Stripped For Florida: Sexualizing Michelle 5

By Willie B.
williebflorida@gmail.com

Copyright 2026 by Willie B., all rights reserved

[5,352 words]

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Sexualizing Michelle

A Stripped for Florida story
By Willie B Florida
Williebflorida@gmail.com

Author’s Note: Readers have asked me how I personally view the Stripped For Florida program; is it a positive or negative thing, utopian or dystopian, empowering or abusive? As a person I am both inspired and appalled by human behavior. As an author I focus on stories that elucidate how ordinary young people navigate the often contradictory circumstances of life in contemporary Florida. WB

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Chapter 5: Miss Morgan’s Finishing Academy for Boys

When we arrived at Miss Morgan’s Finishing Academy there were already six boys milling around the room. Five of them were wearing black shorts and white button up shirts, properly tucked in. It was clear that the sixth boy was stripped. His tanned body betrayed no lines whatsoever and he seemed more at ease than the others.

Miss Morgan strode across the room to greet us. She is a woman of what some might call generous proportions, although I hasten to add that she is not at all obese. She carries herself with an air of relaxed confidence that brooks no dissension. It is almost impossible to imagine that anyone would disobey her instructions. She is wore a calf-length navy blue dress, “sensible” black leather shoes, and a discrete pearl necklace. Her hair was done up in a loose bun.

“Good morning, Brad. You must be Michelle. We’re very happy to have both of you here for this week’s cohort.” She looked up at a clock on the opposite wall. “We’re waiting for one more person, and then we can begin. Boys,” she called out. “I want you lined up in height order, starting right here and about two feet away from this wall. Brad, you can make yourself comfortable in any one of the chairs over there. Michelle, you will be standing to my right hand side.”

At that moment another girl arrived. She was of a very different build than Michelle. Short, slightly pudgy, with soft, rounded breasts and a short bob of dirty blonde curls. Her skin had the pink, pasty look of a girl who had only recently been stripped or who had assiduously avoided being outdoors in the Florida sun.

“Alexa,” Miss Morgan said, “you’ve arrived none too early. Please stand here on my left side.”

“Lads, that’s you, boys,” Miss Morgan instructed. “Get your line in order, please.” With that Miss Morgan strode forward with a pack of stickers in one hand. “Your parents have left these strip stickers. They are specific to each one of you and fully authorized. I will read out your name. Please confirm it is you, As soon as I apply the sticker behind your ear you are to remove your clothing, fold it properly and stack it against the wall over there. Robert McCutcheon, Michael Caron, Ardeshir Shams, Aaron Simon.” After each name the boy nodded in agreement and the sticker was duly adhered. “Ivey Strand, you are already stripped.” The boy grinned at the obvious statement and remained standing in place while the other boys busied themselves with removing their garments.

“Come now, lads. You surely knew to expect this. We haven’t all day. Clothes off, neatly folded and stacked by the wall.”

Miss Morgan now remained the only clothed person in the room.

“As you all know, I am Miss Morgan. I expect all of you to know one another’s names soon enough. Let me tell you briefly of myself and I will then introduce the outlines of what you can expect this week. My family moved from Wales in the British Isles to New Zealand when I was 12 years old. Subsequently I lived for a time in Australia before moving to the United States. That should explain my accent, which seems to fascinate everyone who meets me. Your parents have signed up for one week at my finishing academy. Exactly what is it that we are finishing, you may ask. The word has two meaning. The first is to complete something and to be done with it. After this week you will be done with childhood. You can still be childlike, in the positive sense of the word. In fact, I would encourage you to remain childlike, to see the world with an open-minded innocence, to sense abundance and to experience wonder. But after this week you will experience a new sense of fullness of what is possible and your ability to act with knowledge and agency. Most particularly you will gain this through the experience of sex. The second meaning of finish is to polish something. Something that is polished is more attractive, don’t you agree? A shiny piece of silver or a gleaming gemstone is far more seductive than a tarnished bowl or piece of jewelry. This week we will learn how to polish our interactions with one another. Manners are the mark of a dignified and sophisticated person, which we all must endeavor to become.”

Miss Morgan stood looking at the line of boys. This might have been the time to ask if anyone had any questions, but Miss Morgan was not done.

