A Cheerleader’s Cherry

A Cheerleader’s Cherry

by JesterHaTĀ©

Melissa Haley walked across the 5th wing hallway and felt eyes piercing through her green blouse and tight jeans. A group of geeks drooled as their heads moved with her hypnotizing walk while a group of skateboarders watched her in disgust. She turned her head only to greet few of other cheerleaders and football players, but ignored the rest. Melissa pulled up her purse to her shoulder and winked at a guy that was staring at her wide hips and he swooned to the ground. This was the life of a cheerleader.

Since Melissa became a cheerleader, popularity was no problem for her social life. If she thought someone was worthy of being even looking at, it was so, but if she chose to ignore them, then that was the way it was. She had all the friends she needed in her cheerleading squad and her best friend was the cheerleading captain, Andrea Swanks. Every day, every week, every month, she would have guys drooling over her or girls staring jealously at her strawberry blonde hair, hazel eyes, curving figure, and perfect hips that were as if God Himself specially took His time to craft her body. Her only problem was her small chest, which were approximately 32B, which was probably the smallest section of boobs in the whole cheerleading squad. However, she did not take this as a hindrance at all, since nobody argued Melissa had small boobs.

“There she is,” whispered a boy with curly hair and thick glasses. “Man, she’s a spotlight!”

“You’ll never get her, George,” joked his friend Tommy. “The only girls you get is probably online.”

As Melissa got closed to the exit of the 5th wing, Andrea and her fleet of boys and girls came into view.

“Hey Melissa,” called out Andrea.

“Hi, Andrea.”

“Remember what I told you last week?” asked Andrea excitedly as her friends suddenly began to cheer loudly.

“You mean about the party at the Leaf House? I thought you said there was no way we could take crash there,” Melissa replied.

“But now we can!” screamed Andrea. “I already got all the invitations sent out. It’s going to be, like, a blast!”

The Leaf House was a large condominium that looked more like a mansion than a apartment house. There was also a swimming pool and a large field to play varieties of sports. It was currently owned by Rent-A-House, but it seems that Andrea had tweaked the business around and got a reservation.

“That is so awesome!” Melissa screamed with Andrea but her smile slowly turned into a disappointing frown. “But I have to study and baby-sit my neighbor’s baby.”

Andrea groaned. “C’mon Melissa! This is, like, the ultimate party that everyone has been waiting for.”

Melissa didn’t know how to solve the dilemma. “I don’t know…maybe I should or shouldn’t. It’s not an easy choice.”

“You’re 18, girl,” whispered Andrea and smiled mischievously. “And aren’t you a virgin too? This could also be your chance to pop your cherry.”

Melissa blushed with a shocked look on her face. She couldn’t believe Andrea had said that, but it was absolutely true. Melissa did not know if all the cheerleading squad had lost their virginity, but Melissa had been a virgin throughout her school career. She had gone out with a lot of guys, but it all ended up either in drama or the guy was too boring to be with. However, she never intended to lose her virginity, due to her commitment to lose it to the man she loves most. And the party at Lead House could be the perfect opportunity to meet her destined man.

Melissa smiled and said, “Where do we meet?”

*****************************

After practice, Melissa and the rest of the cheerleading squad went to the girls’ locker room to take a shower and change their clothes. Melissa pulled her cheerleading blouse over her shirt and pulled down her skirt. Her eyes wandered around the locker and saw other girls laughing and playfully touching each other, half naked. Because she was a virgin, she always felt nervous when she saw people touching each other. It looked dirty.

Melissa pulled off her bra and tugged her panties down and went into the showers. The girls seemed more playful and excited in the showers because there were throwing soaps, squirting shampoos, and spraying cold water at each other. Suddenly, someone sneaked behind Melissa with a bucket of cold water and dumped it on her, causing her to scream as goose bumps quickly formed throughout her body. Melissa quickly turned around and saw Andrea, fully naked.

Andrea was a fully-developed girl and Melissa did not argue with it. She had 32D and had a slender figure with a firm butt. She had brownish-red hair and crystal-clear blue eyes that looked like sparks igniting from her pupils. Since she was the head of the cheerleading squad, many girls had begun to bleach their hair red and wear blue contacts just to imitate Andrea. It seemed as if she was hailed as some kind of beauty goddess. She was smiling evilly holding the bucket of water and shrugged when Melissa glared at her.

“Andrea!” Melissa screamed angrily.

“So you’re absolutely sure about coming to Leaf House?” asked Andrea as she turned on hot water in a nearby faucet.

