Please Sir I was a Bad Girl
By
The Disciplinarian

Judy was worried. She needed the grades to pass her examinations but had not been studying hard enough recently and knew that she would do badly today. However she had one help. She had created a 'crib' which she would use to help her through the work. She went into the examination room and worked her way through the questions referring to the answers which she had concealed inside the cuff of her blouse. Whenever the invigilator came round she was able to hide the information with drape of the lace edges over the cuff. The examination ended and she handed in her papers secure in the knowledge that she would now pass.
The dinner break was a much more relaxed affair now this ordeal was over and she returned to the classroom in high spirits chattering with her friends. She was therefore surprised to see the school secretary enter and ask her tutor to release her to see the Principal. She left the room with the secreatary and followed her to the Principal's room. She knocked

"Come in a shut the door Judy as I have seomething very serious to talk to you about."
She entered and stood in front of him and was surprised to see that he had her examination paper in his hands.
"I am afraid that this is a very serious matter young lady. You were seen to cheat when taking the examination this morning."
"N-o-o Sir I didn't."
"I am afraid that lying will get you nowhere. Miss Graham who was invigilating saw everything but took no action until she had spoken to me. What have you to say for yourself?"
Judy started crying:
I'm sorry Sir, but I have not been able to concentrate on my studies and I knew I should fail and I MUST pass to get into medical school next year. Please don't fail me Sir!"
The Principl sat back in his chair and looked at Judy thoughtfully for a free seconds before saying:
"I can offer you two alternatives. The first is that you leave the college immediately with nothing said or you accept my punishment. I can promise you that the second option will not be pleasant."
"I don't mind Sir, anything but leaving."
"Right then you will report to my house at 8:00pm with the books you should be studying. On arrival you will receive twelve strokes of the cane and then you will study for two hours under my supervision. This will be the pattern for the next few weeks until you are up to standard. Do you understand and agree?"
Judy was shocked at the severity but was willing to accept to get her examination grades.
"Yes Sir, I understand and agree."
"Fine I will see you at 8:00pm sharp."

* * * * * * * *


It was nearly eight o'clock and Judy walked apprehensively up to the Principal's house. She knew him to be a stern but fair man and was sure that although she would receive deserved retribution she would be helped to pas her examinations.
She knocked on his door and it opened. He stood there in his shirtsleeves:
"Ah Judy, I am glad to see that you are on time. Come in."
Judy entered his lounge where there was a warm fire burning and saw that a chair had been placed in the middle of the room and on a table at the side was a long thick cane. She placed her books on the table and stood in front of him.
"Now young lady you know why you are here and I suggest that we get the unpleasant part over immediately. Remove your trousers and knickers and bend over the the back of the chair. You will recive twelve strokes of the cane in two lots of six strokes. At any time you may say you wish to cease but understand if you do so you will then have to leave the college. Is that clear?"
"Yes Sir, I understand!"
"Good then we can begin."
Judy unfastened the belt of her trousers and slipped them down and off her feet. She put her fingers in the elastic waistband of her knickers and reluctantly pushed them over her firm bum cheeks and hips. She then removed them so that she was now standing naked from the waist down. Although only eighteen she had a lovely figure with a well-formed and prominent bum while her pubic area was well covered with a blcak bush.
Frank picked up the cane and tapped the chair:
"Over you go legs apart"
As she bent forwards he slipped the cane between her legs and tapped the inside of her thighs spreading them. He could see that she was well formed and the fig of her pussy was prominent between her legs. He tapped her bottom and she flinched.
"No movement or the stroke does nor count"
She had never been caned before and knew it would hurt but was not prepared for the pain as the cane whipped home for the first time. The Principal was not prepared to warm her up and he intended to make these strokes a sharp reminder of her cheating. Judy cried out and rose to her feet as she felt the sting across both buttocks as the cane first sunk deep into her bum cheeks and then was removed.
"Down, I shall not warn you again. If you move then the next stroke will not count. "WHIPPP!!!" CRACKKK!!!",this one was even worse as he measured it a fraction of an inch above the first and watched the cane sink into the white bum cheeks, creating a white line which soon turned to a livid red. "WHIPPP!!!" CRACKKK!!!" the third one turned her legs to jelly and the pain coursed through her body. "WHIPPP!!!" CRACKKK!!!", "WHIPPP!!!" CRACKKK!!!" two more and each one had found a different spot until the whole of her bum was afire. "WHIPPP!!!" CRACKKK!!!"
