Little Miss Perfect & The Headmaster

Outside the heavy walnut door, Serena stood twisting the edge of her plaid skirt nervously in her fingers. Biting her bottom lip, her mind raced trying to fathom what was about to happen to her and if there was anything that should could say or do to get herself out of it.

At 18 years old, she was an abnormally good girl. She had fabulous grades while attending her all girl prep school, the infamous, Weisminster School for Girls. She was never one to cause the usual trouble. She had seen the “wild” girls that are always skiving classes, sneaking out to catch a visit with their boyfriends at the neighboring boys school a half mile away. She didn’t smoke, didn’t drink, and didn’t do drugs. The other students even called her “Little Miss Perfect”, mostly behind her back and out of jealousy.

“So why am I outside the headmasters door with this ball of lead feeling sitting in the pit of my stomach?” Serena asks herself for what must be the millionth time in the past 5 minutes.

The door opened so suddenly that she jumped about a foot in the air, before looking up and seeing the very handsome, but very stern looking headmaster glaring down at her. Mr. Logan, the headmaster, was the youngest (and, according to the girls, the most handsome) headmaster this school has ever employed. He was powerfully built, with thick black hair and eyes so green they looked like emeralds. His dark skin always looked like he just came back from a 3 week vacation in the tropics. There wasn’t a girl, or woman in the entire school that didn’t have a crush on him.

“Come in and sit down, Serena.” Mr. Logan said in a voice that normally made you feel like you were enveloped in warm velvet, but this afternoon, sounded stern, angry, and full of disappointment.

“Thank you, Sir.” Serena said, hoping her voice didn’t give away how very nervous she was. She had never been in the headmasters’ office unless it was to deliver a message from one of her instructors so she looked, in awe, around at the furnishings. The solid maple walls and desk looked undeniably masculine. The book collection lining the book cases where an expensive collection of rare books. Tolstoy, Kierkegaard, Chaucer, Shakespeare, all the greats, made the feeling of the room even more intimidating. Her eyes fell on a beautiful carved cabinet in the corner, and she wondered what mysteries it contained. . It was such an elegant room, and hard for her to imagine the things the other girls said happened in here actually taking place.

Her mind wandered and she almost forgot for a moment why she was there when Mr. Logan’s voice brought her crashing back down to reality.

Slowly walking around the desk, he sat in his chair and just stared at the young lady sitting in front of him. She was the best student in the whole school, the one that had given him hope that there were more than just heathens that were enrolled here. She was a very pretty, shy looking girl. Her auburn hair, held back in a tortoise shell head band, hung down to the middle of her back in curls. Her hazel eyes had a way of looking at you that just made you want to pick her up and shelter her from all the cruelties of the world. She had a wide-eyed, naturally pouting, innocent look that made what he was about to do even more difficult.

“Do you know why I have asked you to my office this afternoon, Miss Cassidy?” Mr. Taylor asked while averting his eyes and glancing at a page in the Discipline Record book lying before him.

“Umm, no Sir, I-I don’t.” Serena replied, nervously.

“Are you aware of the school rules and what the consequences are for breaking them, Miss Cassidy?” Mr. Taylor asked finally raising his gaze to stare directly into her eyes.

“I think so, Mr. Logan.” Serena’s mind was whirling, “What rule could I have broken?” kept repeating itself in her mind over and over again. She couldn’t think of anything.

“Well then, please tell me, Miss Cassidy, what are the consequences for a girl who plagiarizes on a term paper?”

Serena’s eyes widened and her mouth dropped open in shock. She was speechless, unable to reply to his question. How could he have found out? She knew she shouldn’t have done it, but she was just so overloaded with work that she just didn’t have time to do the paper on her own. So she got online while in the library and found a site that sold term papers for a small fee. She ordered one, printed it out and thought that she was good to go. What was the chance of anyone else here using the same site and choosing the same paper, after all, she had thought to herself. Though, she had never done it before she had heard some other girls talking and laughing about how they had done it and gotten away with it loads of times, so why not her? And now, look where it had gotten her!. She does it once, and gets caught? It’s not fair! Her mind screamed.

“Well, girl, I’m waiting for your answer!” Mr. Logan said raising his voice and slamming his hand down hard down onto his desktop; making her jump in her seat.

“I…uh…I can explain, Sir…I was…” She got no further when Mr. Logan interrupted her.

“I did NOT ask for an explanation right now, girl! I asked what the consequences where for such an action! Though, I can tell by your response that you are admitting guilt! Now for the final time, WHAT ARE THE CONSEQUENCES FOR PLAGIARISM?” Mr. Logan said, beginning to lose his temper and patience. His voice rose louder than she had ever heard it before.

“Uh..umm…Sir, ummm…the c-consequences for plagiarism in this school…is ummm.c-corporal punishment, suspension, expulsion or a c-combination of those th-things, Sir.” Serena managed to get out, her heart racing madly. She couldn’t afford an expulsion; she was here on a scholarship. She would lose it if she were to be expelled! She couldn’t imagine being corporally punished though, either, she had seen some of the girls come streaking out of this room, hands under their skirts and tears pouring out of their eyes as they raced to the nearest lavatory. She would have to make him understand what she was going thru at the time. How overloaded she was on homework. Surely he would see how she hated cheating but felt she had no choice! Maybe he would just let her off with a good scolding and lines. He just had to!

“Well, I’m shocked that you know that, Miss Cassidy, since you have apparently blatantly disregarded that rule when it came time to do your English Literature term paper. Do you deny it?” He said while keeping his voice low, but menacing.

