Description: After losing a bet to her friend Zane, Carly now has to deliver the entire cheerleader squad for his pleasure. Fortunately, she has a plan, and it works out far, far better than either of them could have imagined! Virgins, cheerleaders, betrayals, orgies, sex toys all wrapped up in a classic tale of sexual coming-of-age...hotness with a wild ride of the very end!
Tags: teens, consensual, voyeurism, coercion, oral, anal, sex toys, high school, virgin, bisexual
Published: 2018-05-08
Size: ≈ 84,673 Words
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by RedCzar
©Copyright 2018 RedCzar
Tragedy
Toward the end of my junior year, the absolute worst thing ever happened. My beautiful, wonderful girlfriend Jamie decided it was time we started seeing other people, and by "we," she meant "she." I couldn't believe it! Here I thought we were rolling happily along, and then she just dropped this bomb on me out of nowhere. I was stunned.
This is when I discovered that I'm really not as smooth, smart, and clever as I like to think I am. Jamie told me that she knew all along that I had occasionally been sleeping with her best friend, Melissa. She also knew that Melissa was blackmailing me into it. When Melissa told me that she had said to Jamie, "If you don't fuck him, someone else will," what she had actually said was, "If you don't fuck him, I will." So when the opportunity came up, that is exactly what she did. It seems I was a lot more stoned than Melissa was that day during the summer.
I also learned that it didn't really bother Jamie. She said that every time the three of us were together, Melissa would tease me, and Jamie would glare just to watch me squirm. She also said that the whole episode where Melissa was hiding in the corner of the room watching while Jamie and I were fucking away, they planned that. Apparently, Melissa just really got off on watching, and Jamie didn't mind. If only I had known! But apparently, that's how oblivious I am sometimes.
What Jamie said finally pushed her to break up with me was that she heard I was sleeping with some girl from my school. I wasn't. Other than Melissa, I really was completely faithful to Jamie. I have no idea what rumors she was hearing, but that's the excuse that she gave. She never gave me a chance to deny it, or defend myself, or at least lie, just BOOM! Over.
Needless to say, I was devastated. I spent the better part of the next week moping around and being generally unpleasant. Not even the girls I was supposedly sleeping with seemed to be able to cheer me up. Most of my girlfriends at my own school were all paired up at this point, so they didn't have a lot of time for me. Julie pulled me over to the cheerleader table with her for lunch a couple of days, and they all tried to cheer me up. Believe me, that's hard to resist. They did manage to cheer me up, at least during lunch. The rest of the time, I was still pretty depressing to be around.
One afternoon, after I had been sulking around for a week or so, I found myself heading into a study period at the end of the day. On my way there, I ran into Carly, one of Julie's cheerleader friends, in the hallway. She greeted me by throwing an arm around my shoulders and shouting, "Neighbor boy!" That was the nickname Julie and her cheerleader friends had given me the previous summer. It wasn't just because I lived next door to her, but Julie had told them all at camp about her first time with the neighbor boy. When I showed up at her house in the middle of their little party, they realized that I was the "neighbor boy" she had been talking about, and that became my nickname. Personally, as long as the cheerleaders are talking to me, they can call me anything they want.
Carly was in a really good mood. She told me, "End of the day, neighbor boy! I'm outta here!"
I answered, "You do realize there are still two more classes left, right?"
She replied, "Fuck that, I'm blowing 'em off." And then, "OOOH! COME WITH ME!"
I argued that I wasn't a senior and couldn't get away with that, but she said, "Fuck it! You're an A student anyway. Who cares?! Come with me, and I'll take you for a ride in my new car. We can go get fries."
There was a little cafe near our school that made the most amazing fries. It's where everyone went after school. How could I say no to that? So I agreed, slipped out of my study hall after they took attendance, and met Carly in the parking lot.
Riding with Carly
First, let me describe Carly. Carly was a senior. I was just a junior at this point. She was one of the co-captains of the cheerleader squad. She was everything you expect the captain of the cheerleaders to be: long blonde hair, thin, bright blue eyes, a huge smile, and the bubbly personality necessary for all cheerleaders. She also had a PERFECT body. She was five foot six (same as me), had a flat, tight tummy, and a perfect six-pack. Her breasts were big, but not huge. She had the sweetest little bubble butt and legs that you just couldn't take your eyes off of.
