punishment sex stories – Page 8

Caught by Mom and My Aunt

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Mom and dad divorced when I was about ten, it wasn’t a very amicable divorce, so when everything was finalised me and mom ended up living in a small 2 bed apartment near town, and I only got to see my dad about once a month, and on birthdays and holidays. About six months after we moved in to our apartment Aunt Paula moved in with us, to help mom out. For the last five years she shared a room with mom, so I could have my own room. I recently discovered she’s not really my aunt, and being only...

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Tags: nylon, older-woman, punishment

Caught in Mom’s Things

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I was about 6 or 7 when my mom caught me wearing some of her "things". I had taken to trying on all of her stuff that appealled to me, starting when I was about 4 I guess. Perhaps earlier; at any rate, I had great fun trying on her silky panties, bloomers and whatnot. I didn't really like the bras and girdles and all that; they were too rigid and just didn't attract me. But the nylon and satin panties, bloomers, knickers and slips were a turn on, even at that young age. I would put on item after...

Caught Peeping

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I guess I should start out by saying that I grew up a normal boy, interested in baseball, football, and girls. My folks married young, and my big sister Rhonda was born when my Mom and Dad were just 18. I came along just two short years later. Our family lived on a small farm in central Illinois, and the small town I went to school in didn't have a lot of cute girls. Actually, my sister Rhonda was the best looking girl in the school. When I was 13, my Dad was killed in a freak farming accident, so...

Caught Red-handed and Punished

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When I was a teenager, I spent a lot of time alone. I was an only child and my parents were rich and in show business and travelled a lot, frequently being gone for weeks and sometimes months at a time. They never seemed to want to take me with them in their travels, explaining that it would interfere with my schooling, so they left me home with a succession of housekeepers who lived in the house and hired other help to cook and clean. I was kind of a strange, geeky kid and didn't have many friends, so...

Caught With Sisters Panties

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When I was 15 I jacked off all the time. Just like most teenage boys do. One day after school, I arrived home to find that nobody was there. My mom left a note that she would be home in about an hour. Great! I now had some time to jack off without anyone around. I headed to my bedroom, where I stripped down, jumped onto the bed and spread out some porn magazines. I also loved to use a pair of my sisters panties to help in my fantasies while I stroked. My sister is four years older than...

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Tags: punishment

Come in Mommy

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The story that follows is true though I've changed a few key facts (namely the town I live in) to hide my identity. I feel an occasional twinge of guilt, but by and large, I'm pretty damn well pleased with myself. And so is my son! I'm a thirty-two year old mother of one son. John is sixteen. It doesn't take a mathematical genius to figure out that I got myself knocked up when I wasn't quite 16. I dropped out of school and, except for some early help from my parents, I raised John all by myself. Between working...

Carin

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In 1958, when I was twelve, my mother and I went to visit my Aunt Lois in Illinois . The night before we left, she reminded me to pack my suit so that I would have something to wear to church. I hated going to church, and I hated wearing that suit. It was scratchy wool and it felt hot and constricting, particularly in the summer time. I decided not to pack it and see what happened. On Sunday morning, Mother discovered what I had done, and she was furious. Obviously, I couldn't go to church in jeans...

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Tags: nightgown, nightie, nylon, punishment

Brian’s Directoire Knickers Discipline

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It was in the early 50’s when I was at secondary school and my cousin Sheila was at grammar school, that we two cousins used to visit each other and have fun times during our school holidays. I loved to watch Sheila and her friends doing their handstands against a wall. Sheila usually tucked her skirt into the waist-elastic of her knickers when she was doing this and gave us all a good, long look at her gorgeous knickers. The girls’ knickers of the early fifties were rather like adult women’s directoire knickers. However, instead of the lovely, long knicker-legs...

Briefs Encounter 2

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by Nicky London Frank switched off the electric fan at the foot of the stairs to the dining area in his Docklands apartment. Cherry's pettycoats and satin skirt returned to their proper place two inches above her knees. We watched her walk up the highest steps to the upper level. She leaned forward as she reached the top, and we glimpsed for a moment a flash of white knickers from below. The wife of our host, Jenny, followed . The men looked with interest at the straight black seams of her stockings as she mounted the stairs in front of...

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Tags: nylon, punishment, spank, spanking

Be Careful What You Wish For

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Chapter I: Kevin's Shameful Secret As Kevin awoke, the large black nylon panties over his head and face instantly reminded him of the previous nights activities. His right hand instinctively reached down to fondle himself through the silky confines of the pink nylon women's panties he was wearing; as his left hand began to rub the shiney satin cup of the white padded bra that was secured around his chest. His excitement increased upon feeling the stiff nylon of his cum stained panties, as he remembered last nights hour long conversation with his strict telephone dominitrix, Mistress Dawn. Kevin began...

