Dear Auntie Helga,
At our high school dance party, organized the the stern Miss Graham, the theme was 1950s. Boys in suits and bow ties, girls in ankle socks, saddle shoes, and frilly Bobbysoxer party dresses. Miss Graham had announced that there would be a special game this evening. She paid special attention to matching up me, Gus, and Gary with girls who perfectly matched our height as dancing couples. During a break around 8PM, she called us out of the gym where the dance was, to her office.. She invited the girls into an adjoining office and closed the door and explained to us three boys that the fun was about to start. Trouble was, we'd have to undress ... and ask no questions because everything would be clear later on.
"You three just take off all your clothes - including socks and shoes - and lay your clothes on the backs of these chairs."
We were really shocked and stared at each other, but started undressing until we were all standing there in our white briefs - barefoot, embarrassed, and totally mystified!
"Now go out and sit on the bench in the hallway."
We filed out and sat down, asking each other what was the deal? Was this the "game" she had mentioned ? And why the heck did we have to be in our underwear?
After about fifteen minutes of this, the office door opened and the three girls - Betty, Myrtle, and Heather emerged - wearing our clothes! What?? Short Betty was wearing short Gus's tan suit, and Myrtle was wearing Gary's khaki pants, white shirt, and bow tie. Not only had we had our clothes taken away, and not only were these girls seeing us in our underpants, they had put on our clothes!
Out came Miss Graham and ordered us boys back into the office. Auntie Helga, YOU probably have already figured out what came next, but we were still bewildered - until we saw the girls' clothes laid out on the chairs. She ordered us to put them on - I was handed Heather's snowy-white short party dress, Gus was directed to put on Betty's hoop skirt, and so on. We tried to argue but Miss Graham shut that down fast. And then we were handed purses. They had gone through all our pockets and emptied them, and taken our wallets, change, and key rings, and put them in little handbags that matched our outfits. Then we were standing there in dresses, dizzy with humiliation. I was the first to speak.
"Miss Graham, we haven't done anything wrong - we're not delinquents or bullies. We're good boys with great report cards. Why are we being punished?"
"Nonsense, Tony. Sometimes girls like to wear the pants, that's all - and that is even more amusing when boys have to wear the dresses! We girls love springing surprises like this. And life isn't fair, you know. Now let's all go back into the gymnasium to resume dancing. And remember to let the girls lead!"
"Then we'll get our clothes back?" asked Gary hopefully. Now wonder Gary was most nervous - the pink ribbon from Myrtle's pony tail had been tied in a bow to the side of his head, in his short blond curls. "Absolutely. At nine-thirty sharp, we'll come back here and you can change back into your shirts and pants - guaranteed. That's a promise."
You can just imagine the hilarity of our classmates when we walked back in, boys and girls wearing each others clothes. So this was why we had been matched physically! Not for dancing but because we'd fit in each others clothes. I was dying of humiliation as Heather twirled me around to the music - way too much twirling, with hoots and whoops as my dress whirled up, exposing my underwear to the hundreds of spectators.And that silly little purse around my wrist was such an embarrassing touch.
Somehow we survived until 9:30 and the three boys hurried into her office where she and the three girls were already laughing and talking. "We were just saying how much fun it will be for the girls to go home and explain to their families why they are wearing boy's suits - and how much more delightful it will be for you boys to go home and explain why you are dressed up like girls!"
Our eyes bugged out at that! "B-b-but you promised we'd get our clothes back! You promised!" blurted Gus. "Did I? Oh, I suppose I did. Well, it is a woman's prerogative to change her mind. Get home safely, boys. And - life isn't fair. That might be the main lesson you are learning."
Well, after much protesting in vain, we left out the back way. Gary said his family was strict and conservative and he couldn't show up dressed like a girl. He actually took off the dress and left in in the hallway. He would find some excuse for showing up in his briefs.
