Preston's Strip-Humiliation on the Wrong Side of Town: The FINALE

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

Preston just can't win when it comes to what his mean girl tormentors, a couple of sissy classmates, and the boys from the wrong part of town have cooked up for him. Can he finally admit that he almost enjoys it? This is the last installment ... readers will have to use their imaginations from now on. :)

Needless to say, I was not looking forward to the next school day. News of what the girls had done to me at the craft fair awards show was all over town. I was just happy no one knew what had been done to me earlier at the drug den house. Luckily, lots of students and teachers vaguely understood it as some kind of dumb prank I’d undergone connected to a $500 donation to a good cause. Boys did dumb stunts all the time. 

While Sherry, Shannon, and Leslie were pleased with my day of total humiliation, they seemed to have some concerns. The whole project of using petticoat punishment to control and embarrass me was theirs, and perhaps they were thinking twice about how Sully, Rico and Lee were now giving me orders and taking up my time.

That was trouble because it meant the girls needed to take over control more than ever. And they don’t do anything half-way! Rico had told me that they were cooperating with him to “train” me for an evening of sexual humiliation (for profit to him and his crew) this coming Tuesday. But I felt sure the girls were reluctant to hand over their humiliation prey to different predators. 

“You did so nicely yesterday. But just because Sully and Rico’s friends are so into you, there is a danger you’ll get a big head and forget that you are our sissy boy. I’m sure you agree you have some work ahead of you to keep out of trouble. So we are giving you the privilege of a meeting at Leslie’s house at four o’clock this afternoon. There are some administrative matters to deal with. She and her parents are out of town, and she gave me a key. Don’t be late.”

Out of town … don’t be late. This bad news meant they had free rein and control over me at Leslie’s family’s huge house down the street from mine. 

It meant missing another soccer practice, but after what Sherry had asked me in front of 200 people (“Do all the boys on your soccer team wear petticoats?”) to general hilarity, I was happy to avoid my team. I rang the bell at Leslie’s family’s mansion just before 4. A balding butler greeted me with “Master Preston?” and when I said yes, he handed me a cardboard carton and said, “This way, sir.” In my experience cartons were bad news.

And it was. After the butler closed the door leaving me in a kind of music room or library, I opened the carton to find a pink and white organza party dress and a note saying “Strip to your undies and put on the dress. Fold your clothes and place them on the piano bench. When you are wearing your sissy dress, ring for the butler. Don’t put the pink bow in your hair. We will do that.” 

The skimpy, flared party dress left my shoulders bare and hardly covered my Fruit of the Looms. (Yes,I heeded their advice about what brand of underpants to wear among unemployed males.) Of course it had some fluffy layers of petticoats. I rang the bell. The butler knocked, took my clothes and said, “This way, sir!” He led me to another vast boudoir with a desk. Sherry and Shannon were waiting there and smirking, and so was Leo, who I had not seen in months. 

“Princess Preston, don’t you look adorable! Do you feel special today in your pink lace and organza?”

Sherry took the pink bow out of my hand and positioned it on the top of my head for maximum sissy humiliation.

“Yes I do. Thank you so much for such a sissy outfit!’

“Oh gosh, you still make him say stuff like that!? And he still does it!!” laughed Leo.

They loved seeing me blush. Sherry said, “Let’s get the business out of the way first. Here’s the bill. You may read it aloud.”

“’Lace-trimmed pink ribbon neck choker, $20. Lace petticoat with pink bows and ruffled hem, $100. Organza party dress, $100. Pink hair bow, $20. Due and payable immediately.’ I’ll give you a check tomorrow,” I said miserably. Being robbed this way was almost as humiliating as wearing a dress. And this was for just two days’ worth of petticoating.

“Next item of business. Preston, after all the trouble we took yesterday to keep you in your sissy place, you did not do very well up on 40th Street. You hesitated to undress, so they had to take the trouble to strip you. Did you thank them for selling your nice clothes to some trampy women? No. And just as Raul was going to take you upstairs to have some fun with you, you disrespected him by running away. We are disappointed by your bad manners. But we can help you make this right.”

What a crazy misrepresentation of how I had been abused yesterday! But I couldn’t say anything.

“Before we get into the ‘list’ we have compiled [I shuddered—the list of classmates I would have to blow], please seat your pretty ass at the desk.”

I did. There were stacks of elegant notepaper, envelopes and stamps, and pens. Plus a pink leatherette address book. 

“Later on, you will be writing thank you notes to the young gentlemen who hosted you yesterday. First to Sully, who was nice enough to invite you in. Then thank-you notes to Lee and Rico, who undressed you and disposed of your boy clothes. And then to Raul--how disrespectful to a handsome stud of 28 with his dick out! And you tell each one that you regret your bad manners will do everything you can to make up for it.”