He couldn’t believe that his prize student was sitting here in front of him admitting to cheating! He knew what he had to do, and hated having to do it but she left him little room for negotiating. He had to get this school back on track. The students here were running amok, the grade point averages where on a steady decline. He had to set an example, MAKE an example, strike some fear into these students or he would lose his job. What better person to make an example of than the top student of the school? That would show all of them that he meant business and if they didn’t start buckling down they would find themselves in the same position that poor Serena now found herself in.

“I’m sorry, Sir, truly sorry. I was over loaded with homework and term papers that had to be done. I was running out of time so I thought, just this once, I would take the easy way out. I’m sorry, Sir! I felt so guilty but I didn’t know what else I could do! I have never cheated before and I promise I will never do it again. Please Sir, don’t expel me! I will write a thousand lines, do chores, anything but please, PLEASE don’t expel me! I’m here on a scholarship. I’ll lose it if you expel me, Sir.”

Her words came out in a rush, so fast that she didn’t give Mr. Logan time to even try to interrupt her. Her tears falling copiously down her face and dripping onto the front of her blouse, she looked at him imploringly, begging him with her eyes to please understand her reasoning. His face remained stoic, as if set in granite. She hadn’t a clue what he was thinking or if he even heard anything she had said.

After what seemed like an eternity to her, he finally spoke. She held her breath, praying that her impassioned plea didn’t fall on deaf ears.

“Oh, I have no intention of expelling you, Miss Cassidy.” Mr. Logan said allowing her to finally take a breath. She let out a huge sigh of relief.

“Thank you, Mr. Logan, thank you so much! I won’t make you regret your decision. I’ll work extra hard and never cheat again, I promise!” Serena managed to say while drying her eyes of the tears that had fallen.

“Not so fast, girl, I said I wasn’t going to expel you, I did not say you were off the hook. I do not give just lines for plagiarism and cheating. That is two major offenses; no one will get off that easily, even if they had committed only one of them. Did you know you were plagiarizing when you handed that paper in, or did you only know you were cheating?”

“I …umm….plagiarism, Sir, no, I didn’t know. How could it be plagiarism?” She asked her joy of thinking she was off the hook a thing in the past and the chunk of lead that was in her stomach came rushing back, doubling in size.

“Plagiarism, dear girl, because that paper you turned in had been written by someone here, at this very school, months ago. So if you turned in an exact copy without giving that person credit for it, then that is plagiarism. I only see your name on it, not the others. Am I not correct in saying that, Miss Cassidy?” He asked her a sardonic lilt to his voice.

He knew it was plagiary. He knew it because he ran the website with all the papers for sale on them. That is how he finds out who is cheating and who isn’t in the school. Well, at least some of them. All the teachers are aware of it, some actually wrote some of the papers that are for sale, so if they come across one they turn it in to him and he takes care of the rest. It’s quite brilliant really, he thinks, chuckling to himself. The money the students pay for the papers all goes to maintain the school and he is able to try to get a handle on all the cheaters that there are.

“Umm…No, Sir…I mean Yes, Sir, I mean….” Serena stuttered not knowing what to say. Her mind in a whirl, she knew she was really in for it now.

“Well which is it, girl!?! Am I correct or not?” Mr. Logan said his voice raising an octave.

“Yes, Sir you are correct in saying that. It’s only my name on the paper, but I didn’t know that it was written by someone here!”

“Well, you knew it was written by someone else because you sure didn’t write it! So had you known who the author was, would you have given them the proper billing due when you turned in the paper, or would your name still have remained the only one on it?”

She knew she was caught there. She would have had to turn the paper in as her own, regardless. The assignment was to write one, not find a good one, and turn it in.

“No sir, I wouldn’t have put their name on it.” Serena said resolutely.

“That’s what I thought, Miss Cassidy. Now, I don’t want to hear anymore excuses on why you think you were correct in doing this. I’ve heard every excuse in the book and frankly, I don’t think there is any excuse that would make me say that plagiarism and cheating are okay. This school, since I have gotten here, has been chaos. I’m going to get a handle on all of you students if it is the last thing I do. You are the beginning of a new regime that I will be starting here. I’m going to make an example out of you, girl! You will be corporally punished for your misdeeds!”

With that final statement, Serena burst into tears. She had never been punished at school before, and very seldom at home. The hardest spanking she ever had at home was a hand spanking for talking back to her parents and that was when she was seven and it was over a dress, stockings, and panties! She didn’t know if she would be able to handle what the other girls claimed they had gotten in here, and from what Mr. Logan said, she was going to made an example of so her punishment was going to be even worse then theirs!

“Please sir! Please don’t punish me this way! I’ll do anything, I’ll do chores for the rest of the year, I’ll write lines, anything! Please reconsider your decision! I’ve never been in trouble before, that should mean something.” Serena pleaded, tears streaming down her pretty face. The horror of what was in store for her, her mind could hardly comprehend.

“No amount of pleading will change my mind, young lady, so you may as well stop trying. As for you never having been in trouble before, you’re right, that does mean something to me. It means that you knew right from wrong for years and yet you still managed to ignore the good sense that you’ve previously shown and broke not one but two major school rules! I think the rest of the students here would benefit greatly by seeing someone with such a good record punished. They will know that if you cannot get away with such offenses, they most certainly will not. Do you understand me, Miss Cassidy?”

“Yes, I understand, Mr. Logan.” Serena managed to mutter while trying to get herself under control. She was hiccoughing from crying so hard, and her breaths were coming in ragged gasps.

