Cheerleaders’ Spring Break Ch. 01

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My little sister and I were driving home from school, and I was in a pretty bad mood. It was bad enough that I was nineteen, and still in high school. And now it would be one more year of being jealous of all the other kids at school who had amazing plans for the upcoming spring break, which was only about a month away now. I was starting to realize that spring break of my senior year of high school was going to be another boring one. Our parents had never taken us anywhere fun, usually opting to leave me and my little sister home to fend for ourselves, while they went on a trip of their own. They had turned down my sister’s idea of letting me and her fly to Florida alone together, and my sister hadn’t stopped complaining in weeks.

We got home and I knew that only one thing could console me. I hung around in the kitchen as soon as we walked in, pretending to grab a snack, and my sister ran up to her room to change out of her uniform. At our school they wear classic schoolgirl uniforms with the little plaid skirts, long socks, and tight white tops. It’s enough to drive a boy crazy. But my sister hated wearing them, and changed every day as soon as we got home.

I gave her a 30 second lead and then snuck up to my room. Our bedrooms shared a bathroom, and our closets also backed up to one another. Just last week, only a few days after my little sister’s 18th birthday, I’d drilled a hole in the back of my closet to hang a hook back there, and realized the hole went right through her closet wall too. She hadn’t been home at the time, so I went into her room to see how bad the damage was. The hole was just next to one of her closet shelves, hidden in darkness so that she’d never notice it. I was just thinking of patching it up, when I looked at her dirty clothes hamper at my knees. There was a tiny red thong just sitting there on top. I knew my sister often dressed like a slut, but it had never occurred to me that she wore thongs. I picked it up, and saw the wet spot on the crotch that covered practically the whole front of them. I was so turned on. I brought them to my nose and smelled her scent in, and the raw sweetness made my cock leap. I left the room before I got caught, but every day after that, my hormones would get the best of me and I just couldn’t resist sneaking a peek as she got changed.

This afternoon was no different. I got into my closet and peeked through the hole. She already had her shirt and bra off, and was sitting on the chair by her desk wearing knee high white socks and pink panties. My sister had really small tits, and was quite skinny. Maybe almost too skinny. She certainly hadn’t developed the more mature curves of other girls her age. She was the thinnest girl on the whole cheerleading squad, and with her braces, she still looked like she was sixteen. I couldn’t believe she was actually eighteen now. She had a tight stomach and a perfect little ass framed by narrow hips. I could even see the little belly button ring that she had gotten just over a year ago on her seventeenth birthday. Normally I’d enjoy getting a hard-on while watching her briefly change clothes, or check herself out naked in the mirror. But today was something special!

She was already topless, and had her hand down her panties and was rubbing away at her clit. She was writhing around on a chair by her desk, her eyes closed as she frantically worked herself up. She bucked her hips back and forth across the pillow of the chair as she rubbed harder at her clit. Her panties were so sheer that I could just make out the lips of her pussy as she rocked, her breathing growing more ragged.

I hadn’t masturbated in weeks, because of yet another promise to myself that I never would again, but this was just too much. I pulled out my dick which was already rigid and started stroking myself, trying to match her rhythm.

She rubbed her hand over her panties, pushing them into her pussy lips, and leaned back with her legs spread wide. Her arched back accentuated her narrow hips, and her little bright nipples were starting to tighten. She rubbed her hands along the insides of her legs and then reached up and started to pull her panties down. Her neatly trimmed snatch came into view. She had a short landing strip just above her clit, and the rest of her was shaved clean and smooth. The panties came completely off leaving her just wearing those damned knee high socks. I started to jerk away at my cock quicker than before.

Her hand dove back down to her pussy and she resumed rubbing aggressively at her clit with the flat of her hand. She bit her lips and I could make out the shiny wetness of her own juices dripping from her tight pussy and lubricating her flying fingers. She stopped playing with her clit as her fingers rubbed down between her labia, and I could see her hold back a gasp. She drove a finger into her pussy, and started to piston it in and out, a soft moan escaping just at that moment. She instinctively glanced back towards her door, probably wondering if I’d heard her. She canlı bahis added another finger, now pushing two of them as deep as they would go into her sopping hole. I could hear little grunts each time she thrust in, trying to get her fingers deeper than they were already going. She paused long enough to rub her clit a few times, rocking her hips again as she did, then resumed thrusting those two fingers deep inside her. Her moans were growing louder now, clearly audible through the thin walls of the closet.

