[Fiction] The Sleepover Club

[HHHobo]

After reading "Sister's Sleepover" and its sequel, I realized that it reminded me of a long story I wrote four years ago and never posted anywhere. I'll post the first installement below. If the feedback is positive, I'll continue posting every few days. Hope you enjoy it.
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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, Alejandra (Brianna), Bridget, and Rachel. We were all 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 but 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.

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 parents 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 relatively quiet. That made it possible for us to get away with some things.

That first night we all arrived about 7 PM and Brianna’s folks sent out for some pizza and soda. It arrived about thirty minutes later. We took it to the family room and consumed it about ten 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 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. If one person started with fewer clothes than someone else, that was just tough luck.

Brianna spun the bottle and it pointed at Brian. He 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. Still I thought about it, and 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.

[bondageboy]

pretty go so far.

[Daring nemder]

great start please continue.

[ShinyDemon]

This is a really good start HHHobo ! Really well written, well formatted and a good, interesting story. I'm really pleased that my story inspired you to share this one with the readers.

Keep it up ;o)

[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. 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. I’m sure she could feel it through my clothes.

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 Willy’s willy 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. The girls clapped and whistled.

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 she 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. 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 some girl 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.

[Hunterman36]

This story is great I enjoy the development and can't wait for more.

[HHHobo]

For winning the contest Molly got to make the next dare. Rachel and Colleen were out of the running. I whispered in her ear and she chose Bridget and me. Bridget pleaded to be skipped, but Molly insisted. She dared us to have a whipped cream fight. Bridget actually got a little smile on her face. We went in the backyard. There were to be four rounds to the fight. The first round was just a can of whipped cream for each of us. I had felt sorry for Bridget before, and I let her get me pretty good. In the next round we had another can of whipped cream, but one hand was tied behind our backs. Now it was impossible to block your opponent. It was about fifty-fifty. In the third round the hand tied behind the back and our ankles were tied so we could only hop. This made Bridget’s tits bounce all over the place, and I got another woody. It was also a good excuse for me to fall down so that Bridget could really nail me. I even let go of my whipped cream and she got me with two full cans. It looked as if she was perking up, which made me feel glad. In the last round the ropes came off, but we were blindfolded. I made sure to make noise, so that she would know where I was. I even let her steal my can and get me with both cans again. After we cleaned up, she whispered in my ear, “I know you were faking. I really appreciate it. It was a lot of fun.” “No problem”, I replied.

Bridget got the next dare and she returned to Rachel and Colleen. It looked like curtains for them. They only had their panties left, but Bridget made it possible for one of them to survive. She dared them to have a wedgie contest. Brianna and Molly would each give them hanging wedgies. The one that wimped out first would go naked. At first they didn’t want to do it, but finally agree. They had similar panties on that were very elastic. When the wedgies were fully applied, the panties stretched over their heads. Brianna and Molly got their panties well up their cracks and others of us lifted them up and hung them on the wall. They groaned when we let go.

Colleen had the next dare. She went ahead and did it while she was up on the wall. Her choice was obvious – Molly. She dared her to take an enema, but Molly refused and took off her jeans. Molly then dared me and Brian to bounce Rachel and Colleen up and down on the wall. The girls protested, but this seemed a good way to speed up the contest. We went at it. Soon Colleen had had enough and quit. We lifted them both down. They picked their wedgies to our delight. Bridget asked Rachel to do the honors. Rachel slowly rolled Colleen’s panties down, pausing briefly a couple of times until she was past Colleen’s pussy. Then her panties went quickly to her ankles and the number of naked people was six.

This action had gone quickly and I was able to dare Rachel again. After surviving the wall wedgie she was not ready for another dare. I dared her to stick her nose in my asshole. She refused and I yanked down her panties. That left Molly as the winner, but we didn’t stop there. Rachel made short work of the rest of the game by daring all her legal victims. Brian, Colleen and I were out. Brianna, Libby, and Bridget were dared to strip Molly. Molly protested, but the rest of us were ready to end the madness. In no time Molly was also butt naked. Brianna dared everyone to sleep naked, and we agreed. It was now almost 3 AM. We crawled into our sleeping bags, told a few jokes, and went off to sleep.
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This is not the end. This was just the first game. The gang will return with what happened at Halloween.

[molten man]

brilliant story!! it was a great read!!

[ChazzTuck]

i love that this is just the beginning! Looking forward to more!

[Mireille]

Please post more!

[ShinyDemon]

Excellent new installment - this has all the signs of a really good story.

[Dare Man]

A great story and I love it. Maybe put in some more "sexy"details (like Brianna's underwear is). But I love it. Please continue.

