Ruby Hamilton was a wild child. The only child of parents who were both far too busy with their own lives to care about hers, she had basically been on her own for several years. She came and went on her own with very little supervision. So long as she checked in once in awhile to let her parents know she was still alive, that’s all that was required. While this kind of life might be a young girl’s dream, having no one really to answer to, it didn’t lend itself to proper behavior. And idle hands, as they say...

Ruby had been in trouble many times before, and been kicked out of a couple schools altogether. Now she was enrolled in G.W. Jefferson High School, a high school for “at risk” teens – basically their last shot at graduating high school. “G.W.” as it was affectionately called, took in those kids who had been expelled from other schools and tried to help them get through school and get that all-important diploma as well as teaching them skills they would need for the coming job market.

Ruby was a junior there at “G.W.” and had been in trouble four or five times already that year. Now it was getting close to the end of the year and she was, once again, sitting in the principal’s office. She had gotten real familiar with the principal’s office over the years and she was on a first name basis with most of the office staff. When she walked in this time, the woman at the counter just said, “Hi Ruby, have a seat ... he’ll be with you in a minute.”

Right before school let out for the Christmas Break, the principal of “G.W.”, Mr. Baker, retired and the new principal had taken over. Ruby had seen him in the hallways and around school, but she hadn’t been to see him in his office yet. This would be her first interaction with him. But from what she had seen, he was a handsome, younger man about thirty-five or so. And from the gossip around the hallways, he was, as the young girls said, a “dreamy” guy! She would soon find out.

“Mr. Hanson will see you now Ruby,” the lady at the counter said. Ruby walked back into the principal’s office and softly knocked on the door.

“Come in,” came the deep voice from the other side. Ruby stepped into the room to see a man sitting behind the large desk with his face covered by a file folder he was apparently reading. “Please shut the door and have a seat Miss Hamilton.”

Ruby shut the door and took a seat as directed in one of the chairs in front of his desk. She sat there for several awkward moments before he spoke again.

Mr. Hanson closed the file with a snap and set it on his desk. Then he looked at Ruby. “Well, Miss Hamilton, you have quite a file here. You don’t seem to agree with the way we run things here at “G.W.”. I see occasions where you felt you needed to be elsewhere – I believe the mall, the movies, and in the parking lot of the local fast food eatery were a few of your destinations. I also see instances of talking back to your teachers, disrupting the class with various antics, and I am sure there are other things here in your file I would find interesting if I had the time to look through it more carefully.

“But what brings this little visit today is that you were caught smoking in the girl’s restroom, the one next to the cafeteria. Is that correct?” he asked.

“Yes Sir,” she said.

“Well at least we agree on that point,” he said. “You understand that smoking on school grounds is against the rules and the penalty for that is expulsion, even though the school year is just about over. This may seem like a good way to get a head start on your summer vacation, but it also means summer school and/or the possibility of not being able to come back next year and graduate. As you have an extensive record of disciplinary problems already, I can see this ending your school career for good.”

The principal looked sternly at the young woman sitting in front of him. That was hard to do, because she was quite attractive, and he was more inclined to look at her lustfully. Ruby Hamilton was a tall girl with flame red hair that she wore in pigtails, a pretty face with a pale creamy complexion and light blue eyes. She had big breasts and a slender waist, and her hips and ass seemed to flare out nicely from that waist. As he looked at the young miscreant, he had secret thoughts of her being naked and leaning over his desk while he fucked her from behind.

Ruby sat there listening to him speak. She was equally enamored of the man behind the desk. Mr. Hanson was just as “dreamy” as the hallway whispers had indicated. He was six foot four inches tall with broad shoulders, a muscular chest and well proportioned body. He had dark collar-length hair and a scruff beard and mustache. He had a strong jaw and the bluest eyes she had ever seen.

Ruby didn’t want to be expelled from the high school and risk not graduating, especially over something as dumb as smoking in school. She had come too far to not finish. Besides, she had been told her senior year would be the most fun of all her school career. And the idea of summer school wasn’t any more palatable. Summers were hers she felt, and not to be spent making up for school year mistakes.

