Businesswoman Requires Punishment - A Long Weekend Continued
By
The Disciplinarian

In Businesswoman Requires Punishment. Samantha had visited me because she needed to be punished because of her agressive behaviour to her staff. In coming she had discovered an unexpected interest in both the 'pain and the pleasure' which the rod offers and now she has started a full weekend of 'pain and pleasure'

I was up at 5am as always and took the dog out for our usual walk. When I returned Samanatha was waiting for me naked. She had placed a chair in the centre of the room and hasa cane in her hand.
"Please Sir I need to be punished. After you had let me go to bed last night I felt so randy that I played with myself before I went to sleep. I know I am not allowed to without your permission so have prepared myself for my punishment. Please do not be too hard as I could not stop myself."
I looked at her and the chair and though of what I had prepared for the day.
"Over the chair and I will decide how many strokes you are to receive."
She took up her place and gripped the front of the chair hard waiting for me. I inspected her bottom and although their were faint lines there was very little damage so she was ready for a hard caning
I took up my position
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ",
I laid on the strokes hard. I had decided on a dozen strokes and each was to be a full stroke with no holding back
"W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
each stroke drew a gasp from her but she did not move W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
the final strokes landed and I inspected her bottom. I felt her pussy a she was wet and randy so I parted her bum cheeks and saw the puckered rosette of her anus flexing. I told Samantha remove my clothes and to suck me ready. Soon I was naked and she went down and using her fingers and mouth I was soon standing. I told her to bend over again and taking a handful of jelly I pushed it in her anus. I used first one and then two fingers to open her up before presenting the tip of my cock to the hole. I found it immediately and gently pushed easing inside until I was full lodged. Her dark interior was warm and her sphincther muscles grasped my cock. I held her breasts in my hands and began to fuck away gently at first but then as I could see she was getting aroused as well I began to speed up until I was driving in and out like a piston. Samantha was crying out for me to 'fuck her, fuck her' and I was doing just that before I felt my body reacting and my cum welled up and spurted deep inside her. I rested on her back until my cock softened and came out with a plop. Samantha collapsed gasping and thanking me.
It was time for a shower and as we showered together Samantha made sure that my cock was well cleaned and ready for further action later.
She said
"I know I must not ask but is there lots more after breakfast?"
"You must not ask as I am in control but you will have busy day. Now it is time for you to cook breakfast. Put a skirt and blouse on and then this apron while you cook."
We sat an ate an excellent cooked breakfast before Samantha washed up and put the crocks away. By now it was nearly ten o'clock and it was time to begin. I took Samantha into the office and led her to the ladder. I told her to stand on the lower tread and put her hands on the top rung. I took some rope and fastened her hands to the top rung and then strapped her ankles wide spread to the lower rung. I pushed a cushion between her tummy and the ladder and then put a strap round her body. I then blindfolded and put ear muffs on her before leaving her. I had some work to do and it was nearly half an hour before I returned. She was still in position and I walked up behind her and using a feather I ran it up and down her calves. She shuddered at what was happening. and I moved the feather up to her thighs. Up and down the outside and then inside of her thighs. I could see cum oozing out from her pussy and down her thighs. I then used the feather inside her pussy and she bucked and cried out with the erotic feelings being engendered.
Now she was prepared I took my thick soft flogger. It has fifty chamois leather strips each about 30 inches long. I took my position and
"W HI P P ! !", "S P L A T T ! !", I brought it across her back. It did not sting but the shock made her cry out.
"W HI P P ! !", "S P L A T T ! !", "W HI P P ! !", "S P L A T T ! !", "W HI P P ! !", "S P L A T T ! !", "W HI P P ! !", "S P L A T T ! !", "W HI P P ! !", "S P L A T T ! !", "W HI P P ! !", "S P L A T T ! !",
I went on for several minutes before stopping and then going up behind her I felt up between her legs. She was ready and I took a long vibrator and eased it inside. Once deep in I turned the vibrator on full. At the same time I parted her bum cheeks and inserted an anal vibrator. Soon both of them were going at full speed and Samantha was crying out with the delights she was receiving. After two minutes I removed both of them and took up my martinet. This had ten thin leather strings which gave a sharp sting in several places at the same time.