“This is so much fun!” crowed Leo. “Use your best penmanship, Preston!”

“That will be later. But right now, you have something much more fun. Instead of soccer practice, you have another kind of practice. Before we got here, we told Leo and Teddy about the list were on and how they might help you with your homework for Tuesday. Teddy wasn’t available, but Leo is happy to help you out.”

“Oh gosh. Oh please,” I gasped. THEY were on that list?! I knew this kind of outburst was forbidden, but the girls were so delighted to follow up the ridiculous thank-you note business with this new level of humiliation, that they seemed not to care. Leo looked just as excited.

“Preston, do you remember this almost happened the first time we made you wear a petticoat?” Leo asked sweetly.As if I could ever forget that day, thought a couple of years had passed: “You’re a great kisser, Pres. If I take my pants off, will you kiss me down there?”[1]

“You can use the guest bedroom down the hall but be careful to pull down the shades.”

Leo took my hand and led me to a hallway lined with antique furniture and paintings. The room contained a king-size bed and huge windows. He scampered over to the pull down the wide shades, but the room was still light. He lost no time kicking off his shoes and taking off his corduroy pants. He showed no embarrassment at exposing his smooth legs and gingham boxer shorts.

“Can you believe I’ve moved on to boxer shorts and you’re still in white briefs? Not to mention my pants versus your party dress! I don’t mean to tease. I shouldn’t add to the pressure!”

We were exactly the same age, but I had always been an athlete and he had always been a nerd. Gosh, this was embarrassing.

“Do you want to take off the dress? However you’re more comfortable.”

I decided being in the dress was worse than being in briefs, so I pulled it off over my head and laid it on a chair. Leo had taken off his shirt, so we were both in just underwear. I noticed his cock was already out of the fly of his boxers. He escorted me on to the bed. It was crazy how the little nerd was taking charge. We lay down and he put his arm around me. “Hold it while I kiss you,” he whispered. I wrapped my hand around the rigid little thing.

Like I said before, I have no flair for porn. I was there to learn something and I did. I didn’t mind kissing this good-looking boy, but my heart pounded when he reached down to remove his boxers and then pushed down my shoulders. “OK, get started.” He held me by the head and gave me encouragement like “Breathe through your nose.” When it was over—he was a little noisy, in a happy way—he said, “I’ve been waiting years for this! It was worth waiting for!” I thanked him.

“Tell you what,” Leo said, sitting up on his elbows. “They have a list of guys at school you have to do this to. Do you want to go through with it and blow them all, or not?”

I was embarrassed to say that I had to think it over. Then I said “If I could skip it, I would, I guess. This I my second time in two days.”

“Listen. I can tell the girls you did a great job and you shouldn’t over-practice, I’ll tell them you got it all just right. Will you do me a favor in return?” I nodded. “He said, “Please make out with me. I would really love to just hug and kiss you for a little while, after what we just did. Please?”

So we did, embarrassing as it was. Another first for me. As we went on smooching, naked Leo started showing more fervor. “Oh gosh, I love this … oh Pres … I think I’m ready again.” Never underestimate the stamina of a teenage boy at his sexual peak. “And I feel sorry for you because you’ll have to put the dress back on when we’re done. Maybe I should take care of you this time.”


“How did he do?” Sherry asked when we came back, Leo clothed and of course me in the swishy dress. The bow had come out of my hair during all our adventures in there. “You took your time! And that’s quite a big grin on your face, Leo! And Preston, your hair is all messed up, and you lost your hair bow! I guess we all know now what team you’re on, and I’m not talking about soccer.”

They went to a back room to discuss how I did while I sat at the desk to write the embarrassing thank-you notes (“Sully, you were kind enough to make a real priority of getting me out of my dumb preppie clothes.”) and when they emerged, the only thing left to discuss was whether I would put my own clothes now or have to leave in the dress. Sherry decided that Leo could carry my clothes and I should have to wear the dress home, at least as far as Crossbow Terrance, two blocks from my house. “After all,” she said, “You’re going to need the dress for Tuesday.”

“I will?” I was confused.

“Doesn’t Rico tell you anything?” she sighed.


It turns out that Rico was 19 years old. I had thought he was a lot older because of his calm and decisiveness. He was the only drug house guy to keep in touch with me, partly to keep coaching me for Tuesday, but also, I hoped, because he liked being around me. So I took the risk of inviting him to my house. I explained how my evil stepmother Thelma was almost never there. Of course, this time, there she was, glaring at me and trying to size up Rico. I just mumbled that “I invited some friends over” and we went up to my room.

(I also explained how Thelma had helped develop the petticoat discipline for me,[2] and how she hated me because when I turned 21 the house and everything would become mine under a trust, and she would be out, with nothing.)

