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A Regency Rake Part 2
By
The Disciplinarian

My father had now left and I was in charge of the family and the estate. I had to accept advice from our lawyer on running the estate and would also be advised by the butler and housekeeper - the two most important people among the domestics in any stately home - over the arrangements in the house. My sisters and I had discovered the pleasures of sex with each other and, just before my father left, I had also discovered the enjoyment of whacking the female bottom. I intended to indulge myself over the year I was on my own.

I called the housekeeper to my father's study and when she arrived I was rather surprised. Over the years I had not noticed her as she carried out her duties but, when she came to the study, I saw that she was not as old as I assumed but was an attractive woman of about forty who was well formed with an excellent figure. When she stood in front of me I asked her to sit down and explain the running of the household as I wanted a grasp of the principles. She told me about the numbers and types of staff and I was astounded to discover that she was responsible for over sixty girls and ladies while the butler had charge of a similar number of men. The girls ranged from kitchen maids to the personal maids of my sisters and the men from the boot boy to my valet. The outside staff were dealt with by the senior coachman whose staff included grooms, coachmen, stable staff etc. The estate had a Manager who was in charge of making sure that the farmers and their families were all working together to maximize the returns for us and themselves. I would have little to do with him but would meet the other senior staff daily for a report and instructions.

I talked about the use of the rod on the girls and the housekeeper confirmed that she usually disciplined them but in special cases my father dealt with it himself and she assumed I would want to do the same. I agreed that I would. She then seemed rather embarrassed and asked if I would mind if she said something. I told her to carry on and she explained that the cane and strap was used from the highest to the lowest. I was astounded and asked her if she meant what she said 'highest to the lowest'. She nodded and said that she had been disciplined by my father several times and would expect me to do the same. He usually dealt with her at night when everybody had retired and she visited his bedroom suite to be caned. I asked whether she wanted me to do the same and she said yes please and, if I agreed, she would visit me tonight to go through what usually happened. I agreed that this was acceptable and she retired.

* * * * * * * * *

The rest of the day ran smoothly and my sisters and I had dinner together before retiring. I told the girls that I needed my rest tonight and that there would be plenty of time for us over the next year. They agreed and left for their own rooms. My valet undressed me and I retired for the night. I heard a knock on the door and, when I called "Enter", the housekeeper Mrs Rooke, came in wearing just a nightgown. She curtsied to me and explained that my father has a firm way of dealing with any problems which she fully agreed with. If I wished she would like to start the way we would continue. There were a couple of problems which had caused her some concern and she felt that she had not dealt firmly enough. Would I be agreeable to punishing her for her infringements. When I agreed she went to a cupboard in the corner where she took out a long whippy cane which she swished through the air before handing it to me. She then unfastened her gown and let it fall to her feet and I was astounded to see that she was naked underneath.I knew I had been right when I had guessed she had a good figure. She was about five foot six inches tall, shapely calves leading to firm thighs and a well formed, strong bum with white plump cheeks with dimples. I could see slight marks where my father had clearly caned her not so long ago. Her breasts were firm and the nipples stood out from the brown aureoles as though they were ready for sucking. She told me that my father usually gave her twenty four strokes of the cane delivered in groups of six at a time. When he was finished she helped him to relieve himself. I suggested that she took up her usual position and she walked forward and bent over the end of the bed. I was trembling with excitement and I walked forward and caressed her buttocks while she moaned in anticipation.

"When you are ready Sir" she whispered.

I lifted the cane and remembering the way I had dealt with the girls yesterday "WHIPP!!", "CRACKK!!" I lashed in the cane allowing it to sink into the well fleshed buttocks and leaving a white mark plainly to be seen; "WHIPP!!", "CRACKK!!" "WHIPP!!", the second was harder and I had struck, more by luck than judgement, just above the first thus leaving a further line. "CRACKK!!" "WHIPP!!", "CRACKK!!" the strokes hammered home and after six I stopped and looked. The bum cheeks were now well marked and the initial white lines had turned a fiery red and were also standing out from the bum as ridges. I felt her bum. It was hot to the touch and as I massaged it so I let my fingers stray between her thighs. She was already wet and I heard her gasp as I touched her quim. I continued rubbing the bum and thighs before my hands moved up to her breasts where her nipples stood out like iron knobs. They seemed to throb as I touched them.

"Lay on again Sir please!"

