Cheerleader Chronicle Ch. 09

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Rick finds a cheerleader that likes to take charge.
3.9k words
4.62
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Part 9 of the 21 part series

Updated 10/18/2022
Created 09/08/2012
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As usual thanks to my editor Cheer_Smartie526. Please leave comments/feedback/suggestions. I prefer constructive criticism, but if you think it was bad, let me know.


Rick picked up his bag and started to walk out of the gym. Despite the fact school was out for the summer, the cheer team was still practicing. They had one more competition, after that they would be done. The rest of the team was leaving as well.

Lynn watched Rick walk towards the door. She still could not believe the story Courtenay had told her. Quiet Rick was a sex machine. Geeky Rick was a stud in the sack. If anyone knew not to judge a book by its cover, she should. She had been putting notches in her bedpost for months, racking up one sexual conquest after another, and everyone still thought of her as an uptight honor student. She slipped her hand into her gym bag. Her fingers curled around the ball gag, and she felt the muscles in her belly tighten. She began to walk towards Rick.

"Come with me, I've got something to show you." Lynn said.

Rick turned around and looked at Lynn. If she had bigger tits she would just look just like Lindsay Lohan. Unlike Lindsay Lohan, Lynn was the perfect student. Almost to the point of being an overachiever. Rick followed her as she turned down a dark hallway.

"This is a dead end, the rest of the school is locked down," Rick said.
"Oh, don't be so sure," Lynn replied, producing a stack of proximity cards similar to the ones the school staff used.
"Holy shit, did you steal all those?"
"Of course not, "she said innocently, 'I bought them. Then I cloned the card for the principal, the school cop and two janitors. Which one do you think would seem the least suspicious? "
"Principal?" Rick suggested.
"No, he might actually see the report on badge access, and he would know if he had been here. Same for the cop. I'm betting at least one janitor is here today. Let's go with that," she said as she swiped the card over the sensor. The door clicked and she pushed it open. Rick followed her through. She quickly navigated the hallways and soon they were standing in front of the nurse's office.
"So this is my secret, I'm not quite as good as everyone thinks I am," Lynn said proudly as pushed the door open.
"So I guess Courtenay told you..."
"Yes she did," Lynn interrupted," In hindsight I should have guessed most of it. I knew you were in shape; you never seemed to have trouble tossing any of us around. And more than once I saw you looking up the skirt of whatever cheerleader was standing on your shoulders. I was a bit surprised to hear how good you are in the sack."
"Well, I'm glad you were a little surprised," Rick replied.
"I've only got Courtenay's word on that, you still have to prove yourself to me, "she said as she took Rick's bag from him. Rick watched as Lynn searched through his bag.
"I guess you were not expecting a hook up today, that's okay, I brought enough to share," Lynn said has she dropped his bag and opened her own. Lynn pulled out four leather cuffs, each pair joined by a thick rope. Then she pulled out a riding crop. Finally she pulled out a ball gag.
"We can't make a lot of noise, just in case the janitor is actually here. Do I need to put this on you?" she said, dangling the gag in front of Rick's face.
"I think I can behave myself," Rick replied.
"Well, just in case," Lynn said has she fastened it loosely around his neck, "I'd like to keep it handy. Now take off your clothes."

Rick quickly removed his shirt and pants. His erection was already tenting his underwear. He looked over at Lynn. She had stripped down to a lacy black bra and matching thong. When she noticed she had stopped undressing she picked up the riding crop and pressed it to his cheek.
"I want you completely naked, do I already need to start punishing you?" she asked with a naughty grin.
"No, no," Rick answered, quickly sliding his underwear to the floor and pulling his socks off.
"Much better."

Lynn slowly circled him, her eyes covering every inch of his body. The tip of the riding crop slid along his skin. Occasionally he would feel it poke into his flesh.

"Courtenay says you can get it up really fast after you come." Lynn said as she got on her knees in front of him, looking hungrily at his cock," Let's find out how true that is."

Rick let out a surprised gasp as Lynn grabbed his dick and guided it into her mouth. She attacked it with her tongue and fully engulfed it. She held the riding crop in her other hand, rubbing the tip on Rick's chest. She slipped his cock out of her mouth and began to stroke it with her hand.