“Look,” he explained when I told him what Sherry said. “Raul wants revenge for your insulting escape. And he had fun undressing you out of your expensive clothes and seeing you in your underwear. But to cut you down to size, and for a new thrill, you have to report to 40th Street wearing that dress. You can take the bus or I can drive you, but you have to walk the last couple of blocks so that everyone can see you humiliated in the sissy party dress. Sherry texted a picture of it to me to show to Raul, and he says it’s perfect. Don’t worry, you won’t be wearing it long. Have you been practicing like I told you?”

I told him that I had two experiences in the last day, omitting the fact that one of them—Leo on me—didn’t really count to prepare me for Raul.

“I told you two a day. What have you got scheduled for today? I thought you’d be doing the whole soccer team or something.”

“Well, nothing yet. I can’t make guys line up for me, you know.”

“Hell, I can make guys line up for you. I DID make guys line up for you, before you ran away,” said Raul. I didn’t point out that the demographics of the town’s best high school and of its worst drug slum were slightly different. “What are we going to do now?”

“If you want to see the dress, I could show it to you.”

“No, I mean what are we going to do about your learning to suck cocks.”

I didn’t answer for a while, but we looked at each other and both got the idea. He reached over to stroke my neck. “You little devil,” he said. “You little devil.”

“Would it put you more in the mood if I took my clothes off, or wore the dress?” I asked.

“Would it put YOU more in the mood?” he asked.

He had me strip to my Fruit of the Looms and show how the little party dress looked. “It doesn’t cover hardly anything,” he remarked. “Twirl around.” I did. “Damn, that exposes your tighty whities and all the way up your belly button. The girls are hell on you to make you do this. It’s cute seeing a boy like you in that thing but you look so ashamed and sad … I don’t like to see you look sad.” 

So I took it off and sat beside him again and he stroked my neck again. “Here’s the danger,” he said, pulling off his shirt. He stood and up took off his pants and then his boxer shorts. My first look at him naked was a treat—short even black chest hair and a slender soccer player’s build, like me. I hadn’t seen him below the waist in daylight before, and all I can say is that he looked lots more grownup than Leo! “The danger is … “ and he sat down and pulled me towards him and pushed his cock into my mouth, “ … that I might lose my self-control and decide to fuck you.”

I was in no position to say anything. While I was busy on my knees, his cellphone buzzed. “Don’t stop,” said, and looked at the text. “Damn, you thought those girls were evil before? Don’t stop. You won’t believe this. OK, stop. You are pretty great at it. Now take off those briefs and lie down on your tummy. Don’t worry, I’ll be gentle. The heck with Raul and the girls. I’ve been wanting to do this to you since the first minute you knocked on the door in your white shirt and tie.”

As he started, he explained the text. “They want a bigger share of free weed for every guy who does you on Tuesday. You didn’t know that? Oooooh… relax … sweet! ... ”

So that was why the girls were willing to “share” me—Sully and his crew would rent me out in their rear bedroom, collecting cash from every guy molesting me and the girls would benefit each time with free marijuana—I’d be used by nearly everyone I knew. Now THAT is a humiliating thing to find out with my face in the bedspread, and Rico on his knees behind me plowing what had been virgin territory just 2 minutes before.

But it wasn’t the last or worst surprise of the day, because a minute later my bedroom door swung up and Sherry, Shannon, Leslie, Leo, and Teddy filed in. When I saw them, and they saw what Rico was doing to me, I don’t know who screamed louder.


“I can’t believe my eyes!” squealed Teddy. “Look how big and stiff Preston’s cock is—it’s bobbing around!”

“Never mind Preston’s cock,” gasped Leslie, “Look at R—”


(Rico just kept going. I guess in his dangerous and druggy world, a bunch of teenager girls and boys catching him boning their friend was a non-event.)

“Thelma called us and said you said you were having friends over so that we should come right away,” said Leo. “So sorry, Pres—”

“GET OUT,” I begged, and after all five got last longing looks at Rico, they ran out and the door slammed.

“Don’t worry,” gasped Rico, plowing away, and he released his tight grip on one of my hips to reach between my legs to offer some five-fingered encouragement. “I’ll make sure they don’t tell. And when you’re 21 and Thelma’s gone, we can let those girls rent out one of these bedrooms. Someone has to keep you stripped and humiliated, Preston, when this place is ours.”

“Did you say ‘ours’?!”

“Yes,” he replied, both hands back gripping my haunches for his final push. “That’s what I said, loverboy.”





[1] Preston’s Petticoat Punishment, April, 2023.

[2] “More Petticoating for Poor Preston!” April 2023.

Submitted: April 25, 2023

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

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