“Very well, I have already contacted your parents concerning what you have done and they have agreed with me that extreme actions must be taken if you are to stay enrolled her. They had signed a mandatory disciplinary agreement as a condition to your enrollment so I have the final say in what happens to you. The only choice they have is whether they would rather you are expelled. They want you to stay here so you shall be punished.”

Serena’s eyes widened at the knowledge of her parents knowing. They told her before she ever started this school 4 years ago that if she were to ever get in trouble here, she would receive an equal amount of discipline at home during her next school break. That was in 3 weeks!

Now Serena, I have thought long and hard on what to do with you. I want your disciplinary session to be strict enough not only to deter you from ever doing such a thing again but to also make other students not want to follow in your footsteps. Taking that into consideration, I do not feel a simple paddling or caning will suffice. So, I feel that a more prolonged, harsher sentence should be imposed. We shall carry out your punishments this evening. You are too report back here, wearing your night gown and robe at 8 o’clock. Are we clear on that, Miss?” Mr. Logan said while writing down the information in the discipline log.

“Yes sir.” She couldn’t believe she was going to be punished like this. Her stomach was in knots, her throat felt like it was closing up, and her thoughts were whirling.

“Good. Now stand up, and pull your panties to your knees and come lay across my lap. I want to give you a little to think about while you wait for tonight.” Mr. Logan instructed her, still not looking at her but writing everything in the log.

Serena’s heart sank when she heard the order. Panties down! She hesitated for a bit before finally reaching under her skirt and pulling her panties down to her knees. She knew she was in for enough without adding to it in any way. She hobbled over to him, her panties around her knees making walking difficult. She had to stand next to him for a couple of minutes until he was finished writing in the book. Finally, after what seemed an eternity, he put his pen down and scooting his chair back enough to allow her to crawl over his lap.

He positioned her until her head was almost to the floor and she had to reach back and grab the chair legs to stay balanced. Her toes could just barely touch the floor on the other side. He reached down and lifted her skirt, baring her soft bottom. She moaned in embarrassment and clenched her bottom cheeks tightly together in the hopes he wouldn’t see her private areas. He rested his right hand on her bottom and lectured her on the injustice of plagiary and cheating before raising his hand and bringing it swiftly down. His hand flattened her left bottom cheek, her soft flesh absorbing the blow and sprouting a perfect scarlet hand print. She let out a yelp and reached her hand back to cover her bottom.

“You will remove your hand at once young lady, or I shall make this spanking last 10 minutes! I will not permit interference with a punishment! Consider yourself warned, Miss! If it happens again you will pay the consequences for disobedience!” Mr. Logan said very angrily; his tone harsh and unyielding.

Serena immediately removed her hand. She couldn’t believe the amount of pain one hand spank could deliver! Her left cheek felt like it had been branded!

Mr. Logan started spanking her again, first one cheek, then the other, working his way down her bottom. He concentrated most of his attention on her thighs, especially the tender area where they met her bottom cheeks. On and on the spanking continued; until her bottom was glowing rosy red and her tears where forming a puddle on the floor. Never had she felt pain like this! “This was only a hand spanking? Just a taste of what I am to get?” she kept thinking to herself.

Mr. Logan stopped spanking her and rested his hand, once again, on her young, soft bottom. This was just the type of bottom he loved; soft, tender, full cheeks that he could feel his hand sink into with each spank. In fact, he liked everything about this girl over his lap. He secretly hoped that once she graduated, they could continue to get to know one another on a more personal basis, but for now, it was strictly headmaster and student, and he had a job to do. He stopped those thoughts of her, and concentrated on the here and now. He opened the top drawer of his desk and took out his wooden ruler. It was an 18 inch long ruler that was usually used for drafting. The wood was exceptionally hard and it had sharp edges to it, not like the more rounded edges of some school rulers.

Serena glanced back and saw the ruler in his hand and her heart skipped a beat. “What was he doing with that?” She thought, just a second before he brought it down sharply on her tender sit spot. He spanked first on the right cheek then on the left; then repeating it 3 times on each cheek leaving a dark red welt on each. She bucked wildly on his lap trying in earnest to not reach back. She thought his hand had hurt! This ruler was 20 times worse! She started sobbing harder; the pain seemed to radiate throughout her body.

“You may rise now Serena, and pull up your panties.” He told her while placing the ruler back into its drawer.

She rose from his lap, slowly; each movement made her bottom hurt worse. She reached back and could feel the angry weal’s the ruler had left and the heat that seemed to radiate off her bottom in waves.

“You may go now Serena. Remember, back here at 8 o’clock sharp. I wouldn’t be even a minute late if I were you.” Mr. Logan said without even looking at her. He was writing the punishment she had just received back into the logbook.

“Yes, Headmaster.” Serena said and left the office as quickly as she could without causing her bottom further pain. Each step was agony; when she was finally out in the crowded hallway, she took off at a run, hands clenching her tortured bottom cheeks under her skirt. Tears streamed down her face while other students looked at her in shock; not believing that “Little Miss Perfect” had just gotten a licking. Little did they know that it was only the beginning of a very long and painful day for her.

Immediately after Serena left, Mr. Logan (aka: Bryant Logan) locked the door to his office and sat reliving what had just taken place. He couldn’t get the image out of his mind of Serena lying across his lap with her bottom hot and red. Her legs parting after each hard slap of his hand giving him occasional glimpses of her private areas. He had a hard time not allowing himself to become aroused during the spanking but now that he was alone, just the image in his mind made him horny. He undid his pants and started stroking his cock. Reliving in his minds eye, the sounds of her moans and groans each time his hand came down on her soft, plump bottom. He could still feel what it felt like having her squirming over his lap. He stroked himself faster and faster and within mere minutes, the images of her had him arching his back and cumming powerfully. He had never had such an intense orgasm from masturbation before. Afterwards, all he could wonder was if the idea of her could provoke such passion inside of him, what would making love to her be like? He couldn’t help but smile, as he thought that in less than 6 hours, she would be bare bottomed and his hand would be whacking that gorgeous bottom once again. He had quite a bit in store for the young lady, and she wouldn’t be leaving his office without a very blistered bottom.