Carly and I had met at a party at Julie's house the summer before, and we had become very friendly, even flirty, ever since. Carly was actually very drunk the night we met. There was lots of drinking and skinny dipping and chasing and touching. If she hadn't been the first one to pass out that night, who knows what might have happened? Ever since that night, there was always a tangible sexual tension between us, even when her boyfriend was around. Julie has told me repeatedly that Carly would have been all over me that night for sure if she hadn't passed out. I keep in mind how drunk Carly was when she told Julie that.
So today, Carly and I blew off our last class and made our way out to her car. Her parents had given her a pretty new red Mini Cooper when she got her license, and she drove it like it was a rocket. We jumped in, and she peeled out of the school parking lot like a Formula One driver. The girl was a maniac! I was scared half to death, but I was definitely cheered up.
Once we got on the main roads, Carly drove normally. I guess she was just trying to show off on the back roads by the school. Carly is a bit crazy but a lot of fun. As we drove, she asked me why I was such a grouch. Of course, I reminded her of what she already knew and filled her in on all of the other things that Jamie had said. Once again, I was bringing myself down, and Carly was just listening and laughing at me the whole time. Thanks a lot!
She looked at me and said, "Awwwww, poor baby," and then she laughed some more.
While we were sitting at the shop eating fries and sipping milkshakes, Carly told me, "You know Jamie's right. You really are pretty stupid," and then she laughed some more.
I said, "Thanks a lot, just pile on, why don't ya."
"Well, it's true! You couldn't read the signs if we hit you on the head with them!"
"I can read the signs just fine. I get plenty of…"
"Dude, no. You can't. That night at Julie's house, when we were ALL drunk off our asses… if you knew how to read the signs, then you would have fucked all five of us that night. We were all drunk and horny, and you were the only guy there!"
"Oh sure, YOU were the first one to pass out. That would have been fun. Catie and Michelle barely took their tops off when we were all skinny dipping, and they were completely drunk, and Sara apparently never takes her pants off for anyone." (I was sticking with the lie Sara and I agreed to that night; no one ever finds out what we did.)
"Oh please, we all know you fucked Sara that night."
"Didn't happen," I replied.
"We all watched her sucking your dick!" she said, a bit too loud for the little cafe we were in, "…and then the two of you didn't manage to make it back to the party for another forty-five minutes. Are you gonna tell me it took you that long to get dressed?"
"What you saw is all that happened. There was no sex. Trust me, I tried," I answered.
"Uh-huh," she smirked back at me. "Well, you did sleep in Julie's room with her."
"Well, that's not a surprise. You all knew about that already."
Then she added, "We all know you slept with Michelle after her Prom."
"She told you that?"
Again, Carly just laughed at me. "No, we told her. She said she didn't even want to go to her Prom. Julie suggested that she should go with you, and that got her really excited. Then, Michelle and I planned the whole thing. You never had a chance."
"You planned the whole thing?"
"Julie made sure you would say yes, no matter what Michelle asked you. Does that sound familiar? Then we made sure you would come back to Julie's house after the Prom. Then, let me guess, Julie suggested you go back to your house to change out of your tux. And Michelle should maybe go with you if you need help. Do you think it was a coincidence Michelle didn't wear anything under that freaking skin-tight gown? We planned every bit of that right down to getting her on the pill a month and a half before."
"Geez," I said, "I guess I really AM that stupid."
Then Carly leaned over, gave me a squeeze and a kiss on the cheek, and said, "Yeah, but you're cute and really sexy. That's why we all love you." And then she smiled that cheerleader smile.
"C'mon, let's go," she said.
Carly’s House
We got back in her car and hit the road, and I had no idea where we were going. The next thing I know, we're pulling into her driveway. We got out, and she led me into her house and gave me the three-minute tour. As we roamed from room to room, she called out to see if anyone else was home. We got no answers.
