Riding Bareback Ch. 5

Story Info
Jennifer fulfills a legend after the big game.
4k words
4.34
175.6k
59

Part 5 of the 5 part series

Updated 11/01/2022
Created 07/23/2002
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

There was an old football legend at Buckland High based on a story from the ‘70s that had been twisted and exaggerated over the years and was now used mostly to scare the cheerleaders. The last game every year was always against archrival, Lee High School from the next county. Tradition held that the cheerleaders of the losing team had to sleep with the winners. It was total myth, stretched out of proportion, after the cheer captain in ’74 dumped her boyfriend on the Buckland team and went out with the QB of Lee. It was an unbearable affront after Lee had won 35 – 7 and the slighted player started a rumor that he had lost a bet and paid it off with his girl. He promptly, then dumped her for being such a slut. It was too juicy of a story and it grew into a running bet over the years until it included the whole squad, but it never happened. It was great inspiration for the players before the big game and it always was a great game.

This year there was even more on the line. Both teams were undefeated going in and the winner could claim the state championship. The Lee QB, Josh Stevens, had signed to play at Florida. Kyle, Bob and Gerry were each recruited by Ohio, USC and Clemson respectively. Ten thousand people were expected in the stands. Kyle had decided to up the ante and he placed the bet. He had his eye on the captain of the Lee cheerleaders for the last couple of years. When he scouted their team last month he spent most of his time scouting her.

Shannon was her name. She was 5’ 9” with long blonde hair, straight and flowing. Her eyes were clear sparkling blue and her natural smile highlighted her delicious face. She had a perfect body, long lean legs, round firm ass, flat stomach and full D-cup breasts that were so young and firm they could stand up fine with out a bra. Shannon turned heads wherever she went and she knew it. She had dated Josh for two years but had broken up with him when she found out he had cheated on her with three other girls on her squad. He was the only one she had ever had sex with and now, he was willing to give her to Kyle, drunken or drugged, whatever it took to have her ready to fuck. Provided, of course, that Buckland could beat Lee. Kyle would have to provide equal compensation should Lee win the game.

The big game lived up to all expectations. Kyle, playing cornerback, picked off one of Josh’s early passes and ran it back for a touchdown. The Lee QB threw two others for TD’s and at the half it was 14-7, Lee. Gerry ran for two TD’s in the 3rd quarter, but Lee ran for another to tie it up with 1:30 left in the game. Then, on the last play of the game, a hail Mary pass by Buckland for the win was tipped in the air and picked off. The Lee defense made handed off and ladder rolled the ball 8 times while running it 85 yards for the winning touchdown. Buckland went 10-1, for their best season in 20 years, but Lee High School was State Champion.

During the on field handshakes, Kyle couldn’t take his eyes off Shannon jumping up and down in celebration. Her hair and her skirt seemed to float on the wind and even through that white sweater with the red L, he could plainly see the tits of his dreams bouncing away without him. When Josh came to him in line, he gave him the address of the Lee victory party and left with the words, “Bring my prize, pal. Bring my prize.”

Kyle turned his gaze toward the Buckland sideline. The players limped off the field holding their helmets and their heads in their hands. The crowd also walked quietly from the stands and the cheerleaders solemnly packed their gear into duffle bags. As Kyle watched the girls he tried to imagine any of them honoring his stupid bet. He couldn’t pick one to give to Josh for the night. None of them would go for it, but he knew one girl who might.

Outside the fence, walking to her car, he saw her. In cut off jeans that hugged her round ass tightly and a denim halter-top that bared her delicious middle and squeezed her ripe breasts together, Jennifer Fox could give a hard-on to a dead man. Kyle also knew from personal experience that she could fuck like a rabbit. He had had the pleasure of her company several times since he and Gerry double-teamed her after the carnival.


Jennifer knew when Kyle called that he wanted sex and as usual she gave in and agreed to see him. He had a tough game and she felt sorry for him, but she also knew he would take out his frustration on her sweet little body and that was already giving her goose bumps. Her nights out with Kyle were not normally dates. He would pick her up down the street from her house, take her somewhere private, strip her naked and attack that lovely 18 year-old body. Jen would fight a little to keep it interesting, but eventually she would surrender and come all over his thick 9-inch cock. By the end of the phone call, she had mentally prepared herself to once again have her body used sexually by Kyle. She even agreed to wear something slutty for him, although she wasn’t sure what it would be, or how she would get out of the house in it.

