The Secretary Faces a Challenge - Part 2
By
The Master of Discipline

After her Saturday with John Hammond and his wife Mary was all excited when she returned to the College on the Monday. She had remembered what Frances had said about John Finally don't be shy about asking John to cane you at College I am sure he would enjoy doing it Mary listened on her intercom 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.
Mary remembered what had happened and it created a turmoil in her mind until she decided on Wednesday to speak to John Hammond.
The rest of the day went very slowly but at about 3pm she could not wait any longer. She knocked on the Principal's door. Told to enter she walked up to his desk."
"Yes Mary?"
"Please Sir I need to be caned urgently. I enjoyed the experience at your house and am coming back on Saturday but I need a 'College caning' exactly as if I was one of the students."
John Hammond looked at her careully for several minutes before telling her to put the 'In Conference' notice on her door and come back to his room. Eagerly Mary did so.
"Remove all of your clothes and bring the bench to the middle of the room."
She soon stripped and was prepared.
"I am going to deal with you as I would one of the seniors. One dozen HARD strokes is exactly what it means. No crying or moving or the stroke will not count and I will repet it. Is that clear."
"Yes Sir."
"Then bend over the bench. "
Mary bent over and waited. and waited before "W H I P P ! !, "C R A C K K ! !"
she felt as though she had been burned by a red hot bar. The stroke was harder than any she had received over the weekend and fiercer than she had bn prpared for.
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,
She now knew the difference between the pleasura and pain on Saturday and real punishment caning
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
Only halfway through and she wanted to scream "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 ! !"
Line by line the cane dealt its inexorable count. Stroke by stroke her pain level grew until she was sure she could take no more
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !"
The final two blows fell on her bruised and battered buttocks but she remained in position. John hammond came round the front and lifted her head.
"That is a punishment caning with no preparation. Now I think we should finish this session with you pleasuring me. I want you to suck me off."
cock suckingAt this he lowered his trousers and underpants and presented his rigid cock to her face. Mary had never seen a man's cock in this position and was not sure what to do but John left her in no doubt as he offerd the nut to her mouth.
"Suck it and bring me off. "
She took the head into her mouth and was soon sucking away. She found it pleasant and was soon entusiastically sucking. Meanwhile John was rubbing the shaft and it was not long before Mary received a shock as her mouth was inundated with gouts of sperm. She gasped and gagged but kept on sucking and swallowing until there was nothing left. His cock shrunk and he lifted Mary up.
"I think we should do this again sometime you clearly have an apptitude for sucking a cock. Now you had better dress and go into my bathroom and clean yourself up "
Nothing more was said and Mary very sore but also liberated returned to her office and removed the notice from the door. She had even more to think about now before she visited the Hammonds again.
.. When she returned home that evening she had a hot shower which helped to ease the pain in her buttocksand then used her pier mirror to inspect the lines across her bum. John Hammond was an expert and had made sure that every one had found a different space. The bruises were now coming out and there were ridges raised across both cheeks. Thinking about it as she inspected herself Mary was satisfied with what had happened. The 'cold' caning had hurt much more than she had expected but she had found that even now she was looking forwards to what might happen that weekend. She was also pleased that she had visited the Family Planning clinic and had her coil fitted. Frances had told her that she would receive more pleasure if John spent inside her and she was willing to bow to her supeior experience and knowledge.
The next two days passed quickly and Saturday seemed to pass all too slowly as she waited to join the Hammonds but eventually it was time. She arrived at eight o'clock and Frances met her at the door.
"Welcome and do come in. John is in the lounge."
She removed her coat and they went into the lounge where there was a warm fire burning and the lights were low. John was standing in front of the fire and had drinks ready for Mary and his wife. he welcomed Mary with a nod.
"We are both excited to see how he dealt with you on Wednesday. he tells me that he got you to suck him off. I love it but it must have been rather a shock if you had never done it before. before we settle down for the evening I want to sk if you would like to stay for the night. This will allow us more time to play without pressure?"
Mary said she would be happy to stay.
"Good now don't let us waste anymore time in getting down to our skins. At this she stripped her clothes off and watched as John and Mary did the same.
"Let me inspect your bum"
Mary bent over and Frances ran her fingers over the bruises which still showed.
"Hmmmmm! John did a fair job on you but he says you did ask for a punishment caning. Well don't worry we will help."
Mary had found that although normally shy she had no hesitation in undressing in front of Frances and John and felt, in fact, that she compared favourably with Frances. Frances was more mature with full breast with dark aureoles and large nipples. her bush was thick and dark with prominent pussy lips showing through. her bum was full and dimpled offering an enchantin sight. Mary meanwhile had not yet reached full maturity and her breasts still had some time before they were full. Her pussy hair was lighter than that of Frances and it covered the entrance to her pussy while her buttocks were ripe for pleasure and pain. Finally John was about six feet tall with firm calves and thighs, good buttocks. His cock which was soft at present could just be seen through the forest of his pubic hair which extended up his body.

