Sleepover Club

[HHHobo]

I posted this story a few years ago, but now its time has run out. I am editing the original story and adding some additional chapters. I will try to post a new chapter about every other day, as long as people want to keep reading it.

Chapter One

The official beginning of the Sleepover Club came in ninth grade. It wasn’t that we didn’t have sleepovers before that. We just realized how much fun we had together and decided to make it an exclusive group.

There were eight of us living in the neighborhood who got things started. Brian and I (Willy) were the only boys. The six girls were Libby, Molly, Colleen, Brianna, Bridget, and Rachel. We were all about the same age. You will begin to get to know us through the antics of the club.

It may seem strange for there to be a Sleepover Club of both genders. But our parents, especially Brian’s and Brianna’s, were quite liberal. They had grown up through the seventies and the ideas of that time had stayed with them. We were basically good kids and had earned their trust. I’m sure they also felt that we were a lot safer doing things with friends whom they knew in one of their own houses. In any case it was a wonderful arrangement and we had great fun for many years.

Once we decided to form the club, we made it exclusive. Except in very special situations, no one beyond the eight of us was to participate in a sleepover. A special situation might be a relative staying with one of us or a sibling who otherwise had nothing to do and nowhere to go. The latter two presented opportunities to prey upon an unsuspecting victim, but it was also a risk to expose us to an unknown factor.

Our first sleepover after the official formation took place at Brianna’s house. Her parents basically left us alone unless we called them. Their house was built into the side of a hill. The entrance was on the second floor. We had our sleepovers in the family room, which was on the bottom floor, with a walkout into their large, fenced backyard with a pool. Brianna’s rents generally stayed on the top floor in their large master bedroom, which faced the front of the house. So we were safe from parental interference, as long as we kept things relatively quiet. That made it possible for us to get away with some pretty crazy antics.

That first night we all arrived about 7 PM and Brianna’s rents sent out for some pizza and soda. It arrived about thirty minutes later. We took it to the family room and consumed it in about twenty minutes. The early part of the evening was quite tame. We watched some TV, played some DVD’s, listened and danced to some music, and talked a lot about school, sports, and other kids. About 10 PM Bridget suggested we play Truth-or-Dare. We had played it many times before, but recently the level of the questions and dares had been escalating. This night we decided that anyone who refused a question or a dare would have to take off a piece of clothing. A pair of shoes counted as one piece, as did a pair of socks. Jewelry and hair attachments didn’t count. Neither did belts or anything else not made of cloth. If one person started with fewer clothes than someone else, that was just tough luck.

Brianna got to start things off, as she was hosting and she chose Brian to start the game. Brian knew that Rachel had a new boyfriend outside the club. So he asked her T-or-D, and she chose Truth. Brian asked her how far they had gone. Rachel replied that they had only kissed. Well, that was boring. Rachel moved on to Libby. She chose Truth, and Rachel asked her when the last time was that she had masturbated and how she had done it. We all laughed, but Libby said nothing and took off her shoes. When Libby challenged Colleen, she feared the question and took the dare. Libby dared her to let Brian and me feel her up. Colleen chickened out and took off her shoes. She came to me and I wasn’t sure what to do. I hesitated, and Brianna let me know that if I didn’t choose quickly, I would lose two pieces of clothing. I couldn’t get a good idea and I just stammered. Then Brianna yelled, “Times up!” I pleaded, but Brianna insisted that if I didn’t give up my shoes and socks, they would all strip me all the way. I looked around at the others. They grinned and nodded. I knew that they would follow Brianna’s lead, so I reluctantly took both socks and shoes off. Now I only had on my shorts, boxers, and T-shirt. I tried to get back at Brianna. She chose Dare. She’s probably the most uninhibited person I know and would do anything, so I tried to get her by daring her to let Brian put his hand in her panties for three minutes. I thought surely she would back out of that one, but she didn’t. Brian thanked me and slid his hand inside her sweat pants and thong. We could see his hand moving around in Brianna’s crotch and funny looks on Brianna’s face.

