Chapter 1

The late afternoon sun filtered through the filmy curtains, setting the room ablaze with a light red hue that spread across the room. John leaned back in his deep chair, the wide leather seat much larger than he had required. As John had found out, the previous vice principal had been a massive man, over six and a half feet tall and four hundred pounds. Consequently, the furniture left behind was very large.

The mahogany desk in front of him was very large and even though John was just over six feet tall, he still felt small behind it. There was plenty of leg room underneath it and enough space for all the papers and other school crap he wanted scattered across its varnished surface. His office was vast, with two long, deep couches and several similar chairs. The plush carpeting had only been recently installed, something John had specifically asked for so he could walk around his office barefoot. But that wasn’t his favorite part of being the vice principal.

No, the gorgeous teenager riding his cock was his favorite part. She was absolutely stunning, her firm C-cup breasts bouncing with each drop of her perfect hips. He could see the faint outline of a six-pack on her tight stomach and the arms gripping to his shoulders were strong despite their slimness. His hands were clasped on either of her fantastic ass cheeks, clutching each muscular orb as she drove herself up and down. He could feel her pussy walls begin to spasm and knew his orgasm wouldn’t be far behind. With a sudden movement, Sindy, or Sin as she liked to be called, gripped John’s shoulders and pulled herself to him, mashing her lips to his for a deep kiss. It lasted only a few seconds before she threw her head back and let her orgasm overtake her, her mouth open in a silent scream. With her chest forced out and her pussy going into sopping convulsions, John leaned forward and nibbled on her nipple, squeezing both breasts to heighten her pleasure. He could feel her wetness beginning to seep out of their joining and knew his release was going to be coming within seconds. He was never able to withstand her orgasms despite his best efforts, the exquisite heaven that was her pussy overcoming his resistance every time they had sex.

“I’m going to cum,” John choked out.

Fast as a flash, Sin was on her knees and had her mouth descending over his cock. As her lips slid down his shaft to its base, her tongue undulated in a way she knew drove John wild, its slippery length seeming to touch nerve on his cock. He only survived two of these undulations before he blew. Sin didn’t miss a beat though, her throat massaging John’s cockhead as blast after blast of cum shot straight into her stomach. As his orgasm subsided, she slid his cock slowly out of her throat, the last few dribbles of semen landing on her tongue. Several seconds were spent in blissful silence for both as Sin swirled her tongue around his cock to ensure she retrieved all of his seed and that he was thoroughly clean. Satisfied with her work, she let John’s softening cock slip out of her mouth with a small pop. She smiled up at John from her knees, the light shining off her radiant teeth.

“All gone!” she said happily.

John leaned back in his deep chair and smiled down at her. “You’re one kinky cumslut, Sin,” he said, running a hand through his hair. He loved that her name could be shortened to Sin. Almost as naughty as her.

“I know,” Sin said as she stood and sat in his lap.

He loved the way her ass felt on his legs and he loved it even more when she kissed him, which she leaned in to do now. It was a deep kiss, her full lips pressing firmly and fully against John’s as her tongue slithered into his mouth. He loved the way she kissed with such unbridled passion. It belied her youth and allowed John to think of her as more than one of his students for more than a few seconds. Yet it always came back to him, the illicitness of this relationship only furthering his excitement.

Breaking the kiss, John brushed her hair back. Sin let out a huff. “Fuck,” she said. “My parents are going to be here any minute.”

She slid off his lap and began dressing. John watched as she slid on her black thong, followed by her skirt. Next came her lacy black bra and her tight white shirt. Sliding her tie over her head, she settled it into place and slid it up until it was as perfect as when she had walked in thirty minutes ago.

“How do I look?” she asked, turning and popping her hip so her ass stuck out.

“Sinful,” John replied with a smile.

“That’s what I like to hear,” she said. “Could you write me a note please?”

She finished with a pout and John laughed as he reached into his desk to retrieve a legal pad.

“What’s in it for me?” he asked as he ripped off the note.