Big Evil Auntie

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David had just finished his paper round and was feeling a little tired being small for his 16 years. As he entered the house he saw his Aunt Sheila in the living room sitting on the settee crossed legs showing her ample curves, a woman of 40, strongly built about 5'10" 180 pounds, brown hair tied in a bun. David stared at his Auntie as he entered, she looked up at him her huge breasts jiggled, David's Aunties breasts were at least 49DD, in fact her figure measured a whopping 49DD-33-48, she had a broad but tight waist, broad back...

Billy and Aunt Karen (part 5)

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At the Dentist Karen had promised his mother that she would see to Billy's dentist appointment in her absence. Since Mary also was due for a check-up, she made both of them an appointment for the same day. Mary could then provide any support he needed. Karen dropped him off at the dentist's office and then when off to attend to the matters of the day. Billy was sure he didn't need any support, but a chance to be with his attractive nineteen year old cousin was worth the trouble. Well, she was due at any minute. Billy was...

Babysitter

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“Mom, do I really need a babysitter? I mean I'm thirteen, after all.” “Probably not, sweetie, but it would make your father and worry less. And besides, don't you think a whole weekend alone in the house would get lonely?” “I guess so. I just wish you guys thought I was more responsible.” “Alright Josh, I tell you what. If you're well behaved for the babysitter and Sam gives your father and I a good report, we'll think about letting you stay home alone next time we go on one of our couple's weekends.” That was...

Babysitter’s Awakening Part 2

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To say the least I was a bit nervous when I returned to my babysitting job the next week. Everything seemed fine though once I got there. After they left I waited awhile, made sure the kids were asleep and went to the bedroom to return her panties. I could just tuck them back in her drawer and this whole situation would be over with. I opened the drawer lifted up several pairs of panties and slid them in. As I held them in my hand, I realized my heart was racing. I couldn't close the drawer. I...

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Tags: masturbate, nylon, punishment

A Visit With Aunty Brown (part 2)

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I knew that my life was going to be much different. I didn't know exactly what to expect but I couldn't help thinking about the things that had been done to me at Aunty Brown's and the way it had made me feel. It was kind of scary but it also excited me a little. Mommy pulled me out of extracurricular activities at school and insisted that I come right home every afternoon. And when I did come right home that first afternoon she sat me down and said we had to have a talk. Mommy said that I...

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Tags: mom, mommy, mother, punishment, spank

Aunt Shows a Little Kindness

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As an only child in a dysfunctional family I got beaten up a lot by my dad and ignored or scolded by mom. By the time I reached my mid teens I had a serious masturbation problem only then I didn't realize how bad it was. I masturbated frequently and compulsively, and was also an exhibitionist. All I got was punishment. My only friend was my aunt Marge, who was in her early fifties then. I would have liked to visit her more often, only she lived too far away to permit more than the occasional visit. But when I...

Aunty Rosemarie’s Directoire Knickers

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Aunty Rosemarie's birthday fell on a lovely sunny day in mid-April. That day, her 'adopted' nephew, Paul, arrived on his bicycle at her large country cottage, to stay for a few days over the Easter holidays. He looked hot and tired as he had ridden about 30 miles, and so after he had left his shoes and outdoor clothes in the scullery, she took him upstairs for a relaxing bath. She had decided that he must rest in bed afterwards, before enjoying the nice meal that she was preparing for him. "Go and undress," she instructed, "while I run your...

A Visit With Aunty Brown (part 1)

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If truth be told, Jane Bronski had always enjoyed seeing her stepson in the nude. Although she suppressed any conscious acknowledgment of pedophilic tendencies, she never lost an opportunity to treat herself to a peek at his prepubescent body. After undressing him at bedtime an unusually long time would usually elapse while Billy waited naked and nervous for his pajamas to be put on. Mommy would scold if he tried to cover himself or avoid her gaze. Bath time was another occasion for indulging her secret needs. She would sit on the edge of the tub with Billy standing obediently...

A Visit to Grandma’s

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"Damn it mom I don't want to go!" I shouted through my bedroom door. "I don't care your father and I are going away and you are going to your grandmother's!" my mom yelled at me from downstairs. At this point I was extremely angry, slammed my door, and threw myself onto my bed. I went to my computer and went to a porn site, as I always do when I'm pissed. I started looking at MILF's and Mature porn. They were always my favorite categories. I took off my pants and started stroking myself. After a few minutes of...

A Visit to the Doctor (part 2)

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We stopped at the drug store and had my prescription filled which seemed to take forever. The silence between my mother and I was almost unbearable. She didn't yell at me or even say a word. But I could tell she was upset with me - or maybe disappointed somehow. When we arrived at our house my older sister was already home from high school. My mom told me to wait for her in the front room while she put her things away. "Son, we need to have a long talk. You cost me a small fortune today, all because...