Letter 4
From Lara
Dear Miss MacDonald,

Thank you for publishing my letters in the Christmas Annual. I would like to tell you and your readers about the first time that I was exposed to others in my punishment clothes. My wife and mistress Angela first heard of this incident from my mother.

It was early on in my petticoating discipline, and Mrs. Farr my piano teacher, was due to arrive at my house for my weekly piano lesson. I begged Mom to let me put on my boy clothes for the lesson, but to no avail, in fact I received a sound spanking with the skirt of my dress up and panties down, making it an adventure to have to sit on the little round piano stool for an hour.

Mrs. Farr arrived on time, and of course I had to answer the door. She immediately recognised me of cause, although I had on a jumper dress (pinafore style to my English friends) of red and black plaid, and a white button down blouse with a half circle collar with lace around the edges, the sleeves were three quarter length, with ruffles at the end, with knee-length stockings, and a pair of girls' saddle shoes.

Of course all the necessary under things, pink ruffle and lace panties, a white full length slip, but with my hair still as a boy, so my face was easily recognised. Mommy had told her in advance what to expect, and why I was wearing dresses, and further more Mrs. Farr could expect to see me in this attire quite often, and for long periods at a time. The first time was a horrible experience for me; no one other than the family had ever seen me dressed this way thus far. When I answered the door I made the required curtsy, and my face was ten shades of red. She smiled, and remarked I was as cute as she thought I would be, very much to my chagrin.

Mrs. Farr accepted the new me with enthusiasm, much to my dismay. She said my lessons were more accurate, and I played with more enthusiasm, this resulted in all further lessons and practice being done in dresses, if under discipline or not.

A few years later I had progressed well, and took part in the Spring Recital, which was a preliminary for the regional competition for piano and violin, and for which my mother entered me. At the recital the format was for each participant to perform his or her number in front of the audience and judges, then be seated either on the left or right side of the piano facing the judges and audience. I was scheduled toward the end, and this suited me just fine, because it afforded me an opportunity to look straight towards the seated participants, and if I was lucky enough I could see a flash of girly undies. I always made an effort to seat my self in a position for the best look up the girls' skirts as I could possibly get. Sometimes the girls were nervous and would move constantly, sometimes affording me an excellent view.

At this particular recital a few participants had performed and were seated. One girl by the name of Debra was seated straight in front of me (I think she was around 12 years old at the time, I was 13 at the time) and was very nervous and constantly wriggling. I was enjoying the show she was giving me, and not paying any attention to the performers at the time. Suddenly Debbie stuck her tongue out at me, as she suddenly realised I had been staring at her panties, and she quickly closed her legs pressing her knees tightly together.

My mother caught on to what was going on by Debbie's reaction. Later Mom began to give me a verbal scolding in a whispering tone, while painfully tugging at my ear lobe, and she added 'You will pay for this "young lady". Well, as you can imagine, I knew what she meant by the phrase "young lady".

When I got home I was put into one of my little girl nighties, with lace and frills around the neck and collar, with matching panties, and pink slippers, and also given 'Ho Ho', to cuddle, who was my teddy bear I carried to bed with me, when I was Lara. I found it very humiliating to be cuddling a silly teddy bear at the age of 13. I found myself standing in front of a furious mother, and received another oral scolding, as I had gotten many times before, then I was sent for Mommy's slipper, and I was bent over Mom's knee, my nightie pulled up to my waist, my panties down, and I received a spanking on my bare bottom.

That night with a very hot bottom, I laid in bed, and thought that though it certainly stings now, the sting would be mostly gone by morning, but the memory of Debbie's undies burned deeper into mind more than any spanking Mom could give me. As I laid there on my stomach, thinking it will be worth it come morning, and the punishment of wearing little girls' clothes will go on for a while, but what the heck I've done that many times before, and that too will end some time in the near future.

What I did not anticipate was what was to come next. It was the customary for the parents of the competing children to meet together at one of the homes prior to the competition, to ensure every detail was just right. A full program was played out. All participants wore the clothes they would wear while competing, in other words a dress rehearsal with the boys in tux and the girls in their elegant party dresses. This rehearsal was scheduled at, of all places, Debbie's house.

