Roberta

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Cheerleader learns more than cheers.
14.5k words
4.73
648.9k
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Part 1 of the 10 part series

Updated 10/16/2022
Created 01/10/2001
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* A Story from SingerTales *

Roberta was a bundle of nerves as she waited for her turn at the tryouts. Ever since junior high, she'd envied the girls who pranced in front of the crowds during the football games in their shorts skirts and tight sweaters. Today was finally her chance to show off what she had.

She knew she had the shape and the looks, and she certainly had the physical abilities to do the job, but she was also very aware of the politics involved in getting chosen for the squad. The fact that Alan, her older brother was the quarterback of the team might help, but she knew she had her work cut out for her. Also, while she looked much younger than she actually was, she worried that the fact she now eighteen might be a hindrance

As she watched the girls on the field, she could almost pick the ones who she thought would make it, and those who wouldn't. Most of them had the right look, overall, but just didn't have that innocently sexy quality that was almost required these days. Roberta had spent most of her time for the past few years developing that quality. She knew exactly how to tease and please, both with the students and the teachers. Her long, almost waist length blond hair, and her firm, well developed body had made her very popular with the boys, and she used her looks to her best advantage. She rarely wore jeans or slacks, preferring to show off her long legs in short skirts. And she was very proud of her slightly larger than average breasts. She knew her body turned the guys on, and she loved to strut her stuff.

Today she'd chosen to wear the outfit she normally wore for tennis. A very short, pleated skirt, showed her legs to the max, and for a top, she'd worn a thin polo shirt. She'd considered not wearing a bra, for the final decision would be made by Mr. Drew, the assistant coach, but she reconsidered, deciding it would be a bit too obvious.

She'd practiced the normal routines for weeks and weeks, until she knew them all by heart. When she was called to perform, though, her heart was beating wildly in her chest. Nonetheless, she performed flawlessly in her opinion, turning, spinning and jumping in perfect sync to the cheers.

She kept her eyes on Mr. Drew, and saw he was smiling as he watched her. She flashed him a innocently sexy smile as her routine ended and she returned to her seat.

For the rest of the day, she was a nervous wreck. She knew she'd done good, but the final choices wouldn't be announced until tomorrow. She was very relieved when the final bell rang and she was able to head for home.

Walking down the street, she smiled when a carload of guys honked at her as it passed. She recognized them as members of the team and waved excitedly back to them. She grinned as they pulled to the curb ahead of her, and sauntered sexily over to the passenger window. She leaned over with a smile.

"Hi Jeff..." she breathed, smiling at the driver. She knew her breasts were pushing out at the boy in the passenger seat as she leaned over to speak to Jeff, and watched his eyes devour her out of the corner of her own.

Roberta had always gotten turned on when she was being watched and ogled, and the boys were certainly doing their part. The three in the back seat were making comments and laughing, but, on the surface, Roberta ignored them, keeping her attention on Jeff.

"No practice today, guys?" she asked.

"Not till tomorrow, beautiful..." Jeff answered. "But it's our last day off." Roberta smiled to herself when he called her 'beautiful'. She kind of thought she was, but her youthful doubt always enjoyed the reassurance.

"Can't practice without cheerleaders..." a handsome boy from the back added. Roberta looked back at him and smiled.

The boy in the passenger side joined in. "Yeah...it's hard to practice without inspiration..."

Roberta watched his eyes dance over her breasts and she held her pose, leaning both arms on the car roof. She smiled to herself as she realized that every one of the boys were staring at her tits right then and she secretly wished she taken her bra off before she'd left school. If she'd have known this situation was going to present itself, she probably would have, she thought. Roberta had loved to tease boys ever since she realized that she could. And that was quite a few years ago...

Another boy from the back spoke up. "I know I'll be hard at practice if you get chosen, girl!"

Everyone cracked up at his comment and Roberta smiled at his double entendre', glancing back at him with a wink.

She was in her glory as she talked with the boys, grinning as she watched them fight for a better look at the blond beauty leaning against their car. When Jeff offered to give her a ride home, she hesitated just for a moment before agreeing. Politically speaking, it might help her to have some of the team members rooting for her acceptance to the squad. She stepped back as Todd, the boy in the passenger seat, opened his door and got out. He gallantly motioned for her to slide into the front seat, waving his arm in a grand gesture.