“Yeah I’m coming. But I’m not sure about all that virginity talk.”

“Ehh? Don’t tell me you’re not going to try to lose your virginity.”

“Well, are you a virgin?”

“Of course not. I fuck all the time, Melissa. I just had sex with Brad Ginger on Thursday.”

Andrea had a personality that was not afraid to reveal things about herself. Melissa knew she was not a virgin and a long-time experienced woman. Even though Melissa never admit it, she would call Andrea a slut, because of her over-exposed clothing. She always showed her cleavage, wore high heels, and wore skirts or pants with holes in them that at least show one-thirds of her underwear. Even if she had the captain of the football team, Victor Edwards as her boyfriend, she would secretly had sex with other guys. However, Andrea was friendly, funny, outgoing, and full of determination and Melissa looked up to her as a role model.

“Anyways, I hope everything goes alright,” said Melissa and turned off the water and fetched her towel. “Remember Tony Clarkson’s party?”

Andrea laughed heartedly and replied, “Nah, it won’t be like that. This time, the party will be a blast.”

“Something to remember, huh?”

“Uh huh…especially for you, Melissa. You better get fucked that day or I’m going to fuck you myself.”

“Hey, I am not a sex object.”

“Cheerleaders are born to be sex objects.”

Melissa rolled her eyes and dried her hair. Andrea was always joking around but it seemed too extreme. One time, Andrea created a gossip about Mr. Turnip, her English teacher and his secret relationship with a student. Mr. Turnip ended up fired from his job and served time in jail. However, everyone cheered because Mr. Turnip was one of the most grumpiest, oldest teacher in history and nobody like him. In the school, everyone knew about joke of cheerleaders being sex objects and Melissa began to get annoyed by the stupid joke.

“Make sure you shave your pussy, Melissa,” called out Andrea. “Better trim it and dress it up because this week it’s going to go pop!” Andrea put her tongue onto the roof of her mouth and clicked making a popping sound. Melissa rolled her eyes again and quickly dressed as the bell rang.

Secretly, Melissa couldn’t wait for the day to arrive. Even though she never intended to lose her virginity, she always thought about sex since the first day she encountered family life and sex education. She was interested in boys and as a girl, she wanted to experience more and more about the opposite sex. She impatiently waited for the day to come. Leaf House was definitely her last chance for the opportunity for her to become a woman.

*****************************

The week crawled slowly but the day finally came. It was in the evening around 7:00 PM when crowds of people flooded into the Leaf House. There were cheerleaders, old school friends, football players, people from other schools, and many other party-crazed young adults squeezing into the condominium. The party went right to the point; flashing lights were dancing all over the rooms, the bass of the music was thundering across the halls, and liquor, wine, and food were passed around. Some were entranced in the music as they shook their bodies and others began drinking competitions until one of the football players threw up on all the contestants. Melissa entered the party wearing a tank top with short denim and flip-flops. It was a long time before Melissa spotted Andrea in the kitchen area chatting with two boys.

“Oh, hey Melissa,” called out Andrea. “I want to introduce these guys. This is Richard and he’s Ken.”

Melissa shook hands and hugged Richard and Ken. Richard was around 6′2 with huge shoulders and thick legs with blond hair cut into a army style. Ken had short brown hair and also had hazel eyes like Melissa. He wasn’t as big as Richard, but he was definitely much taller than her and Melissa could tell he was fit from the muscles bulging out of his tight shirt. She caught Ken looking at her and winked. Andrea introduced them and Melissa surprisingly realized that both were football players from Melissa’s school, even though it felt as if she never saw them. Andrea and Melissa began to flirt with the two guys until someone started to shout over the loud music and pointed at the large swimming pool.

Everyone began to take off their clothing and ran outside in the cold evening and jumped into the pool. There was laughter and screams which meant the party was going smoothly. Andrea decided to go swimming also and took Richard with her outside. Melissa and Ken continued to chat until Ken put down his drink and smiled brightly.

“Want to go upstairs? There’s a private bath and maybe we can use it so we won’t be overcrowded,” explained Ken.

“Could this be it?” thought Melissa. “Is this finally when I’ll lose my virginity?”

Silently, Melissa nodded and Ken took her hand and led her upstairs. As they walked through the hallway, Ken peeked into rooms, which were mostly occupied by couples that were either kissing their lips out or having their own private parties. Ken finally found a empty place…which was a small room with a bed and a small T.V. set with a large tub in the bathroom. Ken went into the bathroom to fill the tub with hot water and Melissa browsed the room. She opened a closet and was surprised she found a two-piece black bikini set and she smiled as she picked it out.

