Preston's Strip-Humiliation on the Wrong Side of Town, Part 1

I should have known better, but it wouldn’t have mattered even if I did. The toughest boys and the meanest girls were determined that I should never live down my humiliations, and also that my humiliations should keep getting worse, and never end!

It had been nearly a week since my last petticoat punishment, and my suspicions were very strong that my tormenters had started working together. The teenagers at the birthday party wouldn’t have known the fellows on my soccer team, and the totally evil Shannon, Leslie, and Sherry lived in their own little mean girl world, never going to parties and not into sports, just watching TV and gossiping with the evil Teddy and his friend. And yet when I walked through the school cafeteria or rode the bus, I seemed to notice whispers and looks from schoolmates. I just hoped that my embarrassing adventure at the library would be ignored and reports of the depantsing behind the school wouldn’t get around. I mean, would girls actually brag to people about what they had done to me?

Of course they loved keeping me worried and in the dark. And then one day I got a summons from the evil girls to meet them in front of the school. Not in back where they’d stolen my pants and planned out my petticoated future, so maybe I was safe. There would be teachers and crossing guards there so it would be hard to get away with anything.

“Preston, we need your help,” said the evil Sherry with a smile. They were standing there with a small cardboard carton. “This needs to be delivered this afternoon and we’re too busy. We know you’re used to following our orders, but don’t worry, this isn’t part of your punishment.”

I looked at all three warily, knowing that I’d be in trouble if I questioned them. They almost looked innocent and sincere, but I also knew how sly they could be.

“You have to take this box to the address on the letter attached. We have a girl’s group that makes handicrafts and helps out the poor and disadvantaged. You have to put your best foot forward to show how nice we are. You should wear your best clothes, white shirt and nice necktie, and make sure your shoes are polished.”

I looked at the address on the envelope. It was a block up on 40^th Street, not a good neighborhood. People in our wealthy neighborhood never went above 30^th Street. It would be about eight or nine bus stops away.

“I’ve never been to that part of town before. Some people say it’s not safe,” I said, very carefully … not daring to say I didn’t want to go near the high-crime dump.

“Oh, people are so cruel to talk that way about a part of town where the poor people live. This is a needy family that we promised some of our needlework, and a cash donation in the envelope. So can you go home and change into your best suit and get there fast? We really don’t want you to refuse.”

And there was the sly smile. I had a soccer practice, but whether these girls were on the level or not, I know the kind of trouble I’d be in if I even hesitated to say yes. So I agreed, and walked off with the carton and the sealed letter. Could it be that these girls were not evil anymore? And then before I passed out of earshot, I heard Leslie chuckle and say, “You should have told him to wear his best underwear too!”

The bus driver gave me a funny look, once we passed 25^th Street. I was the only passenger, my perfectly pressed khakis, shiny penny loafers, blue blazer, white shirt, and rep tie. And holding the carton and letter in my lap. It was late afternoon, before people got off from work, and there was no retail above 30^thStreet, so why would anyone be going there? Most of that neighborhood was unemployed anyway.

I looked even more out of place once I hopped off the bus. Tough-looking young guys were loitering in the alleys and a few old folks were sitting on their rickety porches, and they all looked at me like I was from Mars! I knew I’d have to deliver this donation to the poor family and get out of here ASAP.

123 40^th Street was one of the dirtiest looking houses on the block, and the doorbell didn’t work, so I knocked. No answer, so I knocked again. The sight of such a well-dressed, clean-cut teenager in this wrong side of town had attracted a small crowd of sullen boys were had followed me and were staring as I stood there feeling awkward. It was a relief when the door finally swung open.

But not a relief for long. Two young men were standing there, maybe 18 or 19 years old, one of them Black, in jeans and a torn T shirt, and a Latino with big black eyes, and he was wearing a polo shirt and just boxer shorts.

“What the fuck do you want?” the Black fellow asked.

“I’m here from Polytech High School, bringing something from the girls’ group,” I said. Something was seriously wrong here!

The Latino turned his head back to shout into the house, “Hey Sully, you expecting one of your white friends?”

“Sully” wandered into the living room behind them sipping at a beer can. Curly-haired punk with a leer that looked familiar. Where had I seen that leer before? … on those girls’ faces of course. This was no poor family needing help from our school!

“I—I—think there’s been a misunderstanding. This is for a family, from Sherry and Leslie and Shannon. Sorry to bother you.” I started to turn and leave, and saw the ragged neighborhood kids still standing there, but now more of them, and grinning at my obvious fear.

“Come in,” said Sully. “Come in and have a seat. Yeah, I’m expecting someone. This is Lee and Rico,” he explained.

I entered the squalid living room but didn’t want to sit down on the ancient sofa. The wall-to-wall carpeting was filthy. There were empty beer cans everywhere.

“Sherry and her friends buy weed from me,” Curly said. “Of course the rich bitches won’t come here. I usually meet them downtown. Aren’t you the fancy boy! All dressed up to deliver my weed money!”

“Doesn’t Mister Pretty Boy want to introduce himself?” asked Rico nastily, looking me up and down.

“Um, I’m Preston, and I don’t need to stick around,” I said, by now panicky at this horrible set-up.

“Just take it easy. Stay here. You’ll just get mugged out there. I’m surprised you didn’t get mugged on your way here. You drive or take the bus?”

