punishment sex stories – Page 2

Trouble for Toby (part 1)

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PART 1 Toby Jones was a 14 year old boy, who recently orphaned, had just moved into his Aunt Margret's huge house in Rottingdean near Brighton. His parents had been killed in a car crash just over a month ago and as Margaret didn't need to work due to a huge inheritance and some excellent investments over the years it was thought it right and proper that she should look after her young nephew. Margaret, a 47 year old spinster had no end of male admirers as she was a very striking woman of 5'10” in her stockinged-feet and a...

Trouble for Toby (part 2)

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PART TWO That night Toby had a fitful sleep remembering what his mature Aunt and his even more mature Headmistress had done to him. He was permanently turned on and his cocked throbbed. He had never felt like this before and he wondered why. He still hadn’t realised that his Aunt Margaret had been lacing his drinks with liquid Viagra. He didn’t hear his aunt come into his bedroom the following morning and only noticed when he felt the bed sink under her weight as she sat down. She stroked his face tenderly. "Good morning Toby," she cooed. Toby looked...

The Wicked Landlady

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***Need House to Share:*** ***Woman and teenage son.*** ***Please call 555-1234*** Tommy and his mother Pat had moved in with Mrs. Carol three months ago. Mrs. Carol quickly called Pat after seeing her ad in the paper. When they came over she told Pat the rent was half what she had originally intended to ask. The reason was Tommy. The teenage boy was simply adorable and she wanted him under her roof. Pat jumped at the chance to rent space in her lovely Victorian home, and Mrs. Molly Carol seemed like such a nice, benign older woman. After they moved...

Tommy’s Wicked Stepmother

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"And I want you to be in punishment position when Miss Caulder arrives Tommy". The boy was mortified upon hearing this over the dinner table. His stepsister Julia looked at him and snickered. What his stepmother was saying was that he would have to be totally nude for the visit from his 7th grade teacher tonight. These punishments began shortly after the death of his father. Whenever his stepmother, Sondra, felt he had misbehaved she would strip off all his clothes and humiliate him somehow. After dinner Sondra said "Julia, be a dear and help Tommy...

Tom Part 1

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Tom was a happy teenager who lived in a city apartment with his mom and dad. He attended Washington Junior High School where he would be graduating in three months. He was captain of the school baseball and basketball teams as well as the debating team. Tom was handsome, athletic, a very good student and was very mature for his age. Although he was very popular with both the boys and the girls in school, he had no steady girl friend but did date frequently. One Friday night when Tom was eating supper with his mom and dad...

Tracy Has a Pizza Delivered

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By Slippy Three nights ago Tracy Hunter was out shopping and headed home when she got an idea what to do about dinner. Since John was out of town and she didn't want to go to a lot of fuss, even as hungry as she was, an idea came to her mind that would prove to be one of the best ideas she had in a long time. " PIZZA! That's it," she thought, "I'll have a PIZZA! Humph, maybe I'll get it with extra pepperoni!" Tracy pulled her sporty little convertible into the Pizza Palace and strutted inside. Of...

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Tags: older-woman, punishment, stockings

Travels with Aunt Leigh

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Part 1 Troy was at that age when a growing boy walks around with a, more or less, perpetual erection. And there’s only one thing on his mind:sex….sex, sex, sex, and more sex! It was driving the kid crazy! And it didn’t help that he lived alone with an attractive “older woman” -- his 40s-something aunt, who also happened to be a good-looking blonde. He remembered when his roommate, Patterson, first met Aunt Leigh, at one of those parents’ days at Hillcrest Academy. Standing at the window of their room, Patterson took a moment to eye up the slender blonde...

The Strict Aunt

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Aunt Cecilia had lived alone until the day her sister died in 1955 she was forced to take in her sixteen year old nephew. She enjoyed living alone and was not offended by the term old maid or spinster, she enjoyed her job as a librarian and thought a good book and a hot coffee an enjoyable evening. At 43 she was still quite attractive but considered plain due to her glasses and the way she wore her hair tightly bunched up in a bun and also for her penchant for tweed skirts and sensible shoes. No freedom was given...

The Panty Teaser

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I think everyone, well, every guy, has a partner in their memory that they just never quite got to have. Not the way they wanted anyway. Mine was Debbie. A beautiful and petite brunette. She had what I would describe as close set eyes which ran in the family. She was so short she seemed to be, like, a little girl to me. Smart as a whip but innocent in a way some girls are. I met her in high school and we got together very quickly. I kissed her on our second date and, on the third, she...

The Pink Nightie

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One summer as I was visiting my aunt Sue, I had confessed of my fetish for silky lingerie and we had a sexually charged encounter with her nighties and slips. Not long after that, she had encouraged me to play with her lingerie on one condition; that I ask first and let her know what I'm wanting to play in. She also didn't want me to lie or keep secrets from her. Well I got "punished" for keeping one desire from her. I was helping around the house when I saw it-a long dark pink nightgown. I was helping her...