As Sin approached, she made a great show of thinking it over. She bent over, showing a delicious amount of cleavage. He spared it a long glance before looking up to meet her lust-filled eyes.

“Well, let’s see,” she said thoughtfully, placing her hands on John’s desk. “I won’t tell my parents that you were shoving your cock into my pussy or that I drank down your cum.”

John raised an eyebrow and gave her the “get-real” look.

“How about this,” she said, a smile returning to her face as the thought began to develop. “I’m Head Girl on my floor, right?”

John nodded. Out of the thirty girls in the senior class, only six girls were being housed on the fourth floor of the high school dorm. The freshmen had the first floor, sophomore had the second, and juniors had the third floor. It was the smallest of the groups, but the board of directors had been adamant that the floors would fill up over the years. Sin, through a random draw, had been named Head Girl. She was currently one of only a half-dozen girls on the campus. The other girls were all younger than ten and were under the watchful eye of professional nannies hired from the richest families in England.

“So that means I’ll have lots of sway over the girls on my floor, right?”

“Yeah.”

“So I’ll see what I can do to convince them that riding your cock and drinking your cum is the best way to spend the year,” she said.

Sin glanced at her watch again.

“Fuck,” she said.

She grabbed the note from his hand and glanced at it. It was some drivel about discussing responsibilities of being Head Girl and organizing class schedules. With a leap, she hopped onto the table and grabbed John’s tie. Pulling him close, she gave him a deep, firm kiss with her pouty lips before sliding off and dashing for the door. She opened it, blew him another kiss, and slipped out.

“Think about what I said,” was the last he heard from her before the door slammed shut. Turning around in his chair, he gazed out the window. His office overlooked the great courtyard that had been installed in front of the school’s main building. A large fountain with two angels slowly burbled and on its side was a Mercedes SL550. Sin’s parents. Damn they were rich.

John had heard they were new to the area, the dad being a big-time surgeon and the mom some hot-shot lawyer. They had incredible money, as their car easily showed, but John didn’t think they had their focus right. They had called and paid a great deal extra to drop their daughter off early. They had given her a great deal of money to spend on food, but as John knew very well, Sin had spent it on a great many other things, chief among them being lingerie and other things that were definitely not food and other necessities.

He swung around to his desk and turned on his computer to review student files. The principal, a doting old man, was away until the start of the school year, which was in two weeks, and John had been left to take care of the final staff hiring and the students’ arrival. He had printed out rosters for all the students, but had not finished the final rooming assignments. He had placed most of the students, but at Sin’s suggestion had decided to ... reaffirm his decisions. There were to be eleven other students on her floor, and as she had both insinuated moments ago and had told him a few times in bed, she was not above enjoying the touch of a woman.

John gave a half-chuckle as he opened up the roster program, his mind wandering back to his first encounter with Sin.

It had been a just over a week ago and John had been in his apartment. He had heard the moving truck arrive, but hadn’t thought much of it. He had assumed it was more of the construction guys, who had been finishing some final details in the lobby to his building. After that, he had heard much of the usual swearing and banging as things were moved, and only once he looked out the window and saw the two BMW 750i’s did he realize that a student was moving in. He remembered then that he had received an early deposit of $10,000 for a family to have their daughter move in early. He knew her name was Sindy, but that was all.

John spent a great deal of time reviewing the headshots of the girls who were attending, a requirement made by the principal, and had masturbated many times to some of the prettier ones. Some of the girls in the senior class were rather normal in their appearance, but there had definitely been some that stood out, but he hadn’t really bothered to get their names. Yet.

Uncaring for the time being, he started his workout. Ten minutes after he finished, and was about to hit the shower, John heard a loud crash from right below his room. Despite his desire to cool down and play video games, his conscience had reared its ugly head and John had descended to see what the problem was. He had arrived at Sindy’s door to the sound of quiet sobbing and had poked his head in.

