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Principal Evans had to use this method to get off as he was not a huge hit in person with the ladies. 47 years old, slightly pudgy and balding didn't make him a prize catch. He was tall at 6ft 2 inches, but had a bland, greasy look to him - some women actually said that he gave them the creeps.

Evans had checked almost all the tapes that evening and was disappointed to find they had nothing on them except the janitor scratching his ass. Evans sighed and dejectedly put his last tape in the VCR in his office. After fast forwarding the first 3 hours he was surprised to see Jessica and Darryl sneak into the supply room. With his mouth hanging open Evans pressed the 'play' button and watched eagerly.

Of all the girls in his school that Evans had wanted, Jessica was at the top of his list. She was on the cheerleading squad, had excellent grades, and was an all around great and well-liked student. She was also the best-built girl too. At 18 she had firm legs and torso from the gymnastics and sports she participated in. She also looked like she had huge, firm tits and a tight ass. On more than one occasion in the halls Principal Evans had seen her white button-down collared shirt gaping open at the buttons, giving him swift peeks at her tits encased in their white cotton bra. On the football field her ass was plainly visible under her short twirling skirt.

Evans moaned as Jessica and Darryl reached for each other.

Darryl and Jessica had been dating for almost a year now, and since they first had sex a month ago they were finding it difficult to keep their hands off each other. They both had a study period that day, and decided to meet for a quick fuck in the little used supply room.

"What if we get caught?" Jessica asked as Darryl quickly pulled her in the room and locked the door behind them. Darryl pulled the string attached to the overhead light and illuminated the room.

"Don't worry, no one would ever think to look in here for us." Darryl quickly assured her. He quickly reached for her and plunged his tongue in her mouth, deeply kissing her. His hands quickly got to work unbuttoning her white school shirt so he could massage her tits. Jessica moaned as his hands rubbed circles around her nipples, making them poke through the cotton of her bra.

"Suck on them Darryl, please!" begged Jessica, disengaging herself from his ravaging tongue. Darryl didn't need another invitation. He quickly undid the front of Jessica's bra and pulled it and the shirt off her shoulders into a heap on the floor. He lifted her up on the table in the room and fastened his lips to her hard nipple, sucking and licking it while his other hand pinched and pulled on Jessica's other nipple.

Jessica could feel her pussy contracting with need and desire. She knew that the crotch of her cotton panties were soaked through with her juices. She ached for Darryl's cock or fingers to be up inside of her, furiously fucking her. As though Darryl could read her mind he quickly reached under her skirt and whipped her panties down her legs.

Principal Evans unzipped his fly and pulled out his hard cock. Unknown to most women Evans was hung. His cock measured a good 9" and was almost 2" in circumference. He slowly rubbed it and masturbated as his eyes first fastened on the sight of Jessica's tits, and then her pussy as Darryl hiked her skirt up and took her soaked underwear off. Jessica kept her pussy trimmed down to almost nothing, so Evans had a good view of her swollen lips. He swore he could almost see her clit poke through - but unfortunately the camera didn't know where or when to zoom in so he wasn't as close as he would have liked.

Darryl spread Jessica's legs wide on the table and quickly shoved 2 of his fingers into her pussy. "My God," thought Darryl "she's still tight as a virgin!" But Jessica was soaking wet as Darryl started to manipulate his fingers in her. Darryl gently moved them in and out as he continued to suck and play with her massive 36C tits.

"More," cried Jessica. The slowness and gentleness of Darryl's fingers frustrated her, but she didn't exactly know why. "I need your cock now!" Jessica said.

Darryl stepped back and undid his fly and dropped his pants. Darryl was a sturdily built 18 year-old on the football team. He kept himself well-groomed and in good shape. His 7" cock sprung into view as Jessica dropped to her knees.

"The slut sucks cock" Principal Evans thought to himself. The cum in his balls started to churn as he watched the sexy near-naked girl drop to her knees in front of the football player. He could hear the sounds of her slurping and sucking as Darryl urged her on with his hands on her head.

"Shit Jessica, I'm going to cum soon if you keep that up." Nothing felt better than hitting the back of his girlfriend's throat with his cock. Darryl wanted to feel himself in her warm pussy though so he pulled her off his cock and told her to bend over the table.

Jessica quickly got off her knees and bent over, unknowingly giving Evans a perfect view of the globes of her ass. It was obvious that Jessica sunbathed in the nude because there was absolutely no tan lines anywhere. Darryl stepped up to her and quickly inserted the head of his cock between her pussy lips. Jessica groaned as he gently pushed into her and started humping her ass.

"More Darryl...fuck me, fuck me good!" Jessica cried out as her hands found her own tits. She loved the feel of her own tits in her hands and pulled and pinched her nipples.

"I'm cumming Mel! Fuck you're tight!" Darryl suddenly jerked erratically and shoved his cock deep into the pussy of his girlfriend.

He quickly withdrew and kissed her on the lips. "We'd better get out of here. I'll go first", Darryl quickly pulled on his pants and was gone.

