The Secretary Faces a Challenge
By
The Master of Discipline

The year was 1956, Mary Green had been Secretary to the College Principal John Hammond for two years now and she found him attractive. He was tall and slim and smiled easily but at Holywood College he was recognised as a disciplinarian and accepted no excuses for slip-ups.. During these two years Mary had typed up many green forms which authorised corporal punishemnt and she had listened over her telephone intercom when the older students, aged 17 and 18 years, had been punished. Today her intercom was on as three students had presented themselves to the Principal.
"John Wright, James Balfour and Peter Rogers you know why you are here?"
"Yes Sir" they replied in chorus
"You know the penalty for actions? The police have left it to me. Do you accept your punishment?"
"Yes Sir"
"Very well you will each receive one dozen strokes of the cane on your bare buttocks. You will strip and stand in the corner with your hands on your head while waiting. John place the bench in the middle of the room . Now prepare yourself."
Mary listened as the students stripped ready.
"Over the bench John and I expect you to count each stroke. Any misses or crying out and the stroke will not count.
As Mary listened she heard
"W H I P P ! !, "C R A C K K ! !"
"One stroke Sir."
"W H I P P ! !, "C R A C K K ! !"
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
By now Mary had her fingers inside her skirt pocket, which had a hole in the bottom, and was rubbing herself over her knickers. She could feel how et she was already and listened again as the cane lashed its inexorable tattoo
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
By now it was obvious from his counting that John was in pain but he did not cry out and then the final two strokes fell in quick succession. "W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,
"Well done. Stand up and return to the side of the room and keep your hands on your head.
By now Mary was so wet that she had eased herself out of her knickers and her fingers were deep inside her pussy.
"Over the bench James and I expect you to count each stroke. Any misses or crying out and the stroke will not count.
As Mary listened she heard again
"W H I P P ! !, "C R A C K K ! !"
"One stroke Sir."
"W H I P P ! !, "C R A C K K ! !"
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
Mary frigged herself faster and faster as James received his final six.
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
Mary heard the preparation for the final two strokes in a haze as she .had a massive climax which she almost cried out over.
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,
"Well done. Stand up and return to the side of the room and keep your hands on your head.
Mary turned the intercom off. She was exhausted with her actions but she knew she had to find a way of getting John Hammond to cane her. She did not know how many she would be able to stand but she did know she need to try..
The three students came out looking very sorry for them selves and moving gingerly through the office. The principal brought the green forms through to her office and told her to file the originals and send a copy to the parents of the students for information.
Mary knew that she had talk to the Principal. She knocked on his door and entered
"Yes Mary?"
"Can I speak to you privately and confidentially?"
"Of course"
"Since I have been working here I have seen many students come to you for the cane and I find that it has a strange effect on me. I feel I would enjoy it but do not want to go to one of the clubs who advertise. I was wondering if you would give me twelve strokes of the cane just like those students who have just left you. I understand that it will be painful and I might wish that I had not asked but I feel I must try. Will you help me."
He looked at her carelly as he thought.
"You are not the only lady who is interested in spanking. My wife enjoys it also. I would not want to o this without her agreement but, if she is happy, I am prepared to do it. I will call you this evening after I have spoken to my wife. How about that?"
"Thank you Sir, that is perfect. I do appreciate the opportunity."
The rest of the day went very slowly and the evening seemed to drag until at about 9pm the telephone rang. She picked it up and gave her number. A woman spoke."
"Hello is that Mary, this is Frances Hammond, John's wife. Let me say first that you are not unusual but in the end you can only tell by trying it. I agree with John that you should be given the chance so I suggest that you come round to our house at 8pm tomorrow evening. I enjoy spanking but I cannot tell how you will react so a private session with John is the best way forward. Will you come?"
"Yes please, and thank you."
"I look forward to meeting you tomorrow evening then."
Mary had burnt her bridges and as tomorrow was Saturday and she was not at the college she would have the whole day to think and worry about it.

