Chapter 2: Betting on Haley

Betting on Haley – Part 1

Skipping Class

Two and a half weeks ago my friend Carly and I decided to skip a couple of afternoon classes and go 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 found the perfect way to accomplish her goal, 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 even locking 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 was 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 sisters 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 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 you want. 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 you know 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 smiled.

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, just the first day that came where both of their parents were going to be gone for the day at some kind of reunion or conference or golf or something, who cares. 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 real quick, and could Haley let me hang out until she got back. She said that Haley lit up when she heard that. She 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 that 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 the abs and shoulders for a change, which I almost never do. She was definitely drooling just a bit.

On the couch

I followed her into the living room where she plopped down on the couch and turned on the TV. I plopped down right next to her, maybe a little closer than she expected. I wanted to be able to touch her. While she was checking out the TV, I was checking out her. I just turned right to her, ignoring the TV completely, and ran my eyes over that body a couple times. Those bare legs were just delicious.

As I sat on the couch ogling her body and feeling my groin start to stir, Haley turned to me, leaned away just a little bit and asked “Are you okay?”

I answered “Oh yeah”

She asked “What are you doing”

Now was the time. I hesitated for a moment, and then said “Okay, now that Carly isn’t here I can finally ask ... how did you like our little show?”

She was nervous. She wrinkled her brow and said “What show?”

I just smiled and said “ ... You know”

I could see in her eyes that she knew exactly what I was talking about. She said “No...”

I grinned at her even harder and said “You remember ... about two weeks ago ... you came home early, even though you were SUPPOSED to be at practice...”

She started to turn bright red and her eyes were getting bigger and bigger.

I continued “ ... then you stood upstairs in the hallway for like half an hour ... peeking through the doorway while I fucked your sister”

Poor Haley’s jaw dropped and she turned the brightest shade of red for a few seconds. I just kept grinning at her and laughed a little bit. She was flustered for a few moments and didn’t say anything. She was obviously shocked that I would just come out with it like that. Then finally she blurted out

“It’s not my fault! She always leaves her door open”

“Always?” I asked. “You do that a lot?”

“No” she answered. Then hesitated a little “well ... sometimes ... besides I didn’t see anything”

I hesitated for a moment, looked her in the eyes and said “How could you not see anything? I did everything but open the door and invite you in”

She gave me that incredulous look again. I could see she was confused. She was having trouble processing that she wasn’t in trouble. She looked at me and said “What?...”

I just giggled as I leaned closer to her, put my hand on one of those sexy thighs and gave it a little squeeze and said “Haley, it’s okay, I didn’t mind.”

She just stared at me with her mouth open.

I said “ ... actually it made it so much hotter knowing you were watching the whole time”

“You knew the whole time?” she asked.

“Oh yeah” I answered. “I saw the door crack open in the mirror.”

Then I added “You should really be more careful, if Carly saw you she would have killed you!”

Poor Haley sat there for a few moments processing what I was saying. Yes, I knew you were there the whole time. No, your sister doesn’t know. Yes, I purposely tried to make it so you could see everything. No, I was not mad about it. In fact, I was very much turned on by it. And yes, that is my hand caressing that soft sexy naked thigh of yours. Would you like to try for more?

Prove it

She sat there thinking for a moment and glanced quickly at my hand on her thigh. Then she looked up at me with a little of that smile returning and said “You didn’t tell Carly?”

“Do you think you’d still be alive if I told Carly?” I answered.

“She’d kill you!”

“Carly still thinks of you like your ten years old. Her sweet innocent baby sister who wouldn’t know what to do with a real dick if it hit her in the face”

I had practiced that line.

Haley reacted exactly as I had hoped, she rolled her eyes and spat back at me with just a little bit of venom in her voice “I’m not fucking ten, I know what to do”

Perfect. Exactly what I wanted you to say. I raised my eyebrows, looked down at that leg I was caressing and gave it a couple very intentional squeezes. Then I looked back up into her eyes and said...

“Really?”

I hesitated slightly. Still locked into her eyes...

“Wanna prove it”

Her eyes went real wide again. Her breathing shortened. She stared right back into my eyes and after a moment answered “Really?”

I leaned in closer, began to caress that thigh. Then I put my other hand behind her neck, and as I pulled her closer to me I said “C ‘mere”

And then I kissed her.

Haley did not hesitate. She just dove right in. The next thing you know our tongues were battling and her arms wrapped themselves right around my neck. I pulled back for a breath, looked down at that hand on her thigh and started moving it higher and higher. I noticed her legs drift apart just a little bit. I don’t think she even realized that she did it, which just made it even hotter. Her breathing quickened. I returned my attention to those lips and resumed kissing for a little while, as my hand continued where it was.

Haley was now rubbing her hands all over my stomach and abs. She was obviously enjoying every moment of this. I was right all along, little sister wanted some action. I slid that hand all the way up her thigh to those tight sexy shorts. Her reaction was automatic. She took in a breath, her legs closed a little on my hand and tightened up, and she suddenly pulled me very tight.

I pulled back from that kiss and said “You said you’d know what to do if you had the chance right?”

She hesitated for a moment and started to say “yeah but...”

I pulled my hand away from her legs. I pulled my hand from behind her head. Then as she watched, I started pushing my pants down.

I said “Okay ... here’s your chance”

I grinned at her, then I just slid my pants off and let my cock fly up in the air. I was so hard by this point that it was such a relief to let it out. It just popped right up like a flagpole. I didn’t care, she’d already seen it anyway.

Haley jumped. Her eyes practically popped out of her head, and she said “OH MY GOD what are you doing?!”

I answered “You said you’d know what to do, now’s your chance to prove it”

Then I gave her the most evil grin, just daring her to continue.

She was staring at my cock sticking up in the air in front of her. She couldn’t take her eyes off it. You could see the thoughts running through her head, but she was still scared.

She blurted out “What if someone comes home?!” as she was looking every which way she could.

I answered “Your parents are gone for the day right? Carly is at Ashley’s house...”

She responded with her eyes still huge. “Oh my god I can’t believe this...”

And then after another moment “it’s so big!”

We sat for a moment with her staring at my cock. I reached around her and pulled her close again. Then with my other hand I reached over and took her hand. Slowly I pulled her hand over and wrapped it around my cock. Very gently she took hold. For all her objections about not being a little girl anymore and knowing what to do, she had clearly never had her hands on a real live cock before, but as she wrapped her hand around mine a smile started to spread across her face. I leaned my head back on the sofa and closed my eyes. Then, slowly, Haley began to explore.

Can you stay?

As I sat there, Haley’s hand began to touch and feel and explore my cock. She could barely wrap her tiny little hand around it. She clearly didn’t know what she was doing, so I gently wrapped my own hand around hers and began to slowly stroke. I started telling her what to do and giving her directions. She followed them eagerly, and she learned fast.

Haley began to stroke the shaft and the head. With some direction, she started to work on my balls as well. In no time at all she learned what worked well and what didn’t. I lifted my head, put my arm back around her and held her close again. I turned to her and softly said...

“Now put your mouth on it”

She stroked it a couple more times and said. “Really?”

I looked at her and said “You did say you knew what to do, right?”

She said “I do! It’s just...”

I knew of course that she had no idea what to do.

I said to her “Haley, do you plan on having a boyfriend at all?”

I also knew she already had plenty of guys asking her out. She answered “Of course I do”

I continued “If you plan to have a boyfriend, I guarantee he’s going to want you to give him a blow job”