Principal Evans sighed now as the near-naked Jessica was left alone. She looked absolutely stunning standing there with cum dripping down the inside of her thigh. She found a paper towel and quickly cleaned up. "Shafted again" groaned Jessica as she started playing with her tits again. She leaned back against the table and started to rub her soaked clit furiously with her fingers. Her hips started to gyrate as she got herself closer and closer to the edge. "Oh yeah....fuck me like that " she whispered as she started to forcefully shove her fingers in and out of her pussy. "Oh...I'm cumming!!" she cried as her hips started to spasm.

Principal Evans started to cum at the same time and splattered the vision of the girl on the TV screen, calling out her name.

Jessica smiled and got dressed and poked her head out the door and was gone.

"Well, well" thought Principal Evans, "Darryl can't satisfy that one. Hmmm." As he rewound the tape for another viewing a plan started to form in Principal Evans' head.

He knew from the guidance counselor that Jessica's single mother was very ill, and the slightest shock to her system could be fatal. Jessica's mother was very proud of her beautiful and talented daughter and lived to see her do well. Her mother scraped every penny together to send her to his private school so that she would have an excellent chance at life.

"I think I could use that information". Principal Evans clapped his hands in anticipation and started rubbing his huge cock again as he sat down to watch Jessica's performance.

"Jessica!! Could you come over here for a second?" yelled Jessica's cheerleading coach.

"Yes coach, what is it?" Jessica asked breathlessly.

"I have a message that you are to go to the principals office after practice today." Said the coach.

"What about coach?" asked Jessica "I'm not in any trouble am I?"

"I wouldn't think so," the coach said "it's probably to do with the award you won in writing last week, he probably just wants to congratulate you in person."

"Okay coach, I'll go there right after I shower." With those words Jessica rejoined her squad and started to practice. She was unconcerned, but didn't relish the meeting as something about the principal gave her the willies.

About an hour later she was knocking on the door to his office. It was after 6:00 and all of the secretaries had gone home for the day.

"Come in Jessica.", she heard through the door. "Uh-oh, he doesn't sound happy." Thought Jessica.

She opened the door and walked into his huge oak-paneled office. This was the first time she had been called there and she nervously looked around. The huge windows had been blocked by curtains that were pulled shut. At the far end of the space sat Evans in his chair behind a massive desk, in front of which sat a lone wood chair. Closer to the door on the right was a long black-leather couch and chair. Just off to the side was a tall stand with a TV and VCR.

Principal Evans watched Jessica look over the room with amusement and anticipation. "Lock the door and come here." The principal said sternly. Jessica quickly complied, though briefly wondered why she was locking the door. She came and stood in front of his desk, nervously looking down at her hands.

"You asked to see me sir?" Jessica asked quietly.

"Yes I did, first of all I want to say that I'm very disappointed in you." Thundered Evans.

Jessica's head quickly snapped up incredulously and gaped at the principal. "But what have I..." Jessica started to ask.

"Silence!" Evans roared. "Until I say you can speak you will stand there, look at me, and listen." Jessica nodded numbly and looked at the man yelling at her, tears starting to form in the corners of her eyes.

"I expected high things from you young lady, and yet I find you acting like a common whore in my school." Evans was starting to enjoy watching the reactions on her face. Her breath was quickening, making her tits heave under her school shirt. She had her hands clasped together in front of her, and was twisting her fingers around and around. As soon as he mentioned the word 'whore', Jessica had an inkling as to why she was in his office.

"Turn around and face the TV" Evans quickly pressed a couple of buttons on his converter and started the video he watched last night.

"Oh no!" Jessica gasped as she watched her encounter with Darryl played on TV. Jessica turned redder and redder as she watched herself being disrobed on the screen. "Oh please turn it off sir!" she asked. Knowing that the principal was watching her, and had watched her in this most private act made her want to throw up. "Oh my God" thought Jessica, "will I get expelled? This will kill my mother!!". Tears started flowing freely down her tortured face.

"Silence!" said Evans "Watch your slutty self perform." Evans was getting hard at watching the scared girl's profile, he quickly reached down and stroked himself through his slacks. Her chest was heaving with the sobs she was holding back.

Evans made her stand there and watch herself from start to finish. When the video came to her own lewd display of masturbation Jessica had to grab on to the chair behind her to stop from collapsing.

Evans turned the TV off and the room was plunged into silence, except for the sound of Jessica's sniffling.

"Now, I am sure you can understand that we cannot let activities of this nature to occur in our school. I will have to call your mother now and ask her to come in to see me. You will sit here as I play this video for your mother and then you will be expelled. The expensive tuition that your mother has paid will NOT be refunded and you will leave the school in disgrace!" Evans advised the shocked teen this sternly, knowing exactly what her reaction would be.

"Oh no!! Please sir, this would kill my mother! Please don't expel me, please don't tell her." Jessica sobbed uncontrollably now, wanting to die. "I'll do anything I can to make this up to you and the school. I didn't want to do this, but Darryl said it was okay. Please please please help me!! Jessica wailed.

"ENOUGH!!" Evans sat forward in his chair in anticipation of what was to come. "Well now, I'm not unreasonable Jessica. If you answer some of my questions and do as I ask I may let this slide under the carpet." Evans said gently.