He was startled to see a stunning blond kneeling on the floor in booty shorts and an incredibly revealing sports bra. Her stunning body had left him speechless, the late afternoon sun streaming in through the windows to illuminate her flawless skin, tight muscles, and mouthwatering curves. Forcing himself to look at the problem and not the girl, at least for a moment, John’s gaze found the emptied dresser and drawers everywhere. Without even needing to be asked, John had set the dresser right side up and began fitting the drawers in place. It was then that Sin found her voice.

“Who are you?” she asked.

“I’m John Anderson, your vice principal,” John replied. “I live on the top floor, the fifth floor, of this building and heard the crash. I apologize for not being more dressed, but I just finished working out.”

John had started to clean up other things that had taken damage or fallen apart in the crash, and he could almost feel Sindy’s gaze ride along his body. He knew he was good looking and in good shape. He had been a football and basketball player in high school and even had scholarship offers for both. But the fun of playing sports was just that for John: fun. He had never wanted to take both any more seriously than he did in high school, and had stuck to that despite many coaches calling him throughout college to reconsider. One thing he had done, though, was to stay in shape. At 6’2”, John could bench press over three hundred pounds and run a mile in less than six minutes. He was in peak physical shape and he knew it.

He let her silently admire him for a few more moments before turning his attention to her scattered garments.

“Can I help you pick these up?” he asked, indicating her clothes with a sweep of his hand while his eyes lingered on some of the more revealing undergarments lying at his feet.

“Okay,” Sindy replied. She dropped her eyes to the floor as she began to pick up her clothes.

“What’s your name?” John asked as he slowly gathered her shirts.

“Sindy,” Sindy replied. “S-I-N-D-Y, Sin for short.”

“Well, Sin, it’s nice to meet you.” John extended his hand and they shook.

“I’m sorry for making such a god-awful racket,” Sin said as they continued to pick up and fold her clothing. “I’m just a little stressed.”

“Why’s that?”

“I’m new to the area and my parents don’t have much sympathy for me. They drove here, looked at my room and told the movers to return to their place as soon as they were done unloading the stuff. My parents are kinda rich, so the movers just put the stuff in here and left. I had to arrange it all on my own.”

“Well, I’m sorry to hear that,” John replied, “but you don’t have to worry about that anymore. Like I said, I live upstairs and as your vice principal, I feel it’s my responsibility to make sure that I solve any and all problems you have.”

“Oh really?” Sindy cocked an eyebrow and gave John’s strong, handsome body another strong once over. “All problems?”

John glanced up from the last shirt he was folding and met her smoldering gaze with one of his own. He had decided as soon as he had accepted this job that he would be willing to take risks. The girls in the pamphlet had been stunning beyond belief and he was only a few years older than many of them. He’d come to the conclusion that if any of the ones who were legal wanted to try something out, he wouldn’t stop them. There was a part of his mind that found it a tad icky to be checking out girls who were only fourteen or fifteen, as that seemed rather young when looking at the age only. Yet looking at the older girls and their lithe, curvaceous, seductive forms very quickly locked him in on several of the senior class girls. They were hot. They looked like adults. And John had gone far too long without sexual contact. Did that make him a scuzzy bastard in many people’s minds? Sure. It made him out to be a pedophile. But they weren’t the ones who were twenty-six and entering a land of pristine female flesh ripe for the picking. He was. He planned on taking advantage of that and it seemed that Sindy, from the way she was looking at him and letting him handle her oh-so-soft underwear, would be a more than willing first subject.

“All problems you feel like letting me assist you with,” John replied, the tone of his reply matching that of her question.

He could see a slight flush creep up the back of her neck, but the seductive smile that glimmered across her face told John that she was enjoying the nature of this conversation just as much as he was.

John’s hands, having been folding clothes for a few minutes now, had accidently strayed to the filmy negligee, G-strings and thongs that were on the floor. He had just grabbed a black lacy bra with neon green designs across the demi-cups when Sin snatched it from his hand.

“Hey mister,” she said in a falsely accusatory tone. “The guy doesn’t get to keep my underwear ‘til the second date.”

“Well, excuse me,” John replied, handing over the bra. He rose to his feet and let his gaze sweep across her impressive pantie collection. “Is there anything else I can help you with?”

