punishment sex stories – Page 9

Aunt Jane

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It had been a year since dad passed away and the mother had become deeply in debt. Aunt Jane came to our rescue. She paid off all our bills and decided to move in with mom, sis, and me. Mother tried everything she could to pay the bills some other way before agreeing to let her move in to which I didn't understand. Aunt Jane was in her early 40s and mom younger sister by a year. She was extremely well built and had a body that made my cock stand out every time she visited which was rare. Sis...

Aunt Karen

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Chapter 1 A Bird in the Hand I was always fond of my Aunt Karen; she was a grown-up for sure, but really not that much older than my sister and I. She occasionally baby sat us and we always had a fun time with her. As I got older and started to have "manly urges," I also noticed that she was a very attractive woman. I thought the world of her. That is, until that summer she spent at my house when she brought that world crashing down around me. I was twelve, and my sister, Carol, was eight...

Aunt Karen part 10

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The next morning I awoke before Aunt Karen. I decided it would be best to go to my own bedroom. I wasn't sure what she would remember from the night before, and didn't want to push my luck. I still had Aunt Karen's big white nylon panties on when I got out of bed. So I slid them off and threw them in her closet before going to my room. A couple of hours later, I woke to find Aunt Karen standing over my bed. She was wearing white stockings, a white garter belt, white panties, a big white bra...

Auntie’s Stocking Slave Ch. 01

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It was 1959 and I was eighteen years old. My mother and father had died over a year ago in a car crash and after spending six months in a foster home my Aunty Jean had taken me in as her ward. Aunty Jean was forty-five and quite an attractive woman for her age. Her body was a little on the large side but she had large creamy breasts and stunning legs for a woman her age. She worked in an office in the city and her work attire usually consisted of skirt, blouse, heels and hosiery; she dressed sophisticatedly...

Auntie’s Stocking Slave Ch. 02

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I crawled out the door and, still naked, I made my way down to the laundry to get a mop and bucket. After filling the bucket with warm soapy water I returned upstairs to my bedroom to find that my Aunty had gone. She had left me a note; it read: 'Wear this.........AND ONLY THIS!!! After you have completed your chores stand in the corner facing the wall and wait!' The note was pinned to a white satin apron, edged with lace. Underneath the apron was a set of clean sheets. I balked at the idea of wearing the apron...

Auntie’s Stocking Slave Ch. 03

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After I had finished my homework I came downstairs for dinner. It felt strange sitting at the table dressed in only in my apron and my cocquette. Aunty Jean was still dressed in her mauve satin blouse and white duchess satin classic-style, pencil skirt, flesh-toned sheer seamed stockings and white high-heeled court-shoes. She had refreshed her perfume before dinner and her scent was delicious. My buttocks still stung a little and the cold vinyl of the dinning room chair against my buttocks did nothing to ease the pain. Aunty said very little during the meal and when we had finished...

Auntie Janice

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Burdened by two suitcases. Robert stumbled up the stairs to AuntJanice's front door. He dropped them on the pavement and caught hisbreath. His arms ached and the exercise, combined with the warmspring day had caused him to sweat through his shirt. Taking a deep breath, he rang the doorbell. After a few moments, Robert heard steps behind the door; he straightened up and tried to look his best. The lock turned and the door swung open. His Aunt did not smile as she stood aside and waved her hand to invite him in. "Just leave you bags here," she said...

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Tags: anal, anus, masturbate, nylon, punishment, rectal, rectum

Auntie Mae

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Billy Spencer had mixed feelings when he was accepted at Lutheran Baptist College. His favorite aunt no longer lived in Roanoke and the only person he knew there from past summers was Aunt Dalia's neighbor, Mrs Mae Osgood. The propect of moving into a dormitory far from the security of home weighed heavily on the shy high school senior. Except for summer visits with Aunt Dalia, Billy had never been away from home. Small for his age, the unatheletic boy was painfully introverted and teased at school as a "mama's boy". He was also frightened of girls. While he...

Auntie’s Panties

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Sam was a bright, 20 year old, radiant young man. He far surpassed his classmates in their studies. Spending long hours in his room completing assignments working many hours into the night. Sam had a somewhat clumsily hidden secret. Sam had a great deal of interest in the underwear of his mother and aunts. He was obsessed. Swiping clothes from the house's only dryer, walking quietly and containing his excitement. Sam would even go as far as to reach into the drawers on his mother's bedroom furniture. But Sam was putting that behind him now. He was behind in his...

Auntie Alice 3

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We got Alice home sometime late Sunday, she was now moved into Gladys's house using the bedroom where I used to sleep. Everything went well, except moving her in a car was a real hassle. Her broken leg was in a full cast from her upper thigh to her ankle. Her badly broken right arm, was encased in plaster from her arm pit to her wrist. Her other arm, the cast went from below her elbow to her hand, her thumb was immobilized. She was in a lot of pain and on some pretty strong medication, she slept through the...