"You can stand up now take a break and rub your bottom."
She stood up gingerly and began to rub her bum cheeks while the Principal looked on. He admired the way she had accepted the cane and also found that he enjoyed looking at her. He saw that her pussy was already well covered with dark hair even at her age and the savage lines he had raised on her bum cheeks. He was not however prepared to call a halt at this point and intended that she should received the full quota.
"Remove your top and brassiere and then take up your position again."
She unfastened her blouse and brassiere and placed them on the table. Her nipples were erect as she took up her position again ready for the rest of the punishment. The pert bum cheeks stared into Franks face with the tramlines red and angry across them. "WHIPPP!!!" CRACKKK!!!" this was fiercer than the earlier stokes and the pain was intense but she found that it was also having an odd effect on her. Although she had masterbated for several years this was even more erotic than fingering heerself and she felt her head spinning and an itch between her legs that she couldn't satisfy. "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!" by this time she could feel her pussy was wet and the itching had become a powerful aphrodisiac which created a throbbing within her. "WHIPPP!!!" CRACKKK!!!", "WHIPPP!!!" CRACKKK!!!". She was bewildered as she found that she was pulled between the exquisite pain in her bum that the cane strokes produced and the heat engendered by them in her pussy and breasts. There was a long pause and then "WHIPPP!!!" CRACKKK!!!" the final stroke. She felt like screaming and lifting off as the Principal made sure that this one would be remembered by applying extra force and a twist into his wrist giving the impact more zip. Through the pain she felt her juices running down her thighs and, without moving from her place she shuddered and had a massive orgasm in conjunction with the pain. She remained bent over sobbing for a few minutes before being gently lifted to her feet. The Principal held her gently, led her over to a sofa and, laying her across his lap rubbed some cream into her tortured bum. She gasped with the discomfort but gradually this changed to pleasure as he did so and she wanted him to go on longer. However he stopped, told her to get dressed, and then they would start on the evening's lessons.
The rest rest of the evening went swiftly and in spite of the pain in her bum Judy found that the Principal was an expert teacher and she learned quickly. It seemed no time at all before he stood up and told her that she must leave as it was 11:00pm. Judy gathered her things together and thanking him prepared to leave.
He smiled and said:
"You have made good progress this evening. Next week we shall go further."
Judy thought as she left that she hoped that this meant in every way - not just in the academic subjects.

* * * * * * * *


Her next session with Frank Williams, the Principal, came all to slowly for Judy, a week was a long time and she dreamed of what might transpire, but eventually it came round. She thought out carefully what to wear and decided that she would dress in more sexy underwear this time to show of her body to him. After all when she was being caned she wore nothing so thick or thin made no difference. As she put on her flimsy knickers and brassiere she though out what might happen while he was massaging cream into her bum. She was not looking forward to the cane, although it had turned her on, but was willing to accept it as part of the package.
She arrived at his front door spot on time, he welcomed her invited her in and they walked into the lounge. Again she saw the chair in the middle of the room and the cane on the side table.
"Hello Lucy. I am glad you have returned for another session. I understand from your tutors that your grades are improving. Again we will get over the unpleasant part first before we settle down to work. Please get undressed - strip fully this time - and then bend over the chair."
Lucy took her time removing her clothes, first she unzipped her skirt and let it slip to the floor leaving her in her flimsy panties, then she unfastened the buttons of her blouse and removed it placing it on the side table so that now she only had on her bra and panties. She unbuckled the bra and shucked it off her shoulders so that her pert breasts tipped with firm nipples came free and she laid that asisde. Finally making sure that she bent well down facing away from him she slipped her panties over her buttocks and hips before finally dropping them over one foot and then the other exposing her charms as she did so.
Frank Williams was not immune to these charms and last week had also made him rethink his strategy. He was captivated by this girl but knew that he was traeding on dangerous ground by inviting her into his home and caning her. He was going to be careful and would let the evening proceed as before but develop as it would.
"Over the chair please and grasp the bar firmly. These twelve strokes will be harder than last time. Again you will receive six , then a break followed by the final six."
Sust took her place and prepared herself "WHIPPP!!!" CRACKKK!!!", but last week had not prepared her for the shock. This was definitely harder and seemed to drive the breath from her body. Frank admired his handwork as he saw the white line change to red. "WHIPPP!!!" CRACKKK!!!" - the second mark was just above the first and she gasped. "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!", the cane lashed down a half inch higher and Judy had difficulty in not crying out. "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!" these last two delivered on the crown of the bum were the final pair at the end of the first six.