“During your time here each of you boys will receive several full body massages, with an added focus on your penis. The goal will be for you to gain full awareness of this organ and how to experience greater pleasure by withholding orgasm until you are fully ready for climax. In order to work on all of you in the time available I have asked Brad, and my friend Fiona to assist. Brad will be here all week and Fiona will be arriving tomorrow. Each one of you lads, as well as our lasses here will have the opportunity to assist. Each of you will have the opportunity to work on self-pleasuring. I know most of you have one burning question, so let me put you at ease. You will not leave here a virgin. You will have many opportunities to have sex. Let me assure you that you will, to use the vernacular, each fuck and get fucked, many times before you go back home. Today, however, we will be devoting ourselves to the fine art of manners. Lads, please meet me in Room B, to your left. Lassies, we’ll be back shortly.”

The boys looked a bit concerned, but it was nearly inconceivable not to obey Miss Morgan’s commands. I remained In the main room with the girls.

Michelle turned promptly to Alexa and introduced herself. “Hi, I’m Michelle.”

“Um, yeah, nice to meet you. My name’s Alexa.”

“I couldn’t figure why my parents were sending me to a place called a finishing school for boys, but you’re here, too!”

“It is weird. I thought it was just my parent’s usual deal. You know, either cheap or not paying attention.”

“Hmm, I don’t think either of those apply to my parents, so there must be a different reason. So what do you think of the boys?”

Alexa shrugged. “Hard to tell, honestly. I guess they’re all in puberty, but a couple of them seem pretty young, although that one guy, I mean he’s tall and developed enough, if you know what I mean. He must be 17 or 18. Anyway, I was surprised more of the boys weren’t stripped. Like, these days it seems like everyone is stripped.”

“I was only stripped three weeks ago. My parents said it was about time I was sexualized.”

“Same with me. My mom literally stripped me right before I walked through that door this morning. That’s why I was late. I was getting out of the car and she says, wait, there’s just one thing I need to do before I drop you off. That’s when she pops a sticker on me and tells me I have to get all my clothes off immediately. It’s so stereotypical. I just didn’t think my mom would do it that way.”

At this point the boys came back in. They’d evidently been directed to start setting up the small round tables that were leaning up against one of the walls. I told the girls to help and all together we set the room up cafe style with two chairs to a table.

“Everyone please have a seat. This is the classroom portion, so it doesn’t matter where you sit.”

There were only eight young people in the room, but everyone seemed hesitant as to where to sit. Closer to Miss Morgan, farther away, at a table alone, or next to another person?

“Places. Now!” Miss Morgan said. Everyone sat down in the closest chair.

“I’m sure you’ve noticed that we’ve set the place up as a cafe. Later today we’re going to learn how to do a proper place setting, how to take orders and bring out food, and how to behave on a date. That includes how to be seated and what utensils to use. But that’s not the most interesting part of a date, is it?”

Heads nodded in agreement.

“How many people here have been on a formal date, where one person invited the other to go out to eat and to enjoy one or more activities before the meal or afterwards?”

“What if we decided together?” one boy asked.

“Good question. That is not only a good way to organize a date, but an excellent way to maintain a good relationship. A relationship is one possible goal of a date, although you might be surprised to know that people go on dates for other reasons as well.”

“Why else would people go on a date?” Another boy asked. The boy seated next to him sniggered.

“Robert,” said Miss Morgan, “you seem to have an opinion on the subject. What reason do you have for people going on dates?”

“I didn’t mean anything by it, ma’am,” Robert replied.

“I’d like to hear your opinion. I’m sure there are several people in this room who might agree with you but are too shy to say anything.”

“To get laid,” Robert murmured.

“Please speak up.”

“To get laid,” Robert said loudly.

“For our event this evening we’re going to follow what is a more typical scenario. For first, second or even third dates people aren’t usually planning everything in an egalitarian way. One person asks someone on a date, hoping the invite will be accepted. It is quite typical that this person pays for the date. We’ll get into the details of that in a bit. Is the person who pays for the date justified in expecting that they might ‘get laid’ as you say. Pay for the date, get sex. Is that a fair description?”

Several boys in the room were nodding their heads in agreement.

“Let me see a show of hands. If someone pays for the date, do they typically expect sex in return? Everyone who thinks the answer is yes, hold up their hand.”