Frances drew Mary across her lap and Mary was surprised to find that she was being spanked by a lady. As Frances began to spank sharply and regularly and Mary soon began to enjoy being spanked by her. She looked up and saw that John was beginning to massage his cock and once it was firm she saw the drop of precum on the tip. John pushed forwards and she took it into her mouth. Frances speeded up her spanking and Mary sucked and rubbed John's cock until he was near cumming. He withdrew and smiling said that it was too early. Frances stopped spanking Mary and slid her fingers deep into a willing and eager pussy which was already awash with her juices. She gave a dozen firm thrusts with two fingers and Mary cried out with pleasure as she came.
Mary stood up and Frances took her hands.
"Now my dear we are going to introduce you to a new fucking. John is going to fuck your anus. Don't look shocked he will be very gentle and you will enjoy it. It has a different sensation but one which is equally as pleasant. The other advantage is that it can be done without any fear of producing babies. Just you bend over the back of the chair and we will do the rest."
Mary was apprehensive but she bent over and felt her bum cheeks parted. She felt a coldness when some cream was introduced to her anus followed by first one finger and then two. The fingers rubbed in an out and she found the sensation unusual but pleasant. Then she felt a hard nut nudge her puckered rosette and then gently begin to enter. She was very tight and found it painful.
"Pretend you are evacuating and relax your muscles."
anal sexShe shut her eyes and did as she was told and soon felt her anal muscles stretched as the head of the cock pushed deeper into her. She gasped as she was spread wider and soon felt his cock was deep inside her. They rested while she adjusted and then he began to move in and out. Mary was amazed at the pleasure she was feeling as his cock thrust in and out and the sensation of his pubic hair on her buttocks. Frances came to her front and held Mary's hands looking into her eyes.. She smiled and then lowering her hands Mary saw that she had a large purple dildo which she had inserted into her cunt and was moving in and out in time with her husband's actions. It was a magic moment and Mary felt a shuddering climax just as John spurted deep into her dark interior. Frances meanwhile gave two more thrusts before she to stood tall with taut thigh and calf muscles and cried out with her pleasure.
Mary felt John easing out of her and in spite of the pleasure she had received welcomed the way his cock shrunk as it left her with a 'plop'.
There was a bowl of water on a side table awith a towel and soap and Mary saw Frances take John's cock and carefully wash and dry it. She smiled at Mary.
"Very important. Whatever the pleasure we receive we must always clean his cock after anal sex. Now you will enjoy yourself. You don't know that John enjoys receiving the cane as well as giving it. It is his turn to be dealt with first tonight.. We are both taking part with me giving him six strokes and then twelve by you before I finish him off. Over the chair John !"
She took up a a cane from the table and handed it to Mary.
"I know you play hockey so you have strong wrists. The way to cane is to lay the tip across the middle of the far buttock - ah I see you are left handed - that is interesting. Once in position do not lash the cane down but a sharp 'flick of the wrist' will do the damage. Watch me !"
"W H I P P ! !, "C R A C K K ! !" ,
the first stroke landed and Mary saw that the action was in the wrist rather than the arm "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 ! !" ,
Five more strokes landed with the full whip before Frances handed the cane to Mary.
"Your turn so make them count"
"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 ! !"
"A good start Mary but use more power. You can see how my strokes have left better lines than yours.
"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 ! !"
"That is better but now really lay it on for the last four. Remember you are caning from the other side which is always more painful." Mary stopped and looked at her handwork. John was well marked but nothing which really had done much damage. Now Frances took the cane
"W H I P P ! !, "C R A C K K ! !" ,
this one lashed home with power and made John grunt
"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 ! !"
Each stroke landed with the full force of Frances wrist and now the marks were looking much angrier
"W H I P P ! !, "C R A C K K ! !" ,"W H I P P ! !, "C R A C K K ! !" ,
The last two were the hardest of all and immediately after John stood up. Mary saw that his cock was rampant and, as she watched, he took his wife, turned her face down over the back of the chair and thrust his probe deep into her. She gasped with pleasure and then Mary saw a 'tour de force' as he fucked and fucked for several minutes while Frances encouraged him His cock drove in and out while Frances pushed backwards to make sure that every time he reached her depths. They were completely oblivious to Mary as they took their pleasure. Mary sat back with her legs spread watching and playing with her clitoris. She took up the purple dildo. She pushed it deep into herself and moved it in time with John's thrusts trying to make sure that she would come at the same time as him. Sure enough she watched his calves and thighs tense as he drove in twice more finishing with a massive surge of cum which drove high into Frances cunt inundating her and oozing out around the edges of her pussy. while Mary gave the dildo a final push which released her emotions and she discharged as well.
John withdrew from Frances and the three of them were gasping for breath as they came off their own particular highs. John poured a glass of wine for each of them and they sat there enjoying the pleasure of their satisfaction.