Meanwhile, Serena had raced back to her dorm room and thru herself across her bed sobbing. She couldn’t believe how much her bottom hurt and couldn’t imagine what it would feel like after tonight. After the pain subsided somewhat, her thoughts drifted back to Mr. Logan. He was so handsome that it made her ache! She felt the familiar twinge between her legs that happened every time she thought of him. She knew what the feeling meant even though, at 18, she was still a virgin. She has masturbated many times and loved the feeling of climaxing but she often wondered if it would be an even more amazing feeling once she experienced it while making love to a man. Her favorite fantasy since Mr. Logan started at this school was making love to him. She heard the other girls talking about things they had done with their boyfriends and she read some erotic stories online so she knew the sorts of things men and women did with one another. She lay in her bed at night, picturing herself and Mr. Logan doing all those things. She longed for him to lie between her legs, kissing her most private areas or his mouth suckling her breasts. She dreamed of him putting his penis inside her and thrusting in and out. All those thoughts swam thru her mind until she couldn’t help but touch herself to relieve the feelings that overwhelmed her.

She found herself thinking about him punishing her, and how it felt when his hand just rested on her bottom. She felt herself blush in humiliation on having him treat her like an errant child and spanking her. How can she get him to think of her as a woman if she had to be across his lap getting spanked like a 6 year old??? Still, she felt herself getting aroused and the pain in her bottom receding a bit when thinking about what had taken place. She couldn’t take it any longer so she laid back on her bed and slid her fingers underneath her panties until she found her hard little nub. Her pussy was very wet and got even wetter when her fingers started massaging around and around her hard clit. She slid her fingers down and worked two of them in and out of her pussy before finally starting on her clit again. She could feel her nipples harden against her bra and the intense feeling in her pussy getting stronger, building and building in strength until finally, with an arch of her hips, she exploded in orgasm. Wave after wave of pleasure raced thru her body until she collapsed, sweating, and breathing hard, onto her bed; totally satiated.

After gaining her composure, she reached over onto her nightstand and set her alarm for 7 p.m. which would give her an hour to get ready and reach the headmaster’s office. Sleep didn’t come easy for Serena though, her mind kept imagining what could happen this evening and the pain in her bottom had returned after her orgasm, though it was now down to a dull throb. Finally she dozed and seemingly seconds later her alarm woke her with its shrill call. She rose slowly and debated over what she should wear. Should she dress in regulation panties or into some of her sexier ones? She didn’t want to incur more of his wrath by not dressing in regulation ones, but her sexier ones may get him to notice that she wasn’t a little girl anymore. After thinking long and hard she slipped on her black satin and lace panties. They were the skimpiest ones she owned. She slipped on her black silk night gown; it wasn’t the sexiest she owned by any means. It hung to just above her knees, but had a plunging back and was held up by the slimmest spaghetti straps. The front had black lace over the silk just over he chest region. Over that she wore a very modest white robe, she didn’t want to come across other students on her way to Mr. Logan’s office wearing anything that would give away what she had on underneath. Giving her hair a good brushing, until it gleamed and wearing the barest amount of makeup, she took a last look in the mirror and was pleased with what stared back. She looked pretty but not over done…besides she was there to be punished not seduce. At the thought of the punishments to come her stomach tightened in dread. She prayed silently that it would be as bad as she was thinking it was going to be and that she would get thru it bravely. Slipping her feet into her slippers, she glanced at the clock and noticed she had only 15 minutes to make her way to his office across campus. She took off, walking fast and all too soon she was standing outside the now familiar walnut door.

In the mean time while Serena was getting herself ready and making her way to his office, Bryant Logan was making preparations himself. He had all the implements he would be using lined up at the bottom of the maple cabinet that sat in the corner. He took one of the two chairs that sat in front of his desk and put it in a corner, getting it out of the way. In its place he put a tall wooden stool. The discipline log was on his desk and waiting for him to record the punishments as they were meted out. After seeing that his office was ready, he went into the adjoining restroom/dressing room and changed into his most intimidating suit. A monochromatic combination;

sharp black suit with black shirt and tie. The combination of the darkness of the suit with his hair made his eyes a startling shade of emerald. The look conveyed power and would leave little doubt in Serena’s mind that he was serious about the task at hand.

He went to his desk and started to do some work concerning an upcoming school function while he waited for Serena’s arrival. Promptly at 8, there came a soft knock on his door.

“Come in, Serena!” He said, gruffly.

“Mr. Logan,” Serena said timidly, “I’m here to report for my punishment like you ordered.”

“Very good Serena, you’re right on schedule. Take your robe and panties off and get your nose pressed into the corner. I’ll be ready to start your spankings in a few moments.” he told her, without so much as a glance in her direction. “Oh, and make sure that you pull your nightgown up so I can see the bare bottom I’m about to beat.” He added as an after thought.

Serena took off her robe and hung it on a hook by the door. She hoisted up her nightgown to remove her panties, hooking a finger in each side; she slowly started lowering them.

Mr. Logan glanced up just in time to watch her peel her panties off. Mmmm…he thought to himself, black satin.