When Jen saw Kyle’s headlights coming up the road she stepped out of the shadows and tossed her overcoat over a fence rail. She could reclaim it there on her way home. Normally in blue jeans or cutoffs, her curvy legs rose out of a pair of cowboy boots, her usual footwear, and barely disappeared under a very short black miniskirt. Above the waist, she wore a thin black nylon top that left all of her flat stomach exposed. There were no buttons fastened, only a knot in the fabric nestled right between her fabulous C-cup breasts held it closed. The tight sleeves ended in bow ties at the elbows. The flared collar was spread wide open exposing her smooth neck and down into the depths of her cleavage. Her long hair was no longer braided, but held back loosely by a thin black ribbon.

Kyle massaged her bare thighs as he drove away and Jen could tell he thought she was hot. She couldn’t believe she had dressed as slutty as she did. She had never made her body so obviously available to anyone.

“Hey Jen,” Kyle said, “Why don’t you help me relax a little while I drive.” He lifted his shirt and loosened his belt.

Jen could see the bulge in his jeans and pressed one hand onto it while leaning in to lick his ear. “Let’s go somewhere and take turns.”

“We are going somewhere and I want you to blow me.”

She couldn’t understand why he was being so direct, but then they didn’t actually have a relationship, so, slowly and quietly, she lowered her head. She bit her lip and held back a tear as she pulled his zipper down and took out his hard cock. Tentatively at first, she licked the head in circles. Her lips opened to let him in and within a few minutes she was bobbing up and down on Kyle’s full length. No longer knowing, she now ran on instinct. She stretched out across the seat, lying on her belly with her boots up against the window. Kyle took the opportunity to rub her fine ass and when he lifted her skirt he was amazed to find her wearing a thin black thong.

Jen’s tan skin glowed in the dashboard light as Kyle squeezed her ass flesh. He slapped her on the butt and Jen pulled off his cock. “Hey, take it easy.”

“You dress like a slut. You get spanked like a slut.” Kyle said just before smacking her even harder. And for the next twenty minutes he alternately spanked and mauled her ass while she pumped her face up and down on Kyle’s throbbing dick. She knew was getting close when his hand left her ass and held her by the back of the head. She tried to pull back but was held firmly as she felt the first of his seed fire down her throat. Rather than fight to get loose, Jen concentrated on swallowing all she could and just managed to keep up with his final pulses.

A few minutes later they were walking into the party for the new State Champion Lee High Bulldogs. Jen clung to Kyle’s arm, very self conscious at the way she was dressed. She wasn’t expecting to be out in public. The other girls wore sweaters and jeans and Jen was nearly naked in her clinging top and micro-skirt. She could feel all eyes on her. The guys imagined peeling off what clothes she was wearing and the girls turned their noses up at her slutty attire. She nearly chugged two drinks and was starting a third when Josh approached Kyle.

“Glad you could make it Kyle. I hope nobody’s giving you a hard time about the game?”

“Not at all. I want you to meet Jennifer Fox.”

Jen shook the tall quarterback’s hand politely, still not knowing why they were there. She thought Josh’s hand and eyes lingered too long on her before speaking.

“Is that your real name? It certainly is appropriate.”

Jen blushed uncontrollably and turned to look up at Kyle. He stared into her eyes for a few seconds and spoke.

“Jen, I want you to go upstairs with Josh.” He made it clear with the determined look he gave her exactly what he meant. Jen could only shake her head as Josh, a man she did not even know, took her by the hand and led her up the stairs. The room grew quiet as everybody watched them climb the steps. Jen looked around the room, searching for a way out, from the cheerleaders who looked away from her to Josh’s teammates checking out her legs and giving high fives, to Kyle who turned to talk to a tall blond with large breasts. Josh made a show of marching her off like a trophy and when they reached the top and turned into the first bedroom there, the room erupted in applause.

Jen was humiliated, but when she tried to protest Josh lifted her off the ground and planted a savage lip lock on her. Jen’s boots hung in the air as he grabbed at her ass under her mini skirt and drove his tongue between her teeth. As she hit the bed on her back, she saw a crowd rapidly forming outside the door. Josh lifted one of her boots and ran his hands down the full length of her leg showing it off to the crowd.