Lynn reveled in Rick's shocked expression. His surprised gasp made her nipples even harder. She liked the way his cock felt in her mouth. She had taken bigger, but did not think of herself as a size queen. She knew deep throating him would not be much of a challenge. Courtenay had told her Rick could get it up pretty quickly after he came, and she intended to find out just how quickly. She raised her head and let his dick slip from between her lips.

"I want you to come in my mouth," she said, and then plunged her head back down, once again taking him in. Her hand pumped up and down furiously as she ran her lips and tongue over the sensitive skin between the shaft and head of his penis. The riding crop tapped on his nipple like a metronome. Rick could not take his eyes off the sight of the honor student that was giving him head. Even though she was not naked yet, she was still very arousing to look at. Rick felt his cock slide down her throat as she took him in completely.

She took her mouth off his cock and gasped for air, continuing to stroke it with her hand. His dick was drenched with her saliva.
"Are you ready to come in my mouth, I want every last drop you can give me. Then I want you to suck on my tits until you are hard again," she panted before inhaling his throbbing erection once again.

Rick put his hand on her head, pushing it down onto his cock. He could feel his orgasm barreling down on him like a runaway freight train. He strained to hold it back so he could enjoy the blowjob just a little longer.
"I'm going to come," Rick said through gritted teeth.

His admission only seemed to encourage her. Her tongue lashed at him with renewed vigor and he exploded into her mouth. True to her words, she sucked down every bit that spurted into her mouth. Only when his penis began to soften did she release it from between her lips.

Lynn stood up. She put both her hands on Rick's head and pulled him down. She pressed her lips to his and slid her tongue into his mouth, the released him. He did not pull away from her kiss. She continued to explore his mouth with her tongue. Her hands pressed against his chest, and her fingers ran through his chest hair. She felt his nipples. They were small but firm. Lynn felt heat building up between her legs. She slide one hand down his body and grabbed his penis. It was firm, but not hard enough to fuck yet. She decided he would just have to entertain her until his erection returned.


"Get up on the exam table. I want you on your knees with your hands behind your back," Lynn said. Rick complied, and felt her putting the restraints on his wrists and ankles. She walked in front of him and removed her bra. The first thing Rick noticed was she had her nipples were pierced. Hanging from each swollen pink bud was a small silver ring. He could not take his eyes off them. He had seen her topless before, but this was new.

"You like? "She asked. "I usually don't wear them to practice; it gets me too turned on. I've had an orgasm from jogging with them in. I want to see if you are as talented as my sports bra."

Lynn took a moment to look at Rick. He fidgeted awkwardly in the restraints. Clearly he was not used to being in submissive position. Lynn smiled to herself, she would set to it that he enjoyed himself. He seemed intrigued by her breasts, and she was more than willing to satisfy his curiously.

Lynn climbed onto a small step, putting her breasts level with Rick's mouth. She put her hands on his head again and pulled him towards her. He pressed his lips on the skin between her breasts. Rick kissed her again and again, slowly moving towards her left breast. Out of the corner of his eye he saw her hand on her right breast. Rick went all the way around her breast with his lips. He was making a trail of kisses the slowly spiraled inward. Occasionally he would stop and blow across her damp skin, raising goose bumps. When his lips arrived it her nipple he gently pressed his tongue against it. The flesh was hard and hot. He took it in his mouth and tugged on the ring with his teeth. When she began to moan, Rick quickly moved his mouth to her other breast. He pinched her nipple between his lips and tapped the ring from side to side with his tongue.

Lynn gasped sharply and her body shuddered. A low moan escaped from her lips and she slowly relaxed her grip on Rick's head.

"Much better than a sports bra," she whispered.


Lynn turned around and bent over, digging through her bag again. Rick could see that her thong was quite wet. Her ass was small and muscular.

"I heard," she said as she stood up, "that you like anal sex."
In her left hand was a small vibrator with a flared base. In her right hand was a bottle of lube. Rick was stunned, and it must have showed in his face. Lynn began to laugh.
"Is that true?" she asked, walking around the exam table.
"Is that what Courtenay said?" Rick replied.
"That's what she said, so do you like it?" Lynn answered from behind him.
"Yes. Fucking Courtenay in the ass was awesome."
"Well, "Lynn said as she finished walking around the table, "It's going to be a little different with me."
Rick swallowed hard, wondering exactly what she had in mind. He looked at the contents of her hands again.
"The difference is," she said,' I've done it before, so you don't have to go quite so slow."
Rick breathed a sigh of relief, and Lynn let out another laugh.
"Silly boy, did you think you were going to be the catcher this time? I have to admit, the idea is intriguing, but I'm not dressed for it today. Now lie down on your back..."

