Bad Boy Gets Birthday Party Humiliation in a Sissy Dress

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

Unruly bully at a teenage birthday party gets his comeuppance in petticoat humiliation for the amusement of all his friends… and then sissy blackmail!

You can consider this to be a letter or a cautionary tale. For me it is my own true story of how a spoiled, cocky rich boy got the comeuppance of a lifetime — petticoat-punished in a way that changed me for good.

It started when my mother sent me to a birthday party for a cousin of mine, a couple of towns over. I would have to go on the bus, and I didn't want to go. It would be mostly girls, and at age twelve I was not yet a fan of silly young females. Also, I was kind of a snob. A whole afternoon with lower-middle class kids attending Sally Sandford's eleventh birthday was no place for a cocky twelve year old (almost thirteen, too!), when I'd rather be playing soccer. But she insisted.

“Preston, please go, and be a gentleman. You can take your friend Eddie to make it more fun.” She added, "Anyway, after all the rain, the ground is too muddy for soccer.”

Eddie was a buddy of mine, a nice kid but kind of a nerd whose hobby was photography. And none of my soccer-playing friends would be seen dead at a girl's party. And so we rode the bus to Milford, though I was not in much of a mood to be a gentleman. I figured I might have fun teasing the girls and bullying whatever dumb eleven or ten-year old boys Sally had invited over. That way, they might let me go home early. 

The Sandfords greeted me and gave cake to me and Eddie. Just as I thought, it was a party out in the yard with squealing girls in party dresses and boys throwing a ball around with no skill at all. I felt superior to everyone.

"What a handsome boy you are, Preston,” said Mrs. Sanford. “The girls will be crazy about you!”

Well, I wasn't crazy about them.  It's true I looked nice in a white shirt, pressed corduroy pants, and my flaming red hair neatly cut short just the day before.

We played tag and it got loud. There were accusations of cheating, and one girl almost got splashed with mud – there was a big puddle of black mud we had to avoid, but I enjoyed chasing the girls near it, to panic them. I was the terror of the schoolyard at school, and here there was no one my own size to challenge me. 

“Mom, Preston is teasing us!" shouted Sally.

“Shut up!" I said. I didn't mind being a troublemaker, but I hate girls who are always trying to involve grownups instead of just taking it.

“Preston, you are out of line. You do not talk that way to a girl!”

Uh-oh.  That was Mr. Sandford's voice.

I had to apologize while the girls smiled victoriously. As soon as he walked away, I told Sally's friend Jane,  "She'll be sorry!”

“Preston is threatening us!"  yelled Jane. Darn—another snitch.

Then it happened. As soon as I started to chase Jane out of the adults' earshot, a third girl came up behind me and gave me a hard shove right towards the mud. I fell forward, breaking the fall with my elbows, landing on them and my knees. All the girls and boys hooted loudly. 

“Oh, Preston," said Mrs. Sandford testily.  I was clearly her biggest headache that afternoon, ruining the party for the girls and now I had ruined my shoes, shirt, and pants.  "Follow me. You'll have to change clothes.” 

The boys had started a stickball game, but they paused to giggle with the girls as I limped up the stairs to the porch, covered with black mud. They all were enjoying my downfall, and the fact that I would have to take my clothes off. Eddie started to follow me, but I told him to stay away. 

“Take off all those muddy clothes, and wash up in there,"  I was told. I went into a bathroom off the living room, undressed, and washed up. Now what?? I was standing there barefoot and in just my underpants! 

“Come out, Preston. We're getting you some dry clothes.” 

Very nervously, I looked around the door and saw Mrs. Sandford standing there holding out a pair of shoes. I stepped into the living room, very embarrassed in just my Fruit of the Looms, but then stopped dead in my tracks. 

“Those are girl shoes!”And they sure were – black patent leather, and the socks were even worse – white and lace-trimmed with pink rosebuds embroidered on them. “I can't wear those!” 

A housemaid had already picked up my pile of muddy boy clothes and carried them away to wash. 

"Don't argue with me," she said.“Put them on. We have three daughters here and no sons. There are no boy's shoes here.”


I sat down and put on the sissy socks and shoes, thinking, "Oh gosh, this is not how things were supposed to turn out."  I had felt sure that if I misbehaved, I would be sent home. I was so busy trying to get the strap through the buckles on the shoes that it took me a minute to see the most horrible sight in the world, much scarier than facing a loaded gun — the Sandfords standing there with a frilly white party dress! 

“No," I said.“Please, no. I can't wear that!”

“There are no boys' clothes here — I'm pretty sure my husband's wouldn't fit you! Come here.” 

I walked over and she made me step into this mass of lace and frilliness. She pulled the puffy little sleeves over my shoulders and buttoned it up the back, then tied the wide pink sash into a huge bow at the back. I could not believe this was happening, and I looked up to Mr. Sandford to see if he might take my side. After all, we were both guys, right? Maybe a sense of male solidarity would make him tell his wife to find something less frilly. 

But no. He was looking at me with the same cold amusement as she was. I had bullied his darling daughter, and he wanted to teach me a lesson. And what a lesson it was. There I stood in a frilly dress so short that it barely covered my briefs. There was no way I could go outdoors like this. 

“I'll wait here until my clothes are cleaned,”I said quietly. 

“Nonsense! It's a beautiful day out there. Come along.”They marched me into the front hallway where there was a full-length mirror.  "How do you think you look?” 