She turned around with her legs straddling the chair back, and reached up her hands grasping the back of the chair and started to furiously buck her pussy hard against the loose pillow of the chair. Her legs were spread wide, straddling the chair, and her pussy had created a slick wet spot on the cushion and she was riding it back and forth, her clit rubbing against the wet spot on the cushion at the back of each thrust. She was bucking at the pillow so hard that it nearly detached from the chair, and she held it down with one hand almost desperately. The sight of her rocking hips and ass peeking out over and over was just fantastic. And to see her rubbing her nipples up against the chairback on each thrust was sinful. My little sister’s body was phenomenal.

I turned away from the hole in the closet, disgusted with myself. What was I doing? What kind of pervert would spy on his own sister, let alone watch her masturbate and totally get off to her. I knew I had to stop doing this and stop fantasizing about her. I shoved my cock back into my pants. I paused as I turned to walk out of the closet when I heard a louder moan, and then the methodic rocking of the chair stopped. I went back to the hole in the closet to see what she was doing.

As I put my eye up to the hole, I could see her slowly rocking on the pillow. She must have orgasmed onto that lucky pillow, her juices dribbling down onto it as she came down from her high. She stood up and ran her hands across the slick spot on the pillow. She picked up the pillow off the chair and brought it up to her nose, inhaling deeply. I just saw her tongue dart out and taste at the wet spot, a smile forming on the corner of her lips.

She walked back to her bookcase, and pulled out an old encyclopedia. She opened the cover of what must have been a hollowed-out book and pulled out a long pink translucent dildo from inside. It was at least 9 inches long, and looked like a bunch of balls stacked one atop the other, each smaller than the one below it.

Almost without thinking she slid the dildo into her mouth, sliding it back and forth a few inches. I figured that my sister slept around, since she dated some pretty questionable guys. But I’d never imagined her giving a blowjob. So to see that pink rod slipping into her mouth was a thing of beauty. Her lips were still red from the day’s lipstick, and her eyes closed as she bobbed the dildo back and forth into her mouth, now sitting on the edge of the chair.

I’d never had sex, let alone gotten a blowjob, so I couldn’t even imagine what it would be like to have some girl do that to me. To grab the base of my dick and feed it into her mouth so tenderly, so carefully. As my sisters tongue slurped out and made circles on the tip of the dildo, I pulled my dick back out and resumed masturbating. She rubbed the dildo across one of her nipples, toying it briefly, before trailing the now-wet dildo down to her already wet pussy.

She slid the dildo slowly across her clit, each bump of the dildo pressing against her wet hole as it rubbed the length of her. She started to moan again, rubbing the hard rod back and forth slowly. She brought up one of her legs onto the chair, her toes pointed in those knee highs, and with her legs now spread I could see the cum from her previous orgasm had dripped down the inside of both her legs. Her pussy lips were spread wide and the dildo glistened as it continued to slide along her lips. She gripped it with both hands and with determination started sawing the dildo furiously across her labia and clit, gasping freely, her eyes still closed. Her body pressed towards the dildo as if begging it to slide up inside her.

She rocked back, and reached the dildo around behind her, and positioned the tip of it right at the entrance to her pussy. She was slower, more methodical this time, than she was with her fingers. I watched as each of those balls pressed up into the folds of her pussy; Watched as her lips slid along each ball as it entered her. Each ball was progressively larger in size, and by the time the dildo was buried half inside her I could see that she was straining to push it in. Damn, she must be tight. She slid the dildo out slowly, and then pressed it back in, more firmly this time. Over and over she sank it in, each time burying it more deeply inside her.

She stopped, pulling the dildo out and brought it up to her lips, her eyes opening. She looked at the cum dripping down it and slowly brought her tongue flat to the side bahis siteleri of the dildo, and licked up it. She practically looked like she was licking a melting popsicle as she licked her own cum from the toy. I could see her working the flavor around in her mouth, and she dribbled her saliva back onto the waiting dildo.

