Preston’s Petticoat Punishment

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Status: Finished  |  Genre: Humor  |  House: Stripping and Humiliation

Preston’s arrogance means total emasculating humiliation at the hands of mean girls and two gay boys. He ends up in petticoats and also stripped to his white briefs at school.

Day One: Humiliated Beyond Belief


How it began: a bunch of us teenagers were fooling around at Sherry’s house, with her friends Leslie and Shannon—mean girls, but fun to watch TV with—and two effete boys, nerdy Teddy and pretty Leo, we were horsing around and swinging my arm, I hit Sherry in the head by mistake. This was a BIG mistake and she was mad, and the others were saying Uh-oh—you’re in trouble… I’m telling on you and so on. A boy who hits a girl gets the worst parental punishment.


So I told them I’d do anything if they didn’t tell on me … anything … I’d give them 5 dollars … even 10 dollars. When the girls heard “anything,” and knowing my reputation for posing as a tough guy, they talked among themselves and then announced that they’d keep my secret but I would have to … dress up like a sissy! 

“But a dress of yours wouldn’t fit over my clothes,” I stammered. (It was worth a try.) 


“Oh no!” they jeered. “You’ll strip down to your undies first.”

So Teddy and Leo led me into a bedroom where I undressed, blushing furiously as these two effeminate boys grinned and folded my shirt and pants and put them on the bed.


“Are Preston's clothes off yet?” one of the girls called from the other side of the door.

“Yes, he’s in just his underwear,” said Teddy, and the door swung open a little. “Oooh, here is the dress.”

“Don’t look!!” I called out in a panic for fear of the girls seeing me in my white Hanes.

“We want his clothes,” said Shannon. “Hand them over.”


“That wasn’t part of the deal!” I nearly wailed. There was discussion between Teddy, Leo and the girls in the doorway. “Sorry, Preston, they insist, they say they’re the bosses now. And you have to take off your undershirt. It’s a sleeveless dress with just straps, and a T-shirt would look dumb underneath.” He giggled. “And they say they want to see your pretty little shoulders.


Numbly, I took off my undershirt. Leo added it to my other clothes, scooped them up, and handed them to the girls. I thought, Teddy and Leo are the worst friends a boy ever had!


The dress had two layers of lace for the short frilly skirt, a sheer middle part, more lace at the top, and two silken straps. I reached up in the air while the boys pulled the dress on over my head and adjusted the straps. They stared at me with grinning delight.


I cannot describe the terrible, horrible, panicky, helpless and slightly wonderful feeling I had. The lace swished around my bare thighs. My clothes had been stolen and now I was dressed like a girl! It was like I had taken a weird, strong drug—my head swam with dizzy embarrassment and fear.


“Come on, beautiful! Time to show you off to the girls!” laughed Teddy.


I followed them out into the hallway where the waiting girls screamed with triumph at the sight of me. They made me walk around and kept giving me orders. I could not believe how evil these girls were. It was like they had been planning this for a year. Maybe they had.


“Tell us you’re a petticoat sissy and you want to wear dresses every day.”


“Please, no,” I begged. And just like that, Sherry slapped me across the face. “Ouch! That hurt!” Tears sprang into my eyes.


She slapped me again, even harder, and I tried to protect my face. “Put your hands down! This all started because you hit me. What’s fair is fair. Come on, girls!” They took turns slapping me, and the shame was too much for me. “Oh look, he’s crying!!” Tears were indeed flowing down my face, red from blushing and the mean girls’ slaps. 


“Look at the sissy crying! Look at the little crybaby in his dress because he’s getting beat up by girls! Now, say what we told you to.”


It was worse than any nightmare. Standing there in my frilly petticoat and sniffling, I said, “I’m a petticoat sissy and I want to wear dresses every day.”


This seemed to go on forever. They decided that I should “kiss the girls” as punishment, but like ladies, they wanted their hands kissed—the hands that had slapped me. “Now you have to kiss the boys,” ordered Shannon. “It’s no sissier than wearing a dress, after all.”


I almost begged not to, but to avoid more slaps, I kissed Teddy on the cheek, and then on the lips after the girls ordered me to. Leo took me in his arms and gave me a long, slow kiss on the lips, like in the movies, and that had the girls jumping up and down in glee.