"W HI P P ! !",
The lash landed and ten thongs traced ten different paths.
"W HI P P ! !", "W HI P P ! !", "W HI P P ! !",
I applied twenty strokes before stopping. She had been on the ladder now for an hour so I removed the blindfold and ear muffs and unfastened her. I helped her down having put my fingers to my lips led her into the bedroom where I lay her on the end of the bed and spread her legs wide. I spread her pouting pussy lips wide. The were enlarged and engorged with the work they had already done. I looked deep inside and saw the coral interior coated with the soft secretions from her spend. I sniffed the interior and the scent of an aroused woman rose into my nostrils. I licked out the cum which oozed down My mouth went down and into her coral interior. I ran my tongue round and round the interior while she squirmed and cried out with pleasure. I then removed my clothes and rubbing my cock to full stand. I stood between her legs searching for the eager opening. I soon found it and thristing forwards drove it up between her legs. She cried out for me to fuck her as I entered and she pushed towards me to make sure that I was deeply lodged. Her legs then went over my shoulders and soon we were fucking hard and long. Each stroke drove deep and each return came back to the edge. Back and forth the heel to toe went on. Now I eased my cock out and ruened her on her face taking her from the back. Her pussy was so wet that I entered with ease and taking her hips in my hands I continued. It was important that this was right and soon was really ready for this and tried to think of other things to take my mind away so that I did not cum too early. Samantha was bucking against me and her vaginal muscles were squeezing me tightly. All good things must come to and end and, after what seemed an eternity, I was ready. I warned Samantha and we drove and drove so that as I felt the welling inside me and with a final thrust I spurted my gouts of cum into her interior and she cried out as her spend mingled with my come. We had reached that ultimate point of perfect union where both parties orgasm at the same time. Half a dozen quick strokes and I was empty while Samantha, not wanting to release me milked my cock with her vaginal muscles until I was drained. Her legs released me and I eased out of her. We both lay on the bed exhausted with our efforts.
Every now and again a fuck is perfect. The partner is right, the libido is right and every part comes together to a perfect whole. It happens rarely , and usually unexpectedly as today.
As we lay there Samantha looked at me and said
"Sir I know I am not supposed to say but that was the best fuck I have ever had. Thank you !"
I looked across at her.
"You do understand that you had no right to milk me like that. You were not given permission. Go next door and select a cane for your punishment."
She left the room and returned with a medium cane. I told her to kneel on the bed and her firm buttocks were soon in position.
"Repeat after me as I cane you 'I must not put my pleasure above my Master's'"
Samantha was still not completely trained and it was necessary to make sure that she did not forget the lesson.
I took up my position
W H I P P P ! ! !", C R A C K K K ! ! ", I
I lashed the first stroke down hard and it dented her bum cheeks as it sunk in forming a white line
'I must not put my pleasure above my Master's'" "W H I P P P ! ! !", C R A C K K K ! ! ",
'I must not put my pleasure above my Master's'" The second stroke was one inch above the first and its white line soon joined the red of the first. I laid on the strokes hard. I had decided on a dozen strokes and each was to be a full stroke with no holding back
"W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
After each stroke she repeated the mantra 'I must not put my pleasure above my Master's'"
each stroke drew a gasp from her but she did not move W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
the final strokes landed and I inspected her bottom. These lines were forming the sort of marks that I wanted and I knew it was time for her to be restrained again so that she could not touch them. I ordered her into her bedroom and told her to stretch out on her face while I fastened her wrists and ankles. When they were fastened I again put on the blindfold and left her. I knew that her bum would be sting and her pussy wet but she could not touch either. I left her alone for half and hour and then returned with the feather and a strap.
I started using the feather on her feet and I could tell immediately that she was in areceptive state as they curled with my ministrations. I used the feather on her calves and then the inside of her thighs. She was crying out as caressed her gently. I felt inside her pussy and she was very wet. She tried to buck on my fingers so she came but I removed them and
"W H I P P ! !", "S P L A T T ! !", "W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !",
I broght the strap sharply across both of her buttocks.half a dozen times. I then returned to my feather and fingers caressing her buttocks and anus. I opened her anus up and inserted the tip of the feather inside. She again cried out and bucked into it.