His house came up first. We shook his hand - Gus and Tony, miserable is our girlie dresses - and thought Hmm! There he goes up the front stairs of his house in his underpants - but how was he going to explain his girlie socks and the saddle shoes and purse, and the pink ribbon he had forgotten to take out of his hair? We could have warned him about that, but we decided his darling hair ribbon would make his talk with his parents even more ... interesting.
Gus groaned when we heard music blaring from his house in the next block. "My sister has all her friends over tonight. Not only did we get outsmarted and tricked out of our clothes by scheming girls - these females are going to give me a horrible evening when they see me like this!" He sighed and headed up the stairs to his humiliating fate.
That left me walking home with waves of humiliation washing over me - a lone boy dressed up like a girl for no reason at all! The wind blew through my bare legs and lifted my light skirt so that I had to gather it in and hurry along taking mincing little steps. I had just learned that wearing a dress forces even a manly boy to walk and act like a girl. He has to walk differently, and sit differently, and really avoids mirrors!
But I did not go home right away. I had this horrible but sweet sensation of public sissy humiliation. When cars slowed down and boys laughed at me, I got excited. I decided that the next morning when I went back to school to reclaim my boy clothes, I would go wearing this same girlie outfit, in broad daylight. I hoped Miss Watson, Betty, Myrtle and Heather would see me like this and make me curtsy to them. I knew all the teenage boys and girls would never let me forget my "public petticoating"! Did Miss Graham know that she had touched a nerve - that she had turned me into a dress-wearing sissy boy not for an evening, but for years to come? These tough ladies must be very smart, I thought.
Well, of course I did get a sense of the motivations the next day, when I did - shaking with fear! - put the dress back on and walk to school. Miss Graham was a little taken aback - but smiling - when she saw me, and explained that Heather had left my clothes at home, so she could not help me. It turns out she had a very strong bond with a couple of those girls, who thought it would liven up the dance to humiliate some boys. They made the decision not only to de-pants a few of us but to make us wear their clothes. They also thought it would be fun to choose us at random rather than to go after bratty boys who needed to learn a lesson. And that made the prank easier - bad boys might have resisted or refused, but we were straight-A students and respectful boys who obediently undressed and took part in our own sissification!
I asked Miss Graham if she and the girls were satisfied with their "game," and she invited a few girls in to view me in the frilly dress and ask if it had been a success. They looked delighted at seeing me still dressed up, and listed their favorite moments - seeing us stripped, seeing us humiliated in the petticoats that had been forced on us, seeing the whole student body react to our sissified state, and of course the worried and scared looks on our faces when our boyish hopes were crushed by these dominant ladies - when we learned we'd been cheated out of our boy clothes and would have to walk home dressed like girls.
Of course Miss Graham did ask why for goodness' sake I was wearing the dress? Of course I couldn't give an accurate answer like "Because it's a thrill feeling petticoats tickling my bare thighs," or, "It's exciting to be teased by boys and outnumbered and humiliated by girls," or "I thought this might be the last chance I'd ever have to be dressed up like a sissy" (ha!) so I gave a totally stupid answer: "I was afraid you'd make me strip down and wear a dress anyway, and I didn't want the embarrassment of being seen in my underwear again. So I figured the only way you can't make a boy dress up like a girl, is if he's already wearing a dress." But I think her intuition told her that, even though I had seemed like a straight arrow at first, only one kind of boy would wear a party dress into a high school in broad daylight! It was so short and girlie that it would have been out of place even on a girl in that setting.
But Auntie Helga - how common is this? I had never heard of boys and girls being forced to exchange clothes, especially when it has nothing to do with punishment - just for ladies to put boys in a predicament.
Thank you for your letter Peter. I must admit that this is rather unique to me as well, though cross dress day in schools is becoming more common though really meant to teach gender equality.
Your strict teachers motivations are a bit of a mystery as well, but whatever the case, the issue is that you learned something about yourself and the fact that you are writing me speaks to your realization about being a sissy.
It could also be that sometimes girls just want to have fun...