Four boys and Alexa raised their hands.

“I hope to broaden your perspective on the purpose of a date. You meet someone you fancy, or perhaps you just want to get to know them better and see if there’s some chemistry. You invite them on a date. This is your chance to put your best self forward. Here at my school our goal is to put a fine finish on your social skills. Learn how to open up a conversation, understand how to use lighthearted stories and humor to tell your date something about yourself, and how to elicit the same from him or her. Improve your listening skills. Being heard and understood is one of the biggest aphrodisiacs out there. I’m not leaving out sex. If you find yourself leaving the date laughing together, arm in arm, not wanting to say good night, wanting to spend the next 24 hours together, then you’re very likely to tumble into bed. This week we will engage you in a lot of activities designed to help you make that time in bed much more enjoyable. It may take a few years to really polish your sexual performance, but we’ll give you a good start. Are there any questions?”

“Do you mean to say that we will be going on dates?” Aaron inquired.

“This very evening,” Miss Gordon said with flourish. “You will be paired up randomly and we will operate in two shifts. For the first shift half of you will go on your date and the other half will wait on your tables. We’ll then switch roles.”

“Does that mean some of us will be on a date with another boy?” Aaron asked. “It seems mathematically impossible for it to be otherwise, I don’t know why you would assume that any particular boy would be gay.”

“In this program we make no assumptions about your sexuality. You are all teenagers. Sometime in your adolescence, or perhaps even later, you may have a clear idea about your preferences. On the other hand you might be surprised at the power of love. As for tonight, we are asking you to go on a date, which is primarily about having a civilized and scintillating conversation with another person. Sexuality need not enter the picture. At this time we will show each of you your individual rooms and give you a chance to get settled in. You’ll be going on a date this evening so I highly recommend that you take a shower and attend to your ablutions. As my mother would have reminded me, don’t forget to clean behind your ears. I will be checking on each of you at some point, so please be so kind as to answer the door when I knock.”

Miss Morgan handed me a clipboard. “Brad, if you would be so kind, please show each participant to their room. It is all clearly marked on the list. I need to attend to some business in the office.”

With that Miss Morgan stepped out of the room and I began ushering people down the hallway to the residential area.

* * *

True to her word, Miss Morgan visited each adolescent prior to the evening’s event. In the meanwhile she and I had worked hard to transform the main room into an intimate cafe. The first group to be brought from their rooms were the four that were to wait tables in the first shift. They gasped at the room’s transformation. The room glittered with small twinkle lights strung from the ceiling. The little cafe tables were covered in blue and white tablecloths. Two crystal glasses and a lit candle sparkled on each table. Even though Miss Morgan had clued me in ahead of time, the transformation of the boys was equally spectacular. Each boy sported a prominent erection, the result of Miss Morgan’s administration of the infamous SFF “shot” to each boy earlier in the evening. Miss Morgan gave the boys a tour of the kitchen, went over the menu and instructed them in the formalities of acting as servers for the first part of the evening. She then went to fetch those who were to go on their dates.

Miss Morgan knocked on the door of the person who had been chosen to be the host of the date, told them the name of the person they were inviting and instructed them to go to the correct bedroom, knock on the door, and escort their date to the cafe.

As Aaron had predicted, boys were paired with boys. In fact, Michelle was asked to invite Alexa as her date, so there were no boy-girl couples. Whether anyone was happy with their date match-up or not, all were as amazed by the cafe setup as the servers had been. The boys’ erections strained upwards, catching the light and casting shadows. The girls’ nipples seemed more prominent than usual. I couldn’t make out their clitorises in this light, but I suspected that Miss Morgan had given the girls arousal creme to daub on their clits and nipples. In keeping with the training earlier in the day, the date hosts escorted their dates into the room and helped seat them at the various tables. Eyes glittered in the candlelight and the magic of the setting put everyone into an anticipatory mood.

Miss Morgan and I sat at a table some distance away by the wall and observed our charges. The servers poured drinks, took orders, brought in appetizers, removed dishes, brought in the next course, and so on. The boys had no choice but to be on full display, naked and erect. The boys at the tables may have had their lower anatomy somewhat hidden by the table cloths, but they were fully aware of their skin taut erections. Florida boys are typically given the shot to induce extreme erections for the first days after they are stripped. The idea is to get them over their embarrassment as soon and as dramatically as possible.