"Stop that !"
"W H I P P ! !", "S P L A T T ! !", "W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !","W H I P P ! !", "S P L A T T ! !",
again I punished her for daring to decide her own experience.
I waited for another ten minutes or so and then removed the blindfold and unfastened her. I told her to pleasure me.
"Yes Master"
Getting off the bed she went down between my legs. She was learning and soon she was sucking away at my cock. She was also improving with this and soon she had taken my ball sac in her mouth while her fingers gently caressed the shaft. Now she took it all in and my cock was deep in her moutha and throat. She rubbed my shaft faster and faster until I felt my cum welling up and gouts of it invaded her mouth and made her splutter as she tried to swallow all of it. She went on sucking gently until she had emptied me.
I told her to stand and have a shower. I would be there to help her and then we would have some tea. She went into the shower cubicle and I joined her and soaped her between her legs making sure that I played with her pussy but warning her not to come. I then told her to bend over and I parted her bum cheeks before I washed her anus preparatory to taking it later in the evening.
We rested for the next few hours resting and watching television. She was perfectly happy sitting their naked while I fondled her without allowing her to orgasm. I certainly needed a rest and I was sure that Samantha did. She was still not a fully trained slave yet and needed to be lead gently to her destiny.
Late in the evening I told her that we were going to shave her pussy. She was very hairy and I was sure that when she was shaved she would find it liberating. I told her to fetch a bowl of hot water and a large towel. I collected a pair of scissors, a cut-throat razor, shaving cream and an electric razor. We placed the towel on the sofa and Samantha sat on the towel. I started by cutting the thick bush with the scissors until it was just a fringe of hair. Now I took cream and wetting the hair rubbed some cream into it. When it was well rubbed in I told her to be careful not to move and took the razor. I gently drew it over her pubis making a singing sound as it sliced through the rough matt. I continued until the main area was clear and then told her to open her legs wide as I shaved the hairs that were around her pussy and anus. I wiped the surplus cream away and took up the 'ladyshave' razor and switching it on cleaned up the whole area. He pubis was now clean and white with not a hint of hair around or on it. Her full pussy lips now showed clearly . She looked down in surprise and then pleasure with what she saw. I fetched a mirror so that she could see everything clearly and she exclaimed with enthusiasm.
"Oh Sir, I love it. I wish I had done it before."
"Now we need to test it so prepare yourself to be fucked. Go to the bedroom and wait for me I will want to be undressed and prepared. "
Samantha preceeded me and was standing by the bed waiting for me when I arrved. She removed my shirt and then unfastened my belt and lowered my trousers and underpants. She folded them and placed them on a chair. She went down between my legs to get me prepared. Shee took my cock in her mouth and rubbed it until it was standing out like a flagpole.
"Get on the bed and spread your legs wide."
Samantha did as instructed and for the first time as she lifted her knees and spread her legs I saw the full result of her shaved pussy. Her pubis was white but her pussy lips which were aroused were a darker colour and were still soft and warm. I parted her lips and saw the early signs of come oozing down. I knelt across her body between her legs and Samantha guided my cock into her. I knew the route well and found no difficulty in arriving at my ultimate destination. The route was well signposted with the slippy interior fully available. I rested there.
"Can I put my legs around you Sir?"
"Yes but you do understand that this will mean six strokes of the cane after for asking."
"Thank you Sir I will deserve the punsishment."
She wrapped her legs round me drawing herself on to my cock. However deeply I had thrust she found more space. I began to fuck slowly and deeply; I had already fucked several times today so was sure I could sustain myself. In, out, In, out I moved while Samantha gasped with pleasure. I am sure that she had never experienced such sustained sex over a couple of days and her appetite was endless. I knew that she was a sub not a slave and I could not deny her the full pleasure she deserved However she would receive her punishment afterwards.