The Gypsy’s Curse

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Virginia Fearnley was the sweetest, kindest young woman you could imagine. She worked as a sales assistant at a shoe store, but in her spare time she volunteered at a local charity that fed and clothed homeless people. So when she saw the shabby little homeless man, while walking from the shoe store to the car park at the end of a long day, she immediately dug for her purse. She had hoped to offer the man a five-pound note, but her face fell when she found that she did not have nearly that much loose change. "Here," she said,...

The Church Lady 2

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by Stockingtops At dinner that evening, Miss Betty was still wearing her terry cloth bathrobe. The waist was tied with a loose overhand knot that seemed to be working its way looser. As she moved about the kitchen cooking, I set the table with dishes and silverware, constantly watching her, and willing her robe to open further. And that it did. The top began gaping more and more. As I viewed her from the side, I could see her heavy breasts swaying back and forth with her movement. Then she opened one of the upper cabinets and tried to reach...

The Church Lady 4

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by Stockingtops I went to the kitchen to join Miss Betty for breakfast. I had found another nightgown to wear, as she had instructed. It was a long pink nightgown, made of sheer nylon material. My nude body was somewhat visible beneath the material. As I thought of appearing before her dressed this way, my youthful erection returned, tenting out the material in front of me. As I walked into the kitchen with my erection bobbing around, I watched Miss Betty's eyes focus on my erection, which she could plainly see beneath the see-through nightgown. "That's a very nice choice,...

The Aunt and the Nephew (part 1)

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a First Imagining or Some Like It Hot The nephew has already been staying with the aunt for several weeks when she begins to suspect that medically speaking he is not really taking good care of himself. Of course as an adolescent she does not expect him to be a paragon of diligent and conscientious virtue, but she does wish that he would adhere to at least a minimum of healthy habits. Nosy as she is, an inherent trait that has its bad as well as its good sides, she cannot fail to conclude that the nephew is...

The Aunt and the Nephew (part 3)

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a Third Imagining or Cosi Fan Tutti For undisclosed reasons an older niece comes to reside at the aunt"s household. She is almost two years older than the nephew, beautiful and lithe, nubile and finely proportioned, a delight to behold and watch. But being older, she has no time nor interest in her male cousin. The poor fellow is ignored by the niece, glossed over, unnoticed in the daily scheme of things. Now to be sure she is conscious of his presence, but it is an annoyance at the best of times, something she can do nothing about. She...

The Barter System

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Doreen May and her nephew Tyler watched the woman behind the desk carefully. It was Friday afternoon and they were in the office of the Loan Officer at the First National Bank. Doreen had applied for a car loan and now waited to find out if it was approved. The loan officer was an attractive woman in her forties. She had dark hair and deep brown eyes. Tyler also noticed her long red fingernails. She tapped them on her desk while she was on the phone. The 13 year old boy looked away quickly whenever she smiled at him. The...

Tell Mommy What You Want

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Sharon Taylor had a dirty little secret; she was constantly horny and loved to act like a submissive, sex crazed slut! Her fantasies involved being dominated, having all of her dirty little holes filled, and being ordered to do naughty, depraved sexually acts. But, after becoming pregnant at a young age, caused by living out those same fantasies, she gave it all up, moved away, and has since lived a respectable life. She was now thirty-two, but if anything, she was sexier than before. She was 5’ ‘4”, with long black hair, large firm tits, a generous ass and a...

Thanksgiving

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* Danny "Danny, are you sure you have all the emergency numbers?" my mom asked as she ushered my two kid sisters into the car. "Don't worry, mom, I'll be OK," I said waving back to her as she got in herself. "It will only be a couple of hours until dad gets home anyway." That was the plan. Mom's part of the plan was taking Pam and Amy to my aunt's house for the Thanksgiving weekend early, and I would wait at home for dad to get home from work and ride up with him. I was happy to...

The Accident

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Me ?? Oh I was a senior in high school and it was a couple weeks to graduation! I was partying real hard with my friends, drinking...doing a little smoke and getting ready to find the most fuckable girl and do some serious lovemaking. Heh heh. Hey, I waited 12 years for this day!! Sure all of us knew that driving and drinking was a no-no, but how do you tell seniors this? Ya can't! Anyway, it happened. An accident. All I remember was Tom saying we were gonna roll and then I must have blacked out. I woke up...

SUMMER VACATION AT AUNT KAREN’S

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The summer I turned 17 was a very special one that I will never forget. It was spent at the summerhouse of my Aunt Karen, and it helped me discover the full extent of my long time attraction to maternal discipline. Aunt Karen was married to my mother's younger brother, and was hardly 40. She was a very attractive woman, and although young and inexperienced I instinctively sensed that she was much more erotically oriented than most of the women in my family. She always wore make-up, and she dressed in a sensual and even sexy way. And I was...