The situation may have been contrived and the partnering done by random selection, but for the teens this was a very real first date, with all the awkwardness, anxiety and excitement. It took the boys awhile to get into the groove. They fidgeted in their seats, attempted to hide their nervousness behind humor, or sat in silence.

At the girls’ table Michelle sat upright, her conical breasts extending prominently forward from her chest. Alexa’s breasts rested like pink cushions on the softer curves of her body.

“So tell me,” she asked Michelle, “who are you being sexualized for?”

“Sexualized for?” Michelle replied with confusion. “I guess for myself?”

“That’s not exactly what I meant.”

“I mean, it is my parents who arranged it. Are paying for it. They have lots of ideas about how it’s supposed to shape my life.”

“But who is the specific person it’s for?” Alexa insisted.

“I don’t understand. Are you being sexualized for a someone in particular?”

“Yeah. It’s my mom’s best friend’s nephew. I’m supposed to be his present. ‘Well,’ my mom says, ‘not really present, if you know what I mean.’ This boy’s mom thinks three girls should be stripped for his party to make it more festive, I guess?”

“That’s really weird.”

“It’s pretty common, I’m told.” Alexa replied. “Kids get stripped to be in someone’s wedding, happens all the time.”

“Oh, yeah, you’re right. I have two cousins who were stripped to be ring bearers.”

“Or some famous person is coming to town, so a bunch of kids are stripped in their honor.”

“Right.”

“So, this mom of this boy, whom I’ve never met, wants girls stripped for her son’s sweet 16. That’s not all, though,” Alexa went on. “I’m pretty sure he’s going to want to have sex with me. They’re stripping him for his birthday, and you know how those parties go. The stripped kid has sex with everyone who’s already been stripped.”

Michelle nodded. Alexa was probably right.

“So,” Michelle brightened. “Have you talked to your sexualizer about it?”

“Sexualizer?”

“You know, the person your parents hired to…sexualize…you?”

It was Alexa’s turn to be confused. “They didn’t hire anyone. There is no…whatever you’re calling it…sexualizer.”

Michelle looked across the table at Alexa. The girl seemed in earnest. “So, if there is no sexua…person, then how are you being sexualized.”

Alexa turned her hands palms upwards. “I don’t know. I’m here, right? My mom stripped me right before I came in. She’s picking me up at the end of the week and we’re going straight to the birthday event. ‘Don’t say anything about the week at Miss Morgan’s, okay,’ my mom tells me. ‘It’s supposed to look like you got stripped 10 seconds before you go on reveal at the party. I just couldn’t do that to you, honey. So, please enjoy the week. I got a special deal on it and…well, I hope its fun.’”

Michelle nodded, speechless.

“Do you have one of those people, sexualizer?” Alexa asked.

“Yes, in fact he’s sitting right over there.”

“That guy?” Alexa asked incredulously. “Who’s been hanging around Miss Morgan since we got here?”

“His name is Brad. He’s been working with me for three weeks now.”

“Working with you?”

“Yeah, taking me places, special events, having sex…”

“You’re having sex?”

“I’ve had so much sex in the past few weeks you wouldn’t believe it.” Michelle enthused.

“Are you having sex with that guy, or with boys your own age?” Alexa asked.

“Both. But lots of sex with Brad.”

“But, Michelle, that’s pedophilia,” Alexa whispered across the table.

“Actually, he’s stripped,” Michelle answered in a normal voice. “He’s allowed to have sex with any stripped kid in Florida. It’s completely legal.”

Alexa gave a brief glance across the room. Miss Morgan and Brad were chatting amiably and observing the youngsters on their dates. “How often do you see him?” Alexa asked.

“Every day.”

“I’m glad it’s not me,” Alexa declared, “Besides, my parents could never afford it. It must be frightfully expensive. Come to think of it, this place must not be cheap, either. I don’t know what kind of deal my mom got.”

“I’m not sure why I’m here, either,” Michelle answered. “At first I thought it might just be a way to get more boys to fuck me. Yes,” Michelle noted Alexa’s look of alarm, “my dad, well, my mom, too, they have this idea that I should have sex with as many boys as possible. I think they said something like fifty in three months.”