“Those do not look like the regulation panties that this institution insists must be worn at all times, young lady!” He said in a gruff manner. He had a hard time speaking over the lump in his throat that those panties and her sexy bare bottom had caused.

Startled, Serena looked over her shoulder at him quickly. Her eyes widened and a faint blush rising to her cheeks.

“I …umm…I only wear these when classes are over, sir.”

“Well when you report to my office young lady, especially when you are to be disciplined, classes are to be considered still in session. Finish removing your panties, fold them up and hand them to me.” said Mr. Logan.

Serena calmly finished taking off her panties, folding them neatly; she brought them over and handed them to him. Her face was hot in embarrassment, but she thought she detected a trace of desire in those green eyes of his. She hoped so, maybe her plan was working somewhat and he is seeing her more as a woman than an errant schoolgirl.

Taking the panties from her, he slipped them into the top drawer of his desk. He had no intention of giving them back to her; he planned on keeping them as a remembrance of this night. Every time he looked at her, whether fully clothed or bare bottomed, he found himself getting aroused. Although, one look into those eyes of hers had more of an effect on his heart than any other part of his anatomy.

“Now into the corner with you, I have a few things to do before I beat your bottom.”

Serena walked to the only empty corner that she seen in his office and pressed her nose in it, she reached back and hoisted up the back of her nightgown until her bottom was visible to him from his desk. Her face burned in humiliation, but she also hoped that he liked what he saw. She was developing much deeper feelings for the man than mere lust. She had seen him having fun and laughing at school functions and knew that this gruff side he was presenting now was because he had to. She couldn’t wait until the 6 months were up; bringing an end to the school year and she could graduate. She planned to pursue him until she won his heart over and did not care how long it took.

She stood there for what felt like hours, listening to the faint sounds his pen was making as he kept working at his desk. In actuality, only 20 minutes had passed before he finally spoke to her.

“Come and stand before me, Serena.” said Mr. Logan as he put his paperwork away and got out the discipline log. When she was standing before him, he looked long and hard at her.

“Young lady, I have thought long and hard about ways to get thru to you and the other students. Try as I might, I still can’t get any of you to take me seriously as a headmaster. I fully intend to make all of you start adhering to the rules and regulations here at Weisminster. You girl, are just the unlucky one that I intend to make an example of, but I am sure you will not be the last student that will find themselves bent over my desk receiving the cane.”

Serena couldn’t help but pale a bit at the mention of the cane. She couldn’t imagine how that would feel on her tender bottom when the ruler and his hand hurt dreadfully.

“You will not be receiving just a caning, however,” Mr. Logan continues, “I intend to beat it into your bottom, in hopes that it will penetrate into your brain just what a horrible thing is plagiarism. Furthermore, tomorrow at morning assembly, I will inform the other students how you were disciplined and why you were punished. That I hope, will make them realize that I am serious about enforcing the rules and regulations here at Weisminster. Now with that being said, come across my lap being sure that your gown is raised so I can spank that naughty bottom of yours.”

Serena walked around his desk and laid herself across his lap, assuming the same position that she was in mere hours before. She could feel the cool air on her up thrust, bare bottom. She couldn’t help feeling like a child as she laid there waiting for his hand to start swatting her bottom.

“Well I see the effects of my hand and ruler have all but disappeared; leaving me a blank canvas to paint red.” said Mr. Logan as he patted her soft bottom. He loved the way it felt on his palms. So soft and tender; a very spankable butt indeed, he thought to himself.

Raising his hand, he felt her tense up as he brought it resoundingly down. He watched as a perfect handprint first rose white then turned a bright pink. Over and over he brought his hand down on her tender, young bottom. Serena moaned and kicked, occasionally scissoring her legs open and closed giving him small glimpses of the virginal treasures that lie there. On and on his hand spanked her bottom until 4 minutes were up and her bottom was on fire. Reaching into his desk, he withdrew the same ruler that he had used on her earlier.

Serena lay across his lap, feeling the sharp slaps raining down on her butt. The spanks just kept coming; she didn’t think it was ever going to end. Her bottom felt like it was on fire and she could barely keep herself from wriggling off his lap. Her tears were dripping down her face and off her cheeks onto the hard wood floors. He finally stopped spanking her, after what must have been hundreds of slaps to her bottom, and rested his hand on her hot bottom cheeks. She heard his desk drawer open and hoped that it wasn’t what she was thinking. Glancing up, her fears were recognized as she seen him take the hard ruler out and raise it, ready to bring it down on her bottom.

“Please sir, not the ruler! Please, it hurts too bad!” said Serena with a touch of panic in her voice. Reaching back with one hand, she covered what she could of her bottom.

“No amount of pleading or crying will keep me from giving you what you have coming. It is SUPPOSED TO HURT! YOU are being punished! What did you think I would do in here this evening, young lady? Give you a couple slaps on the bottom and tell you to be a good little girl from now on? You are not a child any longer, even though what you have done I would expect from a child. You are an adult! Start acting like one! Being an adult means you acknowledge your misdeeds and accept the consequences of them; the consequences you have earned just so happens to be a well blistered bottom!”

With that being said he grasped the wrist of the hand she had placed over her bottom and brought it to the base of her back, holding it there. Raising his arm, he brought the ruler down on her tender sit spot with a sharp crack. She bucked wildly on his lap and let out a short yelp of pain. He held her there firmly and continued bringing the ruler down onto her bottom, doing his best to ignore her cries of pain. Twenty times the ruler came down to deliver its painful bite on her already sore bottom cheeks and thighs making her bottom turn from bright pink to scarlet.