Instead of allowing her to stand Frank went to her rear and gently massaged her buttocks with his fingers. As he did so he let them slip between her thighs massaging down to her knees and up to her crack. She reacted by opening her legs farther to in order to give him greater access.He recognised the signs but refrained from going any further although he had felt the wetness on the inside of her thighs. He stood up again and taking the cane lashing it home "WHIPPP!!!" CRACKKK!!!", making Susy groan, then "WHIPPP!!!" CRACKKK!!!" the next stroke landed on an earlier mark and increased the pain level. "WHIPPP!!!" CRACKKK!!!", "WHIPPP!!!" CRACKKK!!!" she cried out while Frank saw the cane sink deeply into the bruised buttocks. "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!" the final stroke lashed down with extra force and was struck diagonally across the line of the other strokes. She was weeping profusely as she stood up and Frank quite involuntarily took her in his arms.
"All over!"
As he said this he felt her hands down his front fumbling with his belt and, as she unfastened it, she slid his zip down. He remained holding her and felt her hand push down his trousers and underpants which she she found difficult because of his erect cock which she eased out. She slipped down on her knees and gently massaged his cock with her hand exposing the purple knob at the end as she eased the sheath back. The tiny slit at the end oozed pre-cum and she bent her face over it and licked it off with her tongue.
"This is beautiful. Can I play with it?"
He looked down as saw her face and hair covering his cock and making an immediate decision stripped off his shirt so that they were now both naked. He then lifted her up and took her over to the soft carpet in front of the fire and laid her on her back. She spread her legs wide and offered herself to him.
"Please I want you inside me but I am a virgin."
He smiled at her, and with his legs each side of her beautiful body, he presented his cock to her pussy.
"This will hurt at first but then it will become beautiful."
She took his cock in her hand and guided it to the wet lips of her vagina. He pushed in gently and she adjusted herself to his movements. As he eased in he could tell how tight she was but luckily the interior was slippery with her spend and he was able to slide up without much siscomfort until he met the final barrier of her hymen. Susy was helping him by pushing forward and felt the pain as he touched her hymen. She desparately wanted to be fucked and was so exited that taking a deep breath she pushed upwards hard giving a sharp cry as the pain of the tearing hymen shot through her. Frank rested and then eased himself fully inside and said:
"That is it my dear no more pain. We will wait and relax before I take you to heaven."
Susy looked up at him with trust in her eyes and felt herself filled with his magnificent cock. As the pain eased so she felt the warmth begin to flow through her body, and her nipples as she touched them were so sensitive that she shuddered with the emotion. Frank blew in her ear and then gently kissed her mouth.
"Are you ready?"
"Mmmm"
Frank rested on his elbows and began to move in and out of her slowly and gently making sure that she enjoyed every moment. He knew that this was not for his pleasure but for her and it was up to him to make sure that she enjoyed the experience. Time after time he pulled almost clear and then thrust home again gradually moving faster and faster. He felt her legs come up and lock round his back as their coupling continued. It couldn't last long for either of them and she suddenly thrust upwards arching her back andcrying out as she shuddered with a massive orgasm. Frank pulled out and, using his hand, wanked his sperm all over her pubis and stomach. They both lay back and Lucy scooped up some of the sperm which covered her fleece and lifted it up to her mouth where she licked it. "It has a salty taste but I love it. Frank that was wonderful this will not be the only time we do this will it? With the cane as well the whole experience is fantastic. Will you do this every week?"
Frank looked across at her. He bent over and kissed her saying:
"My dear I am glad you enjoyed it. Of course we will do it again. Let us have a shower and then we must return to your books."
He took her hand and led her upstairs to the bathroom where he started the shower. They both entered the stall and under the warm water began to soap each other. It was not long before Lucy was on her knees playing with his cock and inspecting his pubic area lifting his ball sac and running her tongue up and down the shaft. She laughed as she massaged it and found that her ministrations had made it stand out like a rod. The plum head thrust out from the screen of the hood and she kissed it again and again taking it in her mouth working away until Frank stopped her and stood her up. He hugged and kissed her then presented the tip of his cock to her cunt again while she lifted one leg to help him. He lodged it firmly inside her and then rested her against the wall before he started thrusting away with energy. She squealed and wrapped her legs round his thighs while hugging and kissing him.