Roberta giggled and slid across the seat. Her short skirt hiked even higher as she slid in, and she didn't move to adjust it until Todd slid in beside her. But even pulling it down, most of her long legs were exposed in the short tennis skirt. She was loving the attention of these boys. She felt Jeff's thigh press against her own as he pulled into traffic and made a wide U-turn, seemingly taking the long way towards her house.

On the way to her house, she flirted shamelessly with the boys as they did their best to impress her in their young ways. Little did they know that she was already VERY impressed to be riding in the car with them. For a jumior to be getting this kind of attention was a major coup for her, and she grew excited as they teased and toyed with each other. Roberta returned the pressure she felt against her thigh, and looking down, saw a noticeable bulge forming in Jeff's pants. Again, she was actually surprised that she was able to excite these upperclassmen. She had a momentary urge to reach out and touch that bulge, but her common sense prevailed and she contented herself with the thigh contact. Things might get a bit out of hand if she began to stroke his cock in a car full of boys, she thought. She grinned at the vision, though, and continued her flirting.

"Thanks Jeff..." she said sexily as the car pulled up in front of her house. Jeff nodded with a grin.

"Anytime, Roberta....and I mean anytime..." Roberta grinned and poked her tongue out to caress her upper lip, then turned to Todd. She couldn't resist 'innocently' placing her hand on his thigh as she smiled at him.

"This is my stop, Todd...." she whispered. Todd jumped and swung the door open, hopping out to allow her out. As Roberta slid across the seat, she watched Todd's eyes drop to her thighs and she gave him a little show, allowing her skirt to ride up to her panties as she slid out of the car. Her face was eye level with his crotch and she saw he was sporting a full hard-on as he stood waiting for her. She sighed as she brushed past him, letting her skirt fall as she stood.

"Thanks Todd..." she breathed, then turned to the back seat. "Thanks guys...Good luck this season...and wish me luck in the tryouts."

Roberta turned and walked towards the house, aware that every eye in the car was watching her ass as she walked. A huge grin was on her face, and she put just a little extra swing in her hips. She turned and waved as she opened the door, then swung it shut behind her. Her heart was pounding. She'd never been so bold with that many guys at once and found that it excited her very much. As she walked to her room, she remembered the sight of the two hard-on's that had been so close to her. And she imagined that there were probably three more in the back seat, although she hadn't actually seen them. The thought made her heart pound. She simply had to get on that squad!!

Roberta dreamily walked through the house, just to see if anyone was home. When she realized that she was alone, she walked up the stairs to her room. Throwing her books on her desk, she lay back on her bed, her mind twirling as she relived the day. The tryouts were over and there was nothing else she could do about that, she knew. Then, her mind turned to the ride home and she began to wonder what kind of influence the boys on the team might have on who was picked for the squad. And those thoughts turned to the boys, imagining what it must be like inside the locker room with all those boys after a game. Her eyes closed as her mind pictured forty or fifty naked boys showering or walking about. She moaned low in her throat as her hand crept over her breasts. She unbuttoned her blouse as her mind wandered, then her fingers unconsciously unhooked her bra. She sighed a breath of relief as the garment fell away and her hand moved lower, unbuttoning her skirt and finding it's way inside her panties.

Roberta moaned again as her fingers moved over her pussy lips, teasing herself at first, then parting them, gently pushing her finger inside, remembering the sight of Todd's hard cock only inches from her face. As she fingered herself faster, she began to wonder what his naked cock looked like, or Jeff...or the others...

She felt her orgasm overwhelm her as she imagined what it would be like to be surrounded by those five naked boys, their hard cocks Bobbieng in front of her....fingering herself as they stroked their hard-ons...

Roberta pushed a second finger inside her wet pussy, fucking herself with a passion as her orgasm washed over her. She groaned as the noise of her masturbation filled the room, giving her self up to the moment as she coated her fingers with cum.

She was unaware of the spying eyes of her brother as he watched his sister bring herself off from his vantage point in the bathroom doorway. Unbeknownst to Roberta, he'd come home early from school. He'd heard her come in earlier, but just hadn't been in the mood to talk with her. Obviously, his attitude changed as he watched her from his vantage point.

