Preston's Strip-Humiliation on the Wrong Side of Town, Part 3

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

Preston's humiliating day is finally over, but not before some severe public humiliation and an appearance onstage in his underwear and sissy petticoat in front of some of his worst rivals. He learns that his future is not going to brighten at all, thanks to the mean girls controlling him!

Leaving the depressing drug den house, I had mixed feelings. I had escaped molestation, but it was no picnic being in just my underwear and the swishy little petticoat—leaving me mostly naked. It had not even occurred to me to inform those two policemen how Sully and his crew had stripped me out of my expensive clothes and sold them online right in front of me and gone on to line up paying customers for my sexual humiliation. Life felt extra unfair today.


To avoid some approaching pedestrians, I ducked into an alley parallel to Main Street, but only tried that once. The alleys were worse—drunks and crazy-looking guys, old and young, lounged on steps and called out insults or invitations to me. Back out on the street, every who saw me laughed and stared. I’d been stared at a few hours ago, walking these streets because a clean-cut white teenager in a suit and tie was a weird sight. You can imagine how people gaped at a white boy naked except for his white briefs and a ruffled petticoat. 

A number of cars slowed down and guys urged me to get in—twos and threes of grinning men. I had learned my lesson not to do that again. While most of the shop fronts were boarded up with plywood, there was one glass window (pawnshop, of course) that I looked into just because was the only glass shopfront I’d seen. But of course, what I saw was my reflection, looking scared and ridiculous, in a petticoat so thin that that I could see that all the details of my underpants—leg bands, Y-front fly, even the word Jockey repeated all around the waistband—were totally visible! 

I hurried towards 20th Street, which was only a partial relief. The dimly-lit- high-crime, largely deserted ‘hood was behind me. I was entering the safer and wealthier part of town, but because it was well-lit and busier, I was now at much greater risk of being seen, including by people who knew me. 


“Hey sweetie! You look lost!”


Another car was slowing down, but this was a girlish voice, and did I get a shock! It was Sherry and her two friends, Leslie at the wheel.

“Am I glad to see you!” Words I never thought I would say, especially since these witches were responsible for my predicament. “Can I get in?”

“No,” said Sherry. The car parked at the curb and Sherry and Shannon got out. “My, my, you poor boy! Where are your clothes? What on earth happened?”

As always, any sarcasm or “attitude” would mean deep trouble. I took a deep breath and said, “Uh, maybe I got the wrong address. There was no needy family, just guys who deal weed who robbed and stripped me, sold my clothes, and were going to rape me before I escaped in my underwear. They still expect me to come back there for some guys to, uh, get romantic with me. Oh, but thank you for the carton. Without this petticoat, I’d be walking home in just my tighty whities.”

“So you never found the family who needed our help! You need to be punished for that. And I hear there is some missing money. And that you had a brush with the law. Preston, why is so hard to turn you into a nice sissy boy who stays out of trouble?”

Their smirks showed how much they savored this total lie. Even though it was all their doing, I did feet a little safer talking to them instead of being alone on the sidewalk. They were wearing slacks and long-sleeved jerseys, so I did feel embarrassed at being the only boy and yet the only mostly nude and in a petticoat. I had no choice but to respond as submissively as they wanted.

“That was my fault. I was so confused that when three tough guys told me to undress, I didn’t know what to do. A good sissy boy does what he’s told. And seriously,” I added, “That’s the kind of trouble I don’t need more of. You girls are harsh on me, like a boy needs, but thank you for no violence like those guys showed me—pervy men are the worst.”

“And even more than that, we came to find you here. Nice girls don’t go up into that neighborhood, so when we heard you were walking home, we decided to meet you here.” (But not give me a ride home, I thought.) “We’re on the way to the crafts fair award ceremony, that’s why we can’t drive you home. We’re being presented with an award. If you stay in the car, no one will see your … your revealing little outfit.”

