The Dress Punishment

Synopsis: When Jamie gets in trouble at school, he fears the dress punishment.

The Dress Punishment
By K.T. Leone

Being in the principal’s office is never a good place to be, especially after you get caught doing something wrong. It makes you feel kind of nervous when you‘re sitting there waiting for the man in charge to come back in when you know he’s getting all the dirt on you that he could. All I can do is sit here and look at the wood panel walls and watch the second hand of the clock move slowly.

“Tick, tick, tick,” the clock counts down as a sense of impending doom washes over me. I bow my head and imagine the executioner is standing over me with his axe at the ready. Any moment now the second hand will reach zero, the axe will fall, and I will hear the clock no more.

It is almost 2 o’clock, which means half an hour until school lets out. That is, unless you’re in the principal’s office, then the final bell means nothing. Time has no meaning when you are waiting on the judge’s verdict, especially when you know you’re guilty, and worse yet, you know that they know that you are guilty as well. In times like these, all you can hope for is leniency and be prepared to beg for mercy.

Let me introduce myself, my name is Jamie and I am a ten year old boy. I always have to tell people I’m a boy because Jamie can be a name for a girl too and if you went just by looking at me, you still may not get it correct. It’s not my fault that people mistake me for the wrong gender, my mom refuses to fix things or take me to a hair stylist and I have no clue how to toughen up. My name is what started this whole mess anyway today. Well, my name and the fact that Ed Bauer is a stupid bully that won’t leave me alone. See, last year in the fourth grade, Ed started teasing me that Jamie is a girl’s name. Most adults think it is silly that I got mad because of the teasing, but they don’t understand life for a fourth grader. Finally, this year I made it a point not to get upset when Edward would say that I had a girl’s name. But that fink did something really mean. He saw that he wasn’t getting to me by saying that Jamie was a girl name and so he started saying that Jamie was a boy name, implying that I was a girl. He then went on to say that he had proof I was a girl because I had long hair and girl eyelashes. That just made me mad and at lunch I threw my pudding cup at him and ruined his shirt. Of course he tackled me and started punching me in the arm, but what do you expect from a bully who is part gorilla.

“So Jamie,” Principal Malone says as he walks into the room. “Do you think that starting fights during lunch time is a productive way to spend time at school?”

“No sir,” I say, in hopes that this might be something I can get out with just a minimum punishment. Anything less than detention and I can live with that.

“And what do you have to say for yourself?” Principal Malone continues, it’s like every authority figure reads from the same handbook.

“I’m sorry,” I say meekly and hope that I sound sincere enough.

“And what caused all of this ruckus?”

“Edward Bauer said I was a girl.”

Principal Malone gives one of those condescending head shakes that I’m suppose to know means ‘What am I to do with you?’ “That again? What do we say about words?”

I hate being talked down to, but I know I have no way out of this. “Sticks and stones may break my bones,” I recite, “but words will never hurt me.” Which to be honest with you is completely untrue, but I guess adults don’t know that or they completely forgot how cruel and hurtful words can be. I think it’s much kinder to be punched in the gut once than to go the whole year being called a sissy.

“Now what is your response supposed to be when someone is making fun of you?”

“I’m supposed to ignore them and to walk away,” I respond, it’s almost like everything is scripted and there is nothing else I’m supposed to say. I wonder if the principal ever feels like he is a sitcom character and is living his life in reruns.

“And are we suppose to start fights with other little boys?” Principal Malone continues like if I was a five year old instead of being in the 5th grade.

“No sir.” I fidget in my chair. Let’s just get to the punishment part of this so I know if I can at least have a fun weekend. This weekend I have plans, and if things don’t go well with what correction he dishes out, those plans may be ruined.

“And what do you think we should do about this major infraction?”

Ut oh, he said major, which is not good. I was hoping for minor infraction. If he would say minor infraction than that would mean doing extra school work or writing a hundred times ‘I will not fight at lunch.’ But a major infraction can have big repercussions. “Um,” I stammer, trying to figure out what punishment wouldn’t ruin my life outside of school. “Maybe I can spend recesses in your office helping out?”