Auntie Clem and the Clystere

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Mom and I were having breakfast on the patio on a warm July morning. "Oh, by the way," she said as she buttered her toast. "Auntie Clem is arriving on Thursday." I nearly choked on my orange juice. "She...she is?" "Yes. That's two days from now. I thought I'd tell you well in advance, so you'd be sure to be free for her. She'll only be here through the week-end, and of course she'll want to see you." She smiled, and I blushed and looked down at my food"Oh," I said. Auntie Clementine, my mother's older sister, was my favorite...

Auntie Eileen

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Tommy hung suspended from his wrists in the punishment room set up by his Aunt Eileen to correct her own daughter's naughty behavior but now used for his benefit. He had been caught voyeuristically spying on his older sister while she undressed to bathe and his mother couldn't tolerate any more of this ongoing behavior so she packed him off to her sister's stern care. Eileen looked at the boy and licked her lips. The 11 year old boy looked innocent, almost girlish with milk white alabaster skin and light brown hair. His shorts hung low on his hips...

Auntie Erica Catches Rob in Her Panties

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For a couple of months Rob had stayed out of trouble with his dear Auntie, ever since he was soundly spanked and paddled after the unfortunate stealing money from Auntie Erica incident. Since then, his behavior had been exemplary, and in fact Rob had nothing but the highest respect for Auntie, and sometimes felt he had some sort of a crush on her. Her combination of beauty, lovability and strictness somehow really got to Rob. Sometimes he even fantasized about her in a very naughty and erotic way. One early evening Auntie told Rob she was going to the grocery...

Auntie Grace a Cock Tease

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Let me describe my auntie Grace. My auntie is 42, shoulderlength blonde hair, 5 foot four inches and 115 lbs. My auntie Gracehas an hour glass figure. My auntie has very nice legs. Myauntie has a beautiful face, and lovely green eyes. My auntie Grace is also a very sexy sensual smoker. I was about 25 when this happened. I was staying at my auntie's house on vacation. It was summer and most of the family were spending time outside. My auntie always dressed in tight shorts. My auntie always wore nice fitting blouses. My auntie was always catching me...

Aunt Carmen’s Scented Panties

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My Aunt Carmen was the stuff young boys' wet dreams are made of. She'd been widowed for several years by then. While she'd been married she'd been rather dumpy and unattractive, but when she became single again she ditched her frumpy wardrobe in favor of tight jeans and miniskirts, which made her look irresistible even though she was well past forty. Gone were the "sensible" flats in favor of tall stiletto heels. No more erotic woman ever lived! To Mom and my other Aunts, Aunt Carmen was the subject of endless gossip. They never seemed to tire of speculating who...

Aunt Dorothy

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As a teenager I would fantasise over my Aunt Dorothy's mountainous tits - huge melons that jiggled under her jumper as she walked. She was a mature and imposing lady in her late forties, and had a shapely figure, cinched at the waist with wide patent leather belts, which she often wore with flared floral frocks, and taffeta petticoats. And then there were the v-necked sweaters, accentuating her huge, cone-shaped breasts, through which I could occasionally see the circle-stitching of her brassieres. The swish of her petticoats as she walked, and the click of her high- heels never failed to...

Aunt Emily’s Boarding House

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One summer early in Peter's teen years, his mother sent him to stay with his Aunt Emily, who ran a boarding house for young men in the north of England. Peter was quite excited, both at the novelty of the trip and at the prospect of being more "on his own" for the summer. He had onlyrecently discovered the boyish pleasures of masturbation, and he waslooking forward to having opportunity to explore them out of thesupervision of his parents. Little did he know that his mother'ssuspicion of his secret activities was the prime motivation for sending him to the care...

Aunt Emmaline

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My Aunt Emmaline practiced petticoat discipline on me from the time I was eleven years old, which meant at age 13 I was quite used to being dropped off at her house by my mother on a Saturday morning to spend what we called a punishment weekend. That meant I had to take off my boy’s clothes the moment I arrived, stand completely naked before my aunt, and let her dress me as a girl. My dress for the entire weekend was nothing more than a light cotton little girl’s frock, pink or white lace panties, and some shiny...

Aunt Helen

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Helen Strangers was a fine-looking woman in her mid-thirties. A woman of independent means, she lived in some style in a large Edwardian country house set in its own grounds. Inside the house was exquisitely furnished, and she was served by a cook-cum-housekeeper, the taciturn Miss Pring, and the handyman-cum-gardener Allan. When Darren's father got the Consul's job, Helen offered to look after her nephew. It seemed the ideal arrangement since Helen lived not far from Darren's exclusive private school and already saw the boy on a regular basis. Above all the two seemed really fond of each other. So...

Ann 2 – The Secretary Gets a Spanking

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It was the following Sunday and Ann's bottom had recovered from the thrashing James had given her with the cane. Through the course of the week the stripes on her bottom had gone from purple to yellow and now they had almost faded. However she knew that she would have to return to James apartment tonight, one week on, to receive the rest of her punishment. She had really been careless not to check her stocking seams. James always spanked her if they were not straight. It was 6 o'clock. She was not due at James until 8 o'clock. Suddenly...