Sindy acted as if she was seriously pondering this for a moment before replying. “Since I’m new to town, I think a tour would be nice,” she said.

John thought about her request for a moment before replying. “How about I show you some of the restaurants in town?” he offered. “That way you can start to show your parents around and find some places where you and some of the friends you’re going to make can eat. There are several good ones, and when we’re done I can show you where the grocery store is so you can pack your refrigerator.”

Sindy smiled. “It’s a date,” she said. “I only have one problem.”

“Yes?”

“I can’t move my fridge.”

After moving Sin’s fridge, John returned to his room. She had agreed to meet him in the building lobby at 7 for their dinner date, and John had left at 4. He had taken a quick shower and napped before waking, taking another quick shower, and dressing. He wore a simple black and gray-striped button down shirt with khakis and his brand new black Nike’s.

He waited in the lobby for only a few minutes before he heard the elevator bing. Around the corner came Sin, looking as sinful as he had imagined she would. She wore a tight black dress that hugged her mouthwatering figure. A plunging neckline revealed her deep cleavage. Whatever bra she was wearing, if she was wearing one, pushed her breasts together, the perfect globes seeming to have been gifts from the gods as they threatened to burst from her dress. The dress shimmered as she walked toward him and her hips popped with each step. She held a silver clutch in her right hand and had a small gold bracelet on either wrist. Her makeup was done to perfection and John began to harden at the mere sight of her.

“Is this okay?” she asked demurely, stopping in front of him.

They were nearly on top of each other and had anyone else seen them, their proximity would have definitely been considered a bit too close. Yet they were alone and John took a moment to drink in Sin’s beauty. Her radiant blonde hair fell in small ringlets around her model-esque face, her light red lips gleaming in the early evening sun and her eyes speaking to a deep-seated lust that stirred John’s loins. He took a moment to glance down between her breasts. The milky half-orbs looked amazing and he let a smirk tug at the corner of his mouth before returning his eyes to hers.

“You look stunning,” he said. “How’d you know to dress like this?”

“A girl has to look good,” she replied with a wink. “Plus I did some research on the restaurant. You didn’t tell me it was the most expensive place in town.”

“You didn’t ask.”

“But I would’ve looked silly if I had listened to you.”

“I said to wear something nice,” John said with a shrug. “I didn’t think you’d show up looking...”

Sin raised a curious eyebrow and put her hands on her hips as she waited for John to finish his idea.

“Looking like what?”

“A goddess.”

The statement caught Sin somewhat off guard, and John was pleased to see his statement had hit its mark.

“Not what you thought I was going to say?” he asked.

“No. I’m used to boys my age saying “oh, you’re hot” or “look sexy.” You’re ... different.”

“Is that good?”

“Oh yes,” Sin said quickly. “Most boys would have gawked at me like an idiot if they had walked in on me like you did earlier. Then they probably would have tried to snag a pair of my panties like a pervert.”

“How do you know I didn’t?” John said with a sly grin.

“Because I watched you,” Sin replied with a sultry smile of her own. “Your eyes were on me the whole time. I could feel them.”

John’s grin broadened and he winked at her. “A gentlemen never tells,” he replied. “Are we still on for dinner or have I lost that honor in the last few moments?”

Sin smiled. “I think we could still go out to eat, as long as you’re still hungry.”

John caught the suggestive tone and glint in her eye. He didn’t know what would happen, but he had no problem playing along. After all, he had left his conscience in his old apartment the moment he took this job. If these girls wanted to play, he would be the MVP.

“Oh, I think I’ll be able to find something to eat. After all, the menu is full of ... mouthwatering options.”

He smiled and so did Sin as he pushed open the doors and ushered her outside.

He had pulled his car up out front and opened the door as Sin slid in. It was a new Nissan, so nothing nearly as nice as what Sin’s parents drove, but it was fresh nonetheless. Sin complimented him on the small, compact car on the ride over to the restaurant.

“Sometimes it’s nice to see a car that isn’t going to break if you touch something and my parents won’t freak out if I get a ding in,” Sin said.