Wow! Wary I never trusted the girls, I thought they might be making up for the misery they’d caused me. And they weren’t lying—everyone knew about the final night of the crafts fair and the awards ceremony. The stage and seating had been set up by Boy Scout volunteers and a local soccer team—I’d heard that through my own soccer team. And I could stay in the car! This sounded lots better than walking two more miles home in a petticoat. But I’m sure there was a catch, though if I asked “What’s the catch?” I’d be asking for trouble.

“Anything else I need to know?” is how I put it.

Three boys with liquor on their breath emerged from the shadows and whooped when they saw me. “Cute undies! Hey ladies, can we borrow your sissy friend?” One of them lifted my petticoat as I turned around. “I want to keep your underpants after I do you,” he laughed.

“OK, you can get in,” she said, and I scrambled into the back seat. “Wow, thanks! Congratulations on the award! What’s it for?”

“Most funds raised,” said Shannon. “And thank you for taking us to the best total of all the girls’ clubs!”

I was confused. And confusion with these girls only resolved itself in the same horrible way … usually.

“Why yes Preston! When we heard that you promised Sully that you’d happily give him $500, we figured you can give at least as much to a good cause as you’d give a weed dealer so we put you down for a pledge of $500. You also own us for the petticoat and choker you’re wearing. Don’t you want to thank us?”

(It was one of their rules that not only did I only accept petticoat humiliation, I paid for it—every ruffle, ribbon, and petticoat they put me into was paid for with checks—for inflated prices—in my name with my having to write “For petticoats” on the lower left. They never missed a chance for blackmail.)

“Uh … thank you. Good thinking.” Ouch! $500 for these witches? But if I could buy my way out of trouble …

“I mean, don’t you want to thank us at the fair?” Sherry turned to Shannon. “Please take out your phone and make a video of Preston’s answers” Shannon, opposite me in the back seat, did no.

“Uh, where exactly? When?” And the biggest question—what had I fallen for now?

“In about twenty minutes on the stage at the fair. Well, don’t you want to thank us in front of all those high school girls and their older brothers, and the Boy Scouts and soccer team that did all the work? Don’t worry, it’s not your team, the Comets, we’d never embarrass you in front of them. It’s the Tornadoes from across town at Altamont Prep. And I hope you did not forget your best friend, Rico! He’ll be there. He has something to tell you.”

I was speechless--luckily, because saying the wrong thing would lead me into deeper trouble. The Tornadoes had set up the stage and the 200 folding chairs? They were our biggest rivals. Teenage boys are good at prioritizing the terrors that face high school juniors in suburban America, so I knew that however much Raul could humiliate me by having me make love to his eight inches of cock (which I had held in my hand, ewww!) was nothing in comparison to what eleven boys of the archenemy Tornadoes could do to my reputation after seeing me publicly shamed in my underwear and a petticoat. I, Polytechnic’s star goalkeeper, had blocked a hundred Tornado shots on goal and made us the city champions. I was their number one enemy. And I had to appear on stage in front of them like this? I was looking into Shannon’s iPhone camera.

“I would love to appear onstage to confirm my $500 pledge and thank you,” I said numbly. “May I please have that privilege?”

“For just a ‘brief’ appearance’ (they all laughed at the corny joke) or for a nice long speech in your tighty whities and petticoat? Answer in complete sentences.”

“I would like to be on stage as long as possible in my tighty whities and petticoat, please, not for a ‘brief’ appearance I said numbly. Any other response would get me severely punished. “May we please make sure that all the athletes at Altamont Preparatory School understand that I am a dress-wearing sissy boy?”

“If you insist, Preston! It’s a craft fair though, and so many girls will be so good at sewing, and they’ll feel sorry for you and offer you joggers and tops they’ve made in denim, and I really think you should accept any offer of boy clothes.” All three of them gave me mirthful but hateful warning looks, even Leslie in the rearview mirror. I stammered.

“I think a sissy should wear nothing but his little-boy underpants and girlie petticoats. I hope no one offers me any other clothes.”

“We’re ready for the fair,” Shannon told Leslie. “Hit the gas.”