When the three minutes were over, Brianna challenged Bridget, who has been going out with the same boy for over a year. I’m sure that Bridget was afraid that Brianna would ask her about what they did with each other. So she chose dare. Brianna looked Bridget over. Bridget was wearing red shorts and a white T-shirt. Brianna calmly dared Bridget to pour a pitcher of water over her T-shirt. Bridget refused and off came her shoes. Bridget now turned to Brian. Brian chose Truth. Bridget asked Brian if he had ever crossdressed. When he heard the question, he knew that he had blundered. He had confessed to Bridget and me another time that he had lost a bet to his older sisters and had to be feminized for a day. Now Bridget was using it to embarrass him. He couldn’t lie, so he told us all about the experience. He blushed crimson as he told about having to strip naked in front of his sisters, put on a thong and a bra, and get made up. A dress, a wig, and some high heels completed the outfit. They drove Brian all over town – to the mall and McDonald’s and a park. It was the most embarrassing event in his life, and now he had to tell us about it.

Brian would have loved to get back at Bridget, but the rules didn’t allow an immediate reverse. The only one not yet challenged was Molly. Brian chose her and Molly chose Dare. Brian dared her to let the rest of the group redo her hair without cutting any of it. Molly agreed and fifteen minutes later Molly had hair that was pink on one side and light blue on the other. The pink side was done up in a whole bunch of little pony tails, while the blue side was curled up at the bottom. Brianna produced a couple of cameras and Brian and I shot video and stills of the whole process. I don’t think that Molly expected us to do so much, but she took it like a good sport.

[Hunterman36]

I remeber this story. I'm glad to see it back, I hope to see more. Keep up the great work.

[HHHobo]

Molly looked at me and said, “You’re next!” Fearing a question that I might have to skip and lose more clothes, I chose Dare. Molly looked at me and turned to the rest of the group and said, “I hope this fits the rules. Willy, I challenge you to a game of backgammon. The winner gets to make a sundae on top of the loser’s head. All except the loser can then help eat the sundae. The only thing the loser gets is any drippings of the sundae that find its way to his or her mouth or anything fed to him or her by anyone else.” There was unanimous approval and a backgammon board was produced and the game began. At first I had great rolls and I moved out smartly and was building good blocks for Molly’s back men. Then my luck changed and Molly sent several of my men back and I was severely challenged to get them back in. In the meantime, Molly moved her pieces around the board. When I finally got my men back in play, it was too late. Molly won easily. They covered my body with a garbage bag with a hole cut out for my head. Then on came the ice cream and syrup and whipped cream and nuts and cherry, some of which ran down off the top of my head. OMG, it felt so cold. The compilation was attacked by the company. My face was messy to the extreme. An occasional plastic spoon found its way into my mouth. Naturally my embarrassment was captured by the cameras.

I would have liked to try Brianna again, but our normal rules didn’t allow us to come back to the same person repeatedly. Instead I chose Rachel. Rachel didn’t like the dare I had given Brianna, so she chose truth. I asked her to describe her most embarrassing moment. She paused for a moment and chickened out. Off came her shoes.

One of the ways to avoid Brianna’s evil mind is to challenge her, so that she can’t challenge you back immediately. That was Rachel’s choice. Brianna smiled and chose Dare. Rachel dared her to give me and Brian each a lap dance. That was tamer than her first dare, so she readily agreed. I got one song and Brian got the other. I don’t know about Brian, but I had a good boner by the time Brianna was done. As it grew, Brianna turned and gave me a knowing look. She squirmed even more and I was afraid I might erupt. The song ended just in time, and I breathed a sigh of relief.

The problem with Rachel’s tactics is that it exposes the rest of us to Brianna, but that certainly didn’t bother Rachel. Brianna especially likes to nail the guys and I looked especially vulnerable. I knew she would come up with some really humiliating dare, so I went for Truth. She asked me how long my schlong was when it was soft. “Come on”, she said, “We’ll all see it later anyway.” I replied that chances are it would be hard then. Now my penis is pretty big when it is hard, but it is tiny when it’s soft. Whatever I did, I would be embarrassed. I chose not to be specific, chickened out, and took off my shirt. Brianna turned to the other girls and said, “He must have a real microdick.” I blushed and the girls laughed loudly. Brian just looked away.

