Bad Night for Brittany

Brittany Green pulled the cover over her as she lay on the thin mat on the floor of the dorm room. The beautiful 18-year-old high school senior was serving as chaperone for the ten high school girls sleeping in the room.

When you mother is the director of the private religious school and on staff of the church that owns the school, you tend to have such opportunities to be in charge. Even if you are only two months past your eighteenth birthday.

Brittany was already the Captain of the school's girl's basketball team. She was immensely popular. In addition to being very athletic and intelligent, having a 4.0 grade point average. She was a very attractive girl. Brittany was tall, standing 5'10", with a beautiful angelic face, long black hair and a slender, yet muscular 34B, 24, 34 body.

When the school earned a spot for both the boys and girls teams in the state championship tournament they arranged for a school trip for the students to participate. Needing adult chaperones, and falling short, Brittany's mother arranged for her to be the official chaperone for the girl's team itself. It wasn't much of a risk as not only was Brittany very dependable and responsible. But the team was mature and responsible as well. So this freed up the coaches and other adults to chaperone the boys team and several other students who traveled down for the games.

Brittany's girls team won the championship, with Brittany leading the way with 18 points, probably earning her college scholarship. Unfortunately the boys team did not fare as well, losing their championship game.

The games were late, so the school had planned to stay one more night and return home in the morning.

While Brittany was popular and well liked at school, the same wasn't true among the athletes. Being the daughter of the Director, one of the top students, both academically and athletically, and downright beautiful, had gone to her head. Brittany often treated her fellow teammates and other athletes as being beneath her.

Brittany also had something else to laud over her teammates. Four of them had been close friends who took a purity oath with her during their freshman year, swearing that they would save themselves for marriage. Of the five of them, only Brittany had kept her oath.

She hadn't been totally pure. Brittany had given three boys handjobs during high school. And let those same boys fondle her as well. But that was the limit of things.

Brittany passed judgment on her friends for giving up their virginity. And acted like she was superior to them in every way now. Which caused a serious rift between them during her senior year.

For her part, Brittany didn't care. She was proud of her success and of her virginity. But that didn't stop her from flirting and teasing the guys at school. She knew that her flirtatious behavior had caused several boys to masturbate after dating or just hanging out with her. She knew that some of them called her a "Prick Tease" but didn't care. She found it amusing to be able to manipulate the boys so easily.

Ricky Clark was just down the hall from Brittany. Like her, he was 18. But when he asked if he could be a chaperone he had been firmly denied. Ricky was on the losing boy's basketball team. He wasn't a starter. In fact he had never even gotten into the game tonight.

Ricky was six feet tall with an average build. He wore his hair longer than most of his teammates. He was average looking but somewhat awkward around others.

Ricky had had a crush on Brittany for at least two years. But the popular girl wanted nothing to do with him. While he played basketball, Ricky wasn't very popular amongst the other students, especially the girls. Had it not been for his friendship with Joe Robinson, who was the captain of the boy's team, he probably wouldn't be involved at all.

Ricky's parents had put him in the strict, church run private school after he had gotten into trouble in public school. Most of his friends still went to public school, and that's who he usually hung out with. But Joe had befriended him and helped him get along as best he possibly could during his three years here.

Joe was one of the three boys who had dated Brittany and received one of her rare handjobs. Ricky had been jealous of his friend for dating her. But he was mad at the way she dumped Joe during the basketball season. And was even more pissed at her for the way she bragged on the way back to the dorms about how her team was able to win the championship and the boys team was just a bunch of losers.

Coach Lewis, who was chaperoning the boy's team, was a sound sleeper. Ricky and Joe had both sneaked out and hung out with some of the other students the night before. Ricky decided to do the same tonight. But Joe wanted only to go to sleep and try to forget about losing the big game.

Ricky was surprised when he realized that no one was watching any of the halls of the dorm. He freely wandered into the girl's side, wondering how long he could prowl the hall before being run off by someone. He had just barely missed getting caught when Brittany exited the bathroom down the hall. He ducked behind the corner just as the door had opened.

