Naked at Grandma’s 1

By Kahuntwm

Copyright 2024 by Kahuntwm, all rights reserved

kahuntwm1588@outlook.com

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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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Naked at Grandma’s Ch. 1
By
Kahuntwm1588@outlook.com

CFNM, OON, Straight and Gay

I make no apologies for my lifestyle and behavior. Not a single lad gets hurt. Embarrassed? Of course. Humiliated? Without a doubt. But not hurt or injured.
But I do have a problem. I mean, other people might see it as a problem but I don’t.
My name is Ursula Remsky and I am 56 years old as I write this. My husband, whom I loved deeply, passed away four years ago. My children are now adults with their own families. My kids live within an hour of me in the Sarasota area and I see them often. But once they all flew the coup and my Henry died, I became very bored.

My problem, if you must call it that, is quite simple. I love teenage boys and I love them naked. I like naked teenage girls, too. But not as much as l like teenage naked boys. I do not see this as a problem. It is my hobby.

And I formed a group of ladies, all around my age, who have the same ‘problem’. We all have one goal: get a teenage boy and get him naked and embarrassed. We never have sex with these teenagers - that is a no-no with all of us. But we do like to look and to touch these teenagers. This is our fantasy and we have the money and means to bring our fantasies to fruition. All we need are the boys (and girls)

Just a quick background note: I live in a large mansion on Longboat Key. And my group of ladies are Peggy, Lauren, Trudy, and Marie. All are in their fifties or sixties, all are grandparents, and all are rich like me. Most importantly, all are bored - like me. And all like naked teenage boys. Marie, who is a lesbian, and I, who is bisexual, love naked girls, too.

What do we actually do? How do we get these boys into my mansion and get them naked? Best way to show you this is to tell you about my first experience with a naked lad which happened before our group formed. The boy was fourteen years old and he was my grandson, Brett Remsky, son of my son Paul. And he was beautiful.

Brett was at that age when he was still more boy than young man. He was well past puberty and positively glowed - light brown, curly hair, big eyes, snub nose, and sensuous lips. His parents, my son Paul and my daughter-in-law Mabel, were loving parents who doted on him (they actually doted on all their children, but he was their only boy and he was, well, special). They lived in Naples, Florida, which is about two hours from Sarasota, so I didn’t see them as often as I would have wished. But I have seen young Brett grow up and now I wanted something more.

And the opportunity to get closer to my grandson arose when he was accepted into an exclusive prep school in Sarasota. Tamiami Academy was a day/boarding school and I was asked if I would let Brett live with me when school was in session. I played hard-to-get but, of course, I said ‘YES!’

In fact, I helped pay his tuition (Paul and Mabel were, and still are, teachers at a small liberal arts college in Naples and so were not in the high income bracket that I was) and did not ask for any rent and, in fact, said I would take care of all Brett’s financial needs. The family was most grateful.

When Brett called me to personally thank me for all my help, I told him how much I loved him.

“And I love you, too, grandma,” he said. “I don’t know how I will be able to repay you.”

“Well, don’t you worry about that,” I said. “You should know that I will, at times, ask special favors from you. Just little things. You don’t have to do them if you are uncomfortable, and you must feel free to decline. Even when you say ‘no’, nothing will affect the arrangement we have with you living here, nor will it affect my love.”

Brett laughed. “I don’t know what all that means, but I will always be there to help you when you ask.”

Brett arrived in early August and got his sweet fourteen year old self settled in his rather large bedroom (I have a large mansion with large rooms). We spent two weeks (before school began) doing all sorts of things - visiting museums like the Ringling, seeing plays at the Asolo Theatre, traveling shows at Van Wezel, and using my small yacht. In fact, that yacht was when I first got a close look at my grandson’s pretty body. He was built like Adonis. Except for a small touch of hair under his arms and wild, curly light brown hair on the top of his head, his body was essentially hairless. Just gorgeous. Of course, I couldn’t see everything as he was wearing a bathing suit. You know, one of those bagging suits that hide everything special. Whatever happened to speedos?

Brett and I grew very close during those weeks in August. My grandson was a hugger and whenever he hugged me, I was sure that I rested my hands on his butt. He must have noticed but he never said anything. Before school began, I began to plan how I was going to get my grandson naked. And the large pool I had in the lanai, very private with the growing bushes and trees surrounding the lanai, was the pathway to the stripping of Brett.

