Chapter 3: Betting on Haley - Part I

Skipping Class

Two and a half weeks ago, my friend Carly and I decided to skip a couple of afternoon classes and get fries at the local café. I had recently been dumped by my longtime girlfriend, and Carly thought I needed cheering up. Of course, Carly, being the captain of our school cheerleader squad, was the perfect person to do that. By the end of that afternoon, she had found the perfect way to accomplish her goal, and we ended up at her house getting naked.

Needless to say, I cheered up. The only complication was that almost as soon as we got to her room and started getting busy, I spied her younger sister, Haley, watching us through the cracked bedroom door. I thought sure she was going to burst in and bust us or threaten to tell their parents. Instead, the little perv stood there in the hallway watching for at least half an hour as Carly and I did everything we could to each other. Little sister was totally into it!

I didn’t mention anything about it to Carly as we continued our activities, partly because I didn’t want to stop what we were doing, of course, but partly because I was totally getting off on putting on a show for little sister. I did everything I could to make sure she got a good view of the action. At one point, I even locked eyes with her standing in the doorway. She panicked and bolted. She knew she had been caught, but when I didn’t do anything about it, she came right back to watch us finish. I could only imagine her standing in the hallway with her hand down her pants, working herself into a frenzy.

Carly was both shocked and panicked when she found out. Her first thought was that Haley would tell their parents, and they’d take her brand-new car away. She was also shocked that her innocent little sister would stand in the hallway peeping on us the whole time. I recognized right away that Haley wasn’t as innocent as Carly thought. I told Carly she didn’t have to worry about her little sister. She wasn’t going to say anything to anybody except maybe her friends.

After we got dressed and slipped out of the house, Carly and I continued talking about the whole situation. Carly was still convinced Haley was going to blackmail her. I was convinced Haley was a horny little freshman who wanted some of what her big sister was getting, and I had decided to give it to her. By the time Carly dropped me off at home, we had a bet on whether or not I could bed her little sister.

The Bet

The bet was simple. My goal was to take her sister’s virginity. (We were assuming she was a virgin). The hard part was deciding the terms. At first, Carly argued that if I succeeded, then I’d already won because, after all, I got to fuck her sister. I argued that Haley was the goal, not the prize. I was going to do it anyway, but I wanted some icing on this cake!

Eventually, Carly offered up the entire cheerleader squad as a prize. She said that she could arrange things so that all of the cheerleaders would be fighting to jump in bed with me. I didn’t really believe she could deliver on that promise, but who could resist an offer like that?

For my part, I didn’t really care. I was so confident that I would succeed that I gave Carly a blank slate. If I fail, I’ll do whatever she wants. Anything. I saw the look on Haley’s face as she was watching us. I saw the glazed look when we locked eyes through the doorway. That wasn’t planning blackmail. That wasn’t shock; that was lust, pure and simple. The girl wanted to join in the fun. I had no doubts at all.

The only rule I insisted on was that Carly couldn’t say anything. Not to anyone, especially her sister. She was forbidden to reveal that she knew about Haley’s peeping. That was a secret between the three of us, kind of.

Teasing Haley

Over the next two weeks, any time I saw Haley, whether at school or at their house, her eyes would glaze over as she checked me out. You just knew she was remembering what she saw through that doorway. If I stopped by their house, Haley’s eyes would light up when I walked in the door. I would catch her looking me over and just smile, maybe give her a wink, and turn back to my conversation. She would usually flash me back a naughty little grin herself.

I had visited their house before Carly and I had put on our afternoon show, but Haley seemed to look at me a lot differently now. Now, she had a whole different image of me in her mind. I had an image of her in my mind as well, and it was very, very naughty.

Sometimes, I would be able to give Haley a friendly greeting when I arrived with a quick little hug or a squeeze. When I could, I would sneak a little grab at that ass. She would jump a little, but she liked it. Haley was shorter than Carly by at least six or eight inches; she only came up about to my shoulders, but she fit perfectly right under my arm. She had long dark hair, very silky, down to the center of her back. She also has these deep brown eyes that still manage to sparkle and light up whenever she smiles.

Haley played lacrosse and volleyball. Don’t ask me how a girl barely five feet tall managed to make the volleyball team, but damn, did she look good in those tight little shorts! Needless to say, she had a very tight, athletic body. Toned legs, flat tummy, and strong arms. Her breasts seemed small but still a perfect size for her, at least as far as I was concerned. Last but not least, she had that same perfect little bubble butt that her sister had. I loved that ass on both of them! Any time I saw either of them in school, I just wanted to run up behind them and grab hold. I’m sure I wasn’t alone.

... and we’re off!

Finally, the day came to put my plan into action. It wasn’t really a plan; it was just the first day that came when both of their parents were going to be gone for the day at some kind of reunion, conference, golf, or something. All I knew was I could get Haley alone. It was a Saturday, around eight in the morning. Carly came and picked me up, then dropped me off a short walk from their house. Carly had told Haley that I was coming over but that she’d gotten a call from her friend Ashley and had to run to her house really quickly. Could Haley let me hang out until she gets back? She said that Haley lit up when she heard that.

She had just smiled and said, “Of course.”

When I knocked, Haley, expecting me, opened the door and let me in. I greeted her with the same friendly hug I’d been giving her for the last couple of weeks and added a quick little kiss on the forehead. I’m not sure she even noticed. The first thing I noticed was the perfume. I don’t know what it was, but it was intoxicating. I’d never known her to use perfume before today.

She invited me in and told me that Carly would be back soon. She just had to get something from her friend’s house. She offered me something to drink, so I followed her to the kitchen, taking in that sexy little ass in the shorts she was wearing. They were so tight and showed off her ass to its absolute best. This was not something she just threw on for a casual Saturday morning at home. These were tight and sexy. I suspected that as soon as Carly told her she would be alone with me for a while, she ran upstairs and “got sexy” for me. I could feel my groin stirring already.

We made some small talk in the kitchen for a short time. I asked her what her plans were for the day, and she said she had practice later, so she was probably going to work on homework until then. Can you believe that? Such a good student.

Every chance I got, my eyes would roam over that sexy body. I would check out every inch, stop while I was checking out that sweet ass, and make sure she caught me doing it. In return, I caught her eyes traveling over my body. I was wearing loose gym pants and a tight shirt, showing off my abs and shoulders for a change, which I almost never do. She was definitely drooling just a bit.