Chapter 02 – Lilly Meets the Football Team
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The light filtered in softly through the drawn blinds in Lilly’s room illuminating her face and pulling her out of the gentle embrace of sleep. She slowly opened her eyes and stared at the crisp white paint of her ceiling letting herself wake slowly. She rolled over and cringed in confusion at the pain flooding from her pussy before reality sunk in. Her trip to the headmaster’s office the previous day had starched her formerly virgin pussy in ways she never could have imagined possible before and it was taking its toll on her body now.
Lilly made her way carefully to the bathroom, each step blissful agony. Lilly’s introduction to the world of sex had been a bit rough, but she had thoroughly enjoyed every second of it. Lilly stripped out of her night clothes, missing the hamper with her casual toss by a fair bit. She hoped that with a long shower, and some masturabtion, she might be able to work some of the soreness out of her aching pussy, not to mention starting the day off with a bang.
She groaned as the hot water streamed off her body. Sliding her hands over her full breasts she paused only momentarily to graze her erect nippled with the palm of her hand before seeking out the cleft between her legs. Wasting no time Lilly pumped her fingers in and out of her protesting hole. With skill born out of luck rather than experience Lilly quickly worked herself to her limits.
Her body shook and convulsed as the waves of her orgasm rocked through her, bringing relief to her sore muscles. Finishing up the rest of her shower she quickly dried off before heading back to her room. She considered herself lucky that her parents hadn’t heard her in the shower, she dreaded having to explain herself to her father.
Walking over to her closet, she began assembling the pieces of her wardrobe, taking careful care to ensure that she wore panties this time. She wasn’t quite sure if she wanted to repeat the previous day’s activity, or wait for another day, but she was positive that she didn’t want to do it while she felt like this. Standing in front of the full length mirror attached to the back of her closet door she paused to admire herself, she had full lush breasts, which seemed to run in her family, large C’s, closely bordering on D’s. While her mother fell more on the voluptuous side, 6 years of sports and strenuous exercise on her part had removed the majority of the fat from most of her body, while also tightening and toning her shape. The result was a figure which any man, or woman, would kill to get 
their hands on.
The gentle curves of her hips led her eyes down to the dark cleft between her legs where the pouty lips of her pussy peaked back at her. While never having much of an inclination towards sex before the last few month, Lilly had always made sure to keep her pussy cleanly shaven.
“I wonder if I should grow a landing strip?” Lilly mused to herself, running a finger over the smooth outer lips of her still exposed pussy. Although she had noticed that a lot of girls her age had started to leave a small tuft of hair between the tops of their vulva and below their underwear line, Lilly had always enjoyed being completely smooth down there.
Cutting her musings short Lilly pulled on a white satin thong. Putting on the mandatory plaid skirt and white blouse, which were mandatory for her school, Lilly rushed to get the items she needed for the day together. As she was getting ready to leave her room the small black bag sitting by her bed caught her attention. Reaching inside of it she pulled out the vibrator she had purchased the day before.
Though she had been shocked by her encounter with the headmaster, it had awoken something in her which she had never known was there before. She decided that she would put the little thing through its paces during her free period later in the day and slipped it into her back pack.
The headmaster put down the report he had been reading an tapped his chin in consideration. He had been getting additional complaints about the girl he had “punished” the other day; it seemed several of the teachers had seen her making out in one of the hall ways with her girl friend again, despite the firm school policy that there was to be no physical interactions in the halls… that was for behind closed doors after all.
“Some people never learn.” he said to himself “I guess I will have to come up with a better punishment this time the last one doesn’t seem to have been very effective.” he paused
Trying to think of something that would deter her from continuing her reckless disregard for school rules “I will have to make an example of her” he said. Looking under his desk he spoke to his secretary, “Please tell the football coach that I want the team pulled out of their normal classes during fifth period and assembled in room 169 for a morale building exercise” he said
“Right away Sir.” she said, careful to articulate her words without pulling his cock out of her mouth.
“Oh and send a note to Miss Anderson as well summoning her to the same place and time.” he added
His secretary nodded, swallowing the load of cum he left in her mouth and taking the two notes, she hurried out of his office to deliver them before the first bell rang, smirking to herself at the thought of the fun the two girls would get to have that day. Although she was a little jealous that she would not get to be part of the excitement, she always felt special that the headmaster always insisted on keeping her all to himself.
