off, feeling the full smoothness of my now completely hairless balls and cock. Then looking in the mirror, I was made aware of the almost rectangular strip now effectively pointing down at the base of my hard dick. The sight was both embarrassing and deeply erotic at the same time. I dried myself off, and then looked down at the clothes I'd brought with to the shower to wear for the day. A simple white T-shirt, jeans, belt, and then simple black socks and white trainers. A simple grey hoodie completed the outfit, except for the last item that had kept me enthralled and awake for virtually the entire night before. Katie's panties, hidden amongst all of my other clothes, were peeking out from the pile and may as well have been the only thing in the room for all of my fixation. Yesterday morning I had spied on her lifting her skirt for Ms. Berkowitz's underwear inspection, and last night while the rest of the house was sleeping I washed them by hand, imagining the next day when I would be wearing them. I had initially thought that they were silk all round except for a lace trim. Turns out the lace dipped deeper down the font, in a V-shape I tried to continually delude myself, reminding my own dirty conscience that this was all Ms. Berkowitz's idea. That in itself was true, but the excitement and lust I felt while thinking about the silk and lace cupping my now smooth dick and testicles... it was almost too much to bear, and that was all me. To make matters more intense, I was set to be shopping with Katie today! She knew full well what I'd be wearing, what we were shopping for, and had already had a good look at me in a pair of tight, pink satin panties. We were shopping for more underwear, well...panties... for me! Then we had to meet Ms. Berkowitz back at the school (on a Saturday?!), and I had no idea what was in store for me after that. Now was the moment I couldn't take a step back from. Despite having spent the entire day before wearing pink satin panties (with 'I must wear proper panties' printed on the front), I knew that this was really the moment where I could no longer say there was any will in play but my own. Despite knowing that I could not predict the full magnitude of this decision, I picked up the panties and held them open before slipping one foot... then the other...into the openings. I pulled them quite quickly up my legs, having committed to my decision, and immediately felt my groin stir with incredible stimulation. The silk on my balls, the combination of silk and lace on my dick, as well as the mental realization that I was wearing Katie's panties, all nearly made me shoot my ejaculate everywhere. Somehow, after a few moments, I managed to regain my composure, and put everything else on over the panties. This seemed to calm me down, and softened my full hard on to a now semi-erection. Having dressed, I grabbed my wallet and keys, and left the house. ... Standing outside the toy store as Katie and I had agreed, my ears were basically ringing, and I'm sure I was completely out of breath. This was almost worse than school the day before. Here I was, wearing a pair of silky white panties with nothing but my jeans over them. Despite having tried to make sure my belt was on tightly, I was still paranoid that someone might see the lacy waistband peeking out. "Michael!" I heard a voice shout. I turned around and saw Katie striding confidently towards me, a huge smile on her face. She looked amazing. Some tight (very tight) jeans, subtle ugg boots, a loose fitting shirt and tight black jacket, all completed with sunglasses which she took off before giving me a big hug. It was a great sensation for me, and in many ways made me feel comfortable. It felt like this was something we'd organised on our own and were just to good friends catching up. Gently leaving my embrace, she looked around nervously before asking in an excited but low "Have you got them on?" All I could do was nod. "Oh my GOD! You have to let me see!" Before I could do anything, she'd grabbed my hand and pulled me away to the nearby bathroom. Quickly deciding that the Ladies was best she took a quick look in, then back behind us, and yanked me by the arm and took me inside. Once we were in a cubicle, she locked the door behind us and put a finger to her lips. Then she flicked her eyes down to my belt and back up to me as if to say 'Go on!' I was obviously a bit too hesitant for her as the next thing I knew she was on her knees undoing my belt buckle, then the button of my jeans, and then slowly...very slowly... pulling down the fly. My jeans dropped to the floor as she tried to hold back a gasp and yet another of those seductive, wonderful giggles that I'd now heard several times before. I couldn't believe that I was here in the Ladies' bathroom; pants down in front of my high school crush...wearing her underwear. "They look even better