While I expected to be petticoated for my offense, I knew I was never was taken out of the house dressed, but this time was to be very different. Much to my humiliation I found myself in a party dress of very elegant design. Made of white satin, a high lace collar, (that itched my neck), half length sleeves with lace on the cuffs, pulled in at the waist, and the skirt came about two inches above the knees, ending in ruffles and lace. It was a party frock that a sissy little girl of 6 would wear.

My undies consisted of matching lacy panties, (also the lace on my panties itched my legs terribly) and slip, and half-petticoat underneath. Frilled and laced ankle socks, with white Mary Jane shoes. My hair was kept in short boy style, parted on the left, and combed back on the right. This was for the reason that I was not to be seen as a girl, but a boy wearing a dress. When I discovered I was to wear this to the dress rehearsal at Debbie's house, I rebelled in anger and fright, but my only reward for that was another hot bottom, with no sympathy from Mom.

At arrival we pulled into the driveway, and got out of the car. I was in total fright as to what was in store for me; seven other kids around my age would be there, three boys and four girls. As I stepped out of the car, I leaned back in to get my music case, a sudden gust of wind caught my dress and it flew up around my back, it was a shock to me, as this had never happened to me before. I suddenly raised up to back out of the car and bumped my head, still trying to grab the skirt and airy petticoats to put them back in place. Mother was giggling helplessly at my predicament, I finally got my case, and Mom said look, I looked up and saw some of the other kids looking out the window, I was so embarrassed wondering if they saw my problem at the car. Finally getting it all together, I still held back, and Mom again grabbed my ear and started hauling me toward the house, with me yelping, and she finally let go of my ear.

As I trudged toward the house, the wind gave me more trouble, this time it blew up the front of my dress, and as I grabbed to pull it down I dropped my music case, which resulted in more fumbling around. Mom was laughing so hard at my awful state of confusion, trying to keep my dress down, and hang on to my case; she had tears in her eyes.

Then the dreaded moment was upon me, and I found myself ringing the doorbell, and they all stood staring at me. I wanted to fall through a crack, any thing to get out of this horrible state of affairs, but there I was a 13 year old boy, all dressed up in a very pretty party dress any little girl would kill for. I thought right then and there that never again would I try look up another girl's dress.

Once inside the humiliation was the most I had ever encountered up to that time. The remarks and teasing were so very vicious. During the program I was so upset, I performed in the most terrible manner. Which brought on more teasing. But the ordeal was not over yet.

I was made to stand in the middle of the room and tell everyone there in my own words why I was in this predicament. Debbie was in her glory and loved every moment of it. And finally I was made to sit on a chair in the middle of the room with knees and legs apart, in the most unladylike manner, while all had a good look at my undies, and the jeers where the worst I had ever heard. Mom and the other mothers scolded me for peeking at their daughters' unmentionables, which made it all the worse in front of everyone there. And now I knew how it felt to have people looking up your dress, and I was made to tell how it felt to me.

The final blow was yet to come. The girls suggested I receive a sound spanking for peeking at their undies, and of the course the boys thought that was a great idea. I was horrified, as all my previous spankings were on the bare bottom, and the thought of that brought instant tears, but Mom agreed.

She made me lay across her lap, up came my skirt. But to my relief the panties did not come down. She started spanking me with her bare hand over my panties, under other conditions it would not have stung very much, but because of the recent spankings on my bottom, it still stung. But the worse was the humiliation of the whole ordeal, a thirteen year old boy wearing a frilly satin party dress, and the spanking in front of every one, especially the girls, they roared with laughter, a good time was had by all, except me of course.

What frightened me in the future was I thought I would have to be in the competition dressed this way. But it not turn out that way. I was registered as a boy as any distraction from that would ruin my chances for points. As awful as this experience was, and the memory haunts me to this day, I admit I still like peeping at girls' panties. Just so no loose ends are left to this story, I placed fourth in the regional competition, and went on to the state and placed seventh there, in a tux that is. But I think that you would agree that this was petticoat punishment at its most thoroughly effective.


This is one of the most detailed and exemplary letters about boyhood petticoating that I have received in a long time. Your mother certainly knew how to deflate a silly little boy, especially with the help of the girls whose pretty 'unmentionables' he had been surreptitiously peeping at. I hope that in future you were a much nicer little boy, and certainly the effect has been a lasting one, on the evidence of your first letter.

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Letter 5