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Valerie's Greatest Moments

Story Info
A high school cheerleader finally gets the man of her dreams.
3.6k words
4.41
37.2k
59
4

Part 1 of the 2 part series

Updated 06/10/2023
Created 05/06/2020
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Despite being the head cheerleader at West Houston High, and being in a relationship with the second best player on the school's football team, Valerie was not your average 18 year old. Sure, she was stunning, with strawberry blonde hair that went all the way down to her shoulder blades, perky C-Cup breasts, and a tight ass that made even the men in her family uncomfortable; but deep down she was more than that. She was a young woman who was in love with another man, but settled for second best. Why? Because the man she yearned for was her 19 year old brother, Lucas, who was the star Wide Receiver, and the only reason her boyfriend Gerald was able to connect with over 500 connected passes over the past four years.

Valerie hated that she loved her brother so much. She knew that he was forbidden, especially by society's standards, but she couldn't help it. Lucas was just so handsome. His body was built like a god, with washboard abs, strong biceps, a charming and handsome smile, and dirty blonde hair that was just gorgeous to look at. And from what she had overheard, he was also well endowed. Oh what she wouldn't give to be the one who he took into his room late at night, after getting home from a game. She would die, if it meant her last moment was to have her legs wrapped around his naked body while he fucked her like a slut.

Laying awake in her bed, at an early 3:35AM on a Saturday morning, Valerie felt nothing but depression and hormones. Her body was hot, her pussy was soaking in her own juices, her fingers were rubbing her clitoris for all it was worth, and all she could think about was her brother. She had already had 3 orgasms in the last hour, and she was still unable to stop. Oh to be young and horny, it was a nightmare for a woman her age.

As she tried and tried to get her last orgasm to burst through, she just couldn't do it. It frustrated her, because she was right there. She was so close, and it wouldn't happen. She had tried everything from sticking in her fist, to laying on her stomach with her ass up, to even using her hair brush to fuck her ass while she played with her clitoris. Nothing was working. Suddenly, she got a text message on her phone, and all the build she already had instantly left her body.

"Who the fuck?!" She grunted angrily as she rolled over, yanking the phone off the charger, and looking at it. It was Lucas, and he was asking for a ride. She guessed he was drunk, as this was becoming a regular routine for them both. As much as she didn't want to get up, she also would never tell her brother no, for anything. 'If only he knew' she thought to herself, before rolling out of bed. Her naked body was still soaked, and she thought about at least washing up, but she was also tired. She wanted to at least get some more sleep when she got back, and a shower right now would just wake her right up. She decided to at least throw on clean clothes, so she grabbed some pink pajama pants and a "Houston High" pink t-shirt, before slipping them on. Grabbing her phone off the bed and car keys off the dresser, she left the room.

Walking down the hall to the stairs, she heard the unmistakable sounds of bed creaking in her parents' room, and knew what was going on. It was their anniversary, so of course they'd have some fun. 'At least someone's getting off' she said, as she could hear her mother beg for her father to keep fucking her. Turning to walk down the steps, she opened her phone to tell Lucas that she was on the way.

She got to the door, and slipped in her favorite pair of flip flops. They were comfortable, and easy to take off since she drove barefoot. Getting into her car, the head cheerleader started it up, put on her favorite station (the local Rap Station) and started heading to get her brother. She knew her city like the back of her hand, so with a few short cuts, her normal 40 minute drive to the weekly party spot was cut to a mere 15. As she pulled up, she saw her brother's car, and pulled in behind it. The boys and girls at the party all knew the car. How could they not? Valerie was popular, and everyone loved her, even if she didn't party.

"I'm outside!" She said, in a text message to her brother.

"Thanks, be right there!" Lucas replied, and she put the car in park to wait. As she was waiting, she noticed her boyfriend Gerald was there with another girl. He was too busy making out with the girl to notice Valerie, and Valerie didn't care. She could break up with him on Monday, but just in case he tried to deny his cheating, Valerie still quickly snapped a picture.

"You know, that's called spying!" Lucas said as he got in the car, causing Valerie to jump. When he looked over to see what she was taking pictures of, he instantly felt bad. Lucas and Gerald were friends, but Valerie always came first. He went to get out of the car, but Valerie put her hand on his shoulder to stop him.

"It's fine. I'm dumping him anyway. Not being tied down to a loser." Valerie said, as she put the car in drive.

"But he's the best passer in West Houston history," Lucas said, implying more that Gerald is going places than anything else.