During Saturd,ay afternoon Mary prepared herself. She decided on wearing a blouse and skirt with cotton knickers and a bra as well as a suspender belt and stockings. She was not sure of the best clothes but felt these would not seem 'tarty' or over the top.
The time arrived and she drove up to the Hammonds house. When she rang the doorbell she was met by both of them. Frances shook her hand and welcomed her.
"Hello my dear you must be feeling nervous but do not worry as nothing will happen to distress you. Now come in and I will take you coat. Let us go into the lounge where it is warm. "
The three of them went into the lounge and Mary sat down in an armmchair while John and Frances sat on the sofa. Frances produced coffee and as they drunk it talked.
"First of let me say how pleased I am to meet you John often talks about his efficient secretary and I know how much he depends on you. Now to more personal things. You want John to cane you as the caning of the students has created a need. Well let me say you are not the only one and Johm spanks me regularly. I decided that tonight I would join you to help you though the ordeal. Let me explain more about spanking for us. It is a mixture of 'pain and pleasure' which send you to great heights. I am sure that if you heard any of John's canings it had an effect on you. This is 'cold' caning and is purely for punishment. You may want John to do it when you are at College but for tonight we are going to initiate you. So let us begin. John will start on me."
She stood up and lay across John's lap with her head to the left. and her buttocks immediately in front of him. John started spanking over her dress and, as he did so, Mary could already feel a tingle. Soon the dress was lifted and Mary saw that Frances wore a thong and her bare bum ws already taking on a slightly red hue. John continued but now Mary could hear the regular spanking bottom as his hand landed on her bare bottom while all the while massaging ber. The thong came off and John spanked harder and faster but his exploration of his wife became more as she parted her legs to grant him access. It could not last and soon Mary saw Frances buck against his fingers and then with a cry of pleasure subside. back. She lay there and turned to look at Mary. After a minute or two she stood up and removed her skirt so that she was naked from the waist down.
"Now it is your turn to go over John's lap."
Mary took her place and felt John caress her buttocks over dress before "S P L A T T ! !" his hand came down on her right buttock. She gasped with the shock not with the pain and then as John got into a rhythm she found that she was beginning to enjoy herself. After several minutes she felt cold air on her buttocks and thighs as John lifted her skirt.. His hand continued with its its tattoo first on the right then the left ,soft and hard, fast and slow all the time maaging. Mary soon found that she waa getting very wet between her legs.
John put his hands in the waist of her knickers and gently eased them down over her buttocks. These were a little sore now but she helped him until the were off her feet.. vagina playMary looked across at Frances and saw that sitting in the armchair her legs were spread wide and her fingers busy at her nub.
John gently massaged her buttocks before starting again to spank. "S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !" his hand rose and fell. This on her bare bum was much stingier than before but as he did so he also massaged and she felt his fingers gently ease between her thighs. She parted them to allow him gteater access and between the spanking she felt her thighs geting damper and damper as she felt him. Then after a couple of dozen sharp stinging strokes she felt his fingers seeking to enter her and his thumb found her clitoris and began rubbing it as it came out of its hood. She could not wait and after a bounce and bounce she cried out with pleasure as his fingers slid deep into her and her explosion produced a huge spend which covered John's fingers. She gasped with pleasure and then as John's fingers left her she eased herself up.
Frances meanwhile had stood up and removed the rest of her clothes. She then went over to John and unfastened his belt and eased his trousers off before pushing his underpants down. She then lifted his shirt so that he was naked. his chest was well covered with hair and Mary gasped as she saw his cock standing out rigid from his forested loins. Frances looked at Mary
"Before the rest of the evening John needs the chance to exercise himself so if you just sit back................................!"