She had reclined her seat and had stretched her long, strong legs out, eyes closed. John guessed her to be about 5’9” and every inch of her was on display for him to ogle. Pulling up to a red light, he took a moment to do so. Intending to only sneak a peek, he stared long and hard at her smooth skin, perfect breasts and taut stomach. A car horn woke John from his reverie.

A smile pulled up the corners of Sin’s mouth, but she said nothing as the car began to move. She opened her eyes and raised her seat a few moments later to view the town as John drove through. She noted several stores and landmarks that she had first seen when her parents had first driven by. There were several small, local restaurants, a pastry and ice cream shop, and a bakery. In addition, she also saw a mall off in the distance and made a note of its location. She hadn’t seen it her first time through and knew it could be very important to maintaining her sanity in the very near future.

A few minutes later, John pulled up in front of the restaurant and parked. He walked around the car and opened the door for Sin, who accepted his hand with a smile and thank you. As she walked past him and toward the door, he had to make a conscious effort to keep his eyes raised, lest they fall and cause him to lose control then and there. They made it to the front door without incident and John opened the door for her.

“You’re such a gentlemen,” Sin said with a smile.

“I heard it earns me brownie points.”

“Oh, it does.”

The restaurant was called La Luna, a small, Italian eatery that was known for its exquisite food and romantic atmosphere. John had brought a date here once, but she hadn’t been as big a fan of Italian food as she had let on, and summarily dismissed the place when she couldn’t find a single dish she could pronounce.

Sindy, however, was captivated by it.

Seating no more than twenty people at hand-made tables, the restaurant had a rustic atmosphere aided by the great frescoes painted on the walls. The chairs were thickly cushioned and likewise unique to the table they were placed at and were among the finest crafted pieces John had ever seen. The lights radiated at a low setting, combining with the closed curtains to create a very dim room. It took a moment for Sin and John’s eyes to adjust, but when they did, the teen let out a small noise of approval.

“This is beautiful,” she said. “Even better than I imagined.”

“May I help you?” asked an elderly woman off their right.

“Yes,” John replied. “Reservation for Sin at 7 for two.”

Sindy turned to John and raised a silent eyebrow, but said nothing.

“Yes, here you are. Right this way please.”

They followed the woman, John making sure to take several prolonged glances at Sindy’s great ass. Even in the dim light he could see each cheek in the black dress, the perfect hemispheres causing him to harden as her hips swayed. He was glad they reached their table quickly, as it would have been rather awkward to stroll through even as small a restaurant as La Luna with a full erection. They were seated and thanked the woman as she gave them menus and departed.

The pair opened the menus and began to peruse the different dishes. After several seconds of quiet, Sindy closed her menu.

“So you made the reservation in my name, hm?” she said.

“I thought you’d like that,” John replied with a smile, setting his menu down. “I hope I wasn’t being too presumptuous by doing it.”

“Not at all. I like a man who can be an independent thinker and surprise me. I also like a man who knows how to treat a lady right, and this is certainly a nice place.”

John smiled and was about to reply when the waiter came over. He was an old man in his sixties.

“Are you ready to order?” he asked.

“Yes,” Sindy replied.

She looked expectantly at John for a moment before he got her silent hint to start.

“I’ll have the bruschetta appetizer and the filet mignon special,” he said. “Medium rare, please.”

The waiter nodded and turned to Sin.

“And for you miss?”

“Fettuccine alfredo, please.”

The man nodded and took their menus.

“Will there be any wine tonight?” he asked.

Before John could reply, Sin nodded. She rattled off one of the more expensive bottles on the menu and for a moment John made to stop her. He didn’t want to get arrested and certainly not before he could accomplish any of his goals.

“Come now,” the waiter said with a smile. “A man with a girlfriend as beautiful as yours should never refuse her.”

A delighted twinkle came to Sin’s eye at this and she nodded. “I quite agree,” she said.

John could see this was a lost cause and relented with a nod of the head. The waiter departed, leaving the pair alone.