“That’s a new boy every other day!” Alexa exclaimed.

“Yeah, so they’re pissed that Brad isn’t pulling it off. That’s probably part of the reason I’m here, but I’m wondering if Brad isn’t doing some kind of favor for Miss Morgan. After all, here are six boys, five of them freshly stripped. They’re going to want these boys to have sex.”

“With us.” Alexa stated.

“Exactly. We’re here for them to practice on.”

“Wow. So that’s why my mom got a discount?” Alexa asked.

“Or free, even, maybe? Either way, I don’t think you’re leaving here without having sex. That’s probably why your mom doesn’t want you to mention it at the party. Hey, honey, I just stripped three fresh girls just for you. Oh, by the way, she just fucked six boys in the past week, but it’s still special just for you, honey,” Michelle did an exaggeration of a doting mother.

“Oh, my, god,” Alexa said.

“My advice: you’ll probably like sex when it comes down to it. Personally, I love it. But, I doubt very much that any of these boys, or birthday boy, either, for that matter, are very good at it.”

Alexa snorted. “Probably not.”

“Don’t let these first experiences put you off. That’s why my parents hired a sexualizer. He’s an expert, he started slow and easy, he knows how to pleasure a girl.”

“I bet. How many girls has he fucked? Hundreds?”

“Scores, at least. But, you know what?”

“What?”

“In all the sex I’ve had in the past three weeks, I haven’t learned a thing about how to make love to another girl.”

Alexa stared at her.

“You’ve never had sex before, right?”

Alexa looked down and shook her head.

“I’d love to spend the night with you, if you’re interested.” Michelle flashed Alexa a bright smile. “I really don’t want one of these boys to be your first. And besides, I know we just met, but I like you. Please say yes!”

Alexa looked across the table directly into Michelle’s eyes. “I like you, too. I’m terribly nervous, so please don’t expect anything too amazing.”

“It will be my first time, too—our first time. We’ll figure it out together. It will be fun.”

* * *

Miss Morgan and I watched the evening’s even with interest. After finishing their shift as servers the two girls slipped out together. Having seen them converse so intensely all evening we weren’t that surprised that they’d decided to spend the night together. Aaron and Ardeshir were the other couple that went to bed together. Aaron was the one who asked how we presumed that anyone might be gay. They are both very animated boys and they make a cute couple. We’ll see how the kids pair up after today’s events.

Fiona arrived after breakfast. She has a Scottish accent and the looks to go with it, pale skin, freckles and red hair. It’s the real deal. It’s rare to see the unshaved look in Florida, on most anyone, but Fiona’s bright red bush and underarm hair suits her beautifully. I took the boys into one room to discuss their perineums and all the muscles they can tone to become better lovers. We’re going to keep those boys on the edge for hours during this workshop, but after that they’re on their own. The longer a boy can hold off orgasm the more time for pleasure. As an added bonus, if your partner’s a girl she’s really going to appreciate that.

Fiona took the girls and discussed how to develop those interior muscles to transform the vagina into something as versatile as a hand. They’ll use dildos first but once they’ve got a real boy with an erection they’ll use that time to practice putting pressure on the tip, middle and base of the penis. Maybe someday they’ll be adept enough to pulse their vaginal muscles like a wave. It’s like giving a boy a hand job, but all internally. Awesome.

After the pelvic sessions we got to work on the boys. For this first round of massages we lined the six boys up on adjacent massage tables and Miss Morgan, Fiona and I moved continually down the line, shifting places every five minutes. This meant that each boy got to experience the different flavor of massage each of us has to offer, and also that the longest any boy was left untouched was five minutes. It is hard to know which was more agonizing, being massaged or being left alone waiting for the next touch. We started with standard massage, working the kinks out of the different parts of the body and working oil into the skin. But fairly soon we transition to the penis. Then back to the toes, before working our way back to the penis. Then the stomach, and…you get the idea. Attention always comes back to the penis.