“You’re a great kisser, Pres,” he teased. “If I take my pants off too, will you kiss me down there?”


At that moment, I was rescued by Sherry’s father’s car pulling into the driveway. There was chaos as I was hustled to the back of the house and stripped of the dress, then pushed out on to the back porch to wait in my briefs for them to throw my clothes out the back door. I staggered home wondering if it all been just a bad dream, but my burning cheeks told a different story. And had Leo been serious, even a little? 


Day Two: In WAY Over My Head


At least THAT was all over … or so I thought. The next day, I was sitting with some friends in the school cafeteria, avoiding eye contact with Teddy, Leo, and the girls, who would look my way and giggle. Suddenly here was Shannon standing by me with a slip of paper, saying, “I think you dropped this.” She walked away and I opened it.


Hi, Petticoat Boy, meet us behind the gym after school at 3 o’clock. Don’t be late, OR ELSE.


My heart sank. The rest of that afternoon was a blur.


When I reported to the lawn behind the gym, plenty early, of course (that OR ELSE did not need capitals to get my attention), the three girls were sitting on a bench, with an air of superiority and control, probably because I had followed their orders and was clearly afraid of them.  I stood in front of them in my brand-new khaki trousers, white short-sleeved shirt, and blue necktie.


(I wished I’d been more casually dressed. Realizing now that these girls loved feminizing and humiliating masculine, affluent boys, I worried that my crisp white shirt, nice tie, perfectly creased trousers, and expensive polished loafers made me a provocative target. That and my perfect haircut. Related—I had a queasy feeling at their wanting to meet in this secluded spot. Would they try and humiliate me in the middle of a high school campus? Surely not. Maybe they’d take away my tie and make me beg for it, or maybe drop my pants to my knees for a quick second, just to make me follow orders?)


“Well, how did you like yesterday?” asked Sherry sweetly.


I was really scared to give the wrong answer. If I said I liked it, they would tease me. If I said I didn’t like it, they’d punish me. The fact is, I had both hated and enjoyed it, and couldn’t stop thinking about the terrible thrill of being humiliated that way … and the fluffy lace tickling my bare legs. 


“Uh, I guess you taught me a lesson,” I said carefully.


“You’re getting another lesson on Halloween, in two weeks,” said Sherry. “You’re going trick-or-treating in a dress, with us. Isn’t that great?” They all leered at me. The dizzy embarrassment clouded my head again. I knew better than to cross these girls. I did not dare say that I had a plan to wear a pirate costume for Halloween.


“My parents couldn’t believe it!” she went on with a chuckle. “I told them you’d be coming over and we’d dress you up to help you get your wish of trick-or-treating as a little girl. My dad said, ‘That’s an odd choice for a boy like Preston. His parents said something about him going as a pirate. Now he’s going to wear a dress out there? Doesn’t he realize all the teasing he’ll get?’ Haha! Just wait.” 


“In a dress the whole time?” This was a million times worse than being petticoated and pushed around in her living room!


“An adorable short party dress, and ankle socks, and Mary Janes.”


“I don’t even know what those are.”


“Ha ha, well, you’ll learn the hard way, by wearing them. And no Halloween mask, or makeup, or wig—everyone will get a good look at ‘tough guy’ Preston in his petticoat, going up and down every street in this neighborhood!”


“But … I don’t think your shoes would fit me.”


“Let’s tell him the best part, girls! Saturday morning at 10, we’ll all be going to Macy’s to get your pretty little party dress, and your other girlie things like shoes. You’ll try everything on right there in the Girl’s Department for everyone to see.”


I paused as this horror sank in. Not wanting trouble, I just said, “Uh, you don’t need to buy clothes for me, Sherry.”


“You bet I don’t! You’ll be paying with your own money. Now, we need you to promise right now that you will go shopping on Saturday with us, and try on dresses, and that you’ll be a little girl for Halloween. Got that? If you don’t … well, girls, think we can tackle him and get that school uniform off him?”


“He’d look so cute running home in just his underpants,” said Leslie with an evil smile.


“I think he’d look even cuter running home naked!” laughed Sherry. “Naked except for his socks. Those shoes are fancy—they’d fit my brother. What’s your answer, boy? Oh, by the way, let’s see how much money you have for your new sissy clothes. Give me your wallet. And your answer.”