Their individual rooms shared a bathroom, Jack and Jill style, and Alan had just stepped out of the shower when he heard his sister enter the house. He'd cracked the door to her bedroom open, hoping to catch a glimpse of her undressing, as he had so many times in the past. He was totally unprepared for the vision that greeted him.

His cock sprang to full hardness as he watched Roberta finger herself to orgasm. Her naked pussy was directed right at him, and he moaned as her fingers thrust in and out, glistening in the afternoon sunlight filtering through her window. Alan wrapped his hand around his cock, stroking himself as he watched his sister masturbate. When her come ended, and she began to stir, he quietly closed the door. He grimaced when the latch slid home, creating a very audible "click". Concerned about getting caught, he wrapped a towel around himself and moved silently into his own room. Roberta, her head still swimming from her orgasm, also heard the click very clearly.

A smile formed on her lips when she realized that her brother had been watching her. She'd always had a thing for him, and knew he liked to watch her dress. Very often, she'd "accidentally" leave the bathroom door ajar, giving him the opportunity to spy. She grinned as a plan formed in her lustfully excited mind. She hurriedly got up from the bed and stripped her clothes off. Throwing her silk robe on over her shoulders, she turned and exited her room, making her way down the hall to Alan's door. She lightly tapped on his door, and smiled at him as he opened it. His face was flushed, from excitement or embarrassment, or both, and he still had the towel wrapped around him.

Roberta smiled as she saw his hard cock still pressing against the cotton.

"I was going to take a shower..." she said innocently, "Are you done in there...?"

Alan cleared his throat and nodded dumbly. As hard as he tried, he couldn't keep his eyes from drifting over Roberta's breasts. She tied the sash around her waist, but only loosely, and the top swells of her tits were plainly visible. Roberta grinned as she watched him look at her. She was also aware of the way her nipples showed clearly though the thin silk of her robe...

"Can I ask you something...?" Roberta asked. Alan stepped back as Roberta stepped into his room, his hand clutching the towel around his waist.

"Sure, Bobbie" he answered, clearing his throat. "What is it...?" He tried to sound conversational and brotherly, which was tough in his present condition. Roberta stifled a grin as she moved to sit at his desk. She pulled her robe closed demurely, but knew her breasts were pushing out from the silk. Aware that his hard-on was very obvious, Alan moved to sit on the edge of the bed.

"You know I'm trying out for the cheerleading squad..." Roberta began. Alan smiled and nodded his head. "Do you really think I have a chance...? Do you think I have the right look...?" Roberta's question was really half sincere as she waited for Alan's answer.

Alan grinned at her, letting his eyes drop to her breasts once again. "God, Bobbie" he gushed. "If you DON'T get picked, then they're blind! You have one of the best bodies I've ever seen in my life!!" He looked at her and grinned sheepishly. "I mean, I think you do...I mean I'd bet you do..." He stopped stumbling and grinned again. "I think you're a shoo-in, Bobbie..." Roberta stood up and walked over to her brother. Her grin expressed her pleasure at his compliments.

"C'mere, ya big lug..." she kidded, taking his hand and pulling him to a standing position. She looked into his eyes and smiled. "Thanks for your faith, brother." she said sincerely. She pulled him to her and hugged him tightly. Her breathing increased when she felt his cock pushing into her, and she pushed her hips against him. Then she pushed him away in mock surprise.

"How do YOU know I have the best body you've seen?!" she said with a mock look of shock. "Have you been peeking?!" She grinned when she saw him blush bright red. She stepped back and gave him an angry look. "Well...I mean...I haven't...I just...." Alan stammered. Roberta grinned and dropped her hand to her sash. She was feeling extremely horny and it caused her thoughts to form quickly. And the sight of her brother's hard-on under his towel was making her crazy with lust.

"Well, I need an informed opinion, Alan...Tell me what you think..." She pulled the sash of her robe, unfastening it and letting it slide slowly through her hand. Alan stared at his sister as the silk folds of her robe unfolded and opened before his stare. Roberta smiled sexily and pulled her robe open. She watched his eyes open wide as she pulled it off her shoulders and let it drop to the floor. She stood before him naked and flushed.