“Melissa, the water’s nice and hot!” called out Ken as he took off his clothes except his boxers. He went into the tub and laid down so the water reached his chin and he sighed with relief. Ken had planned this so he can get to know Melissa and maybe even get inside her panties.

He was shocked when Melissa came in wearing the two-piece black bikini with her legs slightly crossed and her arms behind her back as her face flushed with embarrassment when he saw Ken staring at her.

“What’s wrong?” asked Melissa.

“Oh…it’s nothing. It’s…damn, you’re fine in that bikini,” said Ken and shook his head in amazement.

Melissa laughed and climbed into the tub. She realized that Ken’s body was amazing too. His body was sculptured perfectly with a six pack jutting out of his abdomen. His shoulders were large, as it was typical for a former quarterback and he had tattoos of a dragon in his right arm and a picture of a giant bonsai tree in his left. Both were silent for a long time, staring at each other’s body until Ken took courage and waded close to her and put his arm around her waist. Melissa blushed and playfully pushed him away but Ken did not let go. Ken stared at Melissa as he urged closer and she knew what Ken was about to do. She closed her eyes and accepted his kiss. Ken slowly used his arm to slowly spread Melissa’s legs. He brushed against her thighs and Melissa shuddered as she had shivers, even though they were in hot water. Ken trailed his fingers upwards until it reached her chest and then he began to massage them. Melissa gasped as they continued to link lips and before she knew it her hand brushed against Ken’s erect cock that was bulging through his boxer.

Ken disconnected their lips and he began to kiss her forehead, hair, ear, and neck. She felt a soft moan escape her throat and arched her back as Ken ravished her with barrages of kisses. His fingers quietly pinched at her nipples until they became hard and then they slowly trailed down between her legs. A finger tried to punch through her bikini fabric and she jumped and giggled softly as Ken smiled down at her. He kissed cheek and then he trailed close to her ears again.

“I want to fuck you,” he whispered in her ear.

Melissa didn’t know what to do. First, she tried to remember any advices that Andrea might have given her from the past. Does she question him back? Refuse and run away? Seduce him and accept? All these questions filled her head and finally came out as, “I…I’m still a virgin.”

“But aren’t you a cheerleader?” asked Ken blankly and Melissa rolled her eyes and Ken laughed at joke. “Well, are you going to keep your virginity and become the next 40-year-old virgin?”

“No,” laughed Melissa. “It’s just that I’m…kind of nervous.”

Ken petted her head and said, “Don’t worry. I’ll take you through every step. Now get on your knees.”

Melissa obediently went onto her knees and let half of her body out of the tub. Ken pushed and sat himself down on the edge of the tub. He motioned her to come close to him as he spread his legs and project a large bulge through his boxer.

“Take it off,” he commanded and Melissa did what he said.

Ken’s 8 inch long, 2 inch wide cock stood erect like a fishing pole pointed at Melissa. Ken smiled and said, “Now, Melissa. I want you to suck it. Remember to not use your teeth because my cock’s really sensitive.”

“Wow, it’s really big.”

“Don’t worry; soon you’ll be taking this way up your pussy. It’s much easier using your mouth.”

Melissa nodded and nervously put out her tongue and touched the tip of his cock. She pulled back and a string of precum stretched between her tongue and his cock. Then she opened her mouth and slowly slid it into her mouth, making sure her teeth did not touch his cock. Then as Ken commanded, she began to suck it awkwardly.

“Like a popsicle, Melissa,” pointed out Ken and she obeyed. “Oh yeah…that’s better.”

From her view, it seemed like Ken was being pleasured, so Melissa took this as her first step in accomplishment. For the rest of the time, she would try her best to have the best, memorable sex ever with Ken. Melissa slowly bobbed her head up and down and Ken let out a soft moan as he put his hand on her head. With his hand, he pushed her head in a little deeper but she choked so he quickly made her pull out.

“That’s too bad,” said Ken. “You can only take that much?”

“Ahh…sorry,” apologized Melissa as she wiped her mouth.

“Again.”

Melissa dived into Ken’s cock and sucked more. Ken slowly began to force her to stuff his cock in his mouth and Melissa tried to resist the choking and gagging, but it was no use as she pulled out by instinct of throwing up.

“Sorry,” Melissa said again.

“It’s okay,” laughed Ken. “It’s only your first time.”