“I’ll try on dresses for you in the store on Saturday and I’ll dress up as a little girl for Halloween,” I said, demoralized, and handing over my wallet. Total surrender. Sherry looked through it and said, “Forty dollars! That’s too much money for a sissy like you to be running around with. I’ll just take that. In fact, I’ll keep this wallet until Saturday. Got a problem with that, boy? Isn’t it worth $40 not to be stripped naked, right here and now?”


“It’s fine,” I mumbled. I was in for it. I had no idea what to say next, but very carefully, I ventured, “Will they allow a boy into a fitting room in the Girl’s Department?”


“Hmm ... “ They thought this over. Then they whispered among themselves and laughed cruelly.  “OK, that’s no problem. But you know what is a problem? Your backtalk. So take off your pants. Take them off and throw them to us.”


Even behind the school gym, this was risky, but getting stripped naked would be worse, so I stepped out of my khakis and surrendered them to Sherry. Surely these witches would return my pants when this scary conversation was over. I stood there, my white Hanes briefs and white crew socks exposed, the breeze blowing through my bare legs.


“Now, listen here. We’ll go to the Girl’s Department to pick out a little dress and we’ll explain that it’s for you to wear for Halloween. Then you go to the Boy’s Department, to wait for a fitting room to open up. You’ll put it on, and then you have to walk all the way across the store in your dress, back to where we’re waiting! A hundred total strangers will see Preston the Petticoat Princess. Any questions?”


I didn’t dare ask about my pants, but Leslie spoke up first anyway. “What about after he pays for his dress? They always ask, shall we box it up, or will you wear it home? Maybe they should box up his boy stuff and he ends up walking through the mall in his sissy outfit.”


“Great idea!” crowed Shannon. “He’ll have to buy us ice cream to thank us for such a good tryout for Halloween, right? Oh Sherry, you think those pants of his will fit your brother?


“I’ll let my brother try them on this afternoon,” said Sherry casually, watching me to enjoy the sight of me losing all hope. “Okay, sissy boy, you just wait here a good fifteen minutes while we get away. Next time we see those pretty legs of yours, you’ll be wearing a frilly dress in the middle of the Girl’s Department. And we’ll be doing lots of practice sessions for Halloween. Now thank us for all our trouble.”


Bullied, robbed, humiliated, de-pantsed—in public! These girls were pure evil. I stood there in my briefs and followed her orders: “Thank you so much for stealing my pants and wallet. I was hoping you would.” What a loser … but wait, here came Sherry with a parting shot.


“My dad was right, you WILL take a lot of teasing for being a girl for Halloween. We’ll see to that. But a lot of people will say it’s no big deal, it’s just a Halloween costume, just once a year for kids to dress up, leave him alone. SO … what will they say when it’s days after Halloween and you’re still being sighted in your dress? Maybe at the mall. Maybe we’ll grab you on the way home from school. Or dump you off in a bad neighborhood stripped down to just those cute tighty-whities and a petticoat? Don’t worry, handsome, I have LOTS of plans for you and you’ll have LOTS of explaining to do. And it’s going to cost you—big bucks—down to your last cent. Byee!!”


This threat made my brain reel. They left me to wait several minutes before stumbling home pants-less, hiding in bushes along the way, shamed and excited and terrified thinking of the department store petticoating and much more to come. I was just 14 years old, but I knew my world had changed for good. 


Submitted: April 13, 2023

© Copyright 2023 White Briefs and Petticoats. All rights reserved.

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Add Your Comments:


Robert Brooks

Great first story, WBP, liked it a lot!

One thing I would suggest (not sure if you can change stories once posted?)
is that you only tell us Preston’s age right at the end. He’s fourteen, right?
I would have liked to know the ages of the characters at the start so I can better picture the scenes and know exactly who & what age we’re dealing with and not trying to guess. It wasn’t until the end I realised he is actually younger than I was picturing (which is absolutely fine, fourteen is a great age for humiliation!)

But as I say, great first story and now I know Preston is fourteen I have a much more definite picture of him.

Thu, April 20th, 2023 3:32pm

White Briefs and Petticoats

Thank you, Robert Brooks! I have taken your comment into consideration in my more recent stories.

Mon, May 1st, 2023 6:01pm