When we got to the living room, Carly pushed me down on the sofa. Then she climbed on top of me, straddling my lap and facing me. She put her hands on my shoulders, leaned in real close, and said…
"Let's see if you can read this sign?" and then she kissed me long and hard.
I sat back and enjoyed it. The girl could kiss. I never really got to kiss her last time. My hands wrapped around her and pulled her tight. Then my hands started to wander up her back, then back down. I slid my hands down over that ass, damn that was nice. She stopped kissing and gave me a big, naughty smile as my hands roamed over that ass.
She said, "Well…?"
"Did you plan this too?"
"It wasn't planned, but it was talked about," she said.
"Talked about by who?"
"Well, Julie, Sara, and I all were talking about you after you left us at lunch the other day."
"And?"
She gave me that naughty smile again. "We decided you need to get laid."
"And what, you drew the short straw?"
"No, I ran into you on my way out the door to skip the rest of the day and thought maybe I'd give you a treat."
Then she stuck her tongue in my mouth again. My hands left her ass and started traveling up the front of her body. Her tummy is so incredible, but when my hands reached her tits, she stopped kissing, arched her back, and let out a moan.
I continued to fondle her tits, squeezing and kneading and teasing. What an amazing body.
"What about your boyfriend?"
She looked around, then answered, "Do you see him here? You really need to learn when to just keep your mouth shut."
"C'mon," she said. Then she climbed off me, took my hand, and led me upstairs to her room.
Carly’s room
Carly led me into her room and pushed the door shut. Again, she pushed me down, on the bed this time, and climbed back up on top of me. She leaned down over me, and we got back to the kissing. In no time at all, her shirt was unbuttoned and lying on the floor. When I slid her bra off, and those tits fell out, my cock just about burst through my pants. I just couldn't keep my hands off her.
After feeling up her chest for a few moments, I realized I needed more. I rolled Carly over onto her back so that I could get my mouth on those nipples. Carly reacted with soft little moans and sighed as I licked and sucked and gently nibbled. While I was doing that, her hands were wandering all over me. At first, she was just feeling up over my back and stomach, but every now and then, her hand would wander down to my pants, which were getting very uncomfortable.
Finally, I had to stop. Things were too uncomfortable like this, so something had to come off. I stood up and took off my shirt. Carly's hands immediately went to my abs.
"Ohhhhh damn, that is so nice," she said as she leaned forward and started kissing and licking my abs.
Carly's boyfriend, as you may guess, was a football player. Huge guy. Big and strong and powerful, but bulky. I, on the other hand, was a gymnast and had a gymnast body. I was only five foot six, maybe 120 pounds, but I had very low body fat. I had big shoulders, big muscles, and flat, tight six-pack abs. With dark brown hair and green eyes, I was almost the exact opposite of her big blonde boyfriend. Right now though, she was concentrating on the abs, and I liked it.
As she was kissing and licking my abs, her hands grabbed my pants, and off they went. My cock was hard as stone by this point and just leapt up to greet her. She was ready for it, and her hands were instantly wrapped around my shaft. She started to stroke it, and then I felt her tongue starting to lick and taste. I put my hands on her head, leaned my own head back, and let out a long sigh of pure pleasure.
I remained like that for a while as Carly swallowed my cock. She was so good. I could feel my cock hitting the back of her throat and the suction trying to drain me dry. I opened my eyes to look down at this gorgeous girl sucking my cock. Instead, my eyes caught the smallest of movements on the other side of the room. I looked and saw the door to the room cracked open just the tiniest bit. I looked away but looked over to the mirror on Carly's dresser, and after a few seconds, I saw Carly's little sister Haley peeking through the door. The little perv was watching us!
Haley was a freshman. She was really a very sweet little girl and, as I thought about it, pretty sexy for a freshman. Haley was shorter than Carly, maybe five feet even, otherwise almost the exact opposite of her sister. She had long dark hair, deep brown eyes, very petite, and small breasts, but she had that same great little ass. You could tell they were sisters. I would never have thought about her sexually up to that point, but now…
I kept my mouth shut and let her watch. I wanted to see how long she would stay there. At that point, I also wanted to give her a good view, so I stopped Carly from doing what she was doing. I pushed her back on the bed, which left me standing there in full view of baby sister with my cock standing straight out like a flagpole. Very slowly, I reached down and slid Carly's skirt down those legs. Then I reached up and pulled the panties right down with it. Now all the clothes were on the floor where they belonged, and little sister was still outside the door, peeping on every move.