"What? Oh yes sir, please. I just can't let my mother know, it would upset her too much." The teen was too grateful to comprehend what she was exactly agreeing to. At that moment she didn't care what the punishment would be, she was so thrilled at the prospect of sparing her mother.

"Are you sure?" Evans asked once.

"Of course sir." Jessica said.

"Good. You will do exactly as I say, and answer my questions truthfully." Evans said greedily. "Now, first of all, do you like having your tits sucked on?

"What?" Jessica was shocked, "I can't...you can't...I can't tell you that!" Jessica said.

"Fine" said Evans reaching for the phone "I guess I'll just call your mother since you've backed out of our deal already."

"No wait!!!" Jessica realized that she would have to answer the principals questions in order to save herself and her mother. Blushing from head to toe the tears started again as she said "yes sir."

"Yes sir what?" asked Evans.

"Yes sir I like having my tits sucked on." Jessica whispered.

"Good girl!" said Evans. "Now you're getting the idea! Undo the buttons on your shirt and take it off for me so I can get a better view of your luscious tits. I'm sure they look even better in person."

Jessica reached up to her top button, and with shaking hands undid all of her buttons. She looked at the man before her and felt sick. He was focused on her chest, eyes wide with anticipation. She swore she could see drool forming at the side of his gaping mouth. She closed her eyes and slid the garment off of her shoulders and placed it on the chair beside her. The teen stood there quaking in her cotton bra. Unfortunately for her the bra enhanced the fullness of her breasts and emphasized her cleavage. The principal groaned and she saw his hand go to the front of his pants under his desk. "Gross!" she thought standing there, "He's going to masturbate while I stand here". If that was all that was going to happen she should have been relieved, but this was only the start of her torment.

"Take off the bra now" she was instructed to do. Jessica complied and stood there, feeling her nipples harden in the air conditioning of the office. "Jesus, you have the best tits I've ever seen!" Evans stood up and came around the desk standing in the small space between her and the desk. "Now show me how you play with your tits when you frig yourself off." Jessica reached up to grope her own tits. She held them in her hands and squeezed them gently. Her nipples hardened further and she started rubbing her thumbs over them in a circular motion, tugging on them and pinching them. She couldn't help but notice the huge bulge in the ugly principals pants, and shivered noticeably in revulsion. The man grinned and mistook her shiver for that of one of pleasure.

"Gee...what a slut. You are totally getting off on feeling yourself up aren't you?" Evans rubbed himself in pleasure. "I knew you'd enjoy this." He leaned back against his desk.

"Now take off all of the rest of your clothes and hurry up." Jessica reached around and unbuttoned the skirt and let it fall to the floor. She slowly hooked her thumbs in her waistband and eased the cotton panties down her legs. She kicked off her shoes and now stood there completely naked.

"Oh ya...I can smell your pussy from here" the principal enthused. "I bet you're soaking wet now aren't you slut? Put one leg up on the chair and spread your pussy lips for me so I can get a good look." The principal dropped to his knees in preparation for the view he was going to get.

Jessica slowly raised one leg and put it on the chair, but kept her legs slightly closed. "Spread those legs wide you slut! I want to see every inch of that soaking snatch!" she was ordered. She closed her eyes and did as she was told. Her small thatch of pubic hair was now inches away from the ugly man's face. He sighed as she took her two hands and spread her outer lips to expose the pink pussy to the man's raking gaze. "Oh ya...you've got the most luscious pussy I've ever seen. Does Darryl eat this luscious cunt out?"

"No sir." Jessica said in a shocked voice.

"Has anyone ever licked your slit?" asked Evans.

"No sir." Jessica whispered shakily.

"Well don't worry. I'll fix that before the night is through. However, we do want you nice and wet don't we?" Evans got up to his feet and went back to his leather chair behind the desk. "Come and sit in front of me on the desk. That's a girl. Now put both feet on the desk with your legs spread wide." Jessica ashamedly spread her legs, now even wider than they were before. "Now finger yourself like you did in the supply room. Show me how you can cum like a good slut. Make sure you spread that honey pot nice and wide and give me a good view. Don't even think of stopping until you cum for me."

Jessica knew better than to protest. She slowly moved her hands down to her pussy and started to rub her slit. She gently started caressing her clit, but she needed some moisture to get going. Jessica took her index finger and started putting it in and out of her pussy, working the moisture up. Principal Evans groaned as he saw her pussy getting wet and swollen. "That's my girl. Look at that lovely pussy. Work it for me."

Once wet Jessica went back to rubbing her clit. She wanted to get this over with as soon as possible and knew from experience that this would be the fastest cum for her. She closed her eyes and concentrated on the small spark in her loins that started growing into a larger pit of warmth. Evans watched Jessica's pussy intently, every once in awhile looking at her heaving tits, and the expression on her face. He stopped rubbing himself through his pants, knowing that he would cum if he continued, and he didn't plan on just cumming in his pants this time.

(next)

This story was split into 2 parts. Jump to any of the segments from here:
1|2
Note: This story was originally submitted as one long story
and it was only broken into 2 parts for faster page loading.

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