It helped that Brett was not particularly shy. As with most Florida kids, he dressed loosely and minulary - baggy shorts and light shirts and around the house, floppers or barefoot. He had his own bathroom with a large shower so I had no excuse to ‘accidently’ walk in while he was showering. So one day we were having dessert on the lanai after supper. It was warm but comfortable when I caught him eyeing the pool.

“Looking to swim?” I innocently asked.

“Sort of but too lazy to go upstairs and change,” he said.

“So don’t,” I said.

He laughed and said “Well, I can hardly skinny dip.”

“Why not?” I asked.

Brett got silent, not something my fourteen year old grandson often did. “I can’t swim naked,” he mumbled

“Why not?” I asked again.

“Because you’re my grandma.”

“That is a reason why you should,” I said. “You know how much I love you and you know I would never be judgemental.”

“I mean - you would see me naked,” he said, again mumbling.

“So what? Any surprise behind those shorts?”

“Are you serious?” he asked.

“Very - I love you very much, dressed or not.” I could see him contemplating. The fact that he was thinking about the possibility of skinny dipping meant to me that he would do it, if not today, then someday soon. As it turned out, my adventurous grandson decided today would do. He shrugged his shoulders and got out of his chair and took a step toward the pool.

“Brett, dear,” I said. “Take your clothes off here, with me.”

He looked at me and took his shirt off. “Are you sure?” he asked.

“Very, sweetie,” I said. “I want to see you naked.”

So, standing there and looking me in the eye, Brett slowly pulled his shorts and boxers down. I looked him right in his eye and then slowly lowered my gaze so that he knew I was going to look down right at his sex organ. Oh, and what a sight that was. The lad was a good three inches long and his balls were prominently displayed in his hairless scrotum.

“Wow,” I said. “My grandson is beautiful - all over.” I stood up and kissed him on his blushing cheek. “Now off you go, I said.” And I watched his butt cheeks bounce around as he walked to the pool and jumped in. I brought my chair over to the edge so I could watch him swim. Imagine, I could watch my grandson swim in the nude.

When he came up for air, I asked him if he was going to swim for a while.

“If you didn’t mind,” he said.”Why?”

“I thought I would join you - I will be right back.” I walked to the downstairs bathroom where I kept my one piece swimming outfit and quickly changed. When I returned, he did not see me grab my goggles and slip into the water. Now with great clarity, I could see Brett’s cute body, watch his ass cheeks swirl, momentarily split open exposing his butt hole, and watch his penis and testicles bounce this way and that. It was a beautiful sight.

When we both came up for air and he saw me with my goggles, he blushed a bright red and lowered his eyes in embarrassment. I didn’t help him much when I said “You have a cute package, Brett.”

“Package?” he asked with a confused expression.

“Your sex organ, silly,” I laughed. I dove under to get another peek but he quickly swam away. For the next few minutes, we chased each other as Brett relaxed now that he knew that his grandma had seen everything. When we got out of the pool using the small ladder , I told him to go first. He knew that he would be exposing his ass and his hanging balls to me, but he went up first anyway. What a pretty sight his ass and balls were.

Nor did he object when I grabbed a towel and began to dry him. He seemed dumbfounded but he no longer looked confused. His grandmother liked seeing his nakedness and he accepted that. He jumped a little when I dried his butt, but he closed his eyes and looked upward as dried his sex. I didn’t actually touch him since it was the towel drying him off but I enjoyed it anyway. So did he as I noticed his penis was acquiring a lift of its own. Brett noticed it and gave me a quick ‘thanks’ and rushed to put his boxers and shorts on. Once he had covered his precious sex, he looked at me. I smiled at him, he smiled back, and then left to go upstairs. By the time I had changed, he was back down, dressed in different and more substantial clothing. We sat back on our chairs and for the rest of the night, we acted as if nothing special had happened.

But, of course, something very special had happened, and so a couple of days later, I brought up the subject.

“You aren’t upset about the other night?” I asked.

“Just profoundly embarrassed,” he mumbled.

“You will get over that. Come, have another swim,” I suggested.

“Bathing suit?” he asked.