Rick awkwardly lay on his side, then rolled onto his back. The restraints made the maneuver difficult. The rope between the cuffs was long enough that he could have his hands at his sides. The thick rope pressed into the small of his back.

"I hope you don't mind," she said has she rolled a condom onto his cock, "but Courtenay is a bit of a slut, I don't know where she has been. Who knows what she gave you. You dick might fall off next week."

Rick eyes opened wide. He had not even considered what Lynn was saying.

"Relax, I'm kidding. Courtenay is very careful, "Lynn said with a smile," plus I am much more of a slut that she will ever be."

Lynn climbed on top of him. Rick noticed her thong was gone and she was naked. Both her hands were behind her back, and he heard the faint buzz of the vibrator.
"I thought about doing this before practice, but doing it in front of you is a little more exciting,' Lynn said. Her voice changed a bit as she pushed the toy inside herself.

Lynn felt a shiver travel up her spin as she penetrated herself with the vibrator. She put the hand holding the riding crop on Rick's chest to steady her as she slid the toy in and out. The toy was not quite as big as Rick's cock, so she would have to stretch even more to accommodate him, a thought that thrilled her. She lowered herself slightly, pressing her wet labia against the length of his erection. Lynn wondered what it would be like to fuck him the vibrator still in her ass. She wondered what it would feel like to Rick. Lynn felt the muscles in her vagina spasm, begging to feel the cock that was so close. Lynn withdrew the toy and gently tossed into her bag. It was time to fuck Rick.

Rick felt Lynn's hand on his cock. She was guiding it between her legs. In her other hand she held the riding crop. He was glad he was wearing the condom; just the sight of her straddling him with his dick barely penetrating her sex had pushed him to the edge or orgasm.

"Don't disappoint me,' she said, tapping the riding crop against his cheek. She slowly lowered herself onto him. Even through the layer of latex she felt incredible. The leather pressed into his cheek helped him back away from the edge. Rick closed his eyes, trying to think of something beside sex.

"That's cheating," Lynn said, tapping him with the crop a little harder,' I want you to look at me while I am fucking you."

Lynn leaned forward, pressing her breast into his mouth. Rick flicked his tongue against the loop and closed his lips around her nipple. He focused all his attention on what his mouth was doing, trying to ignore the feeling of her hot pussy around his cock.

"Don't wear yourself out," Lynn warned, "I have plenty of things to keep your mouth busy."

She put her free hand on the back of his head, pulling his hair and pushing him against her firm tit. Rick strained against the cuffs on his wrists. He wanted to grab her tight little ass and hold it still. He wanted to pound her pussy with his cock, but right now he had to surrender to her desires. She put her other breast against his lips, and he started over.

First he gripped the metal ring in his teeth and pulled on it gently. Then he swirled his tongue around her erect nipple. Finally he pressed his lips to her skin and began to suck her tit into his mouth. Compared to Nancy or Courtenay, Lynn's breasts were slightly smaller and firmer. The word that came to mind was perky. Rick felt her sinking further down onto his cock. Lynn's legs were at some impossible angle, and her clit pressed into the wedge between the shaft of his dick and the rest of his body. He felt her arms under him; she was gripping him by the shoulder blades. Rick held still has Lynn held her body against his, sliding up and down. She began to move faster. Lynn was bouncing up and down. Her breasts slapped against his chest as she pounded herself against him. Her breathing was quick and shallow. She moaned quietly. Finally she stopped moving and Rick felt her vagina grip him tightly.


Lynn felt muscles all over her body begin to burn from excursion. The lure of her orgasm kept her going. Each time she plunged down onto Rick's throbbing cock she inch closer to her climax. Each time Rick struggled against his restraints he moved her a bit closer. She could feel it building from her toes to her scalp. She pushed herself down on him as far as she possibly could; she enjoyed the feeling of him filling her. She was so wet there was almost no friction between them, just the feeling of her body stretching around his. When she finally came it was like a dam burst. Lynn collapsed onto Rick. Her pussy tightened around his cock. She buried her face against his shoulder, inhaling he scent. A feeling of euphoria spread throughout her body in waves, first building to a crescendo. Slowly the waves faded and she found herself lying motionless on top of him. She felt drunk.