“Bus,” I said weakly. Lee and Rico were staring at me with amusement as Sully ripped open the letter and read it.

“What the hell’s going on here?” he asked. He glared at me, looking really angry. “What the fuck are you trying to pull here, Preston, if that’s your real name?”

“I don’t understand,” I murmured, and trust me, and I really didn’t!

As Sully read the letter out loud, the other too glared at me even more fiercely and my heart sank like it never sank before.

“Hi, Sully, here is the $500 we owe you. Thanks so much for the weed! And thank Jimmy for delivering the money. The cardboard carton is for him. PS, I hope he didn’t steal the money, we’re never sure if we can trust him. If all the money isn’t there, be sure to search him. Jimmy is too afraid to carry a wallet around, so it might be hidden in a secret pocket. PPS, if he stole the money before going to your house, it won’t be on him. But his expensive clothes and his watch are worth around $500. Good luck and have fun!” He looked straight at me. “There is no money in this envelope. Where’s the money, pretty boy?”

Oh no. My head was swimming. 

“He lied and said his name’s Preston. He took the cash. Hand it over, you big stuck-up phony!”

“Frisk him! Empty your pockets and take off your jacket,” said Lee.

I turned my pockets out threw my blazer to Lee who quickly went through the pockets. Rico came over and ran his hands all over my chest, arms, and legs.

“You little thief!” Curly approached me menacingly. “You’re not leaving here until we have that $500, if we have to turn you inside out, you little pansy. You got that?”

“It’s a trick—those girls tricked me! Please don’t fall for it, guys. Please let me go.”

“She was right, he hid it somewhere, but I frisked him pretty good,” said Rico. “I would have felt $500 in cash, that’s a big wad.”

“Maybe you should look in the carton?” I said, out of desperation, although confusingly, the note had said that was for me.

“Maybe you should shut the fuck up,” said Sully. “Either it’s in his clothes, or if it’s not, we take his clothes as a down payment. Start with your wristwatch, Jimmy, or Preston, NOW!”

I hurriedly pulled off my gold watch and handed it over. Sully was impressed and handed it to Lee, who said, “We got ourselves a RICH little pretty boy here. Who needs to learn a lesson not to steal.”

The leer was back on Sully’s face. “Time to lose those fancy duds of yours, Jimmy. Take off your pants and hand them over if you don’t want to get hurt, and I’m not talking about your feelings!”

Oh hell. I started to unbutton my shirt but couldn’t resist one more try. “Please guys, this is a misunderstanding! Please!”

“This little pansy is going to take all day to undress,” Rico complained. He strode over and started undoing my pants. Before I knew it, all three of them were on me, roughly pulling my necktie and shirt off, and they whipped my pants off over my shoes.

Then I heard screams of laughter … from where? The front windows. Half the neighborhood children had gathered to spy on the mysterious visitor, who to their delight was now wearing nothing but his underwear. A mere two hours after promising the girls I'd do a simple task for them, I was in this scary filthy house across town with three strangers, kidnapped, robbed, stripped to my T shirt and briefs and feeling doomed.

“Take his undershirt too,” said Sully, who was methodically feeling his way around my expensive khakis looking for hidden money.

Lee snapped his fingers and I handed over my T shirt. There I was in this squalid house now in just my white Jockey briefs, white crew socks, and my loafers. Sully was a quick study with all my clothes, and determined that there was no money in them.

“So what do we do with our little naked gentleman here?” leered Sully. “We have the girls’ permission to keep his clothes, not that we need their opinion. But can he ride the bus home in his underpants?”

“He won’t get as far as the bus stop without getting his ass kicked and maybe raped. And the clothes --no one here wears that preppie shit,” said Lee. “You can fence it downtown, and the watch. I say we pimp out our friend here. Nice smooth white boy from a white collar neighborhood, and in tighty-whities! He’s triple white.” All of them laughed but me.

“Raul down the block is a big maricon. He’ll pay money up to fuck him,” Rico said.

“Do you suck dick, Jimmy?” asked Sully.

“Of course not!” I pleaded, preferring to forget what Eddie still made me do on occasional Saturdays.

“HE doesn’t get to decide about sucking dick, that’s for us to decide,” said Rico. “If he’s going to get raped, it shouldn’t be on the street corner out there, it should be here where we make our $500 back on his sweet little ass. We can use one of the bedrooms.”

I felt destroyed. They were all grinning, and the rabble at the front windows had only grown. I had a serious audience out there drinking in the sight of a humiliated rich kid terrified in his underpants. Those evil girls were going to get me killed! Or raped, or both.

“Let me go. I promise I’ll bring you $500 whenever you want it. Just give me my pants and let me go. You can keep everything else.”

“Look who’s telling us what we can and can’t do, guys—the fruity little millionaire in his underwear!” The rhyme made everyone laugh again, but not me. And the laughter had a cruel ring to it. I was sunk.

What could I do? Except make one last desperate try. “Let’s open the carton, the money might be there. It can’t hurt,” I said, buying time.

“Can’t hurt,” shrugged Sully. “Let’s have a look, Captain Underpants.”

How could I know this was the stupidest thing I could have done?

TO BE CONTINUED.

(I have nice plans for Preston, but if readers have any ideas or suggestions, leave a comment! :)