1967 February: The Fabulous Isabella
I had only met Sir Henry once, when his eldest son was a new boy. Since then, Lady Isabella had always brought the boys at the start of term, collected them at the end of term and took them out during term. At the same time, she almost always found an excurse to talk to me. To be sought after by this tall, aristocratic beauty tended to be disconcerting. Her piercing hazel-green eyes seemed to be drilling into me, with unrequited lust. She always wore figure-hugging exquisite dresses that left little to the imagination, especially her well rounded bottom. I felt that I could be playing with dynamite until one Saturday early in the Easter term, when the fuse was lit.
Normally, she came up from London, took the boys out for lunch and an excursion somewhere, and returned them about ten past seven, ten minutes after curfew. But this week-end, she called me to say that she was coming up to watch her son play rugby for the school on Saturday afternoon, then coming back to take them all out for lunch on Sunday.
It was just after half-time and I was leaning on the pole support along the side of the pitch, when the statuesque lady appeared. Lady Isabella always made an entrance. Given the cold, she wore a 1950s style black trench coat, with a brown trim all round and two rows of large gold buttons down the front. Buttoned up to her neck, it billowed out at the bottom, giving way to the last few feet of a polka dot dress. Her long black hair rolled up in a bun, with a large red flower sticking out of it. She could almost be a flamenco dancer. The boys around me faded away as she asked if she could join me. Her second son was playing in the match and she had, purportedly, come to see him play. I knew that she was taking them out to lunch next day, but I was not expecting her just then. “Dr Thurston,” she asked loudly over the cheering, “ I believe you have a splendid house by the river?” I nodded defensively. “I forgot to book an hotel for the night. You couldn’t be a darling and put me up for the night. Henry has disappeared off to Madrid for a few days and I really don’t fancy going back to London. I looked her into her eyes and saw nothing but lust. But this aristocratic Spanish beauty also appealed to me greatly, so I reckoned it was mutual.
“It would be my pleasure, but you will need to make your own way there. It’s about three miles down the road. You can’t miss it with the very high hedges in front.”
“No problem. My Aston Martin is parked at the back.”
“Ok, give me half an hour after the match and I’ll be there.”
“Brilliant. Gives me some time with the boys, and then I’m all yours.”
Never a truer word spoken, I suspected. I bet myself that it would take less than an hour before she had hauled me into bed.
I had been back home for little more than five minutes when I heard her car on the gravel outside. I opened the door as she pulled a small crocodile skin travel case out of the boot. I took it and showed her up to the spare room, next to my bedroom. “Cinzano Bianco and tonic for me, please. I’ll be with you in five,” she chimed as she shut the bed room door. I had just made her drink and my whisky dry when she appeared at the door. The image was stunning and dripped sex. I could now see the full white Flamenco evening dress with its large black polka dots. It was right off the shoulder and then hugged her figure until just above her knees where it billowed out, swaying as she walked. It left little to the imagination; her full breasts and her largish, delightfully round bottom, all neatly tucked in at the waist. For a lady nearing forty, she still had a magnificent figure. She swivelled slowly. “People tell me I have a great bottom, n’est pas?” she smiled at me. “I’m looking forward to feeling your hand caress it.”
Her Cinzano went down her throat in one gulp, then she turned her back to me. “My dress is rather tight. Would you be an angel and undo my zip?” she cooed. Happy to oblige, I undid it. The whole dress slid down her body until it was around her lower legs. Being a gentleman, I would have caught it and feigned modesty, but it all happened so fast. Instead, for good measure, I undid her bra and let it drop. As I did so she put her head back on my shoulder. I gently squeezed her full breasts and she shivered at the touch. In turn, she started to rub her bottom against my private parts. One hand remained squeezing her left breast, while the other moved down, into her black silk panties. I parted the thick pubic hair, found her clitoris and rubbed it. Almost immediately her body shuddered, and, if I had not held her tight, she would have collapsed on the floor. I removed her panties and led her to the stair case. Faster and faster, we headed up the stairs to my bedroom. She threw herself on my bed, opened her legs and I plunged inside. “At last,” she almost screamed.
Finally, more than a hour later, we both were exhausted. She lay on top of me, her legs astride me, my semi-limp member still deep inside her. Her head rested on my shoulder as she breathed deeply, while my right hand caressed her bottom. After about ten minutes, she whispered in my ear, “I am a very naughty girl. My bottom really needs to be smacked, not caressed.”