"Only because he has the best receiver in West Houston history. Also, he only has the completed pass record, Dad still has the best QBR in our school's history." Valerie replied matter of factly, before giving Lucas a smile. She wondered if he knew how she felt about him.

As they began to drive home, Valerie decided to take the long way home. Especially since her brother was filling up her car with the smell of weed.

"Roll down the window, let it air out," Valerie said, not wanting to mention what the smell actually was. It would be easier for her to deny it later, if she had to. Lucas nodded and put his window halfway down.

"Have I ever told you that you're like the best sister ever?" Lucas said, implying that he was grateful for her not being a snitch. Valerie was thankful that it was dark inside the car, because she was blushing from ear to ear.

"So how was your night?" Lucas asked as he turned down the radio, so they could chat.

"Well, I went to the mall with Jess and Olivia. Olivia proposed to Jess, so that was fun. Other than that, nothing eventful happened." Valerie replied, trying to focus on the road.

"Yeah? That's good for them. It's honestly a shame they're lesbians, I would've loved to..."

"Okay, I get it," Valerie said, pretending to be disgusted, but she was moreso jealous. She wasn't a lesbian, and the boys at school told her she was the hottest in the school, so she would love have Lucas fuck her. But she couldn't, and that bothered her.

"What? I was just saying that they're lovely ladies," Lucas replied, trying to antagonize his younger sister, on purpose.

"Well they're really not. Jess has terribly mean jokes, Olivia is super bitchy, and neither one of them know how to..." Valerie started before stopping. She knew where this would lead. She'd end up arguing with her brother, and that would mean he'd give her the cold shoulder for a week or so.

"What's wrong? Everything okay? Normally you'd have no problem with me talking about them," Lucas replied, as he leaned against the seat to look at his sister.

"Nothing. It's just... Female problems." Valerie said, lying to her brother. Her period had passed days ago, and she was perfectly fine in that regard. She was just jealous, but she couldn't admit it.

"Oh... Okay... Well, I'm starving, what's open?" Lucas replied, seemingly accepting of the answer he was given.

"I don't know. Maybe McDonald's?" Valerie replied, not wanting to mention the local 24/7 diner because of not wanting to get out of the car.

"Nah. I want some hashbrowns with a lot of eggs. Let's head to the diner," Lucas said as he turned to face the road.

"I'm not dressed, and I also don't..." Valerie stopped, remembering it was her brother in her car, and not Gerald.

"Don't what?" Lucas asked.

"I don't have panties on, okay?" Valerie said, embarrassed. Her pants were see through in the light, and wasn't expecting to exit the car when she agreed to pick up Lucas.

"Why? What happened to them?" Lucas asked, nonchalantly.

"I sleep naked, and didn't want to put any on." She replied, deeply wanting to park the car and fuck her brother.

"You know, it's a shame you're my sister," Lucas replied, which shocked Valerie.

"Why? Would you fuck me and never call too, if I wasn't?" Valerie said, half jokingly and half wanting to just tell him to fuck her anyway.

"No. Because I would just love to see what you look like without panties on is all. Also, you have a nice rack," Lucas replied, and Valerie began to melt. She quickly pulled into the nearest parking lot, which happened to be an empty one. She found a parking spot and parked the car.

"And what do I get out of this?" Valerie said, in a seductive tone. She was calling his bluff, because she knew he was too drunk to tell a lie.

"What?" Lucas said, confused.

"You just said that you want to see me naked. Deal. But what do I get out of this?" Valerie said, beginning to lean in. She gave him her best begging look, hoping he wouldn't freak out.

"Uhm... Uhm..." Lucas was speechless. He hadn't thought this through, and just spoke what his mind told him to.

"Uhmmmmmm?" Valerie replied, before teasing the bottom of her shirt, pulling it up just past her stomach.

Lucas was unable to speak at this time, and in all honesty confused. He had no idea what his sister was doing, and when she made a glance, he swore she was looking at his building bulge.

"Better answer quick, or I'm going to quit," Valerie said, beginning to push her shirt down some, to tease.

"What do you want to see?" Lucas said, his confidence no where near the level it was just minutes ago.

Valerie didn't reply, instead, she simply grabbed the Hem of her shirt, and pulled it up just over her tits. She then rested against the window, and began playing with her tits, while her foot came up and over the gear shift. She placed it on Lucas's bulge, and began rubbing her foot softly over it.

"Oh my, I think it's getting harder," Valerie said as Lucas was stunned. He looked at his sister, unsure what was happening.