“Show me your tits, Bitch.” He pulled off her boot and threw it aside, quickly grabbing her other leg. Jen, still in shock, did the only thing she could do. She slowly reached up to the knot at her breasts and untied her top, spilling her glorious tits out in the open. Her firm C-cup breasts stood up proud, nipples hardening under the eyes of her audience with no tan lines in sight. Josh stared into her eyes as he tossed away her other boot and then flipped her onto her stomach. He reached for her shoulders and peeled her top down her strong arms, baring her back. With a slap on the ass he lifted her onto her hands and knees. He yanked the thin skirt from Jen’s beautiful body leaving her in nothing but a thong.

“Turn around Bitch and suck my cock.” Josh waited as Jen turned in a crawl to sit on the edge of the bed. She looked sadly up at Josh as she opened his pants, letting them fall to the ground. He stepped out of them and lifted off his own shirt as Jen wrapped her hands and her lips around his cock. She expertly worked his cock but began to worry as he continued to grow, finally reaching his full length of 11 inches. The crowd oozed excitement and spilled into the room as Josh pushed Jen down on the bed and tugged the thong off her legs. They surrounded the bed as he climbed on top of her and unceremoniously drove his wet cock into her waiting pussy.

Jen gasped and bit down on her lip in pain as he forced his huge cock into her. She was already wet, but this was by far the biggest cock she had yet taken in her young life and he wasn’t waiting for her to get used to it. Josh pushed steadily into her until he bottomed out and then started wildly fucking his prize. Her ankles were up on his shoulders and his hands were on her tits as he mercilessly fucked his new whore. Jen bit down on the back of her hand to keep from screaming but she still let out a loud grunt with each of his thrusts. It occurred to her that this was the first time she ever had sex in a bed.

Jen had learned recently that she liked to be taken. She had let Kyle and LaRouche use her for sex, basically anytime they wanted. They had struck a cord with her; they knew she thrived on being forced. If you didn’t give her a choice, Jen would let you do anything you wanted with her sexy little body. Kyle had just taken her to the extreme, giving her away to settle a bet. Josh, however, was being rougher than the other three guys and she had never before been fucked in front of an audience. As her body rocked on the bed, she saw there were at least 20 people in the room, mostly Lee football players and a few girlfriends. Josh pulled her ass to the edge of the bed and stood up as he fucked her precious body. The crowd cheered as her tits bounced. She was completely naked with her legs high and wide in a house full of strangers. A chant broke out in the room.

“Fuck that Slut! Buckland Cunt!” Over and over again. Hands clapped and feet stomped. Josh gripped her knees and with five hard thrusts, shot his load deep into Jen’s abused pussy. Jen had let her body be taken and now she let herself have what pleasure she could get from her attacker. To the cheers of “Slut” and “Whore” and her own screams of anguish, Jen’s beautiful body rolled through a long and wonderful orgasm. Her head stretched back, her spine arched and her toes clenched. A shimmer went in waves down her tits and abs and her legs shook as Josh emptied his balls into her.

Josh withdrew his cock abruptly and pulled on his jeans, then announced to the crowd, “Since the bet was ‘Anything Goes’ and it was a team victory, any Bulldog that wants to fuck the pride of Buckland can take his turn.” Then he walked out of the room pulling a short redheaded cheerleader with him. “Have fun with her boys!”

Jen inched back against the headboard as they closed in. She knew she was about to be gang-banged by a group of total strangers. It only took seconds for her to be flipped over onto her hands and knees. Instantly she was filled with two cocks, one in her pussy doggie style and one being pushed into her accepting throat. These two guys were nothing if not eager and they didn’t last long. In less than five minutes, Jen was drinking the cum of one and felt the other splash inside her, joining their team quarterback’s.

Before she could move, two more Bulldogs took their places and Jen was filled with cock again. She may as well have been a hole in the ground, the way she was being treated. The chanting continued as she was passed from player to player. The audience started ribbing the player fucking her now and she realized she had just taken his virginity. She looked back at him and actually smiled, but her face was quickly pulled back to the cock waiting in front of her. Two more loads of come splashed inside her and without thinking she swallowed and cleaned up the cock in her mouth. The virgin continued to fuck her slowly with his softening cock until he was pushed out of the way.