He put the ruler away and gently patted her bottom. His heart ached with what he was doing, but also finding having her over his lap being soundly spanked, quite arousing.

She couldn’t believe the pain that centered around her bottom. The ruler hurt dreadfully and she just couldn’t’ fathom that there was more to come after this. Her crying from the hand spanking had turned to sobs by the second strike of the ruler. The only thing that brought a touch of relief to her was what he said about her being an adult now. Maybe the punishment will be worth it, she thought to herself, if after it he will see me as a woman. Her thoughts of him where swimming madly in her head and her bottom hurt so bad she didn’t notice that he had stopped swinging the ruler and was there just patting her bottom.

“You’re hand spanking is finished Serena, now rise and get your nose back into the corner. Keep that gown up and out of the way of your bottom.” Mr. Logan said, hating having her rise off of his lap since he was enjoying it so much. The bulge in his slacks seemed to be growing in enormity; making sitting for him not very comfortable. He watched her walk stiffly to the corner with her gown raised. He sat, leaning back in his chair, and just stared at her. He couldn’t help but fantasize about her being his. He would love to have her in his life, giving her long, erotic spankings before laying her back on his bed and making love to her for hours. He was lost in fantasy for 15 minutes before he finally came to his senses. He wanted so badly to give relief to his aching cock but he knew it would have to wait. It was getting late and she still had a few punishments to get thru so he figured he had better get back to business.

“All right young lady, it’s time for the second phase of your punishment; come bend over my desk now, and grasp the far edge. Be sure to keep that gown out of the way or we will have to remove it.”

Serena did as she was told, having to rise on tiptoes to reach the far edge of the massive desk. She made sure that the gown was tucked out of the way, as she watched him walk to the cabinet that she had been curious about earlier and withdraw a heavy oak paddle. Her stomach clenched when she realized that very soon that horrid instrument would be making painful contact to her already very sore bottom.

Walking behind her, Mr. Logan watched her clench and un-clench her bottom repeatedly in nervous anticipation of the paddles strike.

“Spread your legs apart Serena, I want a nice, wide target for my paddle.”

Serena followed the command, feeling her face burning in embarrassment when she felt the cool air on her private areas. She could feel herself getting aroused at the thought of him seeing her displayed like this; as if she were waiting for him to enter her from behind. . Her pussy was getting wet and she prayed that he wouldn’t notice the evidence of her arousal.

But, of course, Mr. Logan did notice; he couldn’t help it; his eyes were glued to her private area. He could see her glistening pussy and back passage clearly and had to refrain himself from plunging his fingers into her and exploring their depths. He knew that this was no way for a headmaster to think, but he found himself unable to get his mind and heart disconnected from her. Gritting his teeth, he took a deep breath, raised the paddle, and brought it down hard on her waiting behind.

The sound of the strike and the force of it almost lifting her feet off the ground, startled her and a millisecond later the pain seemed to explode from her bottom. She let out a yell that seemed to reverberate off the walls of the room. It took all of her might to keep her hands from reaching back to protect her bottom, she gripped the edge of the desk until her knuckles shown white and waited for the next blow of the paddle.

Mr. Logan waited 15 seconds in order for the pain to set in and for her to brace herself before delivering the next blow of the paddle. Raising the paddle to his shoulder, he brought it swinging back down onto her red behind. He felt the paddle vibrate in his hands and watched it sink deeply into her flesh when it made contact. It sounded like a gun shot went off and silently thanked the previous headmaster for making this office sound proof, for he was sure the sounds of his paddle and her yelling and moaning would be heard through out the school had it not been.

The pain of that strike had almost taken Serena’s breath away. It seemed to radiate through out her body until all she felt was pain. Clutching the desk tightly, she laid her head down and sobbed.

Watching her sob across his desk was almost his undoing. Resigned to what he must do, he raised the paddle again and delivered another hard swat to her behind. He decided he wouldn’t use as much force but he still wanted her to feel each strike so he gave her a medium blow. It still seemed to have an effect on her for she let out a loud moan and started swinging her legs trying to work out some of the sting. He put his mind to the task and started paddling her behind like a metronome. Counting in his head each stroke and doing his best to ignore the pain that he was causing her. He knew that she had more to deal with than this paddling and if he didn’t get himself under control he may not be able to deliver the rest.

Serena lay across the desk, squirming and crying out with each blow of the paddle. The pain was unlike anything she had ever felt before. She no longer cared if he seen her most private areas, the only thing she could concentrate on was getting thru this ordeal and making it back to her dorm for a good long cry.

Fifteen times the paddle resounded on her behind, and never once did she lose her grip and try to protect herself. Mr. Logan was very impressed by her strength and let her lie across his desk, sobbing for a few minutes. He crossed the room and put the paddle away and went to stand beside her. He stroked her hair and comforted her best he could.

“I’m very proud of you Serena, you are taking your punishments very well. You are a very strong, intelligent woman and I know that you are learning your lesson. I sincerely hope I never have to repeat this lesson to you again. I don’t like having to do this, but if this is what it takes for you to realize there are consequences to actions you take in life, then I will do it anytime it is called for. Go ahead and lie here until you calm down a bit, then go and stand back in your corner. You may rub your behind when you get there, if you would like.” said Mr. Logan, before he went and sat down on his chaise and picked up a magazine to try to focus on.

After 4 or 5 minutes of lying across his desk, Serena stood up and gingerly reached back and ran her hands lightly over her reddened bottom. She could feel the heat emanated from it like an oven. She walked to her corner massaging her bottom, trying to get the pain to ease somewhat.

