Preston's Strip-Humiliation on the Wrong Side of Town, Part 2

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

Preston falls into the clutches of a gang who rob and strip him, escapes in his underwear chased by a mob, and ends up in even worse trouble than before. Of course those mean girls at at the bottom of it!

Of course, I did realize that there was no way the carton contained this imaginary $500 the girls had invented to get me into this predicament. But I had to buy time before Rico advanced his plans to make me a sex toy for his friends. 


“First things first. Money money money! Sell his clothes and get Raúl over here!” Sully reached for the carton and put it on his lap but was focused on his cellphone. “I’m texting our girl Sherry who sent him here. I’m telling her …’Hey doll, you sent us your boy with an empty envelope. So we ain’t got no cash, and your boy ain’t got no clothes on no more!” He seemed to find this hilarious.


“You’re one scared white boy,” chuckled Lee. “What happened to that confident, well-dressed guy who knocked at the door before? Well he ain’t well-dressed no more!”


“I texted Raúl,” said Rico. “Lee, you’re in charge of his clothes. Are we taking his shoes too? 


“Of course we are!” said Lee, who was busy on his phone like the rest of them while I stood there like an idiot in my briefs. But I wasn’t being ignored--the jeering and staring youngsters outside the window had not gone away.


Lee had looked at my clothing labels for some online research on his cellphone and whistled. “Damn, those are expensive threads! The pants are imported from England. The loafers cost $300! Never mind fencing them downtown, I got a connection who’ll buy all of it.” He had already texted photos of all my clothes to this criminal friend of his, who agreed on a price and wanted to know how soon they could pick them up.


“They’ll be here in half an hour,” Lee announced. He looked at me and added, “Sorry, Captain Underpants, these buyers are chicks. You are going to have some ladies checking you out in your skivvies!”


They were all business. As drug retailers, they were fast and savvy and profit-oriented. I was a business bonanza for these thugs! 

Sully directed Rico: “Tell Raul and his network we caught a fag … at least pretty soon he’s going to be a fag. Fair hair, blue eyes, smooth and pretty young white boy. They can line up. If they pay $50 each to fuck him, and we sell his clothes and watch, and if Captain Underpants comes up with $500 like he said, we come out way ahead, in the thousands. I’m starting to enjoy myself!” He reached into his pocket for matches and a joint, and fired it up.

They passed the joint around for a discussion they all found hilarious. Their druggy conversation turned how to control me for Raúl and other sex customers. Tie me to the bed spreadeagled on my tummy? “No,” said Rico,“they’ll want to see his face and those big blue eyes while they fuck him, especially because he’ll be crying, I bet you anything. So we can tie him down on his back. They can lift his legs up and fuck him that way. Also, it’s time consuming describing your boy. Heck, I’ll just text them photos.”

Rico aimed his phone at me and took a few pictures. “Take off your underwear I gotta show them your ass and cock.” I dropped my briefs to my ankles, numb with fear and humiliation.“Wow, I’ve never seen pubic hair that color, kinda golden reddish. I bet Raúl will want to clip some of that off for a souvenir. Nice cock for a white boy. Have you ever been fucked?" 

“No, absolutely never!” I said and at least this was no lie.

Rico stepped over and got his hand between my buttocks. I felt a finger probing me. 

“I’ll buy that, he’s tight. I couldn’t even get two fingers up there! Raul will have to pay extra for getting a first-timer. Hey look, I already have a response! He’s on his way over. Good news and bad news, boys. Raúl wants Jimmy here. But you can’t give his clothes to the buyers yet. Raul is spreading the word that we caught a cute young fag, but he doesn’t want him naked. He likes to strip a boy with his own hands. He says he never got his hands on a young preppie boy this cute, and he wants to enjoy it. So Captain Underpants here needs to be dressed up all pretty in his nice clothes.”

Wow, I’d get my clothes back… for a while anyway. Might this mean a window for escape?

“But the girls will be here soon to take his clothes,” Lee objected.

“Don’t worry, everyone will get what they want. You see, I know Raul’s kink. When his crew were teenage punks, they used to mug the Poly High boys. Grab them in an alley and steal their shoes and pull off their pants. You got a rich kid’s pants, you got his wallet too. They were too embarrassed to go to the cops!”

“Jimmy or Preston, pull up your underpants. I like girls, remember, Rico? I can’t get high looking at some naked dude’s junk,” said Sully.

I pulled the briefs up. With everyone making plans to steal and sell my clothes AND my ass, we had lost track of the carton. “Did you get a WhatsApp answer from the girls?” I asked Sully.

“Shut up and put your clothes on so you look pretty for your date. Lee, give him his duds. He’ll only have them on for a few minutes anyway.”

My relief at actually putting on my pants and shirt was just incredible. Could I make a run for it? They were pretty high after all … but then a new development crushed me again.

Rico was active on his phone and directing Lee, who looked surly at having to let me get dressed. “Raul will be here any minute. Damn! He recognizes our boy! From a picture in the paper. Soccer team champs. You play soccer? And you name really is Preston? … Lee, get on .. Preston Collins Berwyn. What a stuck-up fruity name! That you?”