“Please, Mr. Hanson. I really don’t want to be expelled, and I never smoked in school before. Honest. It was just that one time. Can’t we do something else instead? I’ll do anything. Anything you want me to do.”

Benjamin Hanson didn’t really want to expel the pretty girl either. He looked at her record, and noted that she was 18 years old. Expelling her would do more harm than good and may ruin her future irreparably. There was another way, a way he would much prefer doing with her, and he wondered if she really meant it when she told him she would do “anything,” especially when she repeated it. He decided to look into the possibility further.

“What do you suggest?” he asked her.

“How about corporal punishment?” she said.

“You mean spanking you?” he wanted to be sure he was understanding her correctly.

“Yes, spanking me. Would that work?” she asked.

He thought about her suggestion for a moment. Spanking young students was strictly against the law but, since the girl in question was 18 years old, she could sign a statement giving consent to that form of punishment. That would would probably be enough to cover him, at least as far as the law was concerned.

He doubted he would be fired, even if the school board or anybody else even found out about it, which was unlikely. He was fairly certain that Ruby would be smart enough not to tell anybody, keeping her violation of the rules and subsequent punishment just between the two of them. She had as much to lose as he did, if this got out, she would definitely be expelled and no school would touch her.

“You know, Miss Hamilton, it’s against the law to inflict any corporal punishment on a minor but, since you are 18, and old enough legally to give consent, would you be willing to sign a statement that you accept being spanked with a ruler in lieu of expulsion?” As he spoke, Ben took a thick wooden ruler out of his desk drawer and slapped it against his hand.

Ruby looked at the ruler, but not with fear. Instead, she looked at it with lustful desire. She enjoyed having her ass spanked by her many boyfriends as a preliminary to their fucking her, and the thought of this man using the ruler on her bare ass sent a tingle through her pussy. Anna didn’t think the ruler would be all that much different than his hand and it might even feel better, adding a bit more sting and giving her more sexual thrills. Certainly bending over the desk and being paddled bare-assed by this hunky man added to her thrill-o-meter!

She wondered though if, after her spanking, he would be up to the idea of finishing the job and fucking her. Ruby knew that she would be extremely horny and want to fuck in the worst way. Spankings had always turned her on and half the time she acted up just to get one! The longer and harder he spanked her the more aroused and excited she would get, especially if he gave her a bare ass spanking like she hoped. Those were her favorites because it showed him how wet and dripping her pussy would get!

“Yes, Mr. Hanson,” she answered, trying not to sound too excited about the idea of him spanking her. “I’ll sign your paper and you can spank me.”

Ben was smiling inside, and his cock twitched with excitement, but he still tried to be stern with the attractive young woman, at least to her. He didn’t want her to see that this idea was getting him aroused as well.”Very well,” he said, and took out a pen and paper, wrote a few words and handed it to Ruby.

“I, Ruby Hamilton, give my consent to being spanked by High School Principal Benjamin Dixon in lieu of being expelled from school as punishment for smoking on the school grounds,” she read out loud. She signed the paper and handed it back to him. “Okay, here you go,” she said.

The first thing he did after getting the signed release was place it in the top drawer of his desk and lock it safely away. He didn’t know if he would ever need it, but he wanted to be prepared in case he had to defend his actions. Then he went to the door of his office to make sure it was locked and no one would disturb them. The last thing he wanted was somebody accidentally walking in on them as he was spanking her – especially if it led where he was hoping it would.

He walked to his desk and cleared the top of everything so the beautiful redhead could lay over it while presenting her ass for her punishment.

“Now lean over the desk here and keep your feet together,” he told her, placing the ruler on the desk next to her and watching while she did as she was told.

Ruby kicked off her shoes and bent at the hips to lean across the desk, jutting her ass out and presenting it for his purposes. She was wearing a red plaid skirt and a white blouse with white knee-high socks and flat-heeled black shoes. The school had a strict dress code because a lot of gangmembers and former gangmembers went there. Also, many of the girls had come to “G.W.” because of boy issues and the school wanted to keep any romantic complications to a minimum.