Mr. Logan sat in his chaise, pretending to read his magazine but mostly all he did was stare at the enticing backside that Serena was rubbing in earnest. He wished he could do that for her, he longed to be the one to rub and squeeze those perfect cheeks. He sat watching in longing for 20 minutes, trying to get the stiffness of his cock to ease a bit and give Serena time to prepare herself for the rest of her punishments.

Finally he rose and went to the cabinet to retrieve the final two implements, his strap and cane. He knew that the punishments he was dealing out to her were harsh, but needed. He set them both on his desk for her to see. Looking at her red bottom again and hearing her crying softly, he determined that the lesson was being learned so he would go easy on the strapping. The caning, however, would have to be delivered in the usual manner, considering it is the main punishment in offenses such as this.

He then went to the leather couch that graced the wall in the sitting area and piled two of the cushions in the middle of it before returning to his desk and calling her to him.

“Serena come here please.”

Serena walked to him, being sure to keep her gown raised in the back in case it would upset him if she let it fall. She did not want to take any chances on incurring more strokes. Her eyes fell on what was sitting on his desk and she felt herself pale. All along she knew that she would be caned but it didn’t totally sink in until she seen it lying on his desk. The sight of the strap lying beside it didn’t help her nerves one bit, her stomach felt like it was doing somersaults inside her.

“You have taken your punishments extremely well thus far Serena, I’m certainly impressed. I know I have been harsh on you, but it will soon be over. You have two more to face and then we can put this incident behind us.” Mr. Logan said praising her.

“Thank you sir.” Serena replied, sniffling and her puffy eyes, downcast. Her crying had abated somewhat with only a stray tear falling now and then.

Mr. Logan rose from his chair, walked around the desk and gently took her by the arm; leading her to the couch.

“Lie across the couch Serena, with your hips over the pillow so your bottom will be nicely raised for the strap.”

Serena grimaced as she climbed onto the couch to get into position. The action caused the skin of her bottom to stretch a bit and renew the pain in her scorched bottom.

“Be sure to keep your legs together Serena, I don’t want the strap to hit anywhere but your buttocks and thighs.” said Mr. Logan trying very hard to fight the ever increasing bulge in his slacks.

Her face reddened dramatically when he said this as she buried her head in the supple leather of the seat cushions. She braced herself for the inevitable bite of the strap.

Raising the strap high he brought it down medium force across the buttocks he so longed to caress. The strap struck her leaving a one-inch crimson line across the summit of both bottom globes. She let out a soft cry keeping her face buried in the cushions. The second stroke fell right under the first eliciting a yelp from Serena. She looked at him with tears lingering on her eyelashes silently pleading with him to stop the painful strapping.

“I’m sorry I have to be so rough on you Serena, you have no idea how sorry. I have to do this; you left me with no choice. Be brave, my girl, it’s almost over.”

She silently nodded her head, and buried her face once again. Her heart gave a flutter as said “my girl”. She liked the way that sounded. Maybe one day…

Her thoughts were interrupted with another swish of the strap. This one caught her where buttocks met thigh. She bucked wildly at that one and couldn’t help but yelp quite loudly. It hurt so badly there, twice as bad as anywhere else on her bottom.

“I’m going to deliver the rest of these a bit faster so we can get it over with. Restrain from reaching back, the strap hurts dreadfully across the hands. Some find it helps to tuck their arms under their bodies.” He told her wanting to get the strapping and caning over.

She took his advice and tucked her arms under herself. Gritting her teeth she readied herself for the onslaught of the strap.

Waiting until he thought she was ready he started laying the strap onto her upturned bottom quickly; leaving only a few seconds between strokes. Seven more times he brought it whistling down onto her behind bringing the final count to ten. He originally planned to give her twenty but could not bring himself to do it knowing the pain the previous punishments had caused her and knowing that she still had a caning to get through.

The strokes fell fast and hard, and Serena could not help but cry out with every blow. Sobs racking her body, she writhed, trying to escape fruitlessly. After the final stroke she laid there, sobbing into her arms.

Mr. Logan put the strap away and tried to ignore her anguished sobbing. The sound of it tore at his heart and he had to stay resigned to what he was doing. He waited until her sobs subsided, and told her to rise and place the wooden stool into the middle of the room.

She slowly rose from the couch grimacing in pain and walked to the stool while gingerly holding a buttock in each hand. They felt swollen and hot under her hands and she wondered if they looked as bad as they felt. She picked up the stool and at a snail’s pace placed it in the middle of the room. With a deep sense of foreboding she tried to come to terms with what was about to happen. She had dreaded all of the punishments she knew she would be receiving this night, but the cane was the most dreaded of the lot. She had seen the marks it had caused on some of the other girls and heard tales of how badly it hurt them. She was scared that she wouldn’t be able to handle it but she had no choice now. She steeled herself for what was about to happen and awaited his instructions.

Striding across the room, Mr. Logan picked up the cane.

“Serena, you are now about to get the final phase of your punishment. You are to receive six strokes of the cane across your bare bottom. You are not to reach back at any time. If you do that stroke will not count and you will receive it again. Reaching back three times or more will find you back in my office next week to receive another six strokes. Am I making myself clear?” said Mr. Logan sternly.

“Yes, Mr. Logan.” Serena said softly, her stomach in knots.

“Very well then, let’s get this over with.” said Mr. Logan. “Get yourself well over the stool and grasp the bottom rung.”

Serena did as she was bid, stretching she was able to reach the rung. Her body taut over the stool presenting her bottom perfectly for the upcoming strokes.

Taking the cane Mr. Logan gave a few practice swipes, listening to the angry swish it made as it whizzed thru the air.