Then I regained my composure and returned to the job in hand. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" by the end of the first twelve I could see that her bum was well marked and as I touched I felt the welts already rising so that they felt like the ridges in a ploughed field. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" I continued striking with the new marks overlapping the old ones and as I worked through the second dozen I could see that, like the second girl yesterday, she was having some experience which I couldn't yet fathom. She was twisting her body and rubbing herself up and down but she but not in pain and she didn't seem to want the caning to finish.

She cried out "Please, please, harder. I need it harder!"

I renewed my grip on the cane "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" lashed it down with greater force than before until the full number of strokes had landed. I then stepped back to look at my work and so I made the last ones really tell and was astounded when she thanked me with a gasp,

She stood up slowly and gingerly saying

"Thank you John your father could not have done better. Now off with your nightgown."

She lifted my nightgown over my head and throwing it to the side fell back on my bed pulling me towards her "Quickly I need your cock in me." I was certainly at full stand and within a moment I had thrust high up into her wet warm pussy. Unlike the girls who had been tight to thrust into Helen was an expert and she wrapped fuckingher legs tightly round me and started to push up as I hammered down. We worked fast and hard in and out both of us perspiring with our exertions until I stiffened and, with a jerk, spurted into her cunt while she raised herself and cried out as she also came. She milked the last drop of cum from my cock before she released me and rested.

We lay back and she said that that was the best caning and fuck that she had had for a long time. Whilst we were lying there she explained that she had serviced my father in the same way and also found suitable girls to work in the house who enjoyed the rod and were discrete, the rest she punished herself while my father had enjoyed dealing with that special group. She was sure that they would want me to work on them and she would introduce me to them gradually. She then bent over and went down on my cock. She took it right down her throat as she sucked and ran her tongue round the head. When I was primed again she told me that she wanted me in her arse and took a pot of pomade she had brought with her. She knelt on the bed and and opening her bum cheeks told me to put plenty of the pomade in her arse. I took up a handful and slapped it on making sure that my fingers slipped plenty inside the bum working it well around. I rubbed the head of my cock and presented it to her arse pushing gently at the sphincter as she helped me by pushing back. I heard her groan as I managed to get past and inside but once in it was easier and I finally lodged in the dark recesses. We rested to help her recover before I started to move and thrust home with our bodies slapping together as the tempo built. She was holding my ball sac to stop me coming too quickly as I powered away and she was soon gasping with pleasure, before she finally let go and allowed me to cum into her. I felt myself spurt and spurt until my juices had run dry before my cock finally eased out with a plop and she stretched her arms and threw herself back on the bed. We rested for an hour kissing and cuddling before she teased me into action and we had one final fuck with her on top before she returned to her room.

* * * * * * * * *

For several weeks life progressed normally as I learned my business about running the House and Estate. I decided after my first experiences to take it steadily and met one or two of the maids to cane them and also spent one or two evenings with my sisters before things came to a head. One afternoon I received a visit from our Lawyer to tell me that my sisters had been overspending their allowances and it must be stopped. I promised him that I would deal with it personally and called the girls to me. They laughed when I told them and said that they had only gone over by a few pounds and saw nothing wrong in that. I pointed out that I was in charge of the Estate and I would deal with them in the same way as my father would. They were to report to the study dressed in their night wear and I would cane them severely. They looked shocked but left the room returning in a few minutes wearing nightgown and robe. I went to the cupboard where father kept the instruments of punishment and took out the medium cane which I tested as the girls looked on apprehensively. Always before the caning had been for fun but they understood that this was to be for REAL!

I told Joanna to remove her nightgown and bend over the arm of the chair.

"I hope that it is clear that I will not allow you to take advantage of the absence of father and spend more than you can afford. I intend to teach you both a sharp lesson. I shall be giving you two dozen strokes which would be increased if you fail to remain in position. Do you understand?"

Looking very chastened she slipped off her gown and nightdress and took up her stance. I was excited as this was the first time I was going to work on the girls, although I was sure that it would not be the last, and I intended to push them to their limits. "WHIPP!!", "CRACKK!!" I lashed the cane across both firm white buttocks leaving a sharp line where it had landed. Joanna cried out as she had not expected me to be so firm. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" the next two were just above the first and emphasized that this was punishment not fun as they sunk into the bum and rebounded from the resilient flesh. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" by now my sister was crying as I stopped and massaged her bum cheeks to stimulate them. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" the bum was redder and the lines harder as each stroke fell and by the time the first dozen had been dealt she was promising anything to stop me. I remained resolute however and "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" continued until the last strokes "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" which I made to cross the rest. She was weeping heavily by now and I felt her bum massaging the cheeks which, besides its fiery look, was now a mass of weals and ridges. I told her to stand naked in the corner while I dealt with Angela. I had enjoyed caning Joanna and I was sure that Angela's bum would be as receptive.