“So do you have a girlfriend?” Sindy asked with a smile. “I’d hate to be intruding on someone else’s territory.”

“Not at the moment, no,” John replied. “I’m very single, although I could always be persuaded to change that status should the right person come along.”

“And who might that be?”

“Well, she’d have to be attractive and athletic. She’d also have to be adventurous and willing to try new things. But she’s also gotta be down to earth and able to relax, too.”

“Wow, that sounds like a lot of woman to keep track of,” Sin said with a smile. “Mind if I help you find her?”

“By all means,” John replied.

The waiter returned with their appetizers and John and Sin dug in. They were famished from their earlier work and were happy to see their food arrive. While John was a frequent customer here, Sin was not and was pleasantly surprised at how good her food was.

“This is incredible,” Sin said after taking a few bites.

“Did you expect me to bring you to some sort of shack?”

Sin smiled. “No, I just wasn’t expecting it to be this good.”

John returned her smile.

They made small talk after that while they ate. John found out that Sin had been a gymnast, tennis, and soccer player at her old school, and even a cheerleader for a few years. This startled him, as he had expected her to have a much greater social life than participating in all those sports would allow. She quickly added that, despite such a demanding athletic undertaking, she had maintained a very healthy social life.

She had been quite active in the dating scene, having had boyfriends on and off since her freshmen year. None of them had been serious and the way Sin rattled on about the boys, John got the distinct impression that she was using them for their physical gifts just as much as they used her. And while their conversation never crossed into divulging any sexual experiences, John could tell from her innuendos and points of interest in each boy that plenty remained to be discussed at a later time.

Sin then turned the tables on John and he explained about his past. He told her about his athletics and how it had led him into many relationships, some long, but most short.

“Girls wanted to get in my pants and I was fine with it. A few wanted love, but I wasn’t looking for that then. Now, though...” He glanced at Sin’s cleavage again. “Now my mind is a bit more open to the idea of a longer relationship.”

Their entrees were served a few minutes later.

“Normally I don’t do carbs,” Sin said, twirling her first pieces of pasta, “but I might need some energy stored up for later.”

“Oh? What for?” John had seen the gleam in her eye as she leaned forward to blow on her fettuccine, her delicious cleavage making his mouth water. He let their gazes lock for a moment before letting his eyes drop to the valley between her porcelain globes. “Some sort of physical activity?”

Sin chewed and swallowed before responding. “Well, I’m not sure yet,” she replied as she brought her fork down for more food. “It all depends on the mood I’m in later. For now let’s just say I mean to get in my day’s worth of exercise later tonight.”

John felt himself harden again. Anyone with half a brain and at least one eye could understand that she was not talking about hitting the weight room. John wondered, not for the first time, how this evening would end. It was clear there was some serious flirting going on, but how far Sin would take it still remained a mystery. Would she remain a merciless tease or would she try to step things up? He had every interest in the world in getting his hands on her lithe, lush body, but would never force her. He would only go as far as she let him. If she let him go all the way, he’d use her stunning figure to live out his every fantasy and see her rewarded with pleasure unlike anything she had ever experienced. If not ... then he was down a dinner and would masturbate thinking about her every night for a long time.

But John couldn’t help but think that the first option was more likely. Was he putting too much faith in hopes and horny wishes? Maybe. But so far he’d gotten hired to a very high position at an all-girls with at least one exceptionally stunning student, who by all appearances and actions, was attracted to him. He could only assume that there would be other at least mildly attractive girls attending, which would bolster his hopes more. Adding to that fact was the requirement of head shots and body shots by the board to make sure each girl’s clothes fit properly (Why couldn’t they just ask?), which meant John would have much easier ways of picking out who he would be ... keeping an eye on.

It helped that the board was all old duffs, no one younger than 65, because that meant they would be content to just finance his ideas. He knew because he had already had several trips approved without so much as a query about their reason. Apparently “Social and academic interests and development” was all they needed. All they cared about was their money and how much they could get out of the parents. And after seeing the tuition some of these parents were paying, it was clear money was the main priority.