She sat on the edge of the chair and brought one foot up tight against her ass, her legs spread wider than seemed possible. I silently thanked my mother for all those gymnastics lessons she’d made my sister endure, and the sight of her spread out, so ready, as she plunged that fake cock into herself made me let out a half-moan of my own as I hammered furiously at my cock, so close to cumming.

I froze, hearing myself, and wondered if my sister had heard me, but she just drove that dildo home. She powered it in, not being gentle at all. She rammed it harder and harder into herself, trying to get it deeper and tighter into herself. She was gasping. Her hips bucked again, and she rocked back and forth on the chair. She must have been sure I was downstairs because she seemed to throw caution to the wind and moaned loudly as she nearly slammed the whole dildo into her sopping pussy.

Her phone rang. It jangled some loud obnoxious tune and vibrated wildly on her desk. Once again I froze with my eye glued against the hole in the closet.

My sister grabbed the phone off the desk, slowly easing the dildo in and out of her a few times before she set it on the desk and answered her phone.

“Hey, Riley!… No, Ben and I just got home a few minutes ago. Did you have a chance to talk to the other girls after school?”

There was a long pause as she listened. Then she jumped up out of the chair, her tiny breasts jiggling as she squealed in delight.

“You are the best. I can’t believe we are actually going to pull this off. I’ll go talk to Ben right now. I promise you that he’ll agree to come. It’s going to be a blast!”

She hung up the phone, and went to her drawer to grab some new panties and get dressed. I knew it was only had a few seconds to act, so I quickly tiptoed back downstairs and turned on the TV, pulling a pillow onto my lap to cover the evidence of my lust.

My sister came bounding into the room.

“Ben” she said, her eyes sparkling. “I have the best news, ever!” As always, it took me a second to process what my sister was saying. She was wearing a short loose yellow cotton skirt, and a tight white tank top. It was so thin that I could see her bra-less nipples were still rock-hard, and I tried to not stare at them, and finally answered.

“What’s your fantastic news, Ivana?”

“I talked to Dad, and asked him for one more belated present for my birthday last week , since turning 18 is supposed to be a big deal… and I got him to agree to let me take a bunch of friends to the lakehouse for Spring Break!”

I could see that she was excited, and frankly she should be. Our lakehouse was an amazing 3-story house, right on the lake with nearly 50 acres of secluded woods. There were four jet-skis, and a boat for wakeboarding. I had made some great summer memories there. “But, Ivana, I thought that Mom and Dad were going to Spain for Spring break?”

“They are, idiot!” She replied, slugging me on the arm. Her tits were too small to shake much, but I still watched them while I was pretending to be flinching. “They are letting me stay at the lakehouse with some friends, on one condition.” I raised an eyebrow, questioningly. This was going somewhere. “They told me that my super-responsible big brother has to be in charge and supervise us.”

It was true. I was by far the more responsible of the two of us, even though I was just a year older. I was always one to go to church with my parents, and never broke the rules. I barely had any friends to get into trouble with. Ever since I had been held back a grade as a kid, I’d always been bigger than all the other kids, and rarely fit in. My sister, on the other hand, was a social butterfly. This was doubly embarrassing since we were in the same grade. She had always been cute and outgoing, and was friends with nearly everyone in the school. My parents also suspected that she was up to no good with plenty of her many boyfriends, and she was always getting caught by my parents for sneaking out and breaking family rules. She could get into prolific yelling matches with our dad when she wasn’t trying to butter him up to get something she wanted.

“Wait a second” I said. “Who exactly is this ‘us’ that I’m supposed to be watching for two weeks?”

I started to imagine having to watch my beautiful sister making out with some random guy-friend for two weeks, and the thought of it made me cringe. There’s no way our parents would allow her to invite a boy.

She smiled the most devious grin that I think I’d ever seen. Then she said it: “The cheerleading squad.” She just smiled, letting it sink in.