Angela stripped off and faced me so that my cock began to get excited with seeing the fiery bush she had before she turned and bent over the chair. As a redhead her bum was even whiter than Joanna's and the plumpness of the cheeks would give me extra impetus as I struck. "WHIPP!!", "CRACKK!!" - sure enough the impact of the cane as it sunk into the fleshy orbs made her grunt and I felt the backlash as it bouncied back. What a wonderful opportunity this was as head of the house to test my sisters "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" the lines were already turning a bright red "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" I watched as she moved slightly and I knew that she was in the throes of an orgasm while the cane was landing "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!". How beautifully she marked and as I ran my hands over the area of her bum I could feel the ridges swelling to form raised lines. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" that was the end of twelve and although she was in pain I could also tell that she was building to a crescendo of ecstasy with juices spilling down the inside of her thighs. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" - we were now into the second twelve and I was beginning to overlay the lines already formed while the whole area was now a flaming fiery furnace which almost burnt my hand as I touched it. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" I could hear her moaning and panting with her emotions and I was sure that she needed the final strokes to bring her to her climax so without mercy I struck "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" before the final blow she was rising on tiptoes while her body stretched itself and her head came up so that when "CRACKK!!" I lashed the last stroke she cried out and her hands went between her legs to bring her to a final mind-blowing climax. She stood up with tears streaming down her face but turned to me and kissing me said "Thank you, Brother of mine, that was the greatest experience I have ever had."

I was not sure what to do now. I had caned the girls for their misdemeanors but one was congratulating me on what I had done and even Joanna did not seem very distressed. They put on their night clothes and curtsied to me before leaving the room. I was so 'hot' after this that I asked the Housekeeper to visit me tonight.

* * * * * * * * *

When everybody had retired I heard a knock and Mrs Rooke (Helen) came into my bedroom. As usual she was dressed only in her night attire. Before removing her clothes she told me that tonight I was to be caned as well as her just as she used to cane father. I was finding out more about him by the day and the austere man I knew was becoming more human. Once I had been caned I would then know the reason that she as well as some of the girls and, she believed, my sisters enjoyed it as part of the sexual experience. I agreed and removed my nightshirt so that we both now stood naked. As I looked at her it was more apparent what gifts the more mature woman offered with their softer breasts, fuller bum and fleshier thighs that my sisters had not yet achieved. She told me that she would deal with me first and I bent over the edge of the bed waiting and waiting with my mind in a whirl as she selected the cane. I heard it swish through the air and then a burning sensation across my bum. I jumped up but she told me to take up my position again. I was more prepared this time and I was able to absorb the pain of the stroke. She gave me twelve strokes altogether before she stopped and massaged my bum.

"Enough for tonight John. Next time we will try for eighteen."

As I stood up she clapped and said "Primed and ready I see", pointing to my cock which was sticking out like a flagpole and waving about. She knelt on the bed and spreading her legs she used her fingers to open her quim to the point of my arrow. I thrust and it lodged home slipping into the depths while my balls slapped against her and our bodies met. Before I could start she was moving and soon we had built up a good rhythm with her fingers tickling my balls. I held out for several minutes before I felt my cum welling up and with a final thrust I spurted my jism into her while she finished herself off with her finger. I slipped out of her and she looked at my cock.

"You have an excellent size John. The girls will love it as it is long and not too thick. You will need to learn to pace yourself better but that comes with practice. Now I need that caning".