Principal Malone shakes his head again. “Nice try,” he says with one of those goofy smiles that say he thought what I said was cute. “No, I think for this one I need to call your mother and have her pick you up for the day.”

I just bow my head. There really isn’t anything I can say at this point, but what he just suggested was the worst possible outcome. See, there are levels of being in trouble, and there are some levels I can live with. The level that says I got to do something extra during school is pretty low level and though it’s a drag, I can live with it. The next level is where I have to do something after school, which really sucks, but it really doesn’t affect my life other than for an hour after school, which usually means I get my homework done and miss out on playing with my friends. The next level after that is being drafted to fight in a war in the Middle East, which might be cool if they would give me an AK-47. But the absolute worst level is when my Mom has to be called, because her punishments are worse and may be illegal in some states.

Principal Malone pats me on my head as he walks out into the main office so he can get my home phone number and call my mom. So much for having fun this weekend. I might as well dig ditches on a chain gang than be brought home by my mom. I’d rather a year in solitary confinement than what I know my mom has in store for me.

With my mom, punishments are not too hard to figure out. My mom’s punishments are meant to cause you grief and to teach you a lesson. Usually the punishments are the same for the same offenses. Take for instance, the punishment for not eating your Brussels’ sprouts is always not getting dessert. The punishment for getting into a fight with Edward Bauer is going to be the same as it always is, it’s going to be the dress punishment and I, for one, am not looking forward to receiving it.

To understand the dress punishment, you have to first understand what dress we are talking about. The dress, first of all is pink. Not a cool hot pink either, but a very soft, delicate pink, with little pink flowers in the print that are just darker in color than the dress so that they are distinguishable if a person pays close enough attention. The dress is sleeveless, because it is still early enough in the school year for the dress to be considered appropriate for a girl to wear, even though I ain’t a girl, no matter what the rumors going around the school say. Along the waist of the dress is a matching pink belt and sitting off center there are three little roses designed in the fabric. In the back, just above your butt, the belt makes a pretty big bow that if you tie it tight enough makes you look like you have a little bit of hip. The skirt of the dress is ruffled , of course, because it is a fancy kind of dress and the skirt comes to just above the knee, making it modest enough. Sometimes, there are also stockings involved and always matching pink dress shoes.


About two months ago I had worn the dress and the things that it does to you are quite unmistakable. I remember that weekend like it was yesterday and know what the dress does in its entirety. First of all, you don’t just put on the dress and sit around, that would be too easy. The first thing that happens is that you have to take a bath, a real bath as my mom calls it to wash all the boy off of you. My mom ran the bath a little warmer than usual and added some stuff to the water that made it feel gritty. Then you have to scrub yourself, and doing that in front of your mom is a little embarrassing at first. But if she wasn’t there to know you did it right the first time, you might wind up taking three or four baths and that makes it worse.

After scrubbing in the tub for a good fifteen minutes, my mom then washed my hair, which, like I said, is long. On that day, my mom didn’t use my usual shampoo, but one that smelled like strawberries and flowers. She lathered my hair pretty good and then even added conditioner, which I never use, not ever. Then she rinsed my hair off with water from the bathroom sink, I guess she didn’t want the gritty stuff in the water to get in my hair. After that she let the water out of the tub and had me stand in the tub in front of her.
Let me tell you, being a boy and standing naked in front of your mom is never a pleasant thing, especially when you know that what you have isn’t nearly as impressive as what other boy’s have. Every time my mom sees that particular area she always says the exact same thing, “Maybe we should have the doctor check that out?”

And I reply the same thing every time. “It’s okay mom, it’s supposed to be that way, leave it alone.”
Well, after the water was completely out of the tub my mom started to dry me. The terry cloth towel is always nice, but the most important thing is at least I was able to be covered up. You never know what could happen when you are naked. When I was little, my grand papa used to say I better watch out or a little bird might snatch it away. Now every time I get undressed I always listen for chirping, just to be on the safe side. And right after I was toweled off, my mom put baby powder all over me. I never use baby powder, but I guess my mom thought I needed it for when she put me in the dress.