Lilly pulled into her usual parking spot and walked into the building. Walking slowly through the hall, packed with students joking and jostling each other, Lilly made her way to her first class. Just as her hand reached the knob she heard the bell ring announcing that class would be starting shortly.
She walked into her first period class and saw Mr. Jacobs look up at her from his desk.
“Ah I see you were able to make it on time today.” Said Mr. Jacobs a smirk playing around the corners of his mouth “The headmaster left this note for you” he said
Lilly took the note and quickly walked back to her seat. Unfolding the thick white paper she saw the neat script of the head master. The note said: “Report to Room 269 during 5th Period” and was signed by the headmaster.
“Hmmm… I wonder what he wants” Lilly asked herself.
The first two periods dragged on with insufferable slowness as Lilly waited for her free period. She could picture the vibrator sitting in her backpack and with growing arousal she desperately watched the hands on the clock tick by with insufferable slowness. Finally the bell rang, Lilly jumped out of her seat and rushed into the hallway
“I wonder where I could get some privacy.” Lilly wondered to herself
Lilly hardly noticed as her hand drifted between her legs idly, stroking her aching pussy gently
She remembered that the second floor was currently under construction, some sort of remodeling; only they weren’t allowed to work during school hours because of the disruption to the students so the entire second floor was abandoned during school hours
“Perfect.” Lilly said. She failed to notice that Tom, who had been sitting several rows behind her, had seen the the vibrator in her bag, and had noticed the way her hands had been idly drifting to the pointed tips of her breasts and down between her legs. He picked up his bag, following quietly behind her.
Grabbing her backpack, she wandered down the hall until she found one of the stairways leading to the second floor. Looking around she stealthily ducked under the caution tape baring the stairs and climbed up to the second story. The tap, tap, tap of her shoes on the bare concrete floor sounded almost deafening in the eerie silence of the abandoned hallway. Lilly drifted past the empty classrooms, wandering down a forlorn hallway, covered in heavy construction plastic, searching for the perfect place to be alone with her new toy. Finally coming to the end of the hall she saw a door marked “bathroom”, a large swath of plastic covering the door. Lilly pushed her way past and ducked inside. Though the floors and walls where empty she noticed that all of the furniture which had been pushed to the side to clear the way included a very large and plush looking couch which was perfect for what she was looking for. Pushing the door closed she dropped her bag and started rifling through it until she found the tiny vibrator.
She walked over to the large stall and sat down before reaching under her skirt and pulling her panties off before unbuttoning her shirt. In her heightened state of arousal she could barely keep her hands off herself, deciding to enjoy the moment before using her new toy, she thought she would get herself started the old fashioned way.
Working her way quickly to her second orgasm of the day she sat back, taking a second to breathe. Enjoying the momentary break from her new found, and inordinately powerful, sex drive that her orgasm had bought her she reached into her backpack, pulling out her toy.
She twisted the end of the vibrator counter clockwise until it started vibrating gently in her hand. Laying back against the arm of the couch she spread her legs putting her left leg up on the back of the couch to give herself better access to her pussy. She twitched convulsively with the vibrators first contact with her clit moaning loudly into the empty room. Laying her head back against the arm she lost herself in the pleasure emanating from between her legs.
Lilly started making gentle circle motions with the vibrator slowly circling her clit, she could already feel the moisture in her pussy increasing, deciding that she needed more stimulation she unbuttoned her blouse and pulled her bra down uncovering her large tits, she started mauling her left breast, finely pulling it into her mouth and sucking on her nipple. Switching it to its highest level, she cried out into the empty room filling the silence with her pleasure.
She was so wrapped up in what she was doing that she almost didn’t notice the door crack open ever so slightly, though by that point she was so lost in her pleasure that there was nothing else she could do but continue, but the intrusion never came, the door opened a crack but no further. Lilly looked through eyes half lidded with lust and pleasure and saw the mirror which was positioned against the wall in such a way as to give her a direct view of the slightly open door, and what’s more she realized in shock to give the person who was watching her masturbate a perfect view of her exposed body, but it wasn’t a teacher like she had expected but instead Tom. The feeling of being watched made her even hornier and she decided to give him a show worth watching. She let go of her breast and slid her hand down until both were between her legs, which were spread as far as they could go. Continuing to give the vibrators full attention to her tender clit she then inserted her first two fingers inside her tight pussy and started to thrust furiously. She was pleased at the effect it produced noticing that tom had moved from simply rubbing himself through his pants to taking his cock out and stroking it rapidly. Lilly was surprised by how thick it looked and moaned loudly to herself.
