punishment sex stories – Page 7

Johnny Gets Spanked (part 2)

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On Thursday, after a week of dread and also excitement at the prospect of another trip to the gym teacher, John finally got the expected summons to report to her outside the girls locker room after last hour class. As he walked soberly down the hall, he reflected on his troubling week. He had very little reminder of the soreness in his bottom, yet those first two days he got a stinger every time he sat down. And even more troubling was that was almost always followed by an erection as he remembered the sensual Miss Anderson laying it...

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Tags: punishment, spank, spanking

Johnny Gets Spanked part 3

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John slept little Friday night, lying in bed wondering what was happening to him. When he did fall asleep he had another one of those scary but unbelievibly sexy dreams. He dreamt that Ms. Anderson was the head coach of the Cheerleaders and had decided they needed a mascot. She came to his classroom in the middle of the day dressed in a short cheerleader skirt and tight sweater that emphasised her breasts. She anounced to the whole class that "little Johnny" was to be their new mascot. Everyone, especially the girls, laughed at him and Ms. Anderson grabbed his...

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Tags: anal, anus, humiliation, older-woman, punishment, rectal, rectum, spank, spanking

Julia and Alex Take a Road Trip

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It was Friday afternoon and Julia and Alex were getting ready for a holiday week-end break in a country hotel. Julia was just completing her packing and was adding some extra items of lingerie to her already full suitcase - after all, she thought, a girl had to be prepared! So to her case she added a selection of half and full slips of various lengths and colours, extra sets of bras and panties as well as a few extra pairs of stockings. She shut the case and then turned to get ready for the two hour car journey. As...

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Tags: nylon, punishment, seamed-stockings, spank, spanking, stockings

Julia Burns the Toast

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It was 11 o'clock and Julia sipped her hot coffee and reflected on what had been a disastrous morning. She had forgotten to set the alarm clock the previous night so she and her husband Alex had over-slept. As Alex showered she went down to the kitchen to prepare his breakfast. Somehow she had got distracted and had burnt the toast, setting off the smoke alarm. What a noise. Alex had appeared dripping wet from the shower to discover the false alarm. Because of all the mishaps Alex had only time for a few sips of coffee before rushing out...

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Tags: nylon, punishment, seamed-stockings, spank, spanking, stockings

Julia Gets Spanked

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This story concerns the spanking of my wife Julia and is a true account as best as I can remember. Julia is in her mid 30's, with long brown hair and stands 5ft 5ins tall in her bare feet. We have been married for 15 years and she has been subject to discipline for most of those years. Anyway, about Julia's latest misadventure! Julia had been repeatedly naughty over the course of a week so I informed her that Saturday night was payback time! I am a firm believer in women being as feminine as possible and that the spanking...

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Tags: punishment, seamed-stockings, spank, spanking

Julia Gets the Strap

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Julia and Alex had breakfast the next morning in their room. Afterwards Julia dressed for a day's shopping in the nearest town - Alex idea. Because the weather was warm she decided to wear a long blue floral print dress which had a fitted bodice and flared skirt and which buttoned all the way up the front. Underneath she wore a pale blue bra and matching g-string panties and a pair of black hold-up stockings with lacy tops. On her feet she wore white sandals with three inch heels. Her slip was a very long, pale blue half slip with...

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Tags: punishment, seamed-stockings, spank, spanking

In the Hands of Doctor Palmer

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(A Very Clinical Exam) Not long after I reached puberty, I had the most devastatingly humiliating experience of my life. My step-mother came home unexpectedly early and caught me lying on her bedroom floor, wearing nothing but a pair of her stockings, and sniffing her scent in a dirty pair of her panties which I had removed from the laundry hamper. I was masturbating into another pair of panties, and, right when she stepped into the room, I was at the brink of orgasm. I looked up in horror to see her towering over me. In fact, she was standing...

Jamie Learns His Lesson

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(femdom, spanking, forced nudity, voyeurism, forced panty-wearing, older women) After getting kicked out of a Swiss boarding school for smoking cigarettes and stealing, Jamie had been sent by his parents to a day school in Kent, England for his junior year and placed with a widow who rented an extra room in her home for the occasional foreign student. Mrs. Constance Worthington was a kindly but no nonsense woman in her mid-forties living on a small pension since her husband died in a car crash five years earlier. Unfortunately, Jamie's bad...

Jilly’s Flashing

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by Nicky London I took my new girlfriend to a sixties dance night at a local hotel. We both dressed in some clothes we had in our wardrobes which we thought would be in fashion for that rock and roll decade. There were about a hundred couples there. We sat at a table near the dance floor, and sipped cocktails. A good group played music from that era. The beat was livelier than the modern stuff of top of the pops. A bearded man was jiving with his girlfriend a few feet from our table. As she twirled, I caught...