A few seconds later he peeped around the corner and saw Brittany walking to her room. Seeing her in an oversized tee shirt and panties was a pleasant surprise. He could see her nipples poking through the thin material of the shirt. Her long, sexy legs were beautiful to look at. And the partially exposed left butt cheek immediately caught his attention when she turned to open the door to her room.

Ricky realized that his cock was hard as a rock after watching the pretty girl walk down the dark hall. There was only a small exit light lighting the way. Enough for him to see her as she walked below it. But not enough for her to see him at the other end of the hall.

Ricky knew that these doors were probably unlocked just as the ones on the boy's side. He thought that if he could wait awhile he could probably sneak into Brittany's room and jack off while watching her sleep.

Ricky waited for what seemed like an eternity. But in reality had been no more than twenty minutes. He expected someone to discover him the entire time. Finally he dared to creep down the hall and listen to Brittany's door.

Hearing no voices, he turned the knob, trying not to make a sound. He pushed the door open only slightly, then listened for any sound coming from inside.

Hearing only the deep, measured breathing of several girls he dared to push the door open farther. Still hearing no sound of discovery he stuck his head inside. He could see girls sleeping everywhere about the large room. The room was dark. Much darker than the hallway, but there was enough light coming through the windows to make it easy to see everything even before Ricky's eyes adjusted to the darkness. Unlike the boy's side, where only five boys and a chaperone shared a room, here the entire girl's team slept. There were two bunk beds, but the rest of the girls slept on mats on the floor.

Brittany slept closest to the door, which was to be expected of the chaperones. That way anyone trying to sneak out would have to pass by them. Fortunately Coach Lewis was much older and needed the comfort of a bed, which was why Ricky could sneak out so easily.

Ricky stepped into the room, closing the door silently behind him. He was thankful that Brittany's mat was several feet away from the nearest other girl. Standing there looking at all these sleeping girls was both exciting and arousing. His muscles began to shake from the combination of nervousness and adrenaline.

He stood over Brittany, rubbing his crotch with his right hand. His eyes had adjusted well enough that he could clearly see her beautiful face as she slept. He slowly unzipped his jeans and pulled out his hard cock and began stroking it.

But he wanted to see more. Ricky guessed that Brittany, as well as the other girls, were all physically exhausted from the game and celebration afterwards. He thought that he could probably remove her blanket without her feeling it or waking up.

Ricky kneeled beside the 18-year-old girl. He gingerly raised the blanket and pulled it down to her feet. His heart pounded as he looked at the sleeping girl. Her shirt was raised up uncovering her flat belly and fully exposing her panty covered crotch.

This wasn't enough for him. Ricky figured that he had gone this far, he might as well go a little farther. He reached down with both hands and eased her shirt up over her breast.

Even in the darkness he could make out her firm B cup tits clearly. He dared to rub his right hand over Brittany's right breast. Just a glancing pass at first. Then more of a caress and finally a soft squeeze. When she didn't respond he did the same to her left breast.

Ricky began to stroke his cock while watching over the sleeping beauty. Then he grew even more daring.

"I want to see her pussy." He whispered to no one but himself.

Since Brittany hadn't moved a muscle during anything thus far he reasoned that he could probably remove her panties without waking her. Ricky knew this was more risky, but decided that he had to take the chance. If successful he would be the first male, other than her doctors, to see Brittany Green's virgin pussy.

Trying his best to keep his shaking hands steady, Ricky slowly pinched the material of her panties and pulled it away from her skin enough to slip his fingers beneath it. Then he gradually and ever so carefully began sliding them down.

He had to move with caution but a little force to pull them enough to get them below her butt. But once done the journey down her long, sexy legs was a simple one.

Now Ricky had Brittany Green, perhaps the most sought after girl at his school, naked in front of him. He pulled her legs apart and leaned down to get a good look at her pussy. He was surprised that she kept it trimmed around her lips. She had thick black pubic hair above her snatch, but was bare around the sides. Ricky would have guessed that she would have felt no need for grooming something that she had no intention of showing off. He failed to consider the fact that she would care what would show in a bathing suite had she failed to trim.