The girls led me through a crowd of hundreds of fairgoers. I endured the usual laughter and stares, though unlike in the bad neighborhood I was not called a fag or fairy. As we got near the stage the Fair organizers welcomed us and congratulated the girls and stared at me. “Will your benefactor be appearing … uh .. with no trousers on? It’s not Halloween, you know.” There I was in my petticoat and the lace-trimmed pink ribbon around my neck, just three wooden steps up to the stage and into the view of hundreds of people.

“Why, come to think of it, weren’t you all dressed up in a suit and tie earlier?” cruel Shannon asked me. “How did you end up like this? Do you like wearing sissy clothes?”

“It’s too late to change, so I guess I’ll go out there like this,” I said to the astonished organizers.

When it was the girls’ turn to award their prize, Shannon gave a speech and mentioned that nearly half their total donations had come from a single generous young gentleman. “You all know him as the star of Polytech High School’s champion soccer team!”

“BOOOO!!” yelled all the Atlamont soccer team players from the front row. My heart sank!

“And we insist he come onstage to be acknowledged. And I’m sure can’t wait to hear his remarks! Ladies and gentlemen, Mr. Preston Berwyn!”

The applause turned to loud laughter as I stepped onto the stage. Girls screamed and the Tornado soccer players all pointed and grinned at each other. There were cries of “He’s in his underwear!” “Tighty-whities!” “What’s wrong with him, has he gone crazy?” “He’s wearing a petticoat!” Most of the older women looked amused. I was shaking like a leaf. Ashamed, I looked down, instead of out at the audience, but it was no fun seeing my near nakedness except for my underpants and the petticoat, which was swishing around in the breeze. Because it was nearly dark, the bright lights on the stage (thank you, Boy Scouts!) made the lace and my tighty-whities extra white.

“Thank you, Shannon,” I stammered. I couldn’t think of anything to say. The laughter just got louder. “I am happy to help.” I was staring at the floor. When I looked up, I saw dozens of cellphone cameras being held in the air snapping photos of my humiliation. “That’s all.”

Over to the side, Sherry went to the table where a big desk fan was whirring, to keep the seated committee cool in the warm evening.

“And thank you Preston! May we ask you a question? I think everyone here is wondering why you have no clothes on! Except for your pretty petticoat. Do all the boys on your soccer team wear petticoats?”

Amid the roars of laughter and shouts of “Yes they do!” from the Tornadoes, Sherry shifted the fan low and aimed it at my knees. The lace petticoat flew above my waist, revealing my white Jockeys even more brightly, and I panicked, trying to hold down the ruffled hem. The laughter got even louder and there were more cellphones held aloft. All I could think of was how Shannon’s last witticism would get me murdered by the Comets! I ran off the stage in terror.

It took a long time to restore order, judging by the hoots and laughing, but I didn’t look back. The girls found me cowering by the parking lot, getting an earful from one of the balding organizers.

“Maybe I just don’t want to know what this exhibition was about, young man, but you certainly made a scene out there~! What is your school principal going to say about this? It’s a prank in very poor taste! I hope you don’t enjoy wearing dresses!”

“Don’t worry, we’ll take care of him,” said Sherry. “What do you have to say for yourself, Preston?”

“Um, thank you. I don’t know what to say.”

They led me to their car. It was quite late and it had been a long day, forget that I’d had a whole school day before the contrived adventure that got me stripped and taken here.

“Well, I guess we should give you a break. It’s hard on a boy being petticoated, especially all afternoon, and then in front of all those nice people. So you can take it off now. And your pretty ribbon. We’ll keep these for next time.”

“You know, I think part of your trouble up on 40th Street was your being dressed too nicely.” (What?! These girls had made me go home and change from my good school clothes into a fancier jacket and tie! Of course, I couldn’t say a word.) “Not only your nice shirt and trousers, which just begging to be stolen off your back in that neighborhood, you know, Jockey underpants are pricey. At about $20 for a three-pack. Boys up there wear Fruit of the Looms or Hanes briefs, which are only about $15 for a five-pack.” (I was SUPER embarrassed at hearing girls talk so knowledgably about brands of tighty-whities, especially since at the moment that’s all I was wearing!) “Maybe if you wear Fruit of the Looms next time, they won’t chase you around.”