I looked down at the olive skinned mound resting on me and agreed. My hand rose and fell on her left buttock for a couple of minutes. My member got harder as she slid up and down it with every smack. I could feel the warmth where my hand was landing, but I could not reach the other buttock. I sat up, pushed her to my side, then made her raise her tummy so I could push a pillow under it. I now had a superb target and could easily smack both cheeks. That is exactly what I did, with increasing force and speed. Soon both sides of her rump were a deep pink. When my hand began to hurt, I would stop and push my hand between her legs. My thumb moved inside her, to rub her G-spot. My index finger found her clitoris. The result was dramatic. It was only my right arm holding her firmly that stopped her rolling off the bed. When hand recovered, I spanked her again, before restarting the rubbing. It was only after four orgasms, that she begged me to stop. In fact, my sore and burning hand was telling me the same. “Caramba, what are you doing to me?” she almost screamed at me.
It was after 8pm, and the rugby match seemed a decade ago, when we finally declared ourselves famished. My house-keeper was on standby to produce a couple of fine steaks and the trimmings. Half an hour later, we heard her come in and start cooking, while we indulged in some gentle sex. Another half an hour, the door closed as she left discretely, and we headed to the dining room for the well earned steak, salad and chips. I sat at the end of the dining table and she sat on my right. We wore nothing but a couple of my white towelling dressing gowns. As she devoured her steak, the dressing gown front slowly worked its way apart, revealing ever more of her fabulous breasts and their dark nipples. I tried to concentrate on my steak but it became ever more difficult.
Suddenly she dropped her knife and fork on her empty plate and sat back which caused her entire front to be revealed. “You know, my husband won’t let me beat my boys when they misbehave. Do you agree with him?”
I swallowed the last piece of my steak and asked cautiously, “Did he say why?”
“Something about teenage boys should be beaten by an authoritative male figure, not a woman.”
“Well, I can see where he is coming from? But I am sure you would do a very good job of the task,” I added hastily.
“Huh,” she grunted and then, after a pause, asked, “Can I come and watch you beat one of them sometime?”
“I don’t see why not, but you would have to come up from London quickly. A beating cannot be postponed for more that a day or so. Otherwise, the link between offence and punishment tends to fade.”
“So are you going to beat me today?” Her question threw me momentarily.
“What on earth for?”
“Well, I am not exactly being faithful to my husband” Her gray eyes starred at me, challenging me.
“I don’t see why not, if you think you deserve it.”
“I haven’t been beaten for a long time. When we were first married, Henry used to make up excuses to beat me, always giving me 24 hours notice. The anticipation was exquisite. I’d have to go to bed and finger myself at least a couple of times, the build up turned me on so much. Afterwards, we had great sex - not up to your standard of course,” she added with a wicked smile, “then the memories gave me endless pleasure in bed for at least a month. I suppose it was just a pity about those two minutes in the middle.”
“I shall be more than happy to oblige as soon as we have had our coffee.” We had coffee and nonchalantly talked about trivia, through a atmosphere that you could cut with a knife.
Half an hour later, I stood up, went into the sitting room and returned with a large leather cushion which I placed at the other end of the dining table and turned around the carver so she could kneel on it. I then went upstairs to fetch the cane. Finally, I instructed Isabella to stand and disrobe. Then I led the voluptuous beauty to the other end of the table, made her kneel on the seat and placed her tummy on the cushion. Her bottom was slightly outsized, but beautifully round. It could only be described as a delightful target for a cane. She stretched her arms out to grip each side of the dining table. I caressed her smooth, firm, olive coloured bottom. It had to rate amongst the very top of female bottoms that I had ever chastised. My fingers moved between her legs, parted her public hair to discover a well of sticky moisture. Again, my thumb massaged her g-spot while my index finger caressed her clitoris. The effect was dramatic. Within half a minute, her whole body was shuddering quite violently. Her lower legs were kicking up and down, while her bottom trembled.