"Keep going. Oh please don't stop. God Frank I didn't believe that sex could be so wonderful."
He rammed harder and faster and this time was able to hold for longer while Lucy cried out in her passion. He did not try to withdraw and soon felt a welling up in his loins as he felt his spunk spurt home into her. She worked her bum in her ecstacy as she tried to milk him dry.
They stood under the shower gasping before finally washing and cleaning themselves before they dried each other and dressed. As agreed, they returned to her studies. It was difficult for her to concentrate but Frank insisted that she must and it was late in the evening before they finished. Lucy gathered her books together and before leaving. As he was about to open the door she lifted her skirt and lowered her knickers bobbing and laughing as she presented him with a final picture of her ravaged buttocks to remember. She gave him a final kiss saying:
"Until next week Sir."

* * * * * * * *


Lucy found the waiting time interminable but at last a week had passed and agin she thought carefully before she she dressed for the visit. This time she wanted to shock him so just put a long shift dress over her naked body and books in hand she presented herself at The Principal's door. He greeted her with a kiss and led her into the study. This time there was no chair or cane in view. She looked around for them but saw nothing. He took her hand and said:
"I know what you are looking for but this week it will be different. You will still receive your punishment - as hard as usual - but we shall be in my bedroom so that our play can continue longer. I want you to stay all night." "Darling I would love to and I know that the punishment must come first but a chance to make love to you all night long will be wonderful. When do we start?" He took her hand and led her upstairs into his bedroom where he faced her and putting his arms round her gave her a kiss.
"I am going to undress you now and then you can undress me and then I shall spank your bottom."
He put his hands up to the throat of her dress and began to unfasten the buttons until all undone he was able to release it and drop it from her shoulders. He was astounded that as he slipped the dress off her shoulders she was wearing nothing underneath. He could smell the musky female smell coming from her as he slid down to her hips and pussy. He went to the hairy thatch covering her pubis and finding the pussy lips slid his tongue into the orifice offered finding her clitoris standing out like a small nut at the entrance. He rubbed it with his thumb while two fingers explored the interior. She was already wet and the cum ran on to his fingers.
Lucy pulled him to his feet and whispered:
It is my turn now."
She began by lifting his shirt over his head so that she could see the hairs around his nipples. Not as firm or as large as hers but certainly erect. She then unbuckled his belt and released the button at the front. Down went the zip and the trousers followed to the ground. She removed them from his feet and then looked at him. His unerderpants were tented out as though something was trying to escape and she laughed as she touched it. She then slipped her fingers into the waistband and, by dint of a lot of pulling, eased them over his firm cock. She kissed the tip and took it all in her mouth trying to swallow it as she felt his balls and played with them using her fingers to massage his ball sac.
Frank stood her up and reminded her what must happen first and was she prepared. Lucy confirmed that she was so Frank sat on the bed took her over his knee and "SMACKKK" started to spank her with his hand. She squealed because she had not been expecting this and as he settled into rhythm, first one cheek, then the other, then a massage she began to feel euphoric and slipped into an almost trancelike state. The stinging slaps continued until he decided that her bottom was ready for the cane. One last slap and he lifted her off him.
"It's time for the main session. Are you ready?"
She slipped down, smiled and presented her red cheeks to him:
"At Sir's command."
As he took up the cane she took up her position at the foot of the bed with her bum sticking out and her head in the bedclothes. Frank knew that this was the testing time. He wanted her badly and, in fact felt that in spite of their age difference he was already in love with her. He enjoyed using the cane on her and also the rest of the session so he needed to be sure that she reciprocated his affections and she did not feel it was just a one night stand. he knew that if she could take the hard caning he was proposing and still retained her affection for him then their relationship could be long term.
He looked at the bum as he rested the cane on the cheeks. Pert and well formed she made a perfect target. "WHIPPP!!!" CRACKKK!!!", the first stroke landed and made the inevitable mark , first white and then rapidly changing to red,"WHIPPP!!!" CRACKKK!!!" this one landed on the crown of the bum and was well separated from the first. "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!" he started to fill in with sharp accurate strokes which left dark lines across both cheeks. "WHIPPP!!!" CRACKKK!!!", by now he was using the cane harder and he could see that she was gripping the bed covers firmly burying her head deeply in them. "WHIPPP!!!" CRACKKK!!!" he lashed the cane down. He moved over to her and gently massaged both chheks. This time though after touching her pussy he used one finger to find her anus and gently apply pressure. She moaned as he did so:
"Finish me off I do want you so."