"Do you think i have a chance...?" Roberta teased. Her eyes dropped to his cock which was pushing the towel away from his body. She cocked her leg and stood with her hands on her hips, her heart pounding with excitement. She was amazing herself with her boldness. And amazing her brother at the same time! He said nothing, but let his eyes devour her body. Roberta stood still, feeling the hot blood course through her body. She glanced down at Alan's hard-on, pushing against his towel.

Grinning like a minx she moved forward until she was pressing against him once again.

"I'll take that as a "yes"..." she smiled. She sighed as she felt his hard cock pressing into her again, and dropped her hand to the top folds of his towel. Looking into his eyes, she grasped it and pulled as she stepped back slightly, loosening the knot and causing it to fall in a heap by his feet.

Stepping forward, Roberta groaned as his hot cock pressed against her lower belly. She placed her hands on both his shoulders and continued to stare into his blazing eyes as she moved her hips from side to side, feeling his cockhead roll over her belly.

Alan was beginning to pant. His cockhead began to leak pre-come, coating the surface of his sister's belly. As the slickness increased they both groaned and Alan began to fuck his cock against her skin.

Roberta felt her pussy begin to leak. The feel of Alan's hard cock finally against her, and the slick feel of his pre-come was driving her crazy. She continued to move her hips and belly in the opposite direction of his movements. Both their eyes were blazing hotly as they stared into each other's eyes. Roberta kept her hands on his shoulders, but her belly continued to move against his throbbing cock, making it move back and forth across her belly. She grinned, knowing what was going to happen if they continued this dance....

Their eyes were still locked together when Alan groaned loudly. He pushed his cock against Roberta and she felt it buck. She grinned and moved her hips faster, making his cock slip and slide in the pools of pre-come coating her belly. Her heart began to pound in her chest as she realized that she was going to make her brother come... make him come just rubbing against him... Her breathing came in pants as she increased her efforts and she grinned to herself as she heard him moan low in his throat as his cock bucked against her belly.

"This feels good, doesn't it...?" she panted, "I like your cock rubbing against me... you're so hard...and slippery...mmmmm..." Alan groaned as he stared into his sister's eyes. He knew he was going to come if they didn't stop and wondered if he should until Roberta put his concerns to rest. "It's okay, Alan...." She breathed, "I want to see you come....want to make you shoot off...Mmmm....yeah...I want to watch you shoot off...."

Alan groaned one last time as his cock bucked over and over against Roberta's belly. She squealed as she felt his cum splash against her belly, increasing the sloppy wetness between them.

"Yeah...." she sighed. "Oh Alan...God, you're coming...oh, fuck yeessss....Shoot your cum on me...It's so fucking hot...." Roberta pulled her shoulders back and looked down, feeling a mini orgasm arise within her as she watched Alan's cock buck and shoot his sperm over her belly. She watched as the slit in his cockhead opened then shot out a huge spray of semen, splashing against her and almost hitting her tits. It dripped downwards, covering her pubic hair, and dripped down her thighs. She groaned as Alan took advantage of her new position and wrapped a hand over her right breast. The feel of his palm was electric and Roberta felt her orgasm wash over her.

She didn't touch his cock with her hand but simply let him fuck against her belly as he shot volley after volley of cum over her. The smell of it was intoxicating and Roberta breathed deep as her pussy muscles tightened and relaxed in orgasmic rhythm. Her eyelids fluttered as she gave herself up to the experience. Alan was coming on her belly and she hadn't even laid a hand on him!

It was too much for her. As she felt Alan's orgasm waning, she took a step backwards. She smiled into Alan's glazed eyes and slowly let her hand slide down his chest and over his belly. When she contacted his still hard cock, she wrapped her fingers around it, sliding her fist up and down him as she coated her hand with his semen. Alan groaned again at her touch and pushed his cock forward, pushing it through Roberta's tight grip. Roberta grinned and winked at him. She almost couldn't believe she was doing this, but her excitement urged her on. She stared at his still hard cock as she slowly jerked him off, feeling his thick cum squeeze through her fingers. She had a feeling that if she kept this up, she'd make him come again, just from the feel of his hard cock, but she thought she'd better play it safe.

"Well, now I really have to take a shower!" she kidded him. She released her grip on his cock and stepped away from him. She walked to the bathroom door, but turned as she opened it.