on you than they do on me!" she said, having managed to compose herself. My cock was sporting a semi-erection, having not quite got up to full mast in the rush of it all. That didn't matter for too long, as Katie suddenly started running the tips of her fingers up and down the side of my silk covered shaft! I shuddered from the overwhelming pleasure of it all. "I'm sorry," she said, "I just had to feel it with the silk and everything. God, you're so hard!" I somehow managed to say "Of course I am, if you're going to keep doing that!" She then moved her fingers to rubbing the underside of my balls, resulting in an uncontrollable gasp escaping from me. She laughed almost triumphantly, and then retracted her hand. "Come on, we can't waste any more time. Lots to get through today!" she said. I couldn't believe it. My face must have said it all because she looked at me, laughed, and then whispered in my ear: "Don't worry, if you're very good, I'll do a lot more than what I did just now and you might get some release." That in itself should have made me burst at that point, but once again I held my nerve (and my jizz) and nodded at her. We left the cubicle and on our way out passed a woman, probably in her early forties, coming in. "You shouldn't be in here!" she said, obviously shocked. Katie quickly replied "It's ok, he's wearing my panties". Then laughed, grabbed me once again and ran off, leaving the woman looking completely confused and completely shocked. Once we were clear of the bathrooms, I said "I can't believe you just told her that!" "I'm sorry," she replied "it was just such a perfect opportunity, and did you see the look on her face?!" We both laughed at that. "Anyway, you might have to get used to that. Come on, there's someone I'd like you to meet." Despite getting nervous once again, I couldn't resist following her. We ended up outside a shop called 'Wendy's'. Very clearly a boutique lingerie store. I had stopped outside, too nervous to go in. "Don't worry," said Katie, taking me by the arm "you don't have to worry about anything." Gently guiding me over the threshold, she got me into the store. There was one woman in the shop, buying something at the counter. Having made her purchase, she turned to see us both there arm in arm. She gave us something of a knowing smile, despite not actually having a clue what we were actually there for. In fact, she probably thought we were there to get underwear for Katie, while the opposite was in fact the truth. She walked on past, leaving just Katie, myself, and the shop assistant in the store. Katie and the shop assistant clearly knew each other, giving one another a quick hug hello. Katie then gestured for me to come over. "Michael," Katie said, "I'd like you to meet my cousin, Gina." Gina was another tanned beauty, much like Katie. I guessed she was in her late twenties, with a tight figure, gorgeous curves, and mesmerising dark eyes. Wearing a tight black skirt and white button up shirt, her clothes clung tightly to her almost perfect body. The shirt looked ready to burst its buttons as her large (probably D-cup) breasts tried to escape. She was tall for a woman, and looked me dead in the eye with a smile as she shook my hand. "Pleasure to meet you, Michael" she said, and I returned the pleasantries. "Michael," Katie said "I figured it would be pointless going shopping for you unless we knew what size we should be looking for. It can make all the difference, especially for your, um... requirements!" She said the last part with a huge smile and a bit of a laugh. "Gina is an expert and does sizing and bra fittings all the time, so I thought she could help." "Oh so you're shopping for him today?" Gina said, before bursting into laughter. "Well, let's go into the fitting room and get you measured up." There was a pause. I looked at them both nervously. "I'm not sure about this," I managed to say. "Oh don't be silly!" said Gina. "Come, I'll take you to one of our private fitting rooms." She then came up behind me and gave me a slap on the butt before giving me a gentle nudge in my lower back to get me moving. In a complete trance, barely able to tell whether or not I was in some weird dream, I moved forward, and found myself standing in the middle of a rather large cubicle with nothing but a curtain keeping it open. Katie took a seat on the small bench, next to the mirror. After dashing back out of the room for only a moment, Gina came back in, a tape measure round her neck. "So what are we measuring for today, exactly?" she asked, with her hands on her hips and a huge smile on her face as she grinned first at Katie, then at me. "Are we getting him fit for a bra? Corset? Panties? What's the story?" she continued asking. Katie simply left the question to me. "Well, Michael?" she said invitingly. After taking a deep breath to steady myself, I said "Just