Next in line was a 300lb offensive tackle named Bubba. Jen slumped to the bed and lay on her side watching Bubba get undressed. He was not all muscle. His shoulders were about four feet wide and his arms were bigger around than Jen’s legs. His legs were bigger than her waist and his belly over hung his waist enough to hide his growing 9” cock. A few players taunted Bubba that this would be his first fuck, of a human. His hair was long and hung rather scraggily around his face. He wore a partially grown goatee. Jen was worn out from her previous activities and shook her head “no.” Bubba stepped up to the bed and asked her name.

“Jennifer” she replied meekly.

“Well Jennifer,” he said, “I’ll try not to hurt you, OK.” The look on his face seemed to be of genuine concern. He stroked his large hand up and down her leg and motioned for her to roll onto her back.

“OK” Jen said. What else could she say? What worried her the most was just his immense size. He was huge and he was sweating already. Jen had always prided herself on being able to take whatever was thrown at her, but she was worried about this one. Her little body was barely a third of his size, how could she possibly endure this.

“I love your tits, Jen.” Bubba said. His voice was strangely quiet for such a big man. One big hand mauled both of her tits together and pushed her back into the mattress. “Spread your legs wider for me Jen.” As he climbed on top, he let his weight come to rest, nearly smothering her.

She tried to push him up with her arms but there was no chance. Her little hands just sunk into the folds of flesh on his chest. Revulsion swam through her at the thought of this blob getting inside her. She wrestled with the hand grabbing at her chest, but he brushed her away easily. When she tried again to move him, he grabbed both her wrists in one big hand and held them out above her head. Jen could not move at all.

All Jen could to was grunt against his effort as he reached down between their bodies and aimed his cock, the only hard thing on his flabby body, at her tender pussy. He pushed in quickly since she had already taken three loads of come from his teammates. As Bubba rocked his massive weight back and forth on her squashed body, her whole body was buried beneath him, only her slender legs pushed out at either side. He only lifted up to squeeze and pinch her luscious tits.

Jen continued to gasp for air as Bubba fucked her. She was disgusted at being covered in the big slob’s sweat. Her face was pressed into his chest and with her arms stretched out over her head she could not look away. She had swallowed four loads of come and been fucked four times and now she had to have this jerk’s flabby body rubbed in her face. She was almost relieved when she felt him quicken the pace, knowing he was nearing the end.

Suddenly he stopped fucking her and pulled his cock out. Without letting her hands go, he moved up her body and pressed his cock into her tits. His belly dragged on her face as he rubbed his slimy cock on her tits, already smeared with his sweat. This sloppy titty fuck went on for a few minutes until he reached down and jerked his load into her face. He must have been saving up, after all who would have sex with him, because he fired shot after shot onto her face, her hair and her tits. Then he wiped his cock off on her face until she opened her mouth and resigned herself to lick him clean.

The room had mostly cleared out. Nobody wanted to watch Jabba the hut get it on. As Jen tried to catch her breath, one of the few guys left in the room threw her a towel and she wiped her face with it. Another put down the video camera he had been holding. Jen felt humiliated as she realized her whole ordeal had been filmed. Then it occurred to her, that only her last fuck with Bubba bothered her. She had actually been turned on by Josh and the others. Knowing she had been the first sex for some of these guys gave her a wierd sense of pride. Her humiliation came only from knowing anyone else might see her getting fucked by that massive slob, Bubba.

“You’re a mess, Slut! Why don’t you get cleaned up before I fuck you. I don’t want to catch anything from Bubba.” They led her into the large bathroom attached to the bedroom and she got into the shower. The hot water felt good on her battered skin and she let it run down the full length of her hair, reaching the top of her round ass. The curtain pulled open and she saw the video camera back on her again. Slowly she began to soap up her sexy body, teasing these boys with her long wet hair. She leaned against the back wall of the shower and massaged the soap through her breasts and down to her sore pussy. On camera, she worked two fingers into her cunt and made herself come.

After she dried off Jennifer returned to the big bed and let the rest of the team take their turns with her. One by one they would climb between her tan thighs and shove their eager cocks into her stretched out cunt. Nine virgin players gave her their first fuck. In the end she fucked 23 Lee Bulldogs and gave half of them blowjobs as well. Most of it was captured on video and the tape continues to be played for new team members to provide motivation for the big game. Josh gave Jen a ride home dropping her off at 4:30 am, but only after she sucked his cock one more time outside her father’s house. She snuck in the basement wearing only a Lee Football jersey. The rumors of her gang-bang followed her to college where she occasionally was forced into 4 on 1, but she never had another night like this one.

12