Lynn slipped her arms out from under him and grabbed his head. She pressed her lips to his in a long kiss. She was intoxicating. Her kiss almost tasted like she had been drinking.

"Notice anything?" she giggled.
"Yes, what is that?"
"Nobody knows. I even got into a clinical sex study at the university to figure it out. They said after I have an orgasm there is something in my breath that has not been able to identify. I don't know what it is either, but I like it."
"Me too," Rick replied.
"Well, there is only one way to get more," she said, bringing her legs back alongside him.

Slowly she crawled up Rick, passing her body past his lips. He kissed her on the neck, the shoulders. She pressed his face into her cleavage. Rick kissed her on the ribs, then on the belly. Finally she pressed her slick vagina against his mouth. He strained against the cuffs again, wanting to touch her. Then Rick ran began to explore her sex with his tongue. She was smooth and hot and wet. He craned his head forward, pressing his lips against her body. She put her hands on his head and moaned. Rick did not know what it was that he tasted on her breath after she came, but he knew he wanted more of it. First he wrapped his lips around her clit. When she squirmed away from him he buried his tongue inside her. He looked up at her firm, round breasts as she writhed on top of him. The little silver loops sparked in the light. He could see that she was staring at him.

"Yes, yes yes," she moaned,' "Keep doing that. Don't stop."

Rick could feel her getting hotter and wetter. His jaw ached, but he did not even consider stopping. Her hands relaxed as her climax overwhelmed her. She collapsed on top of him, moaning softly. Lynn held his face in her hands, the kissed him again. It was there, whatever it was, it was there. It was almost ethereal.

"Now I want you to get up on your knees again," Lynn said as she slipped over the exam bed. Rick rolled onto his side, and tucked his legs up, the clumsily laid face down on the bed. With his hands and legs tied, it was a precarious maneuver. Slowly he straightened up. He felt Lynn remove the cuffs on his wrists. She kissed him on the check and then whispered in his ear.

"I'm ready for you to fuck me in the ass," she said, smearing his sheathed cock with lube.

Rick watched in silence as she got on the bed in front of him on her hands and knees He shook his now free arms, and then put one hand on her hip. He gripped his cock in the other guiding it between her cheeks.
"You ready?' he asked.
"Yes, you hold still," she replied.

Rick watched as she pressed back against him and his cock slowly vanished from sight. She felt incredibly tight. She rocked forward, then back again. Lynn moaned as she moved back and forth... Rick closed his eyes; the sight of her was too much of a turn on. In his head he heard her call him a cheater.

It took all of her remaining strength to push back against Rick. Lynn had not expected to mind blowing orgasms to happen so quickly. Despite being exhausted she wanted to feel Rick inside her this way. She loved the feeling of her body adjusting to Rick's girth. It was a very satisfying stretch, like taboo type of yoga. Much to her surprise she felt another orgasm building deep inside her. She wanted Rick to fuck her hard.


"I don't care when you come, but you better stay hard until I am done with you," she said between moans.
Rick reached forward, cupping her tits in his hands. He focused on her, not on the way she made him feel. He gently caressed her breasts as she moved back and forth. He pinched the rings between his fingers and tugged on her nipples.
"Okay," she said, "I'm ready for you to start fucking me hard."
Rick moved his hands back onto her hips. She had stopped with most of his cock still inside. He slowly drew his hips back and the thrust them forward. The sound of flesh slapping against flesh filled the room. Lynn grunted approvingly. Rick did it again.
"Yes, yes yes, Lynn moaned, her voice wavering on each thrust. "Fuck me hard, fuck me hard! Don't stop! You cock feels so good. I want it, I want it. I want it all."

Rick could feel his own orgasm building. He dared not stop. He did not want to disappoint Lynn. Over and over he rammed his cock into her until finally he could not hold back any more. His climax surged through him. Rick stared at Lynn's ass, hoping the sight of it would keep him hard long enough to satisfy her. The view of her on her hands and knees was arousing. Rick allowed himself to take in all the sights he had been avoiding. He looked her tight ass around his cock. He watched her tits bounce each time his hips slapped against her ass. He listened to her ragged breathing and quiet moaning. Rick reached around with his hand and stroked her clit. She responded with a loud moan. He did it again and he felt her clench down on his cock.

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