punishment sex stories – Page 5

Out of Mischief

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A spoiled 10-year-old brat of a boy regrets causing trouble in an hotel when he gets an early introduction to strict bondage and humiliation from women who won't tolerate his tantrums. (FFb, ped, nc, mast, bd) *** Bartholemew lay on his stomach, watching daytime TV in a plush, second-floor hotel room. The volume was way louder than necessary, but the 10-year-old didn't care. Bored, he popped another chocolate in his mouth with one hand while he idly flipped channels with the remote in the other. He wondered where Mrs Baxter had got to. He also wondered about that big house...

Nice Neighbor Lady

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After I graduated from college, I lived in an apartment for about five years. I didn't like living in the apartment because of the lack of privacy, lack of parking, and other little things; so as soon as I could afford it, I bought a small house in the suburbs. The house was located in a safe and well-lit neighborhood. Since it was in a circle drive, there wasn't much traffic. My neighbors were real friendly, and I got to meet all of them. There was one lady who lived two houses down from me who I really liked. She...

Nighty-Ware

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Prologue It all started when mom had hosted a Nighty-Ware party for some friends and neighbors in my house. Instead of plastic storage containers, lingerie of all kinds was sampled and purchased. My first sexual experiences came as a result of delivering these purchases to our neighbors. Since then, I've had more experiences, heightening and strengthening my attention and desire for sex. Part 1 ______________________________ I guess I was just destined to grow up horny. At least, that's what it feels like in retrospect. I thought about sex all the time. My dad had a...

My Step Sisters (part 2)

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The girls who had been behind me when I had been punished wanted to see what it looked like when I jumped up from the front. They stood in front of me and Suzanne flicked the crease of my bottom with her finger. Even though it didn't really hurt I jumped up to please the girls. Suzanne repeated this several times making me jump and the other three girls giggle as my prick and balls bounced about. The four young girls spent quite some time examining my nude body both ...

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Tags: punishment, spank, spanking

My Step Sisters (part 2)

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From that day on the girls became even more confident about the way they treated me. On the last day of the school term, a Thursday, Liz told me to go to her friend's house on my way home from school. When I got there I was told that they knew about the magazine I had been reading and that as I had been using girls for my entertainment I would be used to entertain girls during the summer holidays. They told me that I would have to learn how to strip...

My Summer with Cheryl

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Chapter I - Introductions It was the last week of eighth grade, just before summer. School let out on Thursday. Four more school days until the blissful relaxation of my 13th summer. My teachers were all sick of me, and I was certainly sick of them. I made every effort to let them know exactly how sick of them I was. Each of those efforts landed me in the principal's office, although even Mr. Fontaine was too consumed by the expectation of summer to put any real effort into discipline. My parents had never been into discipline either, which probably...

My Understanding Mother

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Well, I wish I could say it was the first time my mother caught me masturbating. But, it wasn't. And, it's not like I was always walking around the house, pulling my crank out and flashing it around, either. I wasn't trying to get caught, but, she had this uncanny ability to want to barge into my bedroom, or need to talk to me when I was in the shower, and as a result, she periodically caught me with my hand around my crank, pumping it toward orgasm. On top of that, I don't know how many times I'd be...

Nancy’s Panty Slave

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**************************** Part 1 I never considered myself an especially aggressive woman, but in the past few months I've discovered the joys of feminine domination by training my boyfriend to be my own personal maidservant! Ronnie is the most servile, most submissive maid a girl could want. No order is too difficult; no whim too small for him to carry out immediately. He hangs on my every word, eager to obey my every command. He is my utter slave and he loves every second of it! You see, Ronnie has a serious panty fetish, which I put to good use in...

Naughty Stepdaughter

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I came home terribly late one Friday whilst Mother was away visiting and old friend for the weekend. I was prepared to face the inevitable tongue lashing from Stepfather, although I wasn't overly concerned. However, it so happened that he had been visiting the local pub and was visibly fuming as I entered the house. He chastised me severely, and as he ranted and raved, his anger seemed to know no bounds. I stood the abuse for as long as I thought reasonable. "I think you made your point," I said curtly, and started walking away. "Just a second, young...

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Tags: humiliation, nylon, punishment, spank, spanking

My Slip Influence

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Undoubtedly the major slip influence for me occurred when i moved out of the family home when i was 19 years of age and boarded with a family of three, a married couple and their 20 year old daughter. The lady of the house whom i shall call Jean would have been in her early forties at the time. The couple accepted me when i applied for accomodation and i moved in. I was somewhat shy and felt a little unsettled being my first time living away from home. With the efflux of time i started to relax and began...