Melissa tried to grasp the huge cock with both of her small hands and bobbed her head, using her tongue to lick the underside of his cock. Ken groaned and whispered, “Oh yes…that’s a tight mouth.”

It was not long before, Ken’s body suddenly tensed and his cock began to expand as it unleashed strings of cum in her Melissa’s mouth. As he came, he continued to whisper, “Ahhh…I’m cumming, I’m cumming! Keep it all in your mouth, Melissa!” and finally relaxed. Ken ordered Melissa to open her mouth and she did to show him all the cum he had unloaded upon her.

“Swallow it, sweetie,” whispered Ken and Melissa closed her eyes tight and swallowed as she slight coughed from the thickness of his cum.

“How is it?” asked Ken.

Melissa smacked her mouth and wrinkled her nose. “It’s kind of salty and bitter.”

Ken smiled and took hold of Melissa’s hand and both of them stood up from the tub. He led her to the bed and then faced her, looking at her full figure. Melissa’s face was flushed from sucking and from the hot bath. He reached for her shoulders and asked, “Mind if you undress?”

Melissa nodded and slowly pulled the string from the bottom bikini as it loosened and slid down to her ankles. Ken grinned with approval as he examined her wet, bald pussy. He pushed her onto the bed and kneeled down between her legs. He licked the slit of her pussy and she reacted with a jolt. “You’re so sweet that I want to eat you right up. And that’s what I’m exactly going to do.” He wiggled into her pussy as she moaned when she felt the tongue explore into her untouched cave and then hummed, which made her body cringe. He attacked her clit which made her squeal as shock sparked through Melissa’s spine.

“Oh god…”

He could not believe how fast Melissa was getting wet. She was already shriving, waiting for the climax to peak and Ken put one finger (two was too tight for her) and slowly fucked her. At the same time, he suckled on her clit which caused her buck furiously as she gasped. “Oh god, what is this feeling!” It was not long before she unleashed her climax and rode her orgasm and Ken’s finger at the same time. He sucked up all her juices and made sure not a single drop was wasted.

“Mmm, you even taste sweet.”

Ken climbed on top of Melissa and began to kiss her. She had forgotten all about her worries of her virginity being taken because she felt as if she was in heaven. Melissa broke their kiss and she whispered in his ear seductively, “Fuck me.”

“Which position you want as your first, babe?” Ken whispered back and pecked at her cheeks and neck. Melissa shrugged so Ken answered his own question. “You know what, I think this should be easier.”

Ken laid back on the bed and picked up Melissa and sat her down right under his erect pole. “Climb on top and go in slow.”

Melissa sat up and hovered near Ken’s cock. She slowly lowered herself, placing her hands on his abdomen to support herself. As the head squeezed through her pussy lips, Melissa cringed and gasped. “Oh my god…it’s tight.”

“That’s what I love about it!” laughed Ken. “Take it all of it, Melissa!”

Melissa squirmed as his cock took its journey to dominate her cherry. She slowly went in until she felt his cock poking at her hymen. She nervously looked at Ken, but he was too mesmerized at her pussy squeezing his cock. It felt as if he couldn’t believe that he would ever have such a tight twat in his whole life. “You okay, Melissa?”

“Y-yeah…”

“Just let it go and sit down until it’s all the way in, babe,” explained Ken. “It’s going to hurt a bit but I know you’re a big girl and you can take it.”

Melissa nodded and took a deep breath. As she let go of her supporting hands and sat down, she felt his cock tear her innocence apart. Suddenly, all the childhood memories and high school life flashed before her eyes and tears formed in her eyes as she gasped loudly when she felt her butt hit his thighs. She was all way in and felt Ken’s cock squeeze through her cervix. Then there was the pain. She felt a slight pain then a discomfort within her. It felt as she was going to tear apart into pieces. But she hid her discomfort by gritting her teeth in her closed mouth It was quiet for a long time, with only Melissa’s harsh breathing filled the small room. A mirror beside the bathroom was already fogging up from the breath and sex in the air. Ken silently reached Melissa’s back and slowly untied her top bikini. It slowly slid down and exposed her 32B breasts and he smiled with approval. Even with small boobs, he thought that she was still perfectly cute and sexy.

Ken smiled and whispered, “You know what to do, Melissa. Ride it.”

She nodded and weakly lifted her body up and sat down on his cock again. She felt her tight pussy contract every time the cock plunged deep into her and then relax as it left the pussy walls. Since it was her first time, every time she pounded herself on the hard pole it hit her pussy walls causing her to moan and scream lightly in mixture of pain and pleasure. Ken smiled, lifting his hand and wiped a tear off Melissa’s eyes and then cupped her breast in one hand and rested his other hand on her waist.