She imagined that it wasn’t her fingers that were inside of her but instead Toms big thick cock pounding away inside of her. Lilly could feel her orgasm starting to build inside of her and kept her half closed eyes locked on the sight of Tom stroking his cock in the mirror while she continued to pump her fingers in and out of her pussy. Finally she pressed the bullet down hard on her clit and increased her pace until she was pumping in and out as fast as she could go until she jerked her head back and moaned feeling the muscles of her pussy flexing and sweat beading down in-between her breasts she collapsed exhausted. She glanced over just in time to witness Tom cum all over the floor painting it with the thick white ropes of his sperm before quietly pulling up his pants and sneaking away.
“I guess he liked what he saw.” Lilly laughed quietly to herself “Because I know that I sure did.” She said
She wasn’t quite sure why but the thought of Tom watching her masturbate made her feel incredibly naughty and erotic, a feeling that she was starting to enjoy. Fixing her bra and buttoning up her shirt Lilly got ready to return to the dull drudgery of school.
“I wonder if whatever the headmaster has planned for me will be as much fun?” she wondered
The rest of the day sped by for Lilly as things often do when you’re worried about something until it came time for 5th period. Picking up her bag she handed her note to her fifth period teacher and headed down to room 169, which was located in one of the adjoining buildings. Oblivious to the long line of male students she was walking past Lilly knocked lightly on the door before entering. As she entered the small room she noticed that the walls where lined with sports equipment, looking up to see the headmaster waiting
“What is this place? Lilly asked
“It’s the gym teacher’s office” said the Headmaster “Now come along we have some business to attend to in the gym.”
“What are we going to do there?” asked Lilly curiously
“You are going to continue your punishment with some community service” said the headmaster with a wicked smile on his face “There is another student there who you are going to help me wish; in fact” he paused “she is already waiting for us.”
Lilly walked submissively down the hall behind the head master towards the gym “I wonder what I’m going to have to do this time she thought to herself.” She was filled with a mixture of excitement and arousal. She tried to look contrite, this was after all supposed to be her “punishment”, she wasn’t supposed to look like she was excited about it.
As she walked down the hall she started to hear strange sounds coming from the gym ahead of her. At first she wasn’t quite sure what she was hearing, but the noises soon resolved themselves into an orchestra of grunts and what sounded like flesh hitting flesh. Walking into the gym proper she beheld the scene in front of her.
All of the wrestling mats had be spread on the floor. A girl was kneeling on one of the mats. All that Lilly could see of her was the well formed shape of her ass as it stuck straight up in the air. A group of naked students stood around her, all of them were stroking their erect cocks in anticipation. As Lilly watched one of them kneeled down, grabbed her by the waist, and inserted his cock into her. Starting to pound away at her pussy both of their body arched and writhed in pleasure.
Another of the students moved around to her front and slid his cock into her mouth.
Lilly saw the ass on the student clench as he continued to pound her, a tell tale sign that he was dumping his entire load into her pussy. She could tell from the amount of sperm that was leaking out from between her legs that he was far from the first one to have cum in her.
“Alright, alright let us through.” said the Headmaster grabbing Lilly by the wrist and pushing their way through the crowd of students surrounding the girl.
As they approached the other student pulled out of her mouth and covered her face in his cum, and she moaned loudly trying to catch as much of his cum as she could in her mouth. Her aim however was impaired by the amount of cum that already covered her face, resulting in most of his load contributing the the thick mask of sperm that was slowing running down her face and dripping onto her breasts. She smiled suggestively, running a finger through the mess covering her face and breasts before slowing inserting it into her mouth and sucking loudly.
“Now Lilly its time for you to help.” said the Headmaster
“What do you want me to do?” asked Lilly unsure
“You can see how dirty her pussy is?” asked the Headmaster “I want you to get down on your knees and use your tongue to clean it out, oh and you should probably strip down first so you don’t get your uniform dirty I don’t have any spares here.”
Lilly stripped off her shirt and bra in one smooth motion before slipping out of her skirt and panties, standing completely nude in front of the crowd of student. She blushed looking down embarrassed as the guys stood around her stroking their cocks.