Resting the cane across the center of her bottom he measured where the first stroke would fall.

“You will count each stroke young lady, and thank me for its delivery.”

“Yes Mr. Logan.”

She felt the cane lifted momentarily from her bottom. She heard the angry swish and seconds later the pain registered in her bottom. She howled in agony. Never had she felt such pain in her life. It felt like she had sat on a hot poker!

“One Sir, thank you.” she managed to say between ragged gasps.

He waited a full minute before delivering the second stroke to her defenseless rear. Raising the cane high he brought it forcefully down with a resounding crack.

When the second stroke hit her whole body stiffened. Her back arched and her legs swung high off the floor. Her mind could barely comprehend the amount of pain she was going thru. Her bottom felt like a nest of hornets had made a home there, stinging her all a one time.

“T-two Sir, th-thank y-ou.”

Three more wicked strokes landed, Serena shrieking after each. She managed to not reach back, count them, and thank him after each bite of the cane. Her bottom hurt so badly that she could barely move. She swore that the cane had cut her, but there was only five angry welts running from the center of her bottom to where her buttocks met her thighs. “One more to go.” she kept repeating to herself. “Then this horrible ordeal will be over.”

“You are taking your caning exceptionally well Serena, one stroke to go and it will be over. Stay across the stool until I give you permission to rise. Prepare yourself.”

Serena gritted her teeth and waited for the final cut of the cruel cane.

Mr. Logan rested the cane on the junction of buttock and thigh, knowing this is the tenderest area. The final stroke must be the harshest so he always laid it on top of a previous stroke. He watched her wince as the cane touched the welt that was already there before raising the cane high and bringing it quickly down to deliver its final, evil kiss.

The pain of the final stroke was so intense that it took a bit for the sheer agony to finally register. She let out a loud shriek and bucked wildly on the stool, almost unbalancing it. She then went limp and just laid across it sobbing.

Mr. Logan looked at her bottom, seeing the angry welts that had risen over the already crimson globes. He felt a strong urge to pick her up and cradle her to him and it took everything in him not to give into it. He slowly put the cane away and went to sit at his desk to log the punishments that she had received. After a bit he heard her sobs turn to sniffles and called her to stand by him.

Serena rose from the stool and went to stand before his desk. Reaching back to cradle her aching bottom she could feel the ridges the cane had made on her tender flesh. As hard as this night was to get thru she came to the realization that she deserved every bit of what she had gotten. She felt no anger at Mr. Logan at all. In fact she fell more in love with him. He cared for her; she could tell by the way he had treated her. Yes he hurt her by punishing her, but she could tell that it was because he had to, not because he took delight in it. She was more resolved now than ever that he would one day be hers.

“No Serena, I want you to come around the desk and stand before me. Don’t worry you aren’t going to be punished anymore, I just want to speak to you.”

She walked around the desk slowly, not wanting to move much. Her bottom was swollen and felt tight; every step stretched the tender flesh there, causing her pain to increase.

When she was finally standing before him, he took both of her hands in his and looked deep into her eyes.

“Serena, I know that the discipline you received this evening may have seemed overly harsh to you. I hope that one day you will realize why I had to do it. I like you Serena, very much, and I only want what is best for you. Once you graduate and get a taste of what the real world is like, I hope you take the lesson that you learned here tonight with you. Many people out there think stealing others ideas or cheating people out of what is rightfully theirs is the only way to get ahead in life. It is not. Honesty is always the right avenue to take. It may not move you quickly up the corporate ladder, but I guarantee you will feel better about yourself at the end of the day. Anyway enough lecturing, you’re a good woman and I know that you will go far in life. Just do it honestly.” He said with his heart in his eyes. He loved her; he knew it without a doubt now. It wasn’t mere lust. He wanted her in his life forever. He just had to wait six months to make it known to her.

“I really like you too Mr. Logan. I understand why you had to punish me this way and I know I deserved it. I harbor no hard feelings towards you at all. I had a lesson to learn, a painful lesson at that! I did learn it and I will always keep it in my mind. I knew better than to do what I did, but I did it anyway. Instead of thinking things thru I acted irrationally. I’m sorry that I was so much trouble for you. Maybe one day, after I graduate I can make it up to you somehow.” She knew exactly HOW she would like to make it up to him, she thought wickedly. She would too, she just had to bide her time.

“Well maybe one day, Serena, I will let you make it up to me.” He said with a slight grin. “But, right now, let me escort you back to your dorm room.”

After helping her on with her robe Mr. Logan put his arm around Serena’s shoulders and helped support her as they took the long walk back to her room. What was usually a five-minute walk took almost twenty since she was so sore.

Standing outside of her door he turned her to face him. Lifting her chin with his finger he made her look him in the eye.

“I don’t want to see you in my office for punishment again, young lady. I don’t like having to do that to you but I promise you, I will do it again if you earn it!” said Mr. Logan, the hint of a smile reaching his eyes, softening his words. “Now I want you to go into your room, put some aloe and icy wash cloths on your bottom. That should help with the pain and swelling somewhat. You are excused from classes tomorrow but you must report for morning assembly since I will be announcing what occurred this evening. Now sleep sweet, Serena, try to get some rest.”

“Goodnight Mr. Logan.” Serena said softly, walking into her room and closing the door behind her. “I love you.” She whispered, listening to his footsteps fade as he walked down the hallway. She did as he suggested and rubbed aloe onto her buttocks and with a fan pointed at the icy cloths resting on her bottom, she drifted off to restful dreams filled with a man having deep green eyes, dark silky hair…and her heart.