“Shift your body so you can hit it where it feels the best,” advised Ken as Melissa obeyed. She shifted her body right and then went straight down as it slid into her tight pussy and scratched her G-Spot. She moaned and closed her eyes while arching her back as she rode him. Her pain and discomfort was beginning to fade away and pleasure was creeping through along her thighs. She had never felt this kind of feeling before since she had started masturbating two years ago. She screamed lightly as his cock suddenly pounded at her cervix and her body shivered with excitement. She began to ride him faster, her breath changing into sharp moans. Ken leaned his body forward and kissed her pink, hard nipples causing Melissa to buckle with ecstasy until she felt a burst of tense muscles in her stomach and thighs.

“Ahhh…”

Knowing what was coming, Ken said, “Don’t stop, Melissa. Cum for me!”

Melissa rode faster, her sharp moans turning into screams. Suddenly, her whole body tense and trembled as she cried out Ken’s name and felt a strong vibe as she felt the warm rush rushing out of her pussy. She sat down on his cock, holding Ken tightly as she breathed loudly as the feeling caused her body to spasm violently. Ken sighed as he felt Melissa’s pussy squeezing his cock tightly, but he held his cum. He did not want this to stop.

“Just ride the orgasm, Melissa,” whispered Ken as he stroked her cheek and kissed her nipples. Melissa moaned as her orgasm continued. She had never came so hard before and even her body was in shock. Soon, her orgasm subsided and Ken picked Melissa up and pushed her onto the bed on her back. He smiled and slowly pushed her legs open as he observed her owned pussy, with mingled combinations of her virginal blood and her cum flowed down her pussy lips.

“What a beautiful view,” Ken said. “Popping a cherry should be considered an art.”

Melissa blushed and finally thought herself as a woman. Now she didn’t have to worry about being with a boy alone or have to think or talk to her parents about saving her virginity to a special person. Ken got on top of her and kissed her nipples, arousing her again. He went up, kissing her sweetly every time and then whispered in her ear, “Now it’s my turn.”

She nodded and laid her arms on the bed and spread her legs so Ken can fit in between. Ken whispered again, “I’m going to fuck you hard, okay?”

Melissa nodded again and whispered back, “Please, fuck me hard.”

Ken rubbed his cock between her pussy lips and slowly entered. Then he placed his hands side to side to Melissa’s head so her head was in between his spread arms until his view was her tits and above and smiled for her approval. She nodded again and he began to pump his body into her. She closed her eyes and cringed as Ken immediately began to pound her pussy, as screams and moans escaped her throat. Ken smiled as he looked down at her face and her beautiful tits bouncing up and down from the force he was exerting into her. His balls slapped her ass loudly as Melissa tightly squeezed the bed sheets with her hands and let out sharp screams at every stroke from Ken’s cock pounded into her. Melissa closed her eyes and laid her head to the side as he fucked her vigorously.

“Melissa, look at me,” Ken said between grunts. “When someone takes your virginity, you should look up at him as he is fucking you.”

Melissa slowly opened her eyes and looked up at Ken, gasping and cringing slightly at some hard pumps he was forcing into her pussy. He smiled and looked down at her as she looked up in silence. Suddenly, Melissa closed her eyes tightly, moaning, “Oh god…I think I’m cumming again.”

“I want to cum with you, Melissa…but I don’t think we can without contraceptives,” whispered Ken with disappointment. He could feel his balls tensing and his stomach tightened as it was ready to cum.

But Melissa shook her head and answered, “No, cum inside me. Make me feel that I’ve become a woman. Please Ken, cum inside me.”

Ken could not object. His cum was already rapidly flowing through his glands and through his cock. Melissa felt his cock bulge and she came as Ken gave his last strength and pounded deep into her as he also came. Melissa felt strings of cum paint her pussy walls and fill her womb as she rode her second orgasm. Ken pulled out and collapsed next to Melissa. They both look at each other, speechless from gasping with perspiration. They smiled at each other.

“Thanks for making me a woman, Ken,” whispered Melissa and kissed Ken on the lips. “I’ll remember this forever.”

As Melissa and Ken whispered passionately towards each other, the silhouette moved in the darkness of the hallways. The figure was hunched up all that time, listening closely to everything that had happened since Melissa popped her cherry. The silhouette smiled and walked away, almost skipping and sang incoherently but joyfully, “Cheerleaders are born to be sex objects….”