As soon as the baby powder bit was done my mom made me get into a pair of panties. Now panties are completely different than normal boy underwear. For one thing, there isn’t a hole in front for when you got to pee and for another thing they fit completely different. Regular underwear is loose and gives you enough room for everything. Panties, especially the little pink panties my mom had gotten for me, are very tight and they hold everything in tight. When mom put the panties on me, you would’ve thought that nothing existed between my legs. For some reason that made my mom happy, but for me, I was mortified. It was like someone played that magic trick where they make it look like they’re pulling their thumb off their hand, only this time I couldn’t rightly see if it would be put back in place.

To make things really weird, my mom wouldn’t put any cloths on me right away, she had me get out of the bathroom wearing those little pink panties and nothing else. Now, you may not know this, but there is nothing more embarrassing for a ten year old boy than to be seen in his underwear by his mother. The fact that I was in girls’ panties made that embarrassment a gazillion times worst. I just stood there and wondered if girls had the same feeling if they stood in front of their mom and dad in panties. They probably did, maybe it was worse if it was in front of their dad, but at least they wouldn’t have a part of their anatomy disappear from view.

“My, my, my, looks like my little Jamie is turning just as pink as her little undies,” my Mom teased me. She may not have realized this but I noticed she used the word she instead of he and that made me mad even though I didn’t understand why. Problem was, me getting mad made me turn redder and made my mom coo all the more.

So there I was, mostly naked and sitting on the chair in front of my mom’s vanity. A vanity is like a desk with a mirror that girls use to do their makeup and hair and all that stuff. But I was sitting in that little chair and my mom was using the hair dryer. I never dry my hair with a hair dryer, I just towel it off. After all, it’s just hair. But this day, with me in girl panties, my mom wanted to do something extra special with my hair. She used this attachment on the hair drier called a volumizer, which looks like the torture device it is with a bunch of plastic spikes coming out of it. My mom was real happy that my hair was long and with the volumizer it made my hair puffier and softer too.

Most boys don’t like soft hair. Let me tell you that off the bat. And my mom didn’t even comb it straight back like I always do or put it in a ponytail. No, my mom parted my hair down the middle and had my hair drape to the sides and fall on my shoulder. The soft hair tickled my bare shoulders and gave me goose pimples and that made my mom laugh at me. No one likes to be laughed at, especially by their mommy.

To make matters worse, my mom then put this pink headband right on top and it had a pink cloth flower on it. Looking in the mirror was like I was looking at someone else. I almost didn’t recognize myself and I think my mom noticed what I noticed.

“My, my, my,” she said softly in my ear as she squeezed my shoulder, “looks like we do have a pretty girl on our hands doesn’t it?”

I gave a strained grin and hoped things would get better.

Mom then got the dress. It’s the only one we have in the house and the way it got there is a mystery. One day I woke up and it was in my closet and my mom has never told me when and how it got there. I suspect it was bought on purpose, because it is exactly my size and it’s not like I have any girl relatives that come by and would leave something like that behind.

Anyway, Mom had me raise my arms and she carefully lowered the dress on my body so she wouldn’t mess my hair. I don’t think mom remembered it was me, her son; I go half the time without even combing my hair so what would I care if it got messed. Anyway the dress was lowered and it zips in the back. I think mom made sure she got a dress that zipped in the back so I could be trapped in it until she wanted to let me out.

Like I said, the dress fit perfectly, which mortified me. I was partially hoping that the dress would be too big or too small and mom would have to abort our plans for that day. But, no, it fit like a glove. And then my mom made me put on the matching pink girl shoes to match and I was dressed for the day.

Let me tell you about what being me in a dress felt like. At the very moment I saw my reflection in the mirror, with me in a dress and looking nothing like the boy everyone knows that I am, I thought I was dreaming and that at any moment I would wake up, laugh at the odd nightmare and then maybe take my bb gun and shoot something. But I didn’t wake up and it only took me five seconds to realize that I wasn’t dreaming, that it was really me in a dress and nothing was going to change that reality.

My first response took even me by surprise. I started to cry. That’s odd for me because I never cry. It’s in the boy manual that crying isn’t allowed, that tears are for girls. But there I was, looking in the mirror and a tear fell down my face. It was like putting on the dress and shoes and having my hair done like that took away who I was and someone else was there living my life.