One look showed me a very scared red-haired boy in a dress, and, oh heck! my legs totally bare. I thought back longingly of my pants, how they had covered me from waist to shoes, dark and thick, zipped, buttoned, belted, and buckled, like a fortress protecting me. The exact opposite of now — naked from the lacy ankle socks to the pouch of my briefs, which were barely covered by the hem of the frilly dress. And I had yet another horrible thought —This was my punishment. Maybe they had only daughters, but even daughters have shorts, slacks, blue jeans, even bathrobes. The Sandfords could have found some much less way of covering me, but they were hell bent on humiliating me as harshly as possible. With very slow steps, I walked to the front door, which she opened for me. 

“Look, everyone!” shouted Sally, loud enough for the whole neighborhood to hear. “Preston's wearing a dress!” Every grinning little partygoer had gathered at the bottom of the steps. 

“That's not all. You can see his underpants!”laughed one of the boys. And it was all too true — as they looked up to the top step, I knew they could easily look up my dress, which I desperately tried to gather and press against my legs, all too aware what a girlish gesture this was. To say nothing of the embarrassing feeling of lace and crinoline against my thighs.

The next hour was a blur of being chased around by the girls, who missed no opportunity to lift up my skirt, though I tried to hold it down. Every time I raised my hand to defend myself from one girl, another one would expose my Fruit of the Looms to jeers and hoots. 

I tried to join the stickball game, but the boys – a bunch of stupid little eleven year olds! – told me, "This is a game for guys, sissy boy.”So much for Preston, the bully, the tough guy, the rich kid, the terror of the playground! 

So I snuck indoors to the den and sat on a sofa. Eddie had followed me and sat down beside me. 

“As long as you're dressed like a girl, let's practice kissing. I'll need practice later, for when I date girls,”he said, putting one arm around me and the other hand on my knee. 

“WHAT?”I asked him.  "Wearing this dress doesn't make me a girl.” I pushed away his hand, which had nearly reached my briefs, but he had started kissing me. The next thing I knew, he had pushed the skirt above my waist and was almost on top of me. What was wrong with this boy? Did I look that fetching in the stupid dress? 

“Hold on here – what's going on??”This was Mrs. Sandford. Oh, my gosh. Tangled in lacey girliness and with my underwear and bare legs totally exposed. Eddie looked a little sheepish. 

“Just practicing kissing,” he said weakly.“As long as Preston was dressed like a girl, I mean.” 

“I told you boys to stay outside. Eddie, go outside. And you, Preston – well, well! Such a tease and bully, but give you a few minutes in a party dress, and you're quite the little seductress!” 

What a horrible to say to a boy, but I could tell she hated me more than ever. So I had to go outdoors too, where most of the boys and girls seemed to have gotten tired of teasing me. Until that is, it was time to go, because Eddie and I had to catch our bus home. As the party broke up, we were all standing there as the Sandfords thanked everyone for the gifts and said good-byes. There was no sign of my boy clothes, which I noted meekly. Mrs. Sandford laughed. 

“Oh, I nearly forgot! You mean, you don't want to go home wearing the dress?” 

This renewed everyone's interest in my predicament, and soon we had everyone's full, mirthful attention. 

“I can't possibly go home like this. Or get on the bus like this!” 

“But what if your clothes aren't dry yet? Surely you don't want to ride home in your underpants, but I guess we can make that happen.” 

More roars of laughter. 

“There's a third possibility, ”said Mr. Sandford. “Just stay here overnight. We can send you home tomorrow. We can keep you in dresses all weekend!” 

I nearly died at the very thought, and blushed at the loud laughter her remark got from the girls and boys who were again enjoying every minute of my humiliation. 

When they were through teasing me, she finally unbuttoned the dress and I got it off, rushing into my wonderful pants and shirt, and boy shoes. 

I can still see the smirks on their faces as I left their yard. I knew they would have a very interesting talk with my parents. I had learned my lesson. And I wish I could say the lesson, and the humiliation ended there, but not by a long shot. 

“I hope no one finds out about this, "I told Eddie, who was fussing with his camera, an early digital job. “You won't tell will you?” We were sitting way at the back of the bus, where no one could overhear. 

“On condition,” he said.

That was weird – nerdy Eddie making conditions to ME?! 

“Come over my house on Saturday. I want you to try on my sister's petticoats. No one will see but me.”He smiled shyly.“I want to practice kissing you some more.”

I was trapped, but I could not just take this sitting down. 

“No way. I will never put on girl clothes again. Anyway,”I added, trying to regain some confidence,  "I'm busy on Saturday.  We're going to see the Harry Potter movie. We're going to the afternoon show.” 

“The only show on Saturday is going to be when you show me how cute you look in petticoats, sitting on my lap,” said Eddie. Then he showed me the slideshow on the screen on the back of the camera: Preston in his briefs and girly socks and shoes; Preston in a dress, being chased by girls; Preston looking like was going to cry, with laughing girls pointing to his Fruit of the Looms. Eddie had been busy at his hobby all afternoon while I was too busy fighting my survival. And he had a new hobby – blackmail. 

That's how I was cured of bullying. But for better or worse, I got many hours more "petticoating" therapy from darn Eddie and from my parents, who had indeed heard from the Sandfords, and made a shopping trip to the girls department at the mall by the next weekend. Not only that, my ego took a real beating as rumors spread about my humiliation at that party because no tough guy likes being chuckled at as a "fairy" "pansy" and "sissy." Before that party, I would have beaten up any boy who called me a fag, but when got around about my punishment in underpants and petticoats, I just had to shut up and take it.


Submitted: April 14, 2023

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

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Add Your Comments:



lol!Funny story!

Mon, May 1st, 2023 3:24am

White Briefs and Petticoats

Thanks, CMM!

Mon, May 1st, 2023 5:59pm