This was all overwhelming for Ricky. He slid off his shoes and removed his pants and boxers. He decided that he would keep her panties. He guessed that she would panic in the morning when she awoke and found them missing. But knew that she would never say anything to anyone.

He was still planning to jack off. But thought, "Why not at least rub my cock against her pussy."

He crawled between her legs and rubbed his hard manhood on her virgin slit. Then he leaned forward and licked her left nipple.

Ricky's only desire now was to fuck the beautiful virgin lying beneath him. But he knew that doing so would be impossible without waking her.

Brittany felt something touching her nipple. It felt good but wasn't supposed to be there. Her body began to respond to being disturbed. She was very tired and groggy, but her awakening senses realized that something was happening.

She came fully awake with a start, finding Ricky on top of her. She nearly screamed, but caught herself before doing so.

Enraged at the discovery that she was being molested by someone. And more so upon discovery of who it was, she tried pushing him off of her.

"What the hell are you doing?" She said as loud as she dared, not wanting to wake anyone up and have them find her like this.

Ricky smiled down at her. He realized in an instant what was going on in Brittany's mind. Her pride and ego were such that she was not about to call for help for fear of being seen like this by the other girls. Brittany's humiliation of being caught, and perhaps forced to continue by the girls who didn't like her anyway, was worse for her than what was actually going on.

At that moment Ricky realized that he could make his dream come true.

"I think it's time someone taught you what happens to prick teases." He whispered, rubbing his cock harder against Brittany's pussy.

"Please stop." She pleaded. "I'll scream if you don't stop."

Ricky called her bluff. "Bullshit. You would have done so already. You're afraid of being seen like this and everyone finding out how you lost your virginity to a loser like me who's only in your pious school because I got into too much trouble elsewhere."

"What do you want." Brittany asked in growing fear.

"I want to fuck that virgin pussy of yours." Ricky said.

"Please don't. I'll jack you off." She offered.

"Fuck a handjob. I want to cum inside you."

Brittany's mind was reeling. She had to stop Ricky from fucking her. She had held onto her virginity for too long to lose it like this. She wanted to cry out for help but could not make herself do so. The thought of the other girls laughing at her for being molested by Ricky, and them telling everyone else at school was too mortifying for her.

"I'll suck your dick." She said, surprising even herself as the words came out.

Ricky hesitated, giving Brittany hope.

"Yes, I'll suck your dick. I've never done that either so you'll be the first to do that with me."

The thought of watching her pretty face sucking his cock was tempting. Ricky had received many blowjobs, and even fucked a few girls as well. But all of them were cheap sluts from his neighborhood. He had never been with a virgin in any capacity. The idea of Brittany sucking his cock appealed to him.

"Very well." He said, climbing up and straddling her chest. "Suck me off."

Brittany looked at the erect cock in her face. She had no prohibitions against oral sex. She had often fantasized about it after hearing other girls share their experiences. And had even practiced the act using her finger or another object in her mouth while masturbating in bed at night.

No, it wasn't the act that was bothering Brittany. It was the fact that Ricky Clark was going to be the first one to experience such pleasure coming from her.

But it was better than the alternative. So she opened her mouth, raising her head and took his stiff cock between her lips.

Brittany used her right hand to stroke his cock while she sucked it. She wanted to get this over with as quickly as possible. Brittany's first experience with oral sex wasn't going as she had planned. But she figured that she could make the best of it. She tried to pay attention to Ricky's movements, deciding that the moment his orgasm began she would pull her head away and jack him off. She knew he would end up coming on her face, but better that than in her mouth. At least she would save that honor for someone else.

Ricky watched as the adorable angle faced girl swallowed his cock. Her hand stroking his shaft as she sucked only made it feel better. He suspected what she had in mind but didn't care at this point. He was making the biggest prick teaser in school suck his cock and that was all that mattered right now.