“Hardly necessary now,” I said. I think he was worrying about the possibility of getting an erection. So I asked. “Are you concerned you might get hard?”

Brett’s eyes opened wide and I knew that was exactly what he was concerned about.
“I can’t control it,” he almost yelled.

“I know sweetie,” I said. “And I don’t want you to control it. Let nature take its course. I would love to see you all hard.”

He looked at me for a long time, then got up and soon he was swimming in the nude. When I got out, I dried him and his penis began to grow. And for the first time, I touched his sex. He jumped when I grabbed his growing cock but did nothing to stop me.

“I think you need to take care of this,” I suggested. He pulled away but I pulled him back. “No, don’t go upstairs. Let me watch.” And so I got to watch my fourteen year old grandson masterbate. I saw his balls pull up and down, and got to see, close up, his perineum and the beginning of his ass crack. As he got close, his eyes focused on my eyes and then he groaned - loudly - as I looked down and saw his cum ejaculate from his super hard penis.

When finished, he took his hand off his cock and just leaned back in the chair. The look on his face was that of peace and serenity. “Don’t move sweetie,” I said. I got up and got some paper towels and then I gently cleaned him up. He looked at me as I wiped up his cum. He clearly loved it as I carefully cleaned and fondled his sex organ.

“There I said. Now, Brett, I want you to remain naked for the rest of the night- you know, so I can admire you.” And he remained naked and I admired every twist and turn of his naked body.

Brett remained nude the next day - at my request - and after dinner, he volunteered to do the dishes. He did wear an apron for that. While he was at the sink, I put a chair right behind him so that my eyes were staring right at his ass. I reached between his legs and gently grabbed his balls. He continued to dry the last dishes as I fondled his precious testicles.

Then I untied his apron and turned him around and his cock was hard and pointing right at my face. He had precum on his pee slit and I licked it off. He really jumped and I laughed. Grabbing him by his cock, I led him to the sofa where I sat down. I spread my legs and had him sit in front of me. I then reached around and began to stroke his impressive, hot, and pulsating penis. When the time came, he had a most impressive series of spurts as he spread his semen all over the floor.

During all this, neither of us said a word. When he finished, he said ‘thanks.”

“You enjoyed this?” I asked.

“Oh, yes, grandma,” he whispered.

“So did I, sweetie.”

Brett remained naked for me whenever we were in the house alone. As he became more relaxed, I was able to touch him at every fleeting moment. If he was walking by me, for instance, I would stop him and fondle his balls or tug his penis or squeeze his soft ass cheeks. Just for a few seconds. Then I would release him and he would continue on his way. God, I loved that. So did he.

But I had not forgotten my friends, Peggy, Lauren, Trudy, and Marie. Here I had a beautiful fourteen year old boy waltzing around the house in the nude. It was time to share him with my friends. And time to have a discussion with Brett.

“I’m not sure what you mean?” Brett said. “You have a club? Five middle aged women? And you are their leader?”

“Yes,” I said. “And you will love them. They are a lot of fun.”

“What is it that you all do?” he asked.

“We get boys like you naked and admire you,” I said.

He almost laughed till he saw that I was serious. “You want me to get naked for them?”

“Yes,” I replied. “And once you make friends when school starts, I want you to include your friends with us.” The smile that crossed his cute face told me that he was receptive to this idea. I pushed the envelope a little. “You do like me watching you naked, don’t you?”

“Would I sound like a jerk if I said ‘yes’?” he asked.

“No, you would not. That is kind of natural. You are such a pretty lad and I want to share you. These ladies are my closest friends and they want to explore every inch of your body - to see and touch your most intimate parts.”

It did not take much to convince Brett. He thought it was all kind of funny. And I guess he knew, deep down, that no one would make fun of him or of his cock and balls.

That Friday night, my friends arrived for the weekend. They each had their own private room and once we had settled down, we waited for Brett to return from school where he was attending an orientation day for new students before school began on the following Monday.

When I picked him up at the school, I could see that he was nervous. “I hope you aren’t having second thoughts,” I said. “I left my friends relaxing at the pool and they are looking forward to meeting you.”

“I just feel weird about it,” he said.

“That is okay,” I said encouragingly. “They are going to love you to pieces. How did the orientation go?”