panties, nothing else." "Ok." said Gina, slightly disappointed but thoughtful at the same time "Well then, take off your shirt, drop those pants, and let's get measuring!" She had basically taken charge but saw that I was still very nervous and hesitant. "Come on Michael," she coaxed "if I'm going to do this properly, I'm going to need to take accurate measurements around your waist and legs. Here, maybe this will make you feel more comfortable..." With that she unbuttoned and unzipped her skirt letting it drop to the floor. My jaw dropped directly onto my chest as she stepped out of the pool of fabric that had gathered around her ankles. Her long shapely legs were enveloped in very fine stockings, held up in by a lacy black garter belt, the straps of which laced underneath her matching black and white lace panties. Her shiny black heels completed one of the sexiest images from my mind, real or imagined. "Now it's your turn" she said, hands once again on hips and indicating my (now bulging) crotch. "Come on Michael, fair's fair." piped in Katie. Nervously and slowly, I unbuckled my pants, ready to reveal my naughty secret for the second time that day. I let the jeans fall straight down, and then stepped out of them. Gina barely missed a step, apart from raising her eyebrows extremely high for just a second. Then, looking directly at the growing presence in my crotch, she cooed her seal of approval without even acknowledging my package, saying "Ooooo, very nice. Alright, off with your jacket and shirt, your turn to go first." I complied, knowing that the big reveal had already been done. Now standing wearing nothing but Katie's white, silky panties Gina came towards me saying "Right, let's get to work." She knelt down in front of me, pulling the tape measure from around her neck. First, she measured my upper leg, right up at the lacy waistband of the panties. Pulling a notepad from the breast pocket of her shirt, she took down the measurement and then moved to the other leg as a comparison. While moving her hands, the back of one of them brushed the silk that was tightly holding up my super sensitive balls. I shuddered uncontrollably. "Oops, sorry about that" she said. She took the measurement of the other leg and then gave just a light tug on the lace of the leg opening, putting it into place. "Those panties are gorgeous!" she said. "Where did you get them from?" Katie stayed quiet about that one, as I looked to her for support. "Uh, it's a long story" I said, which was partly true. "Well, I hope you didn't steal them!" said Gina, letting that one go. Then she moved up to my waist, taking the tape directly around the waistband. She skillfully lifted the tape over the tip of my erect cock as it poked up towards her chin. She then stepped back to make a note on her note pad. "Alright, Michael," she said, "I'm afraid I can't make a complete assessment about your sizing without knowing what we're working with in those panties of yours. Take them down, and we'll get you measured up." She said this quite matter-of-factly, despite the fact that what she was actually suggesting was measuring the dimensions of my penis. "Excuse me, what?" was all I could say. "Michael, if we're going to find the right size and fit for you to wear girls' panties, we're going to have to know what you're packing behind them!" she said, clearly frustrated at how much time I was wasting. "We wouldn't want to be squashing your bits too tightly now would we?" she laughed. She noticed by my body language that I had started to see it from her point of view. "Come on," she encouraged "pull those panties down, just enough so I can get some measurements for your little friend down there." Before I knew it I'd hooked my thumbs into the sides of the panties, and pull them down to my upper thighs, my dick now pointing hard and straight up into the air in front of me. "There we are!" said Gina, "Nice landing strip by the way, and shaved balls too! You're full of surprises. Now... let's see what we're working with." She put the end of the measuring tape right at the tip of my hard cock, and pressed down all the way until she had it taught at the base, right above my incredibly sensitive scrotum. "Six inches, almost exactly!" she proclaimed loudly. I was quite embarrassed to know that Katie now knew my exact size, while Gina proceeded not only to then measure and record my girth, but also the width of my balls! For a second I thought I saw some kind of lust or craving in her eye, like she wanted to feel my balls in her hand, but she maintained her professional approach. "Right," she said "almost there. We've got you measured with a boner, but we need to know what you're like flaccid, so um...I'm going to step out now, and hopefully you'll have a chance to calm down." With that, she stepped out of the fitting room, leaving me standing there with silky white