I stepped back to pick up the cane and let the orgasm subside. I tapped her bottom lightly a few times and watched it tense. I decided on the traditional six of the best to start with, to see where it got us. The first stroke placed an angry set of red tramlines right across the middle of her bottom, and elicited a loud yelp. I waited for her bottom to stop trembling before applying the second stroke, which produced a second set, neatly parallel to the first. This time there was no yelp but I noticed her knuckles were almost white from her tight grip on the table edge. I also noticed that she had started to roll her buttocks, a frequent phenomenon as a woman becomes aroused during a caning. The third produced a loud sob, but she was clearly becoming more and more aroused. Slowly and methodically, I applied the last three strokes. I was pleased at the lines across her bottom, not one crossing another. By the sixth, her bottom was undulating and vibrating quite violently. “You can get up now, girl,” I ordered.
“No, please, don’t stop. I’m nearly there.” Who was I not to oblige? I raised the cane again and started the next phase. This time the strokes came faster, the yelps restarted and her body shook more violently at each stroke. It was on number eleven when she almost screamed, her body started to shake violently, her legs kicked up and down, and her eyes rolled up so far that I could only see whites. I suddenly realised how shocking such a scene would have been to the Victorian prudes and why they banned to public caning of women.
I slowly helped her up; I had to hold her firmly as her legs could hardly support her. “Jode! What have you done to me. I need a large Cinzano Bianco with double gin.” After she had recovered, consumed several alcoholic drinks, we headed back to the bedroom. We had sex twice more and she woke me up at eight next morning with the expert use of her mouth. She had virtually recovered her composure by lunch time and rushed off to collect her sons from College at the end of Chapel. As it was my week-end off, I sat and read Tolstoy’s The Death of Ivan Ilyich. I had made a big dent in the book when Isabella returned just before 8 pm.
“So have good day? The boys behave?”
“Yes, not bad but they are exhausting. I was quite relieved when I handed them back, in tact of course.” She paused, lust growing in her eyes. “So lover, strip me like an onion and bed me. I need it. I’d say give me a good thrashing, but I don’t think my poor bottom could stand it.” So it was that we returned to bed. I really lost count of the number of times I fired into her, but her rolling eyes at each time was confirmation of her total love of sex. Somehow I made it back to College next morning to supervise breakfast. At the same time, she headed back to London in the teeth of the rush hour. But, before she left, she made me promise let her know when one of her sons was due to be beaten, so she could come and watch.
That only arose three weeks later when Bixley 3 and Henderson were caught in the swimming changing rooms smoking and drinking whisky. The swimming pool area is strictly out of bounds to all boys, except during the summer term. The head of College caught them and came to me for permission to beat them. He looked visibly disappointed when I refused and said that I would deal with it myself. Next day was Wednesday, CCF (Combined Cadet Force) day, and a quite afternoon for masters not involved. Isabella had enthusiastically agreed to come up and would be there at two. I told the two boys to come to my study at 2 o’clock the next day. No sport or CCF activity was allowed before 2.30 to ensure the boys digested their lunches.
Lady Isabella Bixley was ten minutes early, to my surprise. An even bigger surprise was when she took off her coat; she was dressed very differently to what I expected. The Spanish look was well reduced. Instead, she wore a black figure-hugging dress which just contained her full breasts down to a couple of inches above her knees. A couple of straps over her bare shoulders just managed to keep her breasts covered. Her bare, shapely legs led down to white socks and black high healed shoes. Her black hair was pulled back hard into a long pony-tail. Only concession to her wealth were her large gold, hoop ear-rings with small diamonds spread around the hoops at some inch apart. When she turned to sit down, I realised the dress emphasised every inch of her superb bottom. Also there was no VPL (visible panty-line), suggesting that she was not wearing any panties. I was sure that we would verify this in due course.
Henderson and Bixley arrived a couple of minutes late but I ignored this. When Bixley saw his mother, his draw dropped. “Mama, what are you doing here?” He demanded, sounding shocked.
“Well, if I weren’t, you would probably be rusticated. I’m trying to save your education.” She lied and the boy just scowled. Isabella’s presence had knocked the stuffing out of them and they did not deny that they were in the swimming area or offer any excuses.
“Right, Henderson. Put the chairs in place. You know exactly how they go. It’s not your first time.” He did as he was told while I fetched the cane from the cupboard. He was a tough rugby player, a star of the House Colt’s team. He offered a fit, firm rear end, tightly covered by his regulation grey trousers. I administered six hard strokes across his bottom while Bixley and his mother looked on in awe. When Henderson stood up, his composure had evaporated, his face was flushed, his hair slightly dishevelled, and the start of a tear running down his cheek. “Ok, you can go and get ready for CCF.” He left the room, slowly rubbing his bottom.