“Get cleaning girl!” said one of the students, slapping her ass to hurry her
Lilly squealed in surprise at the slap on her bare ass and got down on her hands and knees in front of the girl. She could tell that this girl unlike her shaved her pussy completely, she could see the smooth lips of her pussy leaking cum in a thick stream down her legs and was pooling on the floor beneath her. Lilly leaned close and ran her tongue lightly over the outside of the other girls clit causing her to moan and wiggle her ass closer to Lily’s mouth in an attempt to get her to go deeper. Lilly grasped her by her hips and inserted her tongue deep into the other girls cum filled pussy tasting the cum of a half dozen guys. Lilly ran her tongue up and down over her pussy and then deep inside cleaning it out the cum of all the men who had gone before her she could feel it dripping down her chin and between her breasts. She started to get excited, cleaning out the other girls pussy, she leaned down and started sucking on her clit eliciting a squeal of pleasure from girl
She ground her pussy into Lilly’s face encouraging Lilly to go even deeper than before. Lilly was lost in her own pleasure and didn’t notice that the other students had started to crowd around her and where all stroking their cocks excited by seeing Lilly clean their cum out of another girl. One of the less adept students started stroking faster and faster until he ejaculated all over Lily’s back causing her to jerk back in surprise, noticing for the first time all the guys who had gathered around her. She looked up at a dozen cocks uncertainly.
“Now, now Lilly, don’t be rude you have turned on all these fine young athletes it’s only fair that you help them take care of it.” Said the headmaster with a smirk
One of the guys from behind Lily grasped her by the hips and slammed his cock inside of her tight wet hole and proceeded to start fucking her, grasping her by the hair and fucking her doggy style while the other student cheered. Lily opened her mouth to moan in pleasure at the thick cock that was pressing against the inside of her pussy and one of the students took that opportunity to shove his cock into her mouth. Wresting control of her hair from the other student he used it as a level forcing her head back and forth on his hard cock. The two students timed their thrusts so they could fuck in time sliding her back and forth on their cocks, she was just getting close to an orgasm when the student in her pussy came violently painting the inside of her womb with his cum and causing her to cover his cock in her cum, The man in her pussy pulled out and was quickly replaced by another who picked up right where the first had left off and spread her legs as he got better leverage to pound her pussy. The student in her mouth grabbed her head and shoved his cock as far into her mouth and filled her mouth with his cum.
“On your back!” said one of the students pushing her onto her back. He straddled her chest placing his cock in between her lush full tits, he reached insider her mouth and pulled out some of his friend’s sperm and used it as lube, he grabbed each of her tits and started thrusting in between them using them as a surrogate pussy. Another of the students bent close to Lilly and covered her face with his sperm causing her to squeal in surprise as his cum dripped down her face. The student in between her tits squeezed her tits hard and started cumming in between them covering her tits and her neck with his hot sticky seed.
Another of the students in between her legs came again and she could feel it dripping down her ass in between her legs, and pooling on the floor beneath her. As another student entered between her legs Lilly gasped in pleasure as his abnormally large cock slid into her well lubed pussy pumping in and out of her sliding his cock in and out.
Lilly grabbed him and begged her to fuck her harder, to fuck her like a slut as her back arched as another orgasm overtook her causing more of the cum which filled her pussy to leak out. The student thrust harder and harder inside of her before grabbing her tits and squeezing them roughly while pumping her full of his sperm. Lilly moaned in pleasure as his hot cum sprayed inside her.
He pulled out and Lilly looked up as the remaining students circled around her all stroking their erect cocks quickly. Lilly watched as a dozen men all came at almost the same time covering her face, tits, waist, and pussy with their sperm. The sheer eroticism of it pushed Lilly over the edge giving her an orgasm so large she convulsed on the ground rolling around in the collective sperm of the entire football team as her orgasm rolled through her. As she lay on the ground breathing heavily recovering, she opened her eyes when she felt a tongue on her pussy, looking down she saw that the headmaster had untied the other girl and she was in the process of returning Lilly’s earlier favor and was cleaning the cum off Lilly’s pussy. Running her tongue up and down Lilly’s slit she spread the lips apart and sucked Lilly’s clit into her mouth. The student did a thorough job of cleaning her pussy before working her way up to her tits, running her tongue over her breasts removing all of the built up sperm which Lilly was covered in.
“Ahhh… don’t you feel much better now boys?” Asked the Headmaster
“Much better Sir, thank you.” answered the students
“Now ladies why don’t you adjourn to the showers and get cleaned up and then get back to class quickly.” said the Headmaster.
Lilly helped the other girl up, pulling her naked body against her pulling her to her feet they stumbled together towards the showers.