panties round my thighs and my rock hard cock pointing up in the air. I grabbed the sides of the underwear with both hands, but next thing I knew Katie had her hands over mine, stopping me from pulling them up. She took my hands in hers, and moved them to the back of my head. She then ran her hands down the side of my body, to the top of the panties at my thighs, and slid them down to my ankles. Stepping around me to stand in front, she quickly took my cock in hand, and stroked me firmly but not too quickly. "I bet you're pretty close to shooting your load!" she said. "Seeing my cousin in her panties, while wearing mine, I bet a cheeky perve like you was ready to spurt on the spot. Well...it's your lucky day. I'm going to give you a chance to cum in my mouth, and if you don't do just that in the next 60 seconds, then I'm going to make today far more embarrassing than you can possibly imagine, ok?". I nodded my assent, knowing she meant every word and barely able to remember where I was given the way she was stroking my dick. I was surprised at how quickly her tone had changed from earlier that day, even from the day before. She knelt down in front of me, gave me a very quick lick on the balls, and then engulfed me in her mouth. I could never have predicted that my first blowjob would be this good! Her tongue was at work all over and around my cock, while her hand firmly stroked me at the base. I didn't need the full sixty seconds. I reckon I came in about thirty-to-forty, and it was the best cum I had had up to that point in my life. She must have swallowed, and swallowed, and swallowed, to take all of my pent up sperm from the last couple of days. I could barely stand from the ecstasy of it. With a final gulp, she wiped a little excess off her chin and smiled at me before whispering "Good boy!" in my ear. Her sister suddenly came right back in, with almost perfect timing, asking "Have we finally calmed down now?" She looked at my now softening dick and said "Ah good, that looks considerably smaller now." She proceeded with my flaccid measurement (three-and-a-half inches), and even commented that my balls seemed to have decreased very slightly in size, but said nothing further. I got the impression that she knew exactly what was going on, but was declining to say anything. She then proceeded with some recommendations. "For a guy of your size and, well...size... you'll want to go for briefs and bikini panties more than anything else, and I'd say you'll be alright with Medium for the most part. However, if you really want to wear thongs or g-strings, I'd recommend going up to a larger size, though you may find that they don't hold everything particularly well. Would you like me to help you find some nice sexy panties?" Before I could answer, Katie chimed in. "Actually, Gina, we might come back shortly. Now that we know what size to look for, we need to check off a few items on the list." "That's fine!" said Gina "See you in a bit!" With no further ado we left Wendy's, but before we got too far, I actually stopped and held Katie back. Looking at me with a surprised, if slightly confused expression, she said "What is it Michael?" "I just wanted to say thank you" I said quietly, "that was..kinda my first blow job ever." "Really???" she asked, obviously amazed. "Well, it's a pleasure. I certainly enjoyed it. You've got a nice hard, thick cock!" she said playfully. "It's a nice length too, not small but not scary either. Between you and me, I'm dripping wet, super horny and I'm hoping you can help me sort that out later. But right now, we need to get a move on, we've got to get you some panties before Ms. Berkowitz has us both in serious trouble." Having dropped that incredibly sexy bombshell, we headed off to get our shopping done. Unsurprisingly, we did head towards the women's underwear section of the department store, but ended up browsing the aisles of the pre-packaged section. Browsing through the three-pack options, Katie seemed to have found one that she liked. An Appropriate Punishment Ch. 03 "Here you go," she said "you at least need a couple of pairs of sensible knickers before you start wearing sexy, slutty ones. I'm hoping I get to see you in these soon." I looked at the box, inside was an assortment of three pairs of panties; one white, one pink, and one with an incredibly girly floral print. Each had a subtle lace trim on the waistband and leg openings. "At least you'll have one pair of regulation panties, and we already know you look good in pink!" she said. We both ended up laughing at that. Walking up to the checkout counter, I paid silently with my debit card while Katie stood behind me. Despite the dodgy looks from the checkout lady, Katie refrained from confirming the lady's suspicions out loud. "Now that that's sorted," she said, "let's get you some nice and SEXY girls' panties." To be continued...