I stammered, slowly thinking through some of bahis şirketleri the most impossibly beautiful girls I’d ever seen in my life. Most of the girls on the squad with my sister even put Ivana to shame. I mean, my sister was a cute kind of girl-next-door good looking, but some of the cheerleaders were like supermodels. I had some favorites that I wished might be there, and managed to get out “Which of the girls on the cheerleading squad are coming?” I was hoping that my sister couldn’t tell that my voice was a little bit higher.

“All of them.” She just smiled at me, and I had to actually force my chin not to drop. She continued. “We’ve actually been planning this since we all went to the Regional Cheerleading Competition last summer. We had a lot of fun, but there wasn’t a lot of time to just hang out and relax. So we figured that our lakehouse would be the perfect getaway. All of the girls have already gotten parents to agree, and me asking dad if we could go have Spring Break in Florida was a ploy. I knew that he’d turn me down for that and feel guilty, and that getting him to let me have friends at the lakehouse would be a breeze.”

“That’s actually pretty genius, sis.” I muttered, as I thought it through. “But how did you get him to agree to let two dozen girls stay there at once? There’s barely room enough for all of them, let alone me.”

“Well…” her guilty face made it obvious that she had left some details out for our parents. “I was hoping that you wouldn’t tell them exactly how many girls are going to be there.”

I frowned. “You make it sound like it’s already a done deal.”

“Please, Ben? Pretty please? I’ve put months into planning this, and I will owe you anything!”

I frowned deeper. “And you expect Mom and Dad to just be fine with me supervising a house full of slutty teenaged girls?”

“Actually, Mom totally suggested it” she said, perking up. “She joked that you were probably the only guy in the world that could spend two weeks with girls frolicking all over in bikinis and not try to sleep with half of them. I had been thinking I might have to have one of our uncles come supervise, but you will be so much better.”

I had stopped listening about halfway through what my sister was saying. Half of me totally agreed. I was about as chaste as any kid I knew. I was a virgin, and hadn’t ever really had a serious girlfriend. I’d even gone to my parents for advice the one time I had a steady girlfriend and we’d ended up necking in the car after a date. I felt so guilty that I told my parents the next day, and ended up breaking up with the girl shortly after that. Heck, aside from the rare porn and sometimes spying on my sister, I was a pretty innocent guy.

But the other half of me started to imagine those cheerleaders. It was hard enough not to stare at them bouncing up and down at the football games in sweaters and skirts. Just the idea of them in bikinis reminded me of my raging hard-on, and the fact that I hadn’t quite reached orgasm while spying on my sister just now. I thought of perfect blonde Shawna with her big dimples and perfect fake tits that couldn’t be held back by a sweater; she would practically burst out of a bikini. And Tiffany the brunette model had pretty big boobs too, for a cheerleader. Honestly most of the cheerleaders were on the skinnier side, and pretty athletic or petite, and only a few of them had tits larger than a C cup. I pictured Gigi, a tiny Latina who practically had no breasts at all, but the imaginary thong I started to picture her wearing in my mind showed that tight ass that I’d stared at a few times while the girls stretched down after cheerleading practice. I shook myself back to reality. This was going to be a monumental test that I wasn’t quite sure I was going to get through.

“Yeah, I’m probably the only guy dumb enough to not like girls much.” I said sneering.

“Aww, c’mon Ben. You know that special girl out there that you’re waiting for is going to love that you’ve saved your virginity for her.”

Now she was just pandering to me.

“Alright, I’m in.” I said as I sighed a deep sigh. “BUT… I get the master bedroom to myself, and you guys have to promise to be good.”

She kissed me on the cheek as she skipped out of the room. I watched her tight little body as she went through the door, and fell back onto the couch, cursing myself for being so lustful. I had no idea that my sister was such a competent planner, and with how horny I was right now… I wasn’t exactly in the frame of mind to turn her down for anything.

And I had a plan of my own that consisted of me dealing with this boner. I knew that if I was really lucky I could finish what my sister and I had started this afternoon.

After dinner and a few hours with some homework, I said goodnight to sister and our parents and headed to my room, pretending to be sleepy. I messed around on my computer playing games until I heard my sister come upstairs.

She closed the door to her room, and I was already in my closet, with my lights out, and with cock in hand. She was still wearing that short yellow skirt and tank top and I can’t believe our mom hadn’t given her a hard time about how short her skirt was.

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