Little Miss Perfect & The Headmaster

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.