"Please big brother? Can I just see it?" She teased, while she moved her foot up to the waistband of his sweatpants.

Deep down Lucas had wanted this, and he wasn't about to let the moment slide. Quickly, he pulled down the pants and his boxers, and his 8inches sprung free. Valerie didn't take long before she moved her foot back down to her brother's cock. It was extremely girthy, which is what she always wanted. Anybody can have a long one, but long ones don't stretch the same as girthy ones. Using the sole of her freshly purple painted pedicured feet, she began to massage his cock, as it kept getting harder and harder.

"Lucas, I think you have a foot fetish. Do you like the way my feet look? I just got them done today." Valerie said, realizing her orgasm never came earlier, and if she could live out her fantasy to get it, then she would.

"Oh God," was all Lucas could say as he began to relax. Valerie smiled and realized she had power over her brother. This was her greatest fantasy come to life. She slowly brought her foot off of Lucas's cock, and slowly up to his face.

"Go ahead, big brother. Kiss it." Valerie said, to which her powerless brother quickly obliged by kissing the top of her foot. He didn't move his head at all, as Valerie moved her foot back, so that her toes were by his lips.

"The big one. Suck on it." She replied in a more commanding tone. Her brother's mouth opened, and quickly closed on it. He began sucking and sucking on her toe, loving every second of it. Eventually, Valerie pulled her foot out of his mouth. She was in control now, and she knew it. She put her shirt down, and put her foot back under the steering wheel.

"When we get home, you'll do what I tell you to, and if you do, you can have access to both feet. Deal?" Valerie said, before shifting the car into drive, and leaving the parking lot.

Lucas was hard all the way home, and it didn't help that his sister had been teasing him by stroking his cock on the way home, showing how much of an expert she was. She could feel his climax rising, and every time, she backed off.

When they pulled into the driveway of the house, she parked the car. She then turned off the car, and turned to Lucas.

"Pool house, now." She commanded, before exiting the car. She began walking to the backyard, going slow until she heard her brother following her. She picked up the pace, and once at the pool house she waited.

"You have a key, I don't. Open it." She said, to which Lucas obeyed. Valerie couldn't believe her luck, and grabbed him by the collar of his shirt, bringing him inside. They kept going until they got to the sofa, in front of the television.

"On your knees, big brother." Valerie said, and again Lucas obliged. She then kicked her flip flops off, before removing her pajama pants. Lucas's eyes stayed locked on his sister's box as she dropped to the couch, and spread her legs. She pointed to her pussy, and Lucas knew what he was expected to do.

"I've wanted this for so long!" Valerie stated in her most seductive voice possible. Lucas crawled his way over to his sister, and slowly brought is tongue out, just to tease the folds of her vagina, but Valerie had other plans. She was long over due for this orgasm, so she pushed her brother's head down into her pussy, and began to grind on his face.

Louder and louder, she began to moan as she ground and he licked faster and faster. For all she was worth, the cheerleader used her brother's tongue more viciously than she had ever used any of her fingers or toys before, and definitely more than she'd ever used Gerald before.

"Oh God, I'm about to cum. Yeah, your horny little sister is going to squirt, and you better love it," she ordered, as she felt her body begin to tense up before spasming into the biggest orgasm she could imagine. Her grip on her brother's head tightened, as she forced him to drink and lick up all of her juices.

"Oh fuck, that was so good!" She said, as her body heaved while it began to calm down. Lucas was still stunned, but Valerie just giggled to herself. She brought her left foot up to her brother's face, and placed her toes under his chin, lifting his eyes up to see into her own.

"Now, I want you to fuck me. Fuck me better than you've ever fucked someone before," she ordered, and Lucas only nodded before standing up. Valerie leaned forward, and quickly yanked down the pants and boxers of her brother, before leaning back again.

"Why didn't you..." Lucas started, but Valerie simply put a finger over her lips before letting out a soft "shhh". She then began playing with her pussy, while Lucas positioned himself to her entrance. Lucas was about to go in, when she reached down and grabbed him by his cock, and shook her head.

"That's for marriage, and marriage only," she replied, before moving his massive cock down to the entrance of her asshole. She looked at her shocked brother as she slowly began to work his cock into her ass. It was a tight fit, the tightest she had ever been. So tight she began debating on letting him fuck her pussy, but she knew he had to wait for that.