She stood and walked to the end of the bed where she bent over and I took up the cane. She looked up and said "No John, the medium one please and two dozen hard strokes". I took up a thicker cane and she nodded and settled in position. Her bum was fresh and clear again from the caning I had given her a few weeks ago and I now knew that when she said hard that was what she meant. "WHIPP!!", "CRACKK!!" the cane lashed home and she gave a little nod of encouragement "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" I applied the strokes with vigour and soon the bum was well covered with marks."WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" every stokes was laid on to its maximum effect as I knew she wanted and her bum looked raw and very tender by the time the last ones landed. "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" "WHIPP!!", "CRACKK!!" These were diagonal to cause the maximum pain as they crossed all the others and when I had finished she subsided over the end of the bed, her head down and her bum still exposed. Eventually she stood up and kissed me and seeing that I was at full stand again she told me to lay on my back and she would pleasure me from the top so that her bum was not touched. I lay back and sure enough she squatted facing me sliding my cock into her cunt until it had disappeared completely. It was wonderful seeing my cock absorbed into her body with her pubic bush acting as a screen to its entrance. She smiled down at me and then gently started moving up and down. Each up stroke almost lifted out of me while the down took my cock so deep I felt I had been swallowed. Gradually the tempo increased until I found a response and I was thrusting with her. Faster and faster she moved until with a cry she pushed down for the final time and I felt her juices running down my cock and legs as she came with a fantastic spasm. She straightened up and then as my cock came clear of her body she lay down and turned on her face asking me to rub some lotion she had brought into her sore bum. It was a liquid and I ran it over her bum and massaged it in while she groaned in ecstasy. I loved every minute of this because, although I had spanked plenty, I had not really played with a lady's bum before and the chance to move my hands over and rub them was so stimulating that I found that my cock was standing again. She looked at it and took it in her hand just rubbing up and down gently so that I felt pleasure but there was no danger of me ejaculating before she took it in her mouth and started to run her tongue around the tip . She sucked and tickled finally almost swallowing it before she moved her head up and down on it. I felt myself cumming and tried to take it out but she moved my hand away and worked until I finally came and spurted into her mouth so that she was swallowing and spluttering as the cum gushed out. When she was finished she wiped her mouth and thanked me saying that I had done enough for tonight and should get some rest. She put her gown on and slipped back to her own room. Another night, another experience and I had no idea where it would end.

* * * * * * * * *

It was the two days later when she brought two girls to me to receive the cane. They were both about eighteen and had been found stealing food and taking it to their bedroom. Mrs Rooke knew that both of them enjoyed the rod so decided that I should have the pleasure of dealing with them. When they came in the both gave me bold looks and I could tell that these were ones for my pleasure as well. I told the first one, June, to remove her dress and bend over the chair. She smiled as she slipped her shoulders out of the dress and let it fall to the ground. She had nothing on underneath! I looked at her as she turned round and gave me a good view of her figure. I saw that she was well-developed with a good solid but attractive body her thighs were well muscled and she had a handsome bum.Her cunt was covered by a rich black fur which went almost from navel and between her legs. Her breasts were small but pointed with nipples which stood out sharply. She moved forward to the chair and bent over taking up her position and Helen handed me the cane before stepping back. I took a couple of quick swishes with it and then lining up her bum and "WHIPP!!", "CRACKK!!" the first stroke lashed across her bum."WHIPP!!", "CRACKK!!" the second stroke left a further firm white line across both bum cheeks. She didn't move and "WHIPP!!", "CRACKK!!" I continued striking until all twelve had been delivered and her bum looked fiery with lines and ridges forming across the buttocks. She stood up smiled and thanked me running her fingers across the weals. Mary, although smaller, had larger breasts and a bigger bum than her colleague and her pubic hair was sparse leaving the prominent lips of her vagina on view. Before I started I ran my fingers over the bum cheeks and they twitched in response. I then dealt with her in the same manner and the way her fingers had strayed to her cunt as I finished showed that she was wanting relief. The Housekeeper dismissed them and sent them to their room to clean up. She then congratulated me and suggested, flicking my trousers which housed my rampant cock, that if I followed them I might find something to my advantage. She told me the situation of their room and wished me luck. I hurried upstairs and, as I reached their door, I heard giggling while one was saying that: "The Master knows how to cane and I wonder if I knows how to roger as well?"

Mary replied, I bet he does and I'm going to try to have some!"

They both giggled and gasped as I opened the door. I saw that both girls were again naked and, although I could see the well marked bum of one, as her back was towards me the other was on her back and they were finger fucking and tounging each other. They were obviously enjoying themselves from the noise they were making. I walked up close and it was only when I was beside them that they saw me and broke off in confusion. I told them not worry as I had come to help them and I started to unfasten the buttons on my trousers. Mary told me she would do it while her friend prepared herself and it was only seconds before my cock was clear of my trousers and it was being tested by another mouth. I was learning that each one was different and as soon as I was prepared Mary removed my cock and presented it to June's cunt and I was homing in a a dark gash with well formed lips surrounded by a dark bush. As I thrust home she gasped and pushed towards me to lodge it even higher. She was clearly no virgin and as I thrust in and out she was so eager to help that she was pushing up with vigour. The caning had turned both of us on and it was not long before we both spent bucking and heaving as we came. Her friend meanwhile had been lying with her legs apart rubbing her clit and was watching us so that we all seemed to come together. As we rested I asked the girls if the cane turned them on and they both nodded. I asked if they would like more than twelve next time and again they nodded. I then fastened my trousers and said that next time I would fuck her friend.