“I couldn’t agree more,” added Leslie. “It’s a provocation, a rich boy showing off his Jockeys in front of all those underprivileged young men. And you look so cute in them, no wonder they wanted to get romantic with you. We certainly did our part to help, providing the petticoat to protect your modesty.”

They laughed like witches.

“In fact, hand over those jockey shorts, they did nothing but get you into hot water today.”

My jaw dropped. I really had not seen this coming.

“Or should we take them off you? Not here in the parking lot, naturally, I think back up there on the stage would be lots more fun.”

Blushing … beaten again, I stepped out of my underpants. Sherry snatched them away. Of course, I kept my arms by my side. Any shy attempt to cover myself would earn me a few hard slaps. They liked seeing me in underwear or sissy petticoats, but bareass naked was a special treat.

“No wonder all Rico’s friends want to get their hands on you. By the way, Preston, with all the fun you have being turned into a sissy boy, are you a full sissy boy yet? I mean do you like boys or girls? Remember, if you try and lie, you’re all ready for a spanking, being naked and all.”

“No,” I said. “I don’t like boys, but the boys who’ve seen me in petticoats always call me a fairy anyway. Girls … I’m afraid of girls.”

“Afraid of girls?” crowed Sherry. “And why on earth would that be, my little naked fairy?”

“I’m terrified of girls, because of all the … uh .. training you’ve given me. Every time I see a couple of girls coming towards me, I get panicky because I’m worried they’ll strip me.”

Their triumphant smiles showed pride in this achievement—turning a rich, good-looking A student and athlete in a shivering naked coward afraid of girls. And afraid of what was next … shouldn’t I be getting home?

“You can go home just as soon as Rico gets here—oh here he comes!”

It was Rico from the drug house. Up till not I had seen him only in his old polo shirt and boxer shorts, but now he had on a sweatshirt showing a white tee underneath and gray slacks.

“Sorry to run late and miss the show,” he smiled. He looked at me looking surprised. “So did Captain Underpants do it without his underpants? I didn’t think our boy would be in the buff.”

“He was a little shy, but it was a total success. I’m sure he has a lot more admirers after giving his speech in his petticoat.”

“Fuck, the balls on this boy,” said Rico. Readers will remember it Rico was the one who had taken the lead stripping me, deciding how I should be tied up for his friends, and who had lined up Raul to be the first customer. I wasn’t very glad to see him, and I didn’t say anything. “I’ll take our boy. No, Preston, don’t worry, I’m not kidnapping you. I gotta see this famous address of yours. Girls, like we discussed, get me the list by tomorrow. We gotta get moving.”

The girls assured him Yes and hurried away. There I was naked with the drug guy I feared the most. “Hop to it, Captain No-Underpants,” he said, and led me to his car. Once inside, he was all business.

“Here’s the thing. Raul is very unhappy and we kept his money, so we need to make him happy again. So, first thing—your ass is his--don’t let anyone else fuck you before Tuesday. That’s your date back at the house. Got it?”

“Trust me, I have no plans to get fucked before Tuesday. Or on Tuesday, or ever.” I thought I could be a smartass with Rico, the way I would never dare with the girls. “If you took Raul’s money, how is that my problem? I don’t want to see you guys again, okay?”

“That’s bold talk for a naked rich boy in my car,” said Rico calmly enough. “Don’t give me the tough guy act, Captain No-Underpants. Second thing—it’s a big deal to Raul that he’ll be your first, up your ass I mean. Blowjobs are another thing. You gotta have experience or you’ll gag and ruin it for him. So the girls are making a list of gay boys at your school you can practice on. Like your teammate Percy. They say he has a crush on you.’