“Ok, Bixley. If it wasn’t for your mother, you would be on a train home this evening. Now adopt the position.” Well experienced with the cane, the boy did as he was told, trying to ignore his mother’s presence. The grey flannel stretched across a rather bigger bottom than Henderson’s. In fact, I was surprised to see how similar the shape of his bottom was to his mother’s. “Right, as I am fed up with having to punish you, it will be eight strokes.”
“Oh, Sir, that’s not fair, Henderson only got six,” came from the far end of the chair.”
“He’s not here as often as you are.” Isabella looked completely transfixed as I applied the eight strokes to the boy’s bottom. When he stood up, he looked flushed and clearly crying, “Right, go and put your uniform on,” I ordered. I said to Isabella that I would be back in a minute. I followed Bixley out, through my outer office, to the circular landing at the top of the stairs. Henderson was still there.
“How many did you get?“ he asked Bixley before he saw me.
“Both of you into the dorm and get changed,” I ordered. They disappeared into the dorm from the door opposite. I locked the door into my out office and returned to Isabella.
She looked at me mesmerised as I closed my study door. “You’re next,” I ordered. Without complaint, she adopted the same position as the boys. I raised her dress right up to her mid-back, baring her bottom completely. I was right about the lack of panties. I stood back, cane in hand. By any standard, it was one of the finest bottoms ever presented to me in my study to be thrashed. In response, I could only administer the most accurate six of the best that I had ever administered.
It was not to be. I was too accurate and the end result was a broad red line across her bottom. I had, so to speak, filled in the gaps, so that all the cuts had merged together. The effect, however, was predictable as I administered each hard stroke and waited for her dancing bottom to steady. Each time the rattan landed, there was a yelp, followed by a sob. The firm bottom had limited scope to wobble but each cheek did roll separately. Her legs thrashed up and down after each stroke, kicking off one shoe on the fourth one. By the end, she was sobbing loudly.
I told her to stand up, which she did, and threw her arms around me. She sobbed loudly on my shoulder, rubbing her make-up on my pristine, white shirt. But the pain soon subsided sufficiently for her to insist that we adjourned to the bed room. She knelt her on the end of the bed and there was a sharp intake of breath as I drove deep into her. By five o’clock, we were respectable again and sitting on my balcony sipping coffee. It was actually quite a warm March day, and we watched some of the platoons march through the Quad back to the CCF building. Then to my horror, I saw one of the girls from the Dulcima College tennis committee, Dorothy Wheeler, walking a around the edge of the quad.
“What does she want,” I said my heart sinking.
“Who?” asked Isabella, puzzled.
I pointed to the girl heading to the bottom of my staircase. “She is the rather dopey secretary of the Dulcima tennis team. She’s known as Dopey Dottie because her name is Dorothy. She is always messing things up, then takes six of the best rather than resigning. I think she needs an excuse to come over here, probably seeing a sixth former or even a master in secret, I suppose.”
“You beat girls from Dulcima?” Isabella asked, incredulously.
“Yes, but it is their choice. It the lesser of two evils; being reported to the tennis mistress at Dulcima would a disaster. Probably get them expelled.”
“So you whack them, and take them to bed?” Isabella asked with a wicked smile on her face.
“Some but not her. To me she is utter purity or that is what she portrays.”
Just there was a sharp rap on my study door. “Come in,” I called out as Isabella and I went back inside while Dorothy came into the room. I sat at my desk and beckoned Isabella to one of the large arm chairs. “Well, Wheeler, what can I do for you?”
“Miss Willington asked me to bring these to you. The joint tennis programme for next summer.” She put a pile of leaflets on my desk and I took one, avidly hoping something had gone well.
Dorothy added a bombshell. “A couple of the dates are wrong and Miss Willington is not very happy.”
“How much has the programme cost to print?”
“Seven pounds ten shillings,” she said nervously. (£120 at 2025 prices.)
“And you couldn’t be bothered to check the script carefully for that expenditure.”
“Well, it was a bit late and I rushed it.”
I thought momentarily. “You know the consequences of your incompetence. Six of the best or you and Miss Willington can sort it out.”
“Oh, Sir,” Dorothy painfully pleaded. I just waited. Her elfin face looked pained as she said, “I’ll take the beating, Sir.”
I turned to Isabella. “Mind if I sort this out now.”