The more I thought about it that evening the luckier I knew I was. Until he left all of these cunts and bums had belonged to my father who clearly took advantage of it. Now he was away it was mine to indulge myself with - and I intended to do so!

* * * * * * * * *

It was now coming up towards Christmas and I decided that it was time my sisters and I had another session and my first job was to find an excuse to punish them. This came when they had been out riding one day and I was in the stables when they returned. They came galloping in and I saw that there were whip marks on the flanks of their horses and both of them were blowing hard and were in some distress where they had clearly been hard ridden. The girls jumped off and handed their mounts to the grooms and walked off without bothering to see if the horses were well or not. They laughed to each other as they said that they were going to have a bath.

I waited a few minutes and then going to the study collected a riding crop followed them up to their room. I could hear laughter and opened the door to find that they were both naked and Joanna was in the bath while Angela was waiting her turn. There were several buckets of hot water waiting to be added to the bath for Angela. I turned the key in the lock and told the girls that I had come to punish them for their behaviour with the horses. Angela stood naked before me looking shocked while Joanna told me not to be ridiculous. I told them that both horses had been ridden to the point of foundering and were very distressed and might never be the same again. Such callous behaviour deserved punishment and this they were going to receive. I informed the girls that they would each receive two dozen strokes with the riding crop. I instructed Angela to bend over the end of the bed immediately and I would begin.

She took up her position looking at the riding crop I was going to use. It was the one I took when riding and had a bone centre to make it whippy. From the first stroke I made it plain that this was designed to hurt and the thin red lines raised by the whip had more of a 'cut' to them rather than the heavier strokes of the cane which bruise. After a dozen she was crying out with the pain while the lines of the whip had been laid on as if with a ruler. The next dozen added to the pain and by the time I had finished her bum was sore and she was well aware of the distress she had inflicted on her horse. I told her to stand up and have her bath now. Meanwhile Joanna had come over and was drying herself. I knew that she would feel her punishment even more as her bum had been softened by soaking in the bath. I told her to bend over and, when she was in position, felt the soft bum cheeks that I was now going to deal with. Like with her sister I had no mercy and laid the strokes on hard and fast, the way she had undoubtedly hit her horse. By the end she was crying out loudly and I knew that the lesson would be well remembered by both of them. I eased their pain by telling them that I would visit them tonight and whilst we were enjoying ourselves I would talk to them about Christmas as I had one or two ideas. They kissed me and I left.

When we had dinner that night I saw the girls sit down rather gingerly as their bums were obviously sore but they joined in happily enough and were excited about the possibilities of Christmas. After dinner we retired early and soon I joined them in Joanna's bedroom. They had decided that they wanted me to undress them so I had the pleasant task of unfastening the buttons and bows holding their clothes together while they giggled and undressed me. Finally we were all naked and I could see the marks I had placed on their bums clearly and could tell that they were sore. Joanna told me that they were going to have their revenge first and were going to give me twelve strokes each with the cane before the sex started and I resigned myself to a sore bum as I bent over. Both girls obviously enjoyed the using the cane but fortunately they had not yet got their act together so, although it was uncomfortable, it was not too painful and when I stood up they could tell that I was ready to repay them in other ways. Joanna was on her back and had her legs spread wide as I pointed my dart at her bulls eye. I made it first time and slid in without trouble as I lodged high in her. She wrapped her legs around me and joined me in a long, long steady fuck that was only brought to an end when Angela who had been playing with my balls and bum thrust her fingers up my arse.

Whilst we were resting we talked about Christmas and decided that we would have a 'sex and spanking party' each of us could invite two people so that there would be eight of us - four of each sex - and it would be 'anything goes' for the three Christmas days. We would also allow our housekeeper and two of the maids to join some of the parties.

Part 3 of 'A Regency Rake' shows James at "A Christmas to Remember"