Mary sat back in the chair and watched Frances bend over the arm of the sofa spreading her legs wide. John took his place between them and with one or two rubs of his cock presented it to his wife's spread legs. As Mary watched he gradually inserted it until it was fully lodged in her cunt. He took her hips in his hands and began the heel fuckingand toe action, thrusting and withdrawing encouraged by Frances. The spankings had aroused him and he was unable to keep going for long until after two or three minutes he speeded up and with Mary watching his buttocks clench be gave a final thrust which poured sperm deep into his wife - so much in fact that it spurted out around the sides of her pussy. He lay panting over his wife's back for a minute or two as the both recovered before the two of them parted and Mary sat back wiping between her loins while her husband poured out three glasses of wine. Frances looked at Mary
"Some embarrassing questions my dear but are you a virgin and how have you enjoyed the evening so far?"
Mary found it difficult to answer but to the first question she answered "Yes" and to the second a rather longer answer.
"When I came I expected to be caned but what has happened so far ...............I just don't know. I have enjoyed the hand spanking and it has turned me on but I still hope for the cane."
"I promise you that you will receive the cane before you go but would you also like to lose your virginity. My husband is a supurb lover and I promise you will enjoy it."
Mary gasped. She had not expected this but knew that there would never be another chance like this to lose her virginity. Up to now she had not enjoyed the fumbling of young men she had met and was becoming frustrated with her condition.
"Thank you I think I would enjoy it will you be there?"
"Yes of course I will. Now let us move on to the strap and then the cane. Let John remove the rest of your clothes before we start"
Mary stood up and John came over to her. He unfastened her skirt and removed it; then went to her suspender belt and unfastened her left stocking which he rolled down and off her foot. next it was her right stocking before removing her suspender belt. As he knelt there he played with Mary's pussy hair before standing. Now he removed her blouse and brassiere. Frances and John were very pleased as her full ripe breasts were released and the nipples showed rigid inside their aureoles. Frances told Mary to bend over the back of the sofa and as she took up her positionJohn spread her legs wide. "
"S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !"
John's hand landed a dozen times on her bum cheeks before he took up a flexible strap. He massaged her bottom then
"S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !", "S P L A T T ! !"
The strap rose and fell and Mary felt the sting on her bum as the strap burned it. After two dozen strokes John told her to stand up and wait. Frances told her to watch as she was going to be caned by her husband. She would receive two dozen with his headmaster's cane while Mary would receive a dozen.
Frances bent over and spread her legs. Mary could see her bum cheeks flexing as she waited. John massaged her bum and then pushed a finger in her anus before taking up his cane. He stood beside is wife and
"W H I I P P ! !", "C R A A C K K ! !",
Mary jumped as she saw the cane sink deep into Frances buttocks creating a white line as it landed. Frances didn't move
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
After six strokes John went to his wife and massaged her buttocks. He also felt beteen her legs and Mary could see him frigging her pussy. He then took up the cane again
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
Six more strokes and the lines were beginning to show. As he caned Frances Mary could see that his cock which had been at rest was now starting to stiffen.
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
The lines were now very red and some of them were turning to purple but Frances encouraged her husband to further efforts
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
the final stoke fell and Frances remaining in position said one word
"NOW"
John opening a jar put some cream on his cock and with his wife parting her bum cheeks he anointed her anus. His cock was like an iron bar and guiding it carefully he eased it home into the dark hole while Frances encouraged him. He started fucking away while Frances cried out
"Harder and faster my darling"
They had forgotten Mary who sat watching everything with emotions which veered betweeen pleasure, lust and uncertainty. As she watched John pounded his wife's ravaged buttocks with his pubic hair scarifying them but still encouraged by his wife. After his earlier efforts he ws able to sustain better now and it was several minutes before he cried out
"I am coming !!"
and with a final orgasmic thrust he inundated her. They were both gasping and as his cock shrunk with a final plop it eased out of Frances anus.
Frances looked at Mary
"My dear you must think us selfish but now I promise it is all for you. Come to me and I will prepare you. I suggest we go up to our bedroom."
Mary came over and taking her hand Frances led her upstairs to a beautiful bedroom. The two naked women went over to the bed and Frances drew Mary down She hugged her and kissed her. She then gently felt Mary's pussy slipping her fingers inside until she was blocked by the intact hymen.