I am mesmerized watching Miss Morgan. She handles a boy like she is baking bread. Kneading the muscles, stretching, flipping, working her hands up an erect phallus, flipping the boy over, running her fingers along the tendons and up the penis. She is always in motion, completely focused and at tempo, but working so nonchalantly that it seems she will never tire. Our task is to work that boy closer and closer to the edge of climax, but never letting him cross the line. Miss Morgan has an exquisite sense of where that line is. I can watch the boy’s face and know he is about to ejaculate a jet of semen straight up into the air and at the last second Miss Morgan is pulling the energy down his arms and legs and massaging the boy’s fingers and toes. She does this over and over again.

“How long,” I asked her once, “can you keep a boy on the edge.”

“Forever,” she answered matter-of-factly.

“Theoretically,”

“No, actually,” she answered. “I’ve massaged a boy for up to four hours and there was never a chance he was going to orgasm.”

Girls, of course, work entirely differently. To concentrate all the body’s thoughts, feelings and sensations on a boy’s penis is to put him into a state of exquisite agony. The entire world funnels into his dick; there is no other reality. To give a girl the same type of experience orgasm must not be withheld, but prolonged. Before starting work on the boys, Fiona strapped each girl onto a table.

“Lasses, this is not for the sake of bondage, you understand? It’s merely to keep you from toppling off and hurting yourselves.”

Fiona produced two long dildos and ran one up each girl’s vagina.

“Scream and yell all you like,” she invited them. “We don’t mind a bit.”

She punched a few buttons on the remote controls and with a smile turned her attention back to the boys. For the hour and a half we were busy with the boys, the girls were brought rapidly to orgasm and then kept on the keen edge of what the body can tolerate. Scream and yell they did. If they hadn’t been secured they would have bucked and writhed themselves off the massage tables in no time flat. For Michelle or Alexa the world collapsed into full body orgasm and nothing else. They had no sense of the passage of time or what else was going on in the room. Orgasm was all.

The six boys were quivering on the edge of cumming. Their penises had never been this long or erect. Fiona walks over to the girls and turns off the dildos and releases the straps holding their bodies in place. Alexa and Michelle slowly come out of their orgasmic state, heart rate and breathing returning to normal. I look across the room. Michelle’s skin is flushed red and glistening with sweat. Her hair is matted to her head. Her eyes look dazed, but she meets mine. My penis has been erect since we first started massaging the boys an hour and a half ago. I turn my body back towards the first boy. He is lying on the table face down, his penis aching for release. I position myself and slide into his well-oiled rectum. I pull back and plunge back in. The boy comes instantly I fuck him gently but thoroughly and withdraw. A mess of sticky sperm is leaking out from under his torso. His body is covered in sweat and his breathing is still ragged as he recovers from his orgasm. I leave him to rest and move on to the second boy.

The afternoon is long and slow. The kids are worn out and we let them sleep or simply laze around. In the early evening we rouse everyone. Time to take showers and attend to appearances while Fiona, Miss Morgan and I set up the cafe. Tonight everyone dines at the same time while we adults take the role of servers. Assignments have been reshuffled so everyone has a different date partner.

“It is really remarkable how territorial humans can be,” I said to Fiona and Miss Morgan. “After just one night, I sense some resistance to the new partnering and seating arrangements.”

“Very true,” Miss Morgan remarked, “but it is important that our charges learn the social skills of conversing, not to mention flirting.”

“I suspect Michelle and Alexa will turn down any offers from the boys to spend the night. I’m wondering how many boys will decide they are desperate enough after today’s activities.”

“Do you think any of them are gay?” Fiona wondered.

“90% of them,” I replied, only half joking.

“There are only six boys,” Fiona noted. “So you think none of them are gay, or just one?”

“I think the boys are 90% desperate to fuck a girl, but will take the 10% option if they are horny enough.”

Fiona laughed. “Shall we make a bet?”

“Only if you’re willing to lose. I’m calling 100% match up rate.”

“You sound fairly confident.”

“Consider, the boys spent most of the day being aroused, but weren’t fully satisfied afterwards. They’ve all been fucked in the ass, so that barrier has been broken.”

“I’m sure half the banner we’re hearing is the boys sorting out who’s willing to get fucked,” Fiona observed. “After all, there’s still a bit of a taboo against being on the receiving end.”

“I could tell you which of the boys is already used to taking it up the ass,” I said. “There are two of them. But I’ll leave that to the boys to sort out among themselves.”








   
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