"Wow !! John that was the best for months and I could see you enjoyed the dildo Mary. While John rests before dealing with you you and I are going to pleasure each other. Don't look shocked I am sure you will enjoy it. Come here !!"
lesbian kissingShe held out her hands to Mary and drew her to her feet and into the middle of the room where there was a soft rug. She drew Mary down and hugged her before kissing. She pushed her tongue into Mary's mouth and although she had never been kissed like this before she found that she was enjoying it. The touching of their tongues sent a frisson of excitement through herShe felt Frances caress her breasts and rub her firm nipples. Then Frances slid down and sucked Mary's nipples. These were already hard and the flick of the tongue again drew her to new heights of pleasure. Down to the belly button and then through the pubic hair covering her private parts before she parted Mary's legs. Mary waited and then felt that Frances was between her legs and suddenly she felt the touch of a tongue on her clitty. Frances flicked her tongue back and forwards and Mary felt a new and unexpected wave of sensation. She felt Frances part her labia and slip two fingers into the warm wet interior. Her tongue followed and Mary felt a welling up in her Her back left the floor as she had a massive orgasm and spend which squirted across Frances face. Frances laughed and licked the spend and kissed Mary again telling her, as her tongue entered Mary's mouth, to taste her nectar. She sat up and turned to Mary
"Now it is your turn. I don't think you have ever had sex with a woman but now is your chance to try"
She drew Mary down between her legs which she had spread wide. As Mary opened the full lips she scented the aroma of an aroused woman. Sharp but pleasant. She also saw that Frances had a prominent clitoris the head poking out from its cover. She started by rubbing the clitoris with her thumb and Frances moaned with pleasure. Mary then used her tongue on it and gently tongued it as Frances had tongued her. Then she began to tongue inside the coral interior which was slimy with spend. Her tongue went in and out and picked up the spend. She then slid three fingers inside so that as she moved Frances called out to her to move faster. Mary drove in and out and then finally gave a fast rub on her clitoris which brought Frances to a screaming climax.
As Mary looked up she saw that John was standing rubbing his cock until it was like a pole. He beckoned her to him and when she came he bent her over the end of the sofa. He parted her legs and she felt his cock slip easily into her slippery cunt . He took her hips and started ramming away. Both of them were already on a high but Mary could tell that John was restraining himself although thrusting hard and it was several minutes before she felt her body flush with pleasure as with a dozen more pumps John spurted deep into Mary as he himself came. Now she knew why Frances recommended her coil as the final thrust had jetted sperm high inside and and the warm sperm which inundated her added to her own climax.. As John rested on her back she felt his heart throbbing with his efforts. She herself was finding it difficult to come back down to earth but eventually he withdrew and stood up.
Frances clapped her hands and hugged John and Mary.
"I love watching you and I am sure that the three of us will have lots of lovely times. Now for a shower and then some supper."
They went upstairs and there was room for the three of them in the large shower. John found that his cock was an attraction to both ladies with Mary sucking his cock to a stand. Frances meanwhile bent over so that mary could present his rampant cock to her buttocks and he enthusiastically entered into the spirit fucking Frances to climax. They then dried each other and putting on gowns the three of them went down to supper.
Mary found that John and Frances were good hosts and she enjoyed the meal before they went back into the lounge with their coffee and chatted about everything and nothing. By now it was elven o'clock and Frances looking at the clock suggested that it was time for bed. Mary and John wer ready so they went upstairs to the main bedroom where Mary saw a king-sized bed. She ws also surprised to see that the wall mounted cupboards had mirror sliding panels. Frances took of the covers from the bed and the three of them lay for several minutes. As Mary looked around she could see them reflected in the mirrors. fances noted her interest.
"You look surprised. John and I enjoy watching ourselves and this gives us the chance.to pleasure each other and please ourselves. Why don't we let John bugger you and you can see things you will never see otherwise. Why don't you get John ready?
As John lay back Mary went over the top of him and began to massage the tip of his cock with her tongue while at the same time gently rubbing it. She saw it grow like a flower until her mouth had difficulty in contain the purple head. It had drops of pre-cum on it and Marylicked these as she sucked and tubbed away at hi cock. Now it was standing up pround and true and ready to do its duty.
Frances drew Mary to the end of the bed and bent her over parting her legs and buttocks before putting one finger in her anus. Mary was ready this time and soon felt the cool gel inserted into her by Frances. John came behind her and she felt his cock nudge her as he searched for the dark entrance. Then it home in out the puckered rosette. He push forwards gently and mary helped by loosening her anal muscles until she felt him deep inside. She looked in the miror on the opposite side of the room and saw that Frances had on a massive dildo which she was presenting to John's anus. Sood she was home and as she fucked him and John fucked Mary the three of them felt an electric current running through them. John was thruting away into Mary while he was in his turn being fucked and it was not long before Mary felt John jerk and power home before subsiding as hs sperm disappeared into her interior. His cock gently subsided and left her body but Mary could see in the mirror that Frances was not finished with her husband and the purple dildo flashed in and out of his arse. Eventually he cried out 'enough' and Frances withdrew from him.
The session was ended and after clening themselves the three of them lay back to sleep..

In part 3 Mary is invited to remain over Sunday when they have 'other guests she may like to meet ! 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."