“Do carry on,” she said calmly but I saw fire in her eyes.
I stood up. “Remove your panties, Wheeler.” As she raised her regulation skirt, to obey, I went to the cupboard to fetch the cane. This time I would really make her bottom bounce. She was just too agreeable to a caning.
She seemed reluctant to bend over with Isabella watching. “Bend over the back of the couch,” I said firmly, using the cane to point to the red Chesterfield couch that face the open fire. “Grip the front of the seat.” I lifted her skirt and pushed it to her grey pullover, then both of then up a little further. She was now naked from waist to ankles, where neat white socks and sensible black shoe covered her feet. “Pull your body forward so your tummy in right on the back of the couch.” She did as she was told and moved into position.
I glanced at Isabelle who was transfixed by the situation. I raised the cane almost to the ceiling, and brought it down hard, with a loud swoosh and thwack, a technique that gave the cane extra speed. It was a method that I only used for serious offences but it was time that she took the cane more seriously. She yelped as her hands shot back to grab her bottom as she yelped loudly. “Take your hands away,” I ordered firmly after a few seconds. As she did, I saw the angry red line that had appeared across her creamy white bottom. I also realised how round, full and firm it was, in fact, a smaller version of Isabella’s.
The second stroke landed and this time she kept her hands away, her iron grip on the front of the couch. A neat, second, angry, red tramline appeared across her bottom. This might make her pull her socks up, I mused as I raised the cane for the third time, taking the tip to inches from the ceiling. It sped down with a loud whoop to convey my displeasure for her incompetence with yet another angry red line across her bottom. The forth stroke was accompanied by a gritty determination to achieve something with this otherwise attractive eighteen year old. Other women usually created a situation where I caned them as a short cut to seducing me. She shook her head violently as the stroke landed, her normally neat short blonde hair becoming increasingly dishevelled.
Momentarily I considered stopping there as her sobs became louder, but realised that with this girl it would be just a surrender. I applied the fifth stroke and was pleased to see the red lines all remained parallel. Somehow accuracy was easier with this technique. I had striped the bottom in front of me several times before and felt afterwards that she had won, walking away with a badge of honour across her bottom, to show to her lover, whoever he was. Not this time, and so I raised the cane high and brought it down as hard if not harder than the previous strokes. I let her get her breath back before I ordered her to stand up. Her face was flushed red, tears ran down her eyes, her hair was a mess and she was panting. “Right, Dorothy. That’s the last time. Mess up again and I shall simply ask Miss Willington appoint another tennis secretary. Do you understand?”
Dorothy nodded slightly. “Now take your panties and get out.” She did not hesitate and almost slammed the study door behind her. As she did, Isabella shot up and hugged me, before I could even put the cane down.
“When do I get that treatment?” she pleaded. She rubbed her groin against my privates and kissed me heard. What she had witnessed had turned her on to a very light level. I chucked the cane on the desk and pulled her short black dress up to her waist. I rubbed her fabulous bottom and then administered a couple of hard slaps. It was enough to send her into orgasm.
I would have been happy to take her into the bed room and give her another good rogering, but she was clearly mesmerised by what she had just witnessed. Suddenly, she pulled back, pulled her dress right up and placed herself in exactly the same position as Dorothy had vacated. Her bottom was slightly larger, her skin was darker but, beyond that, it was the same play all over again. I retrieved the cane. She went into orgasm almost from the first stroke. Her bottom wobbled more but the lines were similar even though I had even her six a few hours ago. Her legs kicked and shook violently at the cut. I had seldom seen a woman go into such a violent orgasm during a caning. It was only when I administer the last stroke that her body suddenly went completely limp and I could see a thick sticky fluid dripping from between her legs.
As she stood up, I had to grip her firmly or she would collapsed on the floor. As she regained her composure, she headed for the bathroom while I cleaned up the mess on the floor. She had a bath and I did not see her again for half an hour. On return, she could only be described as back to immaculate. I made her another cup of coffee. “If I have an accident on the way home, it’s your fault.” I did not comment. “and if I’m not pregnant after all that, I won’t speak to you again. You didn’t do a very good job last time.”
In fact, I didn’t see her again for some time. It was only a throwaway comment by Bixley 5 during the summer term that I realised that I had been successful. Talking to the boys one evening, he made the comment. “My parents are thinking of moving house. When the new brat arrives, we won’t have enough bedrooms.”