I kneeled down at the edge of the bed and pulled Carly right up to me. I spread her legs and took my fingers right to that beautiful pussy. She wasn't shaved but was very nicely trimmed, a beautiful little golden blond bush above her sexy entrance. I started to work her pussy with my fingers. Carly started to moan and move around and push her hips to meet my fingers.
Thinking of Haley, I spread Carly's legs as wide as I could and started to lick. I attacked her pussy with my tongue and started to eat like a starving man. Carly's thrusts got even more energetic. Her hands grabbed my head and pulled me into her even harder. Every once in a while, I glanced at the mirror and saw Haley still watching with an incredulous look on her face. This was making me so hot.
Carly finally made me stop. She said, "Oh my god, this is so good I don't want to stop!"
Naturally, I had to ask, "So why am I stopping?"
"I don't know how much time we have before my sister gets home, and I want that thing in me."
Who was I to deny her "that thing."
I asked her if, by any chance, she had some condoms. I didn't generally carry them around school with me, so I didn't have any, but I figured considering her boyfriend, and how long they had been going out, she might have some just in case. Of course, I was right.
Carly pointed out the secret stash where she hid the condoms, and lucky for me, it was practically right next to the door. I walked over there, pulled one out, stood as close as I could, in full view of Haley, and slowly rolled it on. Carly was still on the bed with her fingers working her pussy while she waited for me. I don't know which of us Haley was watching.
I walked back over towards Carly, laying spread eagle on the bed, with my cock standing up, threatening her. She just watched me approach with a huge grin on her face.
"Damn!" she said. "That's bigger than I remember." We had been naked together before, after all.
"You were drunk last time, and it wasn't this hard."
"Just bring that thing over here," and spread her legs as wide as she could.
I pulled her to the very edge of the bed and placed myself right at her entrance. She wrapped her legs around me, and as I started to push into her, she started to pull. We both let out the same long, sensual moan. She was so tight and warm and perfect. She closed her eyes again as I pushed into her as far as I could go. We stopped like that for a moment and just felt our bodies reacting to each other.
Then I started to pump. Pulling out just a bit and thrusting back into her. I did this for a while and just fucked her deep. We got into a hot little rhythm, with her making little moans with every thrust and me grunting to push as far as I could. Every once in a while, I would glance at the mirror to see if our audience was still there. Haley hadn't moved an inch the whole time. She was mesmerized. I couldn't see, but I was imagining her hand down her pants, working her own little mound.
I pumped my way deep into that pussy as hard as I could until I could no longer stand; my legs got so tired. I pulled out and stepped back. I pulled Carly up and laid down on the bed myself. I changed my position so that Haley would be able to see as much as possible. Carly climbed up on the bed, straddled me one more time, and lowered herself onto my cock. I so love that feeling as she just sank that tight warm pussy around my shaft.
Carly then started to bounce and drive herself onto me. She was like a wild animal. She made so much noise. Screaming and moaning. I grabbed her hips and pulled her down onto me as hard as I could. I looked over to the door to see if Haley was still watching. She was, and just as I looked, she was staring straight at me. We locked eyes for the briefest of moments. I just smiled at her. I could see the panic in her eyes as she realized she'd been caught. In an instant, she disappeared, but my smile remained, and I turned it back up to the sister that was riding my cock.
I rolled Carly over on her back again and resumed my place between her legs. I pulled them up and started to drive into her hard again, figuring little sister was gone now, and it was time to concentrate on what I was doing. Carly started moaning and calling my name. I pounded harder. I looked to the mirror and saw that Haley had returned to her spot carefully and was watching intently as I pounded her sister hard.