"Be gentle now, you don't want to hurt your sister," she said, and Lucas nodded before starting to push his way in. Valerie wasn't new to anal sex, as it's the only entrance she's given up in her last year of living, thus the only one she's given up ever... At least to a real cock.

After Lucas slowly got about three inches into her asshole, Valerie put her hand on his chest to let him know to wait. She was used to this ritual, but even still, 8 inches long and half her wrist thick was painful. Not only that, but she was absolutely enjoying the feel of her brother stretching out her asshole. It was a heaven sent blessing, and she wanted to enjoy as long as possible.

After about 45 seconds of waiting, she made a quick 3 count in her head, before looking her brother in the eyes, "All the way," she said before removing her hand off his chest, and in he pushed. She screamed, like they both knew she would, but once he was in she was loving it.

"Now fuck me!" She commanded, and Lucas obliged as he began to slide in and out of her asshole. His pacing made her eyes begin to roll in the back of her head, and she could feel herself knocking on Orgasm Door 005.

"Harder," she whimpered as her brother responded by delivering hard thrusts into her. Her body began to rock with him, coming into a rhythm. Once they were in synch, Lucas began to drive into her at full speed, and her moans began to get louder and louder. She was loving it, as her life long fantasy had finally become a reality.

Instinctively, Valerie went to play with her clitoris, but her brother quickly grabbed both her hands. Her eyes shot open, as he put them above her head, and proceeded to keep fucking her. His eyes told her everything. She may have had anal before, but her ass was now his. She may have him at the tip of her finger, but she was not about to deprive him of this asshole.

"So fucking tight," Lucas exclaimed as he pounded in and out of his sister. She knew she was about to have another orgasm, even if it wasn't going to result in her flooding her brother. But she needed to have her clitoris stimulated for that.

"I'm so fucking close, please!" She found herself begging. It was like a role reversal, she thought, but Lucas didn't let her arms go. She felt his cock begin to thicken up even more, and then he let her hands go. Quickly, she began rubbing her clitoris and soon with a combination howl, both Valerie and Lucas began to cum. Valerie was in ecstasy as Lucas filled her ass with his semen.

Lucas had felt the best orgasm of his life, and his cock began to slowly soften, enough to where he could easily slide out of his sister's hole. Valerie laid there, in her own moment of bliss, as she let her legs fall to the ground. Lucas then sat down beside her, and she rested on his chest.

"It's a shame you're too drunk to remember this tomorrow," Valerie said, realizing that he probably thought he just fucked some bimbo from the party.

"I only smoked, and I will remember this tomorrow," Lucas admitted, to which Valerie sat up to look at him. She was confused, and Lucas laughed.

"I had a feeling you had the hots for me, for a while now. But I couldn't do anything because you were underage, and you also had Gerald. But now..."

"Now I'm 18 and single?" Valerie said, trying to put pieces together.

"Yeah, basically. Also, I don't think we should tell Dad." Lucas said. Valerie nodded, but then realized he only mentioned one parent.

"What about mom?" Valerie asked.

"She already knew I was going to. But she told me to let you make the decision," he admitted, and Valerie was in shock. Suddenly, Lucas leaned forward and grabbed both of Valerie's feet. He began to massage them, but she pulled them away.

"Hey, you said I could!" Lucas reminded her, and she simply smiled and stood up.

"Yeah, but I didn't say when," she laughed as she turned to walk backwards to the door.

"Then when?" Lucas asked.

"When I say so, until then, keep pleading me when I say so. Is that a problem?" Valerie replied.

"Not at all!" He exclaimed, excitedly.

"Good. Because Mom and Dad will be leaving for Vegas tomorrow, and you better not have plans." She said, before opening the door.

"Wait! You forgot..." Lucas tried to reply, but Valerie had closed the door too soon. He leaned down, and picked up the pajama pants she had forgotten. As he looked at them, he noticed a wet spot inside. Without hesitation, he smelled them, and realized that she had been wet for a while. He smiled before closing his eyes and falling asleep.

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  • COMMENTS
4 Comments
bshell47bshell47over 4 years ago
WOW! Loved the story.

Can’t wait for the next chapter .

We’re in for an AWESOME weekend.

linnearlinnearover 4 years ago
Great Start

No lube? That had to hurt. I so hope you give us another chapter.

assman37assman37over 4 years ago
Nice start!

Great start to this story. I can't wait to read future chapters.

AlwaystabooAlwaystabooover 4 years ago
Nothing better than an uninhabited sister.

One sibling has to take a risk before something so beautiful can happen.

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