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Tags: masturbation, nylon, punishment

My Step Sisters (part 1)

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My own Mother died when I was eight. For the next five years I lived with my Father. Then, when I was thirteen, my Father met another woman. After a short romance he married her and we moved in to her house. My new Step Mum had three daughters Liz who was fifteen, Jayne who was the same age as me (thirteen) and little Becky who was just eleven. When we moved in my Step Mum told me that I would be subject to the same rules as the girls and...

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Tags: older-woman, punishment, spank, spanking

My Mom’s Panties

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This won't be an easy story to share, but it is something that happened that i will never forget. My mom would roam about the house at times freely in her bra and panties when I was a youngster. The bra never did anything for me, but it was the sight of her in her panties that truly excited me sexually. I must have been around 11 when I started sneaking in her room and poaching her panties for my own pleasure. I'd put them on and masturbate into them. I was careful to wash them and return them to...

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Tags: masturbation, nylon, punishment

My Mother-in-Law (4)

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I was outside wiping my car with a damp cloth getting the dust off the paint when Gladys came out. She stood on the porch in the sunlight. "Well, what do you think?" I whistled a loud wolf whistle at her as I stood admiring her. "You look fantastic, god, all that just to deceive an old fart!" I said looking at her approvingly, also checking for any flaws. The only thing I could see wrong was the yellow dress needed a slip underneath, I could make out the outline of her underwear effortlessly. Just the slightest hint of stocking...

My New Babysitter (part 2)

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The moment I heard sounds downstairs and realized what time it was, I jumped up from my bed, my mind filling with panic. “My parents!” I yelled, “we have to get dressed!” “Don’t worry,” Debby said, taking my arm and pulling me back on the bed, “just relax.” She put an arm around me. “Everything will be fine.” I couldn’t help wondering just why she seemed convinced that everything would be fine. Yet she appeared genuinely unconcerned, completely relaxed and without a worry in the world. I didn’t understand. Here we were, my babysitter and me, the both of us...

My Friend’s Mom

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When I was 12 years old a friend of mine asked if I could spend the weekend at his house. We asked my mom she said ok. I looked forward to being there. I always loved his mom. She was beautiful and always wore dresses and skirts with white slips under them. I remember one day after school my friend and I were playing in the yard he got angry at me and called me a son of a bitch. His mom came to the door and called us inside. She was angry and said I'm going to the store...

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Tags: punishment, spank, spanking

My House Cleaner

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The phone rang and I picked it up. "Hello Mr. M. This is Tina," I heard come across the line. "Oh, hi Tina. How are you?" I asked. "I'm fine, but I just got a new client. Would it be OK if I switched to Friday mornings instead?" she asked. Tina was my house cleaner. She came in once a week for 4 or 5 hours and straightened the place up. I used to be in charge of cleaning the house, or rather, I took on the job when I was disgusted with my wife and kids making huge messes...

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Tags: anal, anus, punishment, rectal, rectum

My Aunt Sandy

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Part1 My first visit at my aunt's. (age 9) I grew up in a very loving yet strict home. I have an older sister (5 years older) while growing up she was not only my friend but also my protector against bullies and at times my parents. On many occasions she would either cover up for me or talked my parents out of punishing me. She was very wild especially for a girl-- for this reason my parents spend most of the time disciplining her and were more lenient with me. I guess she trained them...

My Aunt’s Huge Tits

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It was my first summer back from my freshman year of college; a year that didn't quite reach my expectations of college life. I had tried over and over, and subsequently failed over and over, at courting a girl as a freshman. This meant I went home for the Summer as yet again a virgin, now 19 years old and as frustrated as I could be. My plan for the Summer was to try to reconnect with some old flames from high school when I got back, and make any other feeble attempts I could to lose my V-card, before...

My Best Friend’s Mother

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CHAPTER ONE I couldn't wait for the weekend to get here. My best friend had invited me to go along on a camping trip with his family. It would be Steve and I together with his parents. Steve's mother's name was Pam. She had light brown hair, a slender, athletic body and a very pretty face. She was a nice lady and easy to get along with. I was looking forward to the camping trip and being close to her because I'd always been secretly attracted to her. In my opinion she was the perfect women figure. It was...

My Brother Joey and I

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This is a true story about my brother and I. Joey was 15 and I was 16 when I caught him in my bedroom that first time. I got home early that day not knowing that he had taken an afternoon off from school. I walked into my bedroom and saw Joey standing in front of my mirror looking at himself. His back was to me and he didn't see me. I could see in the mirror that he was rubbing his crotch. But the shocking thing was that he had a pair of my panties on. He...