“Percy has a crush on half the team, and on the coach, and on the history teacher. If I suck Percy’s cock, he’ll think I’m his boyfriend, and I don’t want a boyfriend, or to hurt his feelings.”

“How touching. You’re going to blow Percy and at least two cocks a day between now and Tuesday. You gotta learn to hide your teeth, not gag, take it deep. Big and small cocks. You got that?”

I didn’t answer. We had entered Country Club Estates and Rico was distracted by the huge houses, wide lawns, and expensive cars. He paused in front of my house but didn’t stop.

“Whoa, that’s my house. I have to get out here.”

Rico kept driving, put his right hand on my knee, slid it up to my cock, and then reached up to grab my chin. “I said I wanted to see the address. I’m not stopping there. I don’t need your fucking neighbors seeing you get out of my car naked.” He drove out of the neighborhood to Main Street and sped north past 20th Street and past 30th. We were getting dangerously near the scary neighborhood. After crossing 35th, he pulled into a gas station—not only closed, but out of business. He parked the car behind it and said, “Get out.”

I was afraid to get out, but who wanted to remain in his car? I got out and he came straight over to me. “OK, Captain No-Underpants, we need privacy, but we got stuff going on at the house. We’re OK here. Now don’t take this personally, but I’m going to give you a lesson. Back at the house we asked you if you ever sucked cock. You said no. Now tell me—has anyone every sucked your cock?”

“No!” Again, no lie.

“Well, your first time is going to be naked in an alley—sorry.” He ruffled my hair and stroked my balls. I didn’t get aroused or shrink from disgust. “Notice what I do. Both lips as far as possible to the base of the cock, and back up again, up and down. Most important, tongue always against the underside of the cock. Tongue action will make him blow his load faster. Pay careful attention because then you get your test.”

I cocked my head in curiosity.

“Your test is going to be sucking my dick. Just a test run. And—don’t get any ideas about running away again. I wouldn’t advise that at this time of night.”

Then Rico dropped down and took my cock in his mouth and stroked my balls again. He looked up at me with his big dark eyes as he showed what he had said—lips down to the base, tongue against my cock the whole time.

I have no taste for porn, so I’ll keep this short and sweet. I liked it. Unlike the queasy sexual sensations I got from the girls humiliating me in public in white briefs or petticoats, this felt 100 percent wonderful. He stopped.

“OK boy, this isn’t a date, it’s a demonstration. Now you do it. Not a blowjob—just give me one minute to show me you were listening.”

I wished he had continued what he was doing. And heck, here I was getting my first sexual experience, in public, and with a guy. I didn’t enjoy it as much as having it done to me, and I couldn’t get as far with my lips as he’d done, but I used my tongue, and unfortunately passed the test, because he said, “You’re learning. Keep sucking cocks between now and Tuesday and you’ll be fine. I can’t give you advice about getting fucked, although … “ he lowered his voice, “If you’re not into getting fucked, give the blowjob your all. Raul has wanted you since he saw your picture in the paper with your soccer team, and you are a very cute boy. If you can make him blow his load with your mouth, he might not be up for a shot at your ass.”

“Thanks,” I said, to this guy who had been a cause of my ruin all day and had just molested me. “Can you take me home now? You can drop me a block or two away. I wish I weren’t naked. You don’t have any extra clothes?”

Raul thought a second and then undid his belt and took his pants off. There were those full-cut boxer shorts again.

“I don’t want you to be naked in your neighborhood. Those are big for you but roll up the cuffs." He paused before kissing me on the lips.

Twenty minutes later I was walking down my street, bare chested but in Rico’s warm gray slacks—the only pants I had worn since this afternoon. My mind was a mess. Petticoated in front of an audience after nearly being raped, chased around in public in just my briefs. I was right telling the girls I was very scared of girls. But mainly, the way Rico had touched me and looked up at me from my cock…his big dark eyes and eyelashes. Oh fuck, I was thinking, I’m pretty sure I might be a homosexual. And falling for a thug. And totally dominated and controlled by girls!  



Submitted: April 19, 2023

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