“Very well,” Brett replied, happy with the change of subject. “I am going to like it there. The teachers seemed nice and I already have made friends.”

“Really?” I asked surprised, “That was fast.”

“They put us in groups and we stayed together for the day. I think Jerry and I are already best friends.”

I pulled over and parked in a bank lot. I could see possibilities here. “Tell me about your friends and I will write down their names.” And so I learned about Jerry Allard, Peter Kingsly, and Connor Mason. I wanted to ask how good looking they were but he didn’t go into that. But when he mentioned Susan Farrell and Carol Norton, he was clear that he thought they were beautiful. All five were Bett’s age (fourteen) and they were boarding students making it possible that one or all could stay with us on weekends. Oh, anything was possible.

“And this Jerry is like a best friend?” I asked.

“Too early to tell but you know, sometimes things just click,” he said. I leaned over and gave my grandson a kiss on his cheek, continued driving, and we soon arrived at my nice mansion. The smiles on my friend’s faces when they greeted my pretty Brett was very satisfying.

“Have you been enjoying the water?” I asked. Oh yes, they had.

“Won’t you join us?” Peggy asked Brett.

“Sure,” he replied. “I will go upstairs and change and be right down.”

“Brett,” I said, “no need for that, is there?”

The expression on Brett’s face was priceless. He knew he would eventually get naked but apparently hadn’t realized it was happening right away. Doubts? Of course. Embarrassment? Hopefully. The poor boy just stood there and so I went over and whispered “Shirt off.” And off it came.

“Why don’t you get naked,” I whispered. Brett gulped and slipped his shorts and boxers down. My beautiful grandson, completely nude, stood before my friends. His face was beet red as he watched the ladies check out his cute sex organ. The pool room was silent. Then suddenly, the ladies grabbed Brett and they all jumped into the pool.

While they all swam around, I got things ready for evening drinks. Soon they all got out of the water and dried themselves. Brett had lost his self consciousness and quickly relaxed. As the only one naked, he was careful not to glorify his nudity (we had talked about that - flaunting his cock and balls could be a big turn off).

But soon, each lady wanted a closer inspection. Peggy sat down and asked Brett to come over. When he did, his sex was directly opposite her face. “Just relax,” she said. She first cupped Bett’s balls in the palm of her hand and then squeezed his penis. Brett’s gasp when she touched him was audible. But he didn’t pull back. I was so proud of my grandson. Sure he was enjoying all the attention being on him and his sex organ, but it still was embarrassing for him, especially with his grandma watching him as his sex was fondled. I watched as each of my friends fondled his most intimate parts but I focused on his cute face. Often his eyes were closed as he just enjoyed the feeling of his penis and testicles being lovingly manipulated. A couple of times he opened his eyes and noticed that I was looking at him. He blushed and quickly looked away. So cute.

Interestingly, while Brett remained naked when just the two of us were in the mansion, he did get dressed when it was time for dinner. Indeed, he remained dressed most of the time for the weekend. But every once in a while, one of my friends asked him to strip his clothes off and he complied without question. For instance, he played ping ball with us while in the nude. We all enjoyed watching his balls bounce all around.

Finally, the weekend ended and Peggy, Lauren, Trudy and Marie returned to their homes. For Brett and me, the weekend ended when he said he was going to shower and then go to bed. I followed him upstairs and told him that I would undress him. He seemed taken aback and stood there as I got him beautifully naked. Then I washed him in the shower, giving special attention to his pretty sex and his soft bottom, for the first time thoroughly cleaning his butt crack. He jumped when I circled his hole. I thought he might have an erection but he controlled that (as he did all weekend). I tucked him to bed and sat by him until he fell asleep. My pretty grandson was beginning school the next day and it was important for him to get a good sleep.

The school year began successfully. Like all good looking students (he was a freshman at Tamiami Academy), he was popular. But he stayed within his tight group with Jerry, Connor, Susan, and Carol (the five members of his ‘Pod’). His friendship with Jerry deepened which concerned me a little. Why? Because Brett told me that Jerry was gay. I was sure that Brett was not gay so I asked Brett if he was comfortable that his friend was homosexual.

“Of course,” Brett replied. “Jerry is quite open about it.”

“It doesn’t bother you?” I asked.

