[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.