At this point, I was ready to shoot the biggest load of my life. I wanted Haley to see the money shot, so I pulled out of Carly, stood up, and pulled off the condom. Carly was immediately on her knees, taking my cock in her mouth. The sensation was almost unbearable. I was ready to explode in her mouth, but I wanted Haley to see me cover Carly with it. I started a pumping motion into Carly's mouth as she sucked and stroked me. Then, just as I was about to explode in Carly's mouth, I pulled all the way out of her mouth, and it shot all over her face. It went on her face, in her hair, over her chest. Carly grabbed my cock, sucked it right back in her mouth, and swallowed down everything I had left.
Hey guess what…
I stood there holding her head for a moment as my cock deflated in her mouth. I then collapsed on her bed. Carly got up and collapsed next to me.
All she said was, "Holy shit…"
I agreed. "Yeah… damn… that was amazing."
"So you still upset about what's her name?"
"Oh, the hell with her. What class do you want to skip tomorrow?"
"Sorry sexy, I got plans tomorrow."
We lay there for a few minutes, just breathing and recovering. She looked so amazing laying there naked, and my hands started wandering over her again. I couldn't keep them off of her. This is the vision every guy in school would have killed to see. The captain of the cheerleaders lying naked next to you with your cum all over her. My hands were just rubbing cum like lotion into her skin. Just as I leaned over and put my mouth back to those nipples, we heard the door to Haley's room close.
Carly jumped up and said, "Shit! Get dressed, sister's home. We don't want her to catch us."
"A little late for that, don't you think."
She, of course, asked, "What do you mean?"
"She was watching us through the door for pretty much the entire time. Didn't you see her?"
She said in a slight panic, "What?! No, I didn't see her, did YOU?"
"Of course I did. She was peeping through the door the whole time; how could you miss that?" Of course, I knew Carly hadn't seen her, but I had to play along as if I thought she did; that way, Haley was still in trouble for peeking, but not me for letting her.
The look on Carly's face was priceless as she looked at the door, cracked open that tiny bit, and realized her baby sister had just watched her fucking like a rabbit for half the afternoon and NOT her boyfriend. Her mouth dropped open, her eyes went wide, and she asked…
"Oh my god, why didn't you SAY something?!"
"I was kind of busy at the time, and I was not going to stop because your little perv sister wanted to watch. Besides, she'd already seen us. I didn't think it mattered if she wanted to watch. I thought, sure, you saw her too. Plus, it was really hot thinking about her watching us. I'm betting she was standing there with her hand down her shorts the whole time," and then I gave her that same naughty smile she had given me earlier.
Carly was panicking. She said, "Oh my god, what if she tells my parents?" and then, "Oh my god, what if she tells my BOYFRIEND!"
"She's not going to tell anybody. She's probably already afraid you caught her watching."
"Ugh, you don't know what a little bitch she can be. If she says anything to my parents, they'll take my fucking car away!"
"Just grab your camera and go burst into her room right now. I'm willing to bet you'll find her on her bed with her hand between her legs, working herself into a frenzy."
She grabbed a pillow and hit me. "That's my little sister!"
"Yeah… who just stood in the hallway for half an hour watching us fuck. She's a little perv!"
Carly thought about that for a minute. "Holy shit," she said, "I can't believe she did that."
"If you want, I'll walk down the hall and jump in bed with her. I'll bet she'd be into it."
Carly hit me. "Shut up!
"What?! Then you could walk in and catch her having sex, too. Then you'd be even."
And then I added, "And I'd be even happier!"
She seemed to think about that for a minute and then said, "No, she'd never do that."
"Yes, she would. She'd be all over my dick. She wants it bad."
"She wouldn't even know what to do."
"Sure she does. She'd just do everything she just watched her big sister do."
Betting on Haley
Carly got up and wiped the cum off her body. Then she threw her clothes back on and walked down to the bathroom to clean it out of her hair as well. On the way back, she apparently popped her head into Haley's room to say hi. I heard them talking but couldn't make out what was said. Carly said she was bright red and seemed very nervous.
She told Haley she was going to see her boyfriend, and we quietly crept out of Carly's room and down the steps. We got into her car and headed back to… I didn't even know where we were headed. To be honest, at that point, I was really picturing Haley's tight little ass. I kept thinking about it for a few minutes and thinking about the whole afternoon and Haley watching even after she KNEW that she was busted.