“Yes,” I said, wary at being fully identified.

Lee was fast. “He lives at 5200 Country Club Drive. Zillow says it cost in the millions---six bedrooms! We got ourselves a rich boy for sure. GoogleEarth shows it with two Cadillacs in the driveway.”

A knock at the outer door and Rico said, “Raúl!” Who strolled in and exchanged fist bumps with all three of my druggy kidnappers. He circled me with a look of utter delight on his face. He was a decent looking guy of almost 30, prematurely balding and Puerto-Rican looking.

He ruffled my hair and said, “You’re even prettier than the pictures!” He kissed me on the lips. “Drop your pants, pretty boy.”

“Drop ‘em!” said Lee. “The girls are ten minutes out and you have to have all those clothes off.”

I unbuckled my belt, unbuttoned and unzipped my khakis and let them fall to my ankles. Raul’s right hand was instantly cupping the pouch of my briefs.

“Pretty legs, nice package … briefs boy naturally. Faggot. You a fuckin’ fairy?” This took me by surprise and I looked scared. He leered and laughed softly. “In this neighborhood where we live, you tell a boy to drop his pants, he’ll give you a beatdown. You’ll be in the hospital. But you soft rich boys just drop them. I have a lot of experience. Fairy. Fuckin’ fairies. Now let’s have that tie off, and all the rest. And you can step out of those pants.”

I tried to look away as I undressed myself, and noticed that the crowd outside the front window had doubled in size and was mostly teenagers, laughing and pointing at me. I felt lucky I couldn’t hear what they were saying!

“Raúl, it’s going to cost you a hundred. He’s never been tapped. Finger him and see. OK?”

Raul did not take his eyes off me as he handed some bills to Rico, and Lee stood there grabbing the clothes I was removing. “I’ll take these out to the girls,” he said. I could hear female voices at the front door.

“We’re getting $400 for your clothes, so kiss them bye-bye,” laughed Sully. “Now you are Captain Underpants for good. Don’t ask me how the fuck you’re getting home. If we ever let you go.”

“My fag isn’t going anywhere, said Raúl. “Except upstairs with me. Right boys?”

“Get the rope,” said Sully. “Use the bedroom in the back. His first time will probably hurt and he might holler.”

Lee and Rico went into a back room while Sully finally paid attention to the carton, and Raul grasped my elbow and escorted me out of the room. The staircase was on the left, and the front door on the right. The women who had bought my stolen clothes had left it half open. On my left, Raul had opened his fly and pulled out his cock, and forced my hand on it. He ruffled my hair and saw me glance at the open door.

“You like cock, faggot? You’re going to love it. I’ll take some nice pics of you sucking on it before I shove it up your sweet little ass, Preston Collins Berwyn.” He lowered his hand to stroke the seat of my briefs. “You lookin’ at the door instead of my cock? Gonna make a run for it, faggot? Just try. Just try it, faggot.”

This was my only chance, with the other three in other rooms. I was wearing nothing but my underpants and white crew socks, but as a soccer player I was light and fast.

“Get him!” yelled Raul. I had bolted out the door and down the steps—right into the arms of a dozen jeering teenage boys. Several hands grabbed at my cock and the waistband of my underpants. I brushed past them and dashed down the sidewalk. “Catch him, and you get $100!”

“We’ll get him!” Some of the boys were on my heels but laughing so hard they weren’t fast. I turned a corner and saw some young toughs vaping on the next corner.

“Stop the white boy!” my pursuers yelled. “He’s running away! Get him!’

“Where are your fuckin’ clothes?” asked one of the vapers, who tried to block my way.

“Get him! Let’s get him naked!” I don’t know who had the bigger adrenaline rush, me or the boys chasing me who wanted to get me naked and would probably give me a beating.

A car cruised up beside me with two young Latinos in it. “You in trouble, mister? Get in.”

It was a split second decision. Get into a car with strangers, or get stripped naked by a mob? I opened the rear door and got in.

“Please hurry!” I said. “To any bus stop, please. Or can you drive me downtown? I’ll pay you anything you want. My family’s rich.”

The driver just looked at me in the rearview mirror. “Rich boy in his underwear being chased around the ‘hood? What’s the story, handsome?”

He started to drive away, but slowly enough that the car was almost surrounded by the boys yelling for them to give up the white boy.

I explained that I had been tricked and lured here by some people who had it in for me, and that a weed dealers, Sully, Lee, and Rico, had stolen my clothes and were going to let me get raped by a friend of theirs. The driver and the passenger looked at each other but said nothing. I noticed that they were not driving in the direction I wanted. Heck. Had I over-shared?

“That’s too bad, handsome, said the driver. “I’d like to help you, but Sully’s crew is a big deal in the ‘hood. Everyone knows them. What do you think?”