Ben walked up behind her and patted her ass as she leaned across over his desk. She felt good to his hand back there, soft but firm, and Ruby lay there offering no protests or objections. He softly stroked her round firm asscheeks, enjoying the feel of them, the heat radiating from them and their firm tightness. Young girls, he thought to himself.

Ruby was also silently enjoying his caresses, the feeling of this man’s strong hands on her tender flesh was very arousing. He was much different than the immature fumbling boys she was more used to. Mr. Hanson knew his way around a woman’s body and she could tell. His actions were sure and confident and she could sense that he knew exactly what he was doing ... and doing to her!

He lifted the hem of her skirt over her waist, folding it, and then tucking it under its own elastic waistband. He reached under her to push the front part of her skirt between her body and the desk, making sure it would not get in the way of the spanking and what he hoped would follow. Ruby raised her body up from the desk slightly to allow him to tuck the skirt out of the way. He smiled when he saw the girl was so cooperative with her punishment.

He smiled upon seeing the lacy black panties she was wearing, and how they contrasted so nicely with the creamy white skin of her ass cheeks and upper thighs. Such racy underthings were a violation of the dress code even though they couldn’t normally be seen. Defiant to the end! he thought, chuckling to himself. He liked her spirit, although he couldn’t condone her infraction.

As he stood there stroking her panty clad ass, he thought about how he would be turning that whole area bright red in a matter of moments and it made him smile even more. He hooked his fingers in the waistband of the skimpy garment and pulled it down over her succulent ass and reached around her body again to pull down the front of the panties. When he pulled them down to her thighs and let go, they slid down her legs to the floor, and she lifted one foot through the waistband so her panties were around only one of her ankles.

Her ass was fully exposed to him now and ready to be spanked, but he took his time to admire the lovely view. As he suspected while she still wore that clunky plaid skirt, Ruby’s ass was truly a thing of beauty. Her hips flared from her waist and sloped down to merge with her legs, while her buttocks arched out from her back, forming a pair of perfect, creamy-white hemispheres before curving around and under to join her legs.

When his hands caressed the lovely bottoms of those hemispheres, the skin was soft and the flesh was firm. Best of all, fondling her in an intimate way like he was doing now, did not evoke any complaints, which made him think his goal of fucking this sexy schoolgirl might just be achieved.

Ruby hoped it would too, although she had no way of knowing what the man behind her was thinking. She did know her ass was alluring and loved having boys and men stroke and fondle her there, especially if their touching was a prelude to a good, hard spanking, and a good fucking after that. She had shaken that ass on more than one occasion to get what she wanted and she hoped that this time would be as equally successful.

Mr. Hanson’s strokes had already lit her fire and she hoped that he would be willing to feed that fire. Wanting to encourage the principal to continue what he was doing, she bowed her back, raising her ass and making it an even better target for his hands and the ruler he would be using for her punishment.

Ruby’s gesture did not go unnoticed. Ben picked up the ruler, pulled back his right arm and swung it hard, striking the young girl on the succulent right cheek of her ass. She gasped in shock and cried out slightly from the sudden pain, but made no effort to escape the blow. His next swing put a second red mark an inch above the first, and he knew it must be painful, but Ruby gave no indication of any distress, except a soft grunt, which could have indicated either pleasure or pain.

In reality it was both, but the young hottie wasn’t about to tell the principal that, at least not yet. The wooden ruler striking the tender flesh of her ass was quite painful, but she turned the pain immediately into pure pleasure. The ruler hurt more than her boyfriends’ open hands, which means it gave Ruby more pleasure. The third blow was to her left buttock, and she cooed in delight, and her ass started squirming.

Mr. Hanson kept the blows coming, hard and at roughly twenty second intervals. This gave enough time for the pleasure to reverberate through her body from every swat, so Ruby derived joy every time the ruler struck her upper thighs or ass. As the spanking continued, the girl’s sexual excitement mounted, and she could feel herself drawing closer to a climax. She resisted the temptation of reaching under her body and playing with her clit, because she fervently hoped the man doing the spanking would do that for her during the fucking she hoped would follow.