He took up the cane again and "WHIPPP!!!" CRACKKK!!!","WHIPPP!!!" CRACKKK!!!" used the first two to get his line straight. "WHIPPP!!!" CRACKKK!!!", for Judy her mind was turning over and over between the pain and her lust, "WHIPPP!!!" CRACKKK!!!" - nearly finished as the pain level rose but her pussy was sopping wet with her cum as she felt more and more randy. "WHIPPP!!!" CRACKKK!!!", - thank god there was only one more - or was she - "WHIPPP!!!" CRACKKK!!!" the final stroke powered home and she screamed as it seared her buttocks. Frank dropped the cane and took her into his arms:
"No more, no more. Bend over again and open your bum cheeks for me as I am going to fcuk you in your anus."
Judy bent back over so that he could see her ravaged buttocks. She used both hands to part her bum and Frank taking a tube of KY Jelly squeezed some into the tiny puckered hole. he inserted one finger in and slid it in and out before widening it with a second finger. She moaned as she felt the surge of eroticism run through her body as his fingers explored her. He anointed his cock and presented it to the anus. As he pressed she groaned with the discomfort but he told her to pretend that she was shitting and relax her muscles. As she did so his cock slid farther home stretching the anus wider and wider. She cried out but because of the jelly his cock slipped home with ease and after he stopped moving the pain subsided and she could feel the warmth and pleasure she received from his cock.
"Are you ready for me to start?"
She nodded and he bgan a gently in and out movement which had her grasping the bedclothes and drawing them towards her as she approached her own climax in unison with his. He speeded up and she sensed him tense before with a final thrust she felt him ejaculating inside her. At the same time the warm erotic glow suffused her from her feet to her head and she tingled with pleasure. Frank lay across her back for a short time before with a plop his cock slid out. They kissed and hugged each other before going for a shower. This time they soon finished and, under strict instructions from Frank, returned downstairs to complete her assignment.
This time however there were no farewells and Judy after a late drink Judy asked Frank if she could go upstairs first and he follow in a fe minutes. At that she went up to the bedroom and, from her briefcase, took out a long see through nightdress which she proceeded to don. When Frank came upstairs he saw her lying on the bed wearing only the nightie.
"I want our first night together to be beautiful so am wearing my wedding nightdress":
Judy said in a small voice.
Frank went over to her and said that it was a wonderful thought and he loved her even more for it. He removed his shirt and trousers and she saw that he was ready for her. He lifted her up and gently unfastened the ties at the shoulders of the nightdress and stood watching as it slipped to the floor. Although this would not be the first time they had made love he knew that it was defining moment in their relationship. Frank sat back and watched as she twirled in front of him. Her breasts were on the smallish side but they were so expressive. Her nipples were a soft pink, but firm like nuts. Frank knew how much she enjoyed it when he touched them and he drew her onto the bed to nuzzle them with his lips. She arched her back to push them farther in his mouth and he sucked on each nipple in turn as though her breasts were full of milk. Her hand came down across his stomach and her fingers twined in his pubic hair before her nails ran up and down the length of his cock. As she did so she felt it stretch and throb in reaction and she bent over with her mouth bringing it down to his rampant cock to kiss the slit in the tip and lick the precum from it. She pushed him on his back and sat astride lifting herself slightly and guiding his cock into her. She felt it ease into the warm slippery interior and, as she gently slipped down, she felt it reach the top of her vagina. She sat back and smiled down at him in triumph before beinning to rise and fall slowly and carefully. She lifted her body so that it almost left his cock before bringing it down to take it full inside. He watched her with her breasts rising and falling in time with her ribcage showing with her efforts. This could not last for either of them and as she speeded up starting to breath heavily with her efforts so Frank pushed against her until finally she drove down crying out in ecstacy while he gave a final thrust with his spunk spurting high up into her in jets which overflowed and ran down her legs. All passion spent they collapsed into each other's arms kissing and hugging in their pleasure.
"I don't want this ever to end. Can I come and stay forever?"
Frank kissed her:
"My darling I never believed that we could form such a wonderful relationship. I love you and want to marry you if you will have me. There is twenty years between us but I hope that will not stop us.
Only time will tell whether they married and produced a happy ending to the story but for now we draw a veil over the rest of the night.