He felt his orgasm approaching much more quickly than he desired. He tried his best to hide that from Brittany. Ricky leaned forward, getting his hands ready for his next move. Then he felt the orgasmic sensation surge through his cock.

Brittany was surprised when Ricky's hands clasped the sides of her head. She felt the first dribble of his cum drop on her tongue just as he thrust his cock deeper into her mouth. She tried to pull away but found her head held tightly in place just as a large gob of his cum splashed into her mouth.

Brittany silently cursed as Ricky came in her mouth. The boy was pumping his cock into her mouth as he blasted his load down her throat. She had no choice but to begin gulping his semen down.

Ricky's legs quivered as he climaxed in Brittany's mouth. He was still unable to believe his good fortune at happening upon this chance to deflower her. Cumming in her mouth was just the first step. He knew that he could go farther now because she would do nothing to stop him if it meant everyone there learning that she had just sucked his cock.

"My turn." He whispered as he pulled his cock free from Brittany's mouth and slid down her lithe body, coming to rest with his head between her legs.

"Get the fuck out of here." She spat in disgust. Trying to push him away.

Ricky grabbed her wrist, then pulled them down to her side and held them there. He looked at her untouched love box and pressed his lips to it, kissing her pussy.

"Stop it." She said, almost a little too loud.

Ricky did not respond. Instead he started licking Brittany's pussy. He started between her lips, then slowly worked his way up to her clit, which was swollen from the unwanted stimulation.

Brittany closed her eyes, trying to ignore the tongue that now massaged her love button. She risked opening them long enough to look about the room, assuring herself that no one was awake and watching her demise. She thought of the snickering comments that would be coming from some of the girls if they were to find her like this.

Ricky licked her pussy, feeling Brittany's juices begin to flow freely. He was determined not to stop until he made her cum for him.

Brittany couldn't believe that her body was betraying her. She could not deny how good Ricky's tongue felt. But she wanted nothing to do with the wonderful sensation. She silently struggled against him; unable to escape his invading tongue no matter how hard she tried.

She felt the familiar sensation growing between her legs that she got when masturbating and could not believe that she could climax while being raped by Ricky Clark. Her hips were rising and falling. Not only in protest, but also in reaction to her own growing need for release.

Brittany clenched her jaws, trying to resist the approaching climax. But Ricky was no newcomer at this and was manipulating her clit with his mouth and tongue like a seasoned pro.

He enjoyed the taste of her sweet, unused cunt and how her juices felt spilling onto his chin. He could tell that Brittany Green was about to have her first male induced orgasm and was too caught up in the moment to stop if he wanted to.

Brittany exhaled as her body convulsed. Her orgasm began and she trembled from head to toe as Ricky continued licking her clit as she came against his face. She was thankful for the darkness that hid her shame and humiliation from being seen in her flushed face as she continued to climax.

Ricky did not stop licking her pussy until satisfied that Brittany's orgasm was indeed complete.

She lay there unmoving and silent as Ricky pulled away. He could see her glistening pussy clearly even in the darkness of the room. His cock was fully erect and wanting action again. Ricky decided that now was the moment to finish Brittany's deflowering.

Brittany tried to get her breathing back under control, unable to believe that she had just cum for Ricky. She felt him beginning to rise and was thankful that her ordeal was about over.

Then she felt him climbing atop her.

"No, get off me." She said as loudly as she dared. "I gave you a blowjob so leave me alone."

"Now I want to break that tight pussy open." Ricky told her.

Brittany had to hold back a scream of rage and frustration. She had already given Ricky too much. Now he was intent on fucking her as well.

Ricky pressed his cock against Brittany's wet opening. The girl pounded at his back with her fist, trying to stop him from going any farther. But Ricky was not going to be denied.

His cock slid inside her pussy. Brittany willed herself to be quiet, still hoping that he would change his mind. But not willing to wake up the others in the room and have them share in her humiliation.

Ricky's cock met the resistance of Brittany's virgin wall. Having never experienced breaking a girl's hymen he wasn't sure just what to do. So he did the one thing that came natural to him. He pulled his cock back a little then slammed forward with all his might.