My mom saw me crying. She took a Kleenex and dried the tears from my eyes. “There, there, little girl,” my mom said softly but to me it sounded cruel. “Remember, you did this to yourself. I’ll let you think about that as you go to your room and get acquainted with your new role.”

I walked, actually more like shuffled, my way to my room. It felt so weird being in a dress. You feel every breeze on your thighs and boys aren’t use to that.
Here is what is totally strange though. At first the dress felt foreign, like it was a part of another person’s life. But as I muddled around my room, it started feeling less and less strange and felt almost normal. I found myself getting comfortable in the dress and that worried me to no end. Not only was the dress feeling less and less weird, but I noticed I was moving around differently. The way I walked changed, I wasn’t taking those long strides that I was used to taking, but instead started taking more measured steps. Also, when I sat on my bed, I sat differently. Instead of sitting with my legs spread open and kind of leaning back and relaxed, I was sitting straight up and I kept my knees together and a few times I noticed that I crossed my legs at my ankles and that is something I never did before. The other thing the dress did was made me not want to play with my regular toys. I was in my room and I had army men and my Xbox, but I decided not to use any of that stuff. The dress almost made me wish that there was a doll around or at least something that was appropriate for someone wearing such an outfit to be playing with. That dress must contain some powerful magic to make me want to play with girl toys.

In fact, after an hour, I was so used to the dress that I almost forgot I was wearing one as I worked on a poem for school. I thought the plan was ingenious, poetry was for girls, and my mom dressed me like a girl, I was sure to get an A, no doubt. My only real concern was that the poem I would write would be so good that the teacher would think someone else wrote it and I might get into trouble.

Just when I thought I would make it through the day though, my mom had another surprise for me; she was going to take me out. I was really scared then, but mom said she wasn’t completely heartless and that we were going to go to a mall 50 miles away and no one would recognize us there.


Principal Malone enters the room while I was mid thought thinking about the last time mom put me in a dress. I hate when that happens, because sometimes it is good to be prepared.

“I just got off the phone with your mother,” he said in that stern voice that says no one is pleased with me. “She will be here shortly. Now, after a brief discussion on the phone we had decided that you will not be suspended for fighting.”

“Phew!” I thought. I dodged a major bullet there. Getting sent home early from school was one thing, but getting suspended could have gotten me punished for life and I wasn’t ready for that. It’s one thing to suffer the dress punishment for a day or a weekend, but getting suspended might mean a lifelong dress punishment and I couldn’t deal with that.

“But, I want no more of this fighting nonsense to go on or I will suspend you the next time. Do I make myself perfectly clear?”

“Yes sir,” I say as convincingly as I can. I don’t know why adults can’t see that it wasn’t me that wanted to fight; it was stupid Edward and his dumb comments. And, since they heard that I threw the pudding cup first, he got off Scott-free and I know for a fact he’ll never have to worry about a dress punishment, the dumb oaf.

“I want you to promise me that you will stay away from Mr. Bauer and make sure he doesn’t goad you into further misbehavior.”

“I promise,” I say in all honesty, but I doubt there is enough space in the school to keep Edward away from me. I don’t know what fascination I hold for the guy, but I know that I’m his favorite target.

“Good!” Principal Malone gives me one of those stupid adult smiles that they give when they think they’ve gotten through. “Let’s not have a repeat performance then. You may wait outside for your mother.”

“Yes sir,” I say and then go to the main office where I get to sit on a hard wood bench and let other kids look at me funny and wonder what I did so wrong.

That’s almost as bad as the punishment that I know is coming up.


Going out in public when you’re a boy wearing a dress is very nerve racking. First off, you worry that people will know that you are a boy, even though my mom said that there was no chance of that happening I didn’t believe her.

We went into this huge mall and for the first time in quite a long while I found myself holding my mother’s hand. I was really that nervous.

“Don’t be such a worry wart, Jamie,” my mom said casually, like this was something we did every other day. “Mommy’s got you, you’re safe.”

I know she said I was safe, but I didn’t feel that way. Every time a boy looked at me I could feel the sweat forming on my brow. I worried that they knew, that they would post about me on the internet, and my life would be over.

“It’s okay, they just think you’re pretty,” my mom told me as we walked through the food court on the way to one of the women’s stores that she likes to shop at.