"You are so ready for this. Your interior is hot and wet. I cannot stop you feeling pain but I promise you that afterwards you will be glad. Here comes John so I will prepare him for you."
John came in and his cock was not yet fully ready, still drooping between his legs. Frances went down on him and sucked and rubbed him until the purple head came out of its shield shining and glowing with health. Now it was ready and Frances took a jar of cream and anointed it. She then parted Mary's legs and opening her pussy put some crem inside. Mary was wet and ready so she drew Mary down the bed and parted her legs making sure they were widly spread.
John eased between her leg and Frances guided his cock until it found the virgin lips. John pushed forwards with his cock entering into Mary. He slid deeper until he found the blockage. Mary felt his cock spread her interior and her breath was short as the head of his cock came up until against her hymen,. She felt him ease back and then there was a sharp pain as he pushed sharply home splitting her hymen as his cock slid higher into her. She felt a sharp pain and cried out but it soon subsided as his cock remained quiescent in her. Her interior throbbed with the pain of his entry overlayed by the pleasure of the feeling of being filled. She felt him ease back and then drive home and soon he had set up a rhythm so that she found that she needed to wrap her legs round him as the pain and the pleasure of the deep thrusts were bringing her to a new sensation - a climax which was different to any she had felt before. She pushed against John and he was able to match her for several minutes before he told her he was ready and he withdrew in time for Mary with one hand to bring him off with gouts of spunk covering Mary's pussy hair and belly. At the same time she also used her other hand to rub Mary's clitty and bring her to a superb orgasm.
The two of them lay back gasping for air and Frances wiped first the blood spots off her husband's cock and then Mary's vagina. She kissed her husband and then hugged Mary.
"How was that for starters. I promise you that from now on there will never be pain but only pleasure !"
Mary sighed and admitted
"It hurt at first but once we got into a rhythm I forgot the pain and the pleasure overode everything. Now I do need the cane to test me."
"Of course you do and John will give it to you. You will have twelve HARD strokes and once John starts he will finish. No stopping in the middle. Is that agreed?"
"I agree"
"Over the then of the bed then and prepare yourself.
Mary knew this was the climax to the evening and the final test so gripped the bed tightly. She felt John gently masage her bum and then a pause before a blinding pain seared through her buttocks. "W H I I P P ! !", "C R A A C K K ! !",
She cried out and grasped the bed more firmly. This was more painful than she had expected.
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
She found that before the pain from the first stroke had subsided the next ones were adding to it and one pain was building on another
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
Six stokes and she knew that she must endure six more. Frances and John massaged her bum and then again that pause
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
She had received ten stokes but now she found that the same effect as had happened when she heard the students being caned was happening and a warm glow was suffusing her pussy which ws overriding the pain.and she knew she wanted more
"W H I I P P ! !", "C R A A C K K ! !", "W H I I P P ! !", "C R A A C K K ! !",
It was finished and her buttocks were throbbing with the pain but she knew that although she had had enough in a perverse way she need more. Frances lifted her up and looked at her.
"Yes you are one of us ! You need the cane for fulfillment but you also need a man's cock. Bend over again and wait."
Mry did as she was told and found that in some way John was rigid again and probing for her pussy. Sore as she was she knew that she needed him again and spread her legs wider so that he could enter her. This time she need no lubricant and he seemed to go deeper than before. he took her hips in his hands and began to fuck her. This time there was no hurry and it seemed he went on forever before finally withdrawing and rubbing himself off over her buttocks. Frances thrust her fingers into Mary and brought her to her climax.
It was ended exhausted as she was Mary knew that if these two would allow her she would be back for further sessions.
Frances suggested that she have a shower before she dressed and left and Mary was glad of the chance. When she was ready to go Frances looked in her eyes.
"Would you like to come again next Saturday. Now we know how to proceed we can have even more pleasure. Confidentially one thing I would suggest is that now you have lost your virginity you should get a contraceptive of some kind, maybe a coil, as much of the pleasure of being fucked is to have the man finish inside you. Finally don't be shy about asking John to cane you at College I am sure he would enjoy doing it."