After a devastating breakup with my girlfriend , my cheerleader friend Carly decides I'm the one who needs cheering.
Carly and I skip class
Towards 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 drops this bomb on me out of nowhere. I was stunned.
This is when I discovered that I’m really not as smooth and 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 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 some times.
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 girl friends at my own school were all paired up at this point and so 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 in the hallway, one of Julie’s cheerleader friends. 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 makes 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, 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 with 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 cheering up.
Once we got on the main roads Carly drove more 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 was asking 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 milk shakes 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”
She said “Well it’s true! You couldn’t read the signs if we hit you on the head with them!”
I said “I can read the signs just fine, I get plenty of…”
She said “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!”
I answered “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)
Carly answered “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”
I said “Well that’s not a surprise you all knew about that already”
Then she added “…and we all know you slept with Michelle after her Prom”
“She told you that?” I asked.
Again, Carly just laughed at me. “No, we told her. She said she didn’t even want to go to her prom. Julie suggested she should go with you and that got her real excited. Then me, Michelle and Julie planned the whole thing. You never had a chance”
“You planned the whole thing?” I asked.
“Julie made sure you would say yes, no matter what Michelle asked you, 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 in case you needed help? 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 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 your cute and really sexy. That’s why we all love you.” And smiled that cheerleader smile.
“C’mon, let’s go” she said.
We got back in her car and hit the road, 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 were roaming from room to room she was calling 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 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 did get to really 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…?”
I answered “Did you plan this too?”
“It wasn’t planned, but it was talked about” she said.
I asked “Talked about by who?”
She said “Well, Julie and Sara and I all were talking about you after you left us at lunch the other day.”
“…and?” I said.
She gave me that naughty smile again and said “We decided you need to get laid”
I said “and what, you drew the short straw?”
She said “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.
I said to her “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. The she climbed off me, took my hand and led me upstairs to her 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 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 sighs as I licked and sucked and gently nibbled. While I was doing that, her hands were wandering all over me. 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 Dam 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 the gymnast body. I was only five foot six, maybe 120 pounds, but very low body fat. I had the big shoulders, big muscles and flat tight six pack abs. With dark brown hair and green eyes, I was almost the exact the 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 had 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. Long dark hair, deep brown eyes, very petite, 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 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 would glance at the mirror and see 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?”
She answered “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 and 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.
“Dam!” she said. “That’s bigger than I remember”. We had been naked together before after all.
I told her “You were drunk last time, and it wasn’t this hard”
She answered “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 to 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”
She asked “so you still upset about what’s her name?”
I said “Oh the hell with her, what class do you want to skip tomorrow?”
She answered “Sorry sexy, I got plans tomorrow”
We laid 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”
I answered “A little late for that don’t you think”
She of course asked “What do you mean?”
I said “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?”
I answered “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!”
I said “She’s not going to tell anybody. She’s probably already afraid you caught her watching”
She answered “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!”
I told her “just grab your camera and go burst into her room right now, I’m willing to be 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!”
I answered “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”
I said “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!
I said “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”
I answered “Yes she would. She’d be all over my dick. She wants it bad”
Carly said “She wouldn’t even know what to do”
I answered “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” I answered.
Carly took her hand off the wheel and just smacked me hard with it. She said “NO, you cannot fuck my little sister”
I answered “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 said to her “I’ll bet you anything that with enough time alone with her, I can get in her pants”
She said “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 asked “She just stood out there peeping the whole time?”
I answered “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.
I said “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 it was all I could think about. Jamie who?) Maybe the two of us could take her sisters 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 that she could hook me up with ALL 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!