I turn over and brought Samantha down on top of me. She smiled as she looked down at me and then proceeded to fuck me to some purpose as she rose and fell while held myself under control. He breats rose and fell in time with her cunt a the whole scene was very erotic. Eventually with her body glistening she moved faster and faster warning me that the time was coming for it to end and sure enough as she vame down and her vaginal muscles squeezed my cock so I came. The infusion was small as I had used up much of my juices earlier. but for all that pleasurable. Samanatha sat still for a minute or two then eased off me , climbed down and fetched the cane.
"I deserve my punishment Sir"
She bent over the end of the bed and waited. I took up the cane and I took up my position
W H I P P P ! ! !", C R A C K K K ! ! ", I
"Why are you being punished ?" 'I must not put my pleasure above my Master's'" "W H I P P P ! ! !", C R A C K K K ! ! ",
'I must not put my pleasure above my Master's'" The second stroke was lowerthe first but still in the main target area. I laid on the strokes hard. I had decided on a six strokes and each was to be a full stroke with no holding back
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
I inspected her bum and was satisfied with the results. I told her to stand up and informed her that she would be sharing my bed tonight so wash and get ready.
I washed myself and when I returned to the bedroom found Samantha was already in bed and waiting for me. She was stretched out naked and was clearly waiting for me to join her. I slid in beside her and cuddled her.
"Tonight you are free of your serfdom and can take the initiative if you wish. There is a penalty however as if you do so you will receive two dozen stokes of the cane after breakfast tomorrow. These will be the hardest yet. Take your time but the decision is yours."
Samantha thought for less than a minute and then laughing said
"OK lover boy let tomorrow look after itself. Tonight we will play. lets rest for an hour or two with some gentle foreplay and then I shall want fucking and your cock up my arse."
We turned to each other and I finger-fucked her and caressed her while she fondled my cock. Then she turned round and told me that she wanted a '69'. I was game and before long I had her pussy over my mouth while she sucked and fondled my cock. I slid my tongue into the orifice and licked the inside and using my thumb to rub her prominent clity before spreading the pussy lips and slipping thee fingers inside. I moved them in and out while she bucked under it while sucking away at my cock. I had to stop her there because I would not be able to bugger her if she had brought me off. To help her I produced a long rubber vibrator which I used for several minutes to bring her off. It was clearer than ever to me that she was actually a very sexy lady who had missed out in her younger days on sexual stimulation and now she needed to enjoy her full sexual opportunities. I was not going to miss this opportunity and I hoped that she would continue visiting regularly.
Meanwhile she wanted to be buggered and I had promised the night would be hers so told her to kneel. She knelt up on the bed and I spread her bum cheeks apart. He anus was flexing already anticipating what was too happen. I took out the jelly and putting some in her anus used two fingers to spread her and prepare her for my cock. I eased my fingers in and out to prepare her. Taking my fingers out I took my cock in my hand and presented it to the puckered hole. I eased it forward and the head touched her hole. I took hold of her hips and pushed steady until I was lodged inside. Samantha groaned but wea cleaarly happy with my entering her. I knelt behind her and grasping her hips firmly I bagan fucking her arse. As I fucked so she encouraged me with words I cannot believe she had ever used before.
"Come on big boy ! Deeper in my arse ! I need this so much ! Don't stop ! Oh ple-e-e-e-se continue !"
This latter as I slowed down. I rested for a couple of minutes still inside her before I continued.ramming my cock into her dark, mysterious interior. She had discovered meanwhil how to help me and was squeezing her spinchter muscles so that they added to our pleasure. Time to call a halt and I gasped out
"I must come in a minute "
Then it was the magic moment when the emotion flooded through me and into the tip of my cock as I pumped the final times spurting deeply inside her. I had had a rest and by balls were fully charged so that besides inundating her insides they also oozed out from her anus. I gasped and rested on her back as she milked me and slowly my cock subsided until with a 'plop' it came out.
Samantha lay back with her hands behind her head
"That was worth a thrashing tomorrow. Come on lets clean up."
We went into the bathroom and she cleaned herself and my cock.