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Tags: nylon, punishment, spank

Hotel Paradise

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'So there we have it,' said the manager of the Hotel Paradise. 'Your son has admitted the theft and Mrs Crenlee told us all when she caught the boy in her room she wants justice. I have no choice but to call the police.' To the horror of the three people sat opposite him the man reached for the phone on his desk and started to dial. 'No, wait,' said Jon Owens, getting to his feet. 'Surely we can work something out. We can talk to Mrs Crenlee about compensation.' The manager stopped dialing and looked at the worried man...

House Arrest

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It was only a few weeks since ten year old Randy first jacked off. His friend showed him how to whack his Willie and thereby have this incredible sensation, his friend having himself just learned the trick from his older brother. The very first time that feeling swept over him, it frightened Randy, thinking that he was about to go blind or even die or something. But he didn't die, he just felt... well, incredible. When he realized that he hadn't died, gone blind, and that nothing terrible had happened, he naturally wanted to do it again, and each time...

Head Dressing

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The title of this short story is a bit strange but it's a punishment the neighbor lady made up and later I was to suffer. But before I get ahead of myself I will start at the beginning. I was a typical teenage boy living with my step mom in a modest duplex apartment. We had a neighbor lady named Madge who lived in the apartment next door. I was just learning about women and would always notice Madge when ever she would come over to have coffee with Ruth. I always loved the way her perfume smelled, how her...

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Tags: hosiery, nylon, punishment

Grandma’s Little Girl

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I remember growing up in the 60's and how my grandmother wore those open bottomed girdles. She was a German woman who came alone to American as a young girl. She loved fine clothing and wore the best dresses, skirts and blouses; and of course, lingerie was always part of that. She was very open and a bit of a nudist too. I stayed with her many weekends after my grandfather passed away. She wore those girdles, like I said. I loved them, although she didn't wear the full ones that had the bra, only the shorter ones. Many times,...

Got Caught Wearing Panties

4/5 - (1 vote)

When I was in high school, I was good-looking but shy. I got laid a couple of times, and I loved pussy and anything that had to do with it. I would beat off a lot at home. When my parents were gone, I would go into my mom's room and jack off to her panties, wipe up the cum, and stash them deep in the drawer. I guess my mom was suspicious because she snuck up on me in my room and busted in on me. I had her panties on and my legs spread, penis in hand, jacking...

Forced to Serve at my Aunt’s Tea Party

5/5 - (1 vote)

When I was 12 years old, my parents went on a two week vacation and sent me to my Aunt's house to stay with her while they were gone. My Aunt Shirley was my mother's older sister. She was about 50 years old at the time. And she was a very imposing woman. She had large breasts, large hips and thighs, and a small waist that was often wrapped with a belt. She was a very strict woman and she informed me upon my arrival that if she was to be responsible for me, then I would not be allowed...

Foster Sister Panty Tease & Forced Wearing

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She was two years older than me, and she loved to tease and show off. I was in foster care, and living at her house. She always had music on in her room and had the door open or at least cracked. I could watch her from the living room. She talked on the phone a lot. She was often on her bed and I spent a good deal of my time infatuated with her panties. Sometimes they would be peeking from the top of her jeans, or they would be pulled way up above them so they were unmistakable....

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Tags: nightgown, nightie, nylon, punishment, spank

Family Friend Jane

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One summer, when I was 18 years old, my parents went on a vacation. My parents were going to be gone for three months and they didn't trust me to be alone for that length of time. I didn't know how to cook for myself, and I didn't know how to keep the house clean. I had lived a sheltered life where my mom had done all of the housework and I just studied and did my homework. So they had a family friend, Jane, who had just graduated from college, come to baby-sit the house and me. Jane's family...

Fantasy: “Aunt Missy”

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I was a lucky kid. When I was 13, my best friend "Dave" lived next door, and he had a pool, and a bunch of cute older cousins who used to enjoy coming over. But I have to admit, I really had a crush on his mother, "Missy." I called her "Aunt Missy," because she had known my parents when they moved here, and had looked after some of the other neighborhood kids and me, especially after Dave was born. She was 36, but had the face of a 30-year-old and the body of a 20-year-old. There was talk around...

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Tags: big-breasts, huge-tits, masturbate, punishment

First Time Dressing in Mom’s Undies

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I still remember the first time I started wearing my moms undies. I was about 7-8 when I was going through her dresser and found her underwear. She had one drawer just full of girdles and one drawer full of bras. I took out a girdle and the feel and the smell I just know I had to try it on. But it was to big for me. But I always remembered that feeling and smell. When I was about 12/13 I was in the bathroom and on the floor was one of her girdles I picked it up and...

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Tags: punishment, seamed-stockings, spank, spanking

Dressed By My Sister

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By Bra Guy This is a true story that set my life for good in dressing in soft silky lingerie. This happened about forty+ years ago. My dad traveled for work a lot. I was mainly brought up by my mom and older sister. My sister was four years older than me, she (I would love to tell her) is the reason for this story. Also I should add her best friend and next door neighbor. I can always remember helping my mother take the laundry from the dryer and help her fold them. ...

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Tags: nightgown, nylon, punishment, seamed-stockings