“Why should it?” he said. “I am not planning to have sex with him so his sexuality is his business, not mine. And he knows that I like girls.”

We talked a bit further but I was proud that my grandson was so open minded. There was no hate in his heart. He admitted that Jerry could not hide that there was a physical aspect to Jerry’s fondness for him but Jerry controlled that very well.

I felt bad for Jerry. How he must yearn for Brett, to touch him all over, and to be denied. Well, it is no more my business than anyone’s, and I was glad that the two boys were best friends.

I also decided that Jerry would be our next target. So I asked Brett if he wouldn’t like to have Jerry over for the weekend.

“After all, he is a boarder and he might like a home cooked meal and a comfortable bed to sleep in.”

“In his own room, too,” Brett laughed. “After all, you have a lot of bedrooms in this place.”

“Do you think he will get naked?”

“In front of you?” Brett asked. “I don’t know. I suppose if I was naked he might. Would you like that, grandma?”

“I would indeed. Two naked boys for the weekend? Sounds like paradise.”

As expected, Jerry jumped at the prospect of spending the weekend at Brett’s grandmother’s mansion with its pool. It certainly beat dormitory life at school. I picked both boys up at the end of school on Friday. Let me tell you, Jerry Allard was one beautiful boy. Tousled curly hair, cute face, nice body (which was too much covered by clothing). I couldn’t wait to see his sex organ. I wondered if his cock was bigger than Brett’s.

I would have to wait till Saturday to find out since the boys swam with bathing suits covering their intimate areas. We still had fun on Friday as Jerry was very outgoing and he and Brett clearly enjoyed each other’s company. We laughed, played games, and ate well. Saturday morning was devoted to working on a project the boys had for science class which they finished up around 10:30.

“Boys,” I said, “time for a swim before lunch?”

They both smiled and Jerry began to go upstairs to change into his bathing suit. Brett grabbed him and led him to the pool. I stayed behind to prepare lunch.

“Jerry,” Brett said as they headed to the indoor pool. “This is going to sound a little weird but we are going skinning dipping.” Now, I could see and hear them from the kitchen and I saw Jerry’s face light up. I assumed that he was excited that he might finally see his best friend in the nude.

I missed the rest of the conversation as I got a phone call from Peggy. Brett told me that Jerry and he stripped and they each looked at the other’s cock and then laughed. Jerry apologized to Brett for staring at his cock and balls. Brett told him that was fine - he knew that Jerry was gay. Anyway, when I next looked they were both in the pool. I finished preparing the sandwiches and brought lunch into the pool room and placed it on the table.

“Time to get out and eat, boys,” I shouted.

I could see Jerry freeze. He looked at Brett. “We can’t get out now - we are naked.”

“That is the way grandma likes it,” Brett said laughing. And just like that my grandson pulled himself out of the pool and Jerry could see that his buddy was naked in front of his grandma.

“Come along, Jerry,” I said. “No secrets around here.” Brett helped pull his friend out of the pool and there it was - a perfectly formed male of fourteen years standing in front of me with the most precious parts of his body on full display. And yes, Jerry’s penis was a bit longer than my grandson’s. But that is okay - I love variety.

I grabbed a towel and went straight to the profoundly embarrassed boy and said, “Jerry, just stand there and I will dry you.”

I could see the boy was shocked - he just stood there dumbfounded. He never said a word or moved his hands while I dried his body. I squeezed his butt and gently fondled his cock and balls with the towel. I looked up and Jerry was just staring at Brett with his eyes wide with wonder.

“Now, Jerry,” I said after the quick dry, “you may dry Brett.” Both boys guffawed at that. I gave Jerry a new towel and said “Get at it - lunch is waiting.” Jerry walked over to his wet friend.

“Are you okay with this?” Jerry asked Brett.

“Yes, I guess so,” Brett said, almost in a whisper.

So Jerry, a gay boy, dried his straight friend. He was so gentle and Brett just stood there. “Brett, honey,” I said, “why don’t you place your hands on the top of your head so that Jerry can do a thorough job.” My grandson gulped but did place his hands up. What a beautiful picture. One boy, completely naked, being dried by another naked boy.