The rest of the night was spent quietly with the two of us on our own sides of the bed but early in the morning I woke up to a pleasant feeling and, when I opened my eyes, I saw that Samanatha was at my side gently sucking my cock. It was not a violent attemt to get me ready but just a gentle suck as though on a stick of rock to arouse me."
"You are back in control again Sir and I am ready for what the day brings."
We both got up and I took the dog out before we had a shower and I dressed for breakfast. Samantha was looking apprehensive as she walked around as she knew what was to happen later. She cooked us breakfast and after washing up stood in the corner while I read the morning paper.
It was now nearly ten am and time for her punishment. I sent her into the office and told her to wait for me beside the flogging bench. I followed her shortly and told her to bend over the bench where she would be fastened down. I reminded her that this was after her decision last night. Did she understand?
"Yes Sir and I don't regret a moment !"
I took my most potent cane, a rattan about three feet long and nearly half an inch in thickness. It had a good handle which would mean that it would not slip in my hands. I measured up and tapped her bottom a couple of times before
W H I P P P ! ! !", C R A C K K K ! ! ", I
We had started. Every stroke in this session would be designed to find out her limits "Why are you being punished ?" "Because I took command last night." "W H I P P P ! ! !", C R A C K K K ! ! ", W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
I stopped and felt her bum. It was glowing red and each line was clearly deliniated.
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
Although there were no wounds her bum was beginning to have ridges raised across it. Samantha whimpered but did not move.
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
I laid on the strokes hard. I had decided that I would push her limits and there was to be no holding back
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
By now I had filled the main area and the next strokes wer overlapping the earlier ones which were now becoming ridges.
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
Her bottom was now looking like a disater area with thick and thin marks covering both cheeks. I was now taking her into new territory and was exploring as I watched her carefully for signs of distress.. I felt her bottom and ran my fingers along the red ridges which wwre now turning to a deep purple and their full effect showed.
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
She was now showing signs of distrss. Not acute but warning me that the next four srokes must be the last four so gripping the cane firmly
W H I P P P ! ! !", C R A C K K K ! ! ", "W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ","W H I P P P ! ! !", C R A C K K K ! ! ",
I heard her crying out as I lay on the last four. I stood back and looked at her bum before releasing her. She was sobbing and buried her head in my shoulder and wrapped her arms around me.
"That was superb ! Those last strokes took me to places I never knew existed. The pain seemed to be in a different me. What does it mean?"
"Come and I will put some cream on your bottom so that it does not harden up and try to explain.
She lay across my lap and I saw how bruised her bottom was as I poued baby oil over them. I began to smooth it in and then massage it. she cried out with the pain but then settled as she felt the benefit.
Why do you feel as you do you ask? I delibrately pushed you to your limits and proved what I thought. You are a flagellant. This means that you enjoy the cane and there comes a moment as you are being caned when your mind switches out of the pain to a different plane. I have spoken to several ladies like you and they tell me that gradually as the pain from the cane increases so they begin to widraw into themselves. After a time they find a dream state where they are mentally orgasming within their mind. When in that state they can receive fifty, sixty or even one hundred strokes so that their bum is severely bruised but until I stop they can accept even unlimited amounts. Of course this does not happen immediately and takes months even years but each visit the number of strokes increases."
As I was talking I was playing with her pussy and now her cum oozed down onto my fingers and I thrust deep into her and moved my fingers in and out rapidly until she cried out with her orgasm.
It was nearly time to finish and I told her to return to the edge of the bed and present herself for my cock. We tried to make sure that her buttocks were on soft cushions and her legs were well spread. I went into her with ease as she was slippery. This was my first of the day and I prepared myself to make sure that I gave her the maximum pleasure. I went deep and held my position. I drew out to the edge and then rammed deeply again. I went on like this for several minutes and then speeded up as Samantha wrapped her legs around me until with the quick heel and toe and the short digs I came with floods of cum while I felt her spend mingling with mine.
It was the finish and we showered and dressed before I escorted Samantha to the door.
"Samantha you are back in control until we meet again. I look forwards to your next visit"
"Thank you Sir for the weekend and I look forward to my next visit."

The final part of the story will be on line shortly