I could now come to Molly to try to exact a little revenge. My hair was still all sticky from the sundae. I think she feared that I would come up with something equally messy, so she chose Truth. Trying to get her to lose her shoes, I asked her to describe her pussy in detail. Surprisingly, Molly launched into a vivid picture of its pinkness, its cute clitoris, the curly black hair that surrounded it, its softness, its sensitivity, and how much she liked it. Everyone was speechless, even Brianna. But Brianna wasn’t quiet for long, because Molly challenged her.

As usual, Brianna chose Dare. Molly dared Brianna to a game of Word Racer, with the loser having to tongue kiss with the boys, five minutes each. Brianna knows how good Molly is at Word Racer. Had Brianna had fewer clothes on, she might have accepted the dare. It was easy to decline and remove her socks and that is precisely what she did. Brianna turned to Brian for the next turn. Brian is incredibly shy about his body, so it seemed to be easy to get him to answer a question or take a dare. This time he chose Dare. Brianna dared him to take a spanking from all the girls for fifteen minutes. Brian thought that his pants and boxers would give him some protection, so he chose the spanking. The music was turned up to cover the noise. Brianna had Brian bend over the back of an easy chair with his butt sticking straight up. I got out the cameras and the girls starting swatting Brian’s backside. As was to be expected, Brianna swatted him the hardest. When the time was up, he had trouble sitting down, but he had taken the spanking well.

Brian and I spoke briefly. It seemed as if two things were going on. All of the girls except Brianna were trying to keep her from challenging them. But Brianna seemed to have other things on her mind, namely Brian and me. We decided to focus on two of the other girls, so we wouldn’t be the only ones victimized. Bridget and Rachel were likely candidates because of their boyfriends. Brian looked up and challenged Bridget. Bridget quickly responded, “Dare!” Brian remembered how Brianna got her before and tried something of the same kind. He challenged Bridget to get a swirlie. Bridget demurred and removed her socks.

Bridget pondered a while. As she looked back and forth she seemed to be considering challenging Brianna or me. Finally she looked at me and said, “What will it be, Willy?” “Dare”, I replied. “OK, let us paint your fingernails and toenails.” I wasn’t ready to lose my shorts, so I gave in. Out came about twenty different shades of fingernail polish and one of the girls started out on each extremity. Each of my nails ended up a different shade. One hand was a variety of pinks. One foot had greens and blues. The others were a mish mash. I was embarrassed, but it was better than being one step from nudity.

Bridget’s challenge opened up an opportunity. I looked at Brian and he nodded. “Brianna, it’s you!”, I spoke sharply. “Dare”, she replied. “Take a double dose of laxative!” I said. “Are you kidding me?” “No!” “Well, I won’t.” She took her top off, stood there with her bra on, and stuck her tongue out at me. Now she had a problem. She really wanted to get at Brian and me. She couldn’t challenge Brian, because he was her last challenge. She couldn’t do me, because I had just dared her. Brianna looked around and realized that Molly still had all her clothes. “Molly”, she cooed. “Yes, Brianna”, Molly replied. “Truth or Dare?” Brianna queried. “Truth”, the answer came back. Brianna had completely expected a dare, and had to scramble for a question. “Hurry up”, I said, “There’s a time limit in this game. You’ll lose more clothing if you don’t ask a question.” “Shut the fuck up”, cried Brianna. The others joined in the chorus, rattling Brianna even more. No one had ever seen her rattled before. She couldn’t come up with a question for Molly. Libby and Colleen made her give up, and I was revenged. Brianna took off her jeans and was down to just her underwear. She and I were the same distance from nudity.

[wedgied]

Nice Story, I look forward to more

[fleetfeetclogger12]

Applause!! Keep it goin! As mcdonalds says....

IM LUVIN IT!

[silverwall]

Great story. I look forward to more posts.