[Daring nemder]

awsome run keep going please

[HHHobo]

Molly had escaped a problem and looked for her own challenge. She could stick to the feminine game plan and go after one of us guys. On the other hand she could look to bring one of the females closer to being bare. Molly is a jock. She plays every sport she can find, and she plays them hard. In that, she shares many traits with males, although she hates males who disparage women. Fortunately, Brian and I didn’t fit that pattern. Bridget is an athlete, too. But Bridget also leans toward being deliberately sexy, which Molly never does. So Molly saw Bridget as being vulnerable to a challenge and called her. Bridget was still afraid of questions relative to her relationship and she called “Dare”. Molly dared her to make a call to her crush and get the discussion as sexy as possible. Bridget thought briefly and declined the dare. She had been wearing a tennis dress, so she had to take it off and be reduced to the same state as Brianna. Brianna immediately claimed that her pink bikini panties were cuter than Bridget’s plain white ones, but we all just ignored Brianna.

Bridget knew that the game was running against her. She had to make some change to deflect the interest in her state of dress. It was clear that Brian, Molly, and I, and possibly Brianna, were likely to choose her. She had to find a different route. After some brief thought she chose Rachel. Rachel also had the boyfriend issue and called “Dare”. Bridget dared her to turn on all the outside lights in the backyard and go out in the middle and pee. Surprisingly, Rachel accepted the dare. The lights came on, the door was opened, and Rachel walked out. She was wearing a miniskirt and a short top that showed her midriff. With her back to the house she lowered her blue-striped panties to the ground. She squatted down and revealed nothing to anyone in the house. If someone were looking into the yard from the opposite direction, they got quite a show. But the chances of that were remote, as Rachel obviously knew. We could see her pee because the ground near her feet began to glisten. When she was done, she pulled a tissue out of her top, wiped herself off, stood up, and pulled her panties into place. Without undue embarrassment she had fulfilled the dare.

Rachel returned to the house smiling at her success. Now she had to decide who to challenge. Should she go for Brianna or me? We were close to being stripped. Should she go for Molly, who was still fully clothed? She didn’t want anyone putting a time limit on her. She looked my way and said, “Willy”. “Dare”, I replied. “Now that you have pretty nails, how about some makeup to go with it?”, Rachel asked as she giggled. I turned her down and took off my shorts. It was clear that I was soon to have my package on display.

“What the hell”, I thought, “Let’s see if I can bring someone down with me.” “Truth or Dare, Brianna”, I shouted. “Dare”, she answered. “If I strip all the way, then you have to do the same.” “I can decline that and just lose my bra.” “But then I still have my shorts.” “Hmmm...”, Brianna thought about it. “Hurry up or I’ll call a time limit on you.”, I warned her. “OK, let’s do it!”, she agreed. “Take your bra off, then we’ll both take our bottoms off together.”, I instructed. Slowly she undid her bra in back, slipped the straps off her shoulders, but held the bra in place with her arms. She rotated to give everyone a view. Cameras were very busy. Finally she let the bra slide off all the way, revealing her large nipples, which were noticeably erect. We looked each other in the eye. Brianna walked over and stood next to me. We faced the others and slowly lowered our underpants. As we did so, we bent at the waist, so it was hard for anyone to get a good look. When we stepped out of our u-trou, we straightened up, putting all of our goods on display. There was a round of applause and cheers. “No covering up!”, ordered Rachel, “or you get a paddling on your bare behinds.” I was blushing, but Brianna seemed to be enjoying all the attention. She is really quite uninhibited.

Now the rules changed for the two of us. Since we had no more clothes to give, we couldn’t back out of a truth or dare. However, we were allowed to turn one down, if we doubled another one immediately. Now Brianna looked around. She clearly wanted to get others to join us in our state. Bridget was the closest, so Brianna chose her. As usual, Bridget went for a dare. Brianna made one that I was sure that Bridget would pass on. Bridget was to go to the far end of the backyard dressed as she was then, in her panties and bra. There she was to point straight up and spin around ten times. Then she had to run straight back into the house. The catch was that Brianna would be waiting for her with the hose, as well as Brian, Molly, and me with Super Soakers. Obviously Bridget didn’t want to be bare, because she took the dare.

Off she went to the end of the yard. She barely made the ten spins without falling down. As soon as she was finished, Brianna hit her with a blast of water that sent her reeling. The three of us with Super Soakers closed in and drenched her. She was very dizzy and could not dodge our onslaught. As she began to recover her balance, she tried to keep one of the three us between her and Brianna. We fixed her by two us coming right at her and splitting to either side. Then she was hit by both of us and Brianna. Brianna was obviously going for her bra and panties. They were white and Brianna wanted to them as transparent as possible, as well as to make them cling to her body. I was really into this. The focus was on Bridget’s predicament, not my nakedness. Finally Bridget gave up trying to dodge the water. It was useless, as she was thoroughly drenched. She just ran straight for the door, taking one last blast from Brianna before she gained the safety of the house.

“Hey, Miss Transparent”, yelled Rachel as Bridget came inside. Bridget instinctively covered up. Libby handed her a towel and she dried off. Her soaked undergarments clung to her body. Bridget sat down, crossing her legs and folding her arms to reveal as little as possible. “I’m not nude; I can cover up.”, she declared forcefully. Bridget was in the middle. She wasn’t naked like Brianna and me. But she was much barer than the rest of the group, who were almost fully clothed. “Is it time for us to be able to dare multiple people?”, she asked.