There was a pause before his friend answered him in Spanish. They talked in Spanish for a while, not smiling, and seemed to be driving around and making turns at random. Or not so random. The driver swung a right, and I saw that we had just entered 40th Street. We had gone in a circle. I had talked too much. If I had just said I’d been mugged, they might have driven me to safety. But up ahead on the right was the house where I’d been robbed and humiliated, with a few teenagers standing around and two uniformed policemen on bicycles. Sully and Lee were out there talking to them. The car pulled up to the police and the driver said, “Get out. Sorry, handsome.”

“Please keep going! Take me anywhere!” I begged. But too late—the small mob of teenagers who had failed to catch me now opened the car door and pulled me out. Everyone stared at me, the cops too.

“Somebody forgot his pants!” said one cop. “You feel a breeze, mister?”

“Officer, can you give me a lift to a bus stop? Or drive me downtown? Or to my home?”

“What’s your address?” asked the cop.

“5200 Country Club Drive. Or anywhere near there.”

“We’re not running a taxi service, sonny. And I’m pretty sure the only reason a boy from your fancy zip code comes to the ‘hood is one reason only, and since I don’t see any narcotics on you, I won’t haul you in.” He turned to Sully. “You’ll keep this young man out of trouble?”

“Oh yes officer,” smiled Sully. “A little prank went wrong. I’m sorry for the misunderstanding, officer. Welcome back, Preston!”

I could not believe that the police were refusing to help me! Leaving a guy stranded in his underpants who’d been chased by a mob! They didn’t leave right away, but ignored me to talk on their radios about how they had been responding to a small disturbance. The noisy crowd in front of the house (enjoying my humiliation through the big window) and my escape had attracted attention.

Sully put his arm around my shoulder as Rico and Raúl came out of the house. Raul looked furious, Rico just looked high.

“Listen up, Captain Underpants. Change of plans. I don’t need police paying attention to my location here. I have an understanding with the normal beat cops, but not these guys. So I’m sending you home. Raul, you’ll fuck Preston for sure, but just not today. And Preston, for the trouble you’ve caused us, you are going to be fucked by a lot more guys than Raul. We lost some profit today and you’re going to earn it back. And don’t ever BS me. We know where you live and Sherry and her friends are keeping tabs on you.”

The cops hadn’t cycled away yet. I couldn’t believe he was talking this way within earshot. Even if they weren’t on the take, they obviously wouldn’t interfere with a drug gang protected by their colleagues.

When I could finally speak, I said, “Thanks a lot. What about my clothes? Can you at least loan me a shirt and pants and some shoes? And some bus fare?”

For some reason they all burst out laughing. What was funny? Or was it just the weed? Then Sully showed me the carton.

“No bus fare for little runaways like you. No pants and no shirt either. But—Lee, go in and get a pair of shoes for pretty boy. Preston, we opened your carton and were just charmed by what you were carrying around. Very smart of you to have a backup set of clothes!”

Man oh man! Had the evil girls known enough to equip me with some backup pants? Very out of character, but welcome.

Sully opened the carton and drew out … a petticoat. A two-layer white petticoat with ruffles and pink bows, entirely see-through. You should have heard the laughter. And then a pink lace-trimmed ribbon with Velcro. That was to go around a petticoated boy’s neck. I was speechless. It was too horrible to have my secret petticoat discipline life exposed in public in front of all these lowlifes! Lee appeared with a pair of scuffed white sneakers and I put them on, still unable to speak.

“Please no” I begged. “Pants. Any pair of old shorts. Please!”

“That would not be Sherry’s plan, Captain Underpants. White boy, white collar, white briefs, white socks, white shoes, white petticoat. You’ll be the prettiest sissy boy on Main Street.”

“But … but ... I’ll get beaten up! Or arrested!”

The police were just starting to leave but stayed for a loud laugh and a last remark: “No, boy, it is not an arrestable offense to dress like a sissy, even if it should be. Just don’t try to rob a bank that way.” And they bicycled away.

I knew when I was licked. I took the petticoat and put it on. Raúl insisted on being the one to fasten the pink ribbon around my neck. Everyone had their cell phone cameras out, snapping away.

“It’s only about an hour walk, Mister Preston Collins Berwyn of 5200 Country Club Drive,” said Lee. “I wouldn’t advise you to try and get on a bus that way. Or to get in any stranger’s car. Just keep walking.”

“I tried to tell you that you were safer indoors than risking getting raped out on the street,” said Rico. “A few fucks and blowjobs and we would have let you go. In your underwear. But you were also the one making all the noise about what was in the carton. You’re a rich boy but stupid. It’s getting dark, and I think you are in for worse than anything we did to you.”

“We’ll get our chance, don’t worry,” said Raul, one hand on his crotch with the other one ruffling my hair and giving my crotch a squeeze. “Look at you in your fag petticoat. Didn’t I know right away you’re a fuckin’ fairy?”

I walked past all the gleeful faces and iPhones taking pictures, hurrying towards Main Street. A car drove by and I heard someone yell, “Look at the fag!” It would be a long walk home … if I made it. 




Submitted: April 15, 2023

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

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