When Jerry got to his friend’s genitals, he hesitated. “Go ahead,” I said, “but be gentle.” The room was silent. Brett clearly was enjoying being dried off by someone else, and Jerry was in seventh heaven doing the drying. I could see how gentle Jerry was when he dried my grandson’s balls. I decided to go for it all.

I walked over and took the towel away from him. “Jerry,” I said, “you can touch Brett if you want. He will not mind as you are his best friend.” I wasn’t sure if Brett minded or not so I looked at him. “For Jerry,” I said. He nodded his head and I kissed him on his cheek.

“Go ahead, Jerry,” I said.

“You sure?” Jerry asked Brett.

“I am,” Brett said with hesitation. “But you are the only boy I would let do this.”

Jerry got on his knees and reached out and touched his friend’s penis. He rubbed his finger over Brett’s pee slit while his other hand cradled and massaged his friend’s delicate balls. I could see from Brett’s expression that he was enjoying being touched by Jerry’s soft hands. I could also see that Brett’s penis was beginning to respond to Jerry’s gentle massage.

Suddenly Jerry stopped and stood up. Both boys were fully erect with their cocks pointing out. “Brett,” I asked, “did you want Jerry to stop?”

Brett paused. Perhaps if Jerry was a girl he would not hesitate. But this was his best friend - Jerry. He loved Jerry but not in the way Jerry loved him. But Jerry’s hands felt so good when playing with his sex.

“Jerry,” I said, “you aren’t going to leave your friend like this, are you?”

Brett laughed at that. No, I’m sure he was thinking - no, I don’t want to be left like this.

“Jerry,” I said, “why don’t you take Brett in your mouth and give him some relief?”

Jerry looked at Brett for some kind of affirmation. Brett gave him more than that. “Jerry, will you suck me off?” Not waiting for an answer, Brett placed his hand on Jerry’s head pushing his friend down on his knees. Brett then pushed Jerry’s head toward him so that his lips were just a millimeter from his cock.

Breathlessly, I watched as Jerry engulfed my grandson’s magnificent erection into his mouth. Brett’s groans were very audible as he gently began to pump his penis in and out. I got behind my grandson and placed my finger down his butt crack and began to massage with a pretty little butt hole. I even pushed my finger in a little. I could tell my grandson was losing it. His legs seem to wobble a little. His groans came faster and louder. He could feel my finger inside his ass and his penis inside his best buddy’s mouth. The explosion, when it came, was so profound that Brett yelled out in joy. Jerry, beside himself with wonder, took in his buddy’s semen, spurt after spurt. Jerry relished the taste and the thick texture of Brett’s essence.

I had placed my free hand on my grandson’s chest to steady him and I could feel his heart pumping. When he had emptied his balls, Brett’s body relaxed and his heart slowed down. I held him up. I released my finger from his ass and Jerry released his friend’s penis and swirled his buddy’s cum in his mouth. I laughed and helped Brett sit down.

But Jerry still had a problem. He remained fully erect and in some pain. “Come here, Jerry,” I said. “Let grandma give you some relief.” I sat on the big leather chair and indicated that he was to sit in front of me between my legs. As he sat down, his ass cheeks split and I got a look at his crack. God, was that hot.

Once he was settled down, I reached around and took Jerry’s penis in one hand and palmed his sweet balls in the other. Brett, exhausted and sitting in his chair, stared intently as his grandmother stroked the pulsating penis of his best friend. Soon Jerry began to groan and then began to shout as I felt his sperm transport through his throbbing cock. Spurt after spurt ejaculated from Jerry’s penis landing on the floor.

We spent a couple of minutes, all three of us, without moving. Just resting, just recovering. Then I said, “Brett, why don’t you get a towel and clean up Jerry cum from the floor. And Jerry, why don’t you help him.”

Jerry got up and I got another close (and quick) view of his ass. I watched as the boys, on their knees, cleaned up the floor. Then, as they remained naked, we sat around for lunch.

Suddenly, Brett said “That was fucking awesome.”

“And you fucking taste so good,” Jerry said.

Yes, it was fucking awesome. And the future looked bright. Soon the ladies would enjoy these two boys who each looked like Adonis. And they each had three more friends - Connor, Susan, and Carol - whom I hadn’t seen yet. Oh, yes. As great as this morning has been, it was only the beginning.

{End of Chapter 1}








   
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