I turned to Carly, and I said, "You know, I really could fuck your sister."
She turned to me as she was driving and shouted, "What?! Shut up! You will not!"
"I didn't say I would. I said I could."
Carly took her hand off the wheel and just smacked me hard with it. She said, "NO, you cannot fuck my little sister."
"I'll bet I can."
She hit me again.
I replied, "Oh look, who's not seeing the signs now? She stood there watching the entire time we were in your room. Everything. She could have just bolted the minute she saw what was going on, but she stayed there peeping the whole time… she LIKED it… she wants to TRY it."
"…and I'm going to give it to her." Again, I flashed that evil grin.
Carly clearly still saw her little sister as a sweet, innocent little thing. I was seeing her a sexy little piece of ass. Now, I wanted her.
"I'll bet you anything that with enough time alone with her, I can get in her pants."
"I am NOT betting on my sister's virginity!"
I laughed. "Oooh, a virgin! Even better!"
Carly was quiet for a few minutes as we drove, but she was clearly thinking about it.
"She just stood out there peeping the whole time?"
"Yup. Even when I locked eyes with her, and she knew she was busted."
"What?" she shrieked.
"Oh yeah," I said. "Locked eyes with here right in the doorway. Then she bolted. But she came right back to watch some more."
"Holy shit. I can't believe that," she said quietly.
"Yeah… she wants me. Kind of like her big sister."
After a short pause, Carly answered. "No, I would have just come in the room and joined in."
That got me laughing and thinking even more! Maybe I can fuck Haley and get Carly to join in! Who's not reading the signs now? I was getting hard again just thinking about both of them. Either of them. Together, separately, whatever, I'd never fucked sisters before.
I turned to Carly and said, "C'mon, bet me. Anything. I'm gonna do it anyway. You might as well get in on the action". (And yes, I WAS going to do it anyway. Right now, that was all I could think about. Jamie who?) Maybe the two of us could take her sister's virginity together! Now that would be fun!
She hit me again. "You are not! You leave her alone!"
We kept talking about it for a while, and I slowly wore her down, pestering her with questions about herself.
"How old were you your first time? Barely older than Haley is now, right?"
"Do you even know how much she has done with any of her little boy toys?"
"Wouldn't you rather her first time be with me than one of these fuckboys always hitting on her?"
By the time Carly dropped me off at my house, we had made a bet on whether or not I could fuck her little sister. Negotiations continued as to the terms. Carly's view was, if I could, then I'd already won because, after all, I got to fuck her sister. I disagreed, fucking Haley was the goal, not the prize.
Eventually, Carly said that if I succeeded, she knew a way to hook me up with the rest of the cheerleader squad. I didn't know she planned to do that, but what guy could pass up that deal? If she couldn't deliver, I could always demand a three-way with her and Haley.
We left my end of the deal open-ended for the moment; she was going to think about it and decide something truly devious to make me pay when I failed. We'd decide before it happened. I was so confident I would succeed that I didn't care. I decided that it had to be soon, though, like that weekend. I wanted today's events to be fresh in Haley's mind, OR we would have to have another little session of our own for her to watch again. I wanted her to still be horny from watching. I was already plotting and planning. This was going to be fun!
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.
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 of 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?"
"Oh yeah."
"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, gave it a little squeeze, and said: "Haley, it's okay. I knew you were there."
She just stared at me with her mouth open.
"…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, though; 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 as turned on by it as you were. 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 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 you're a child. 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 a fucking kid. I know what to do!"
Perfect. That is exactly what I wanted her to say. I raised my eyebrows, looked down at that leg I was caressing, and gave it a couple of very intentional squeezes. Then I looked back up into her eyes.
"Really?"
I hesitated slightly. Still locked into her eyes.
"Wanna prove it?"
Her eyes went really wide again. Her breathing shortened. She stared right back into my eyes and, after a moment, answered, "Really?"
I leaned in closer and 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 I knew, 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 hands away from her legs and 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?!"
"You said you'd know what to do. Now's your chance to prove it."
Then I gave her the evilest 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 looked every way she could.
"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.
"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?"