That comment made me blush, though I wish I hadn’t because it made mom smile so big that it made me think she was up to something. But, just like when I first put on the dress, after a little while I calmed down and things seemed to happen naturally. Luckily, the trip out didn’t cause any damage to me and we almost had a nice time together.


I doubt this weekend was going to be a nice time as I saw my mom walk into the office. She took a quick glance at me, shook her head, and then walked to the front desk. “I’m here for my son,” she said in such a way that made me think she disapproved of having a son and that there was no way I was going to get out of the dress punishment now.

After my mom did a little chatting with the principal that was out of earshot, she signed the big red book, and turned her eyes on me. “Let’s go,” she said shortly.

The walk down the school hallway when your mom just picked you up for misbehaving is a long, lonely one. I bet it feels just as bad as when inmates are walking to the electric chair. Inside my head I imagined the classroom doors were really prison bars. It would be better if I was going to an electric chair; the dress punishment was a far worse fate. We didn’t even say a word between us and made our way to our grey minivan. I climbed in my seat and a few seconds later mom was behind the wheel.

“What do you have to say for yourself, young man?” My mom put an emphasis on the word man that made me gulp.

“It wasn’t my fault, really. Edward started it.”

“And Edward forced you to throw a pudding cup at him?”

“No,” I said in defeat. I know I was wrong for letting someone control my actions.

“It seems to me like someone has a little too much testosterone in their system,” my mom said pointedly as she put the car into gear and slowly made her way onto the road.

“It’s not that mom, I promise,” I started to plea.

“I think it is, and there really is only one solution for this. Since you have so much testosterone and want to behave like a Neanderthal male, then I think we need to adjust our plans for the weekend and teach you a little lesson.”

“But mom,” I said, but that was really all I had.

“No buts out of you. You leave me no choice; your actions have determined dress punishment for the weekend.”

“But that’s not fair,” I stated as I folded my arms and pouted in my seat.

“Maybe with the punishment you will think the next time you want to be a barbarian,” my mom said and left it at that.

It only took five more minutes to get to our house, but it might as well take a year. This weekend I had such great plans and now they were going to be ruined. I got out of the van and walked slowly behind my mother.

As soon as we got in the house my mom stopped by the foot of the stairs. “Go up to your room, go to your closet, and bring it down to me now, mister.”

“Yes ma’am.” I knew what she was talking about. She was going to waste no time with the dress punishment.

I walked up the stairs as slowly as I could get away with. If I went any slower my mom would’ve yelled at me. I went to my room and to my closet and pulled the dress down on the hanger. So pink and feminine, it really didn’t go with anything else in the room and I’m surprised my mom didn’t keep it someplace else.

I walked down the stairs where my mom was still waiting. By the look in her eyes I knew she was disappointed. I made it to the bottom step and stood right in front of her.

“You brought this on yourself,” she said softly. “You have to learn to behave properly and this is the only way I can teach you.”

I start to cry. “But mom, anything but the dress punishment. I’ll do anything. I’ll clean the house, I’ll do the laundry, I’ll cook dinner, and I’ll mow the yard. Anything you want but not the dress.”

“I’m sorry, now hand it over.”

“Please,” I beg.

She stood there and shook her head no and held out her hand.

Reluctantly I put the dress in her hand, knowing that my weekend and maybe my life would be ruined.

Slowly my mom turned to the downstairs closet, hung the dress up in there, closed the door and locked it with a key. “Maybe if you behave next week like I know you can, you will have a chance to wear it again.”

I still cried. I was so looking forward to wearing the dress this weekend and going to the mall with my mom again, we were supposed to pick out a second outfit for me, but it was ruined because of dumb Edward Bauer.

Author's note: This is the first story that I've written since 2005 or 2006 (The other recent post were written prior to then and I've just been typing). I don't know if it is any good or if I have lost my touch. I wanted to do something though to get the creative juices flowing and when the idea for this story popped into my pretty little head and I knew that it wasn't going to be very long, I decided to type it up and throw it out there for everyone.

Please give me your feedback and comments, have I lost my touch?

Also, if you haven't already, would you mind sending a kudo my way. I would really appreciate it.

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