Jamie & Mrs. Gray

4/5 - (1 vote)

I'd been renting a room from Mrs. Gray for almost 4 months. She was an older lady, a divorcee who looked similar to my mother in many ways. They were both tall, almost a full head taller than I stood. They were both sturdily built with broad shoulders, big boobs, wide hips, and thick thighs. And like my mother, they were both kind, but strict at the same time and could become firm if the need arose. Affectionate is not a word I'd choose to describe either of them. Even more, Mrs. Gray never liked to repeat herself or be...

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The Day I Wore My First Pair of Panties

4/5 - (1 vote)

Today started out just like any other day in my life: with one exception. Today I wore girl's Panties for the first time. My Mommy decided to punish me for acting like a sissy , so she pulled my pants down, ripped off my jockey shorts and into a pair of pink, frilly panties I went. My mommy was hysterical laughing at the site of me all dressed up in my cute little panties. She said that she couldn't wait to tell all of her girl friends that her little boy looked great in panties. I shuttered at the thought...

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The Cabin

5/5 - (1 vote)

Tom was headed to his Aunt Susan and Uncle John's cabin in the north woods with his mom and dad for two weeks. He had mixed feelings about the trip. He'd miss hanging out with his friends, but the "cabin" was actually an ultra-modern house next to a beautiful lake and he'd have a very cool room all to himself. And even though his aunt, who was a nurse, was something like 40, she was totally hot. She has a lean, athletic-type body that made his heart beat a little faster just thinking about. And it wasn't like he had...

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Bath – a Mother and Son Story

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Carol hadn't had sex since her husband Ray had left more than four years ago. Strange as it sounds, the thing that finally brought her celibacy to an end was her son breaking his leg. *** Mike was 14 and a natural athlete. Whatever sport was in season, he played. He was good at all of them and great at some. It was at a baseball game where an inexperienced player slid into second base, spiking Mike's left leg and breaking it. There was knee damage as well, so Mike was now laid up with a cast almost hip to...

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Roger’s Auntie Becomes His Mummy

5/5 - (1 vote)

I have always been a fairly mild and meek person and would never get involved in any sort of confrontation and for that reason people seem to treat me rather badly. As an 18 year old in his last year at school I had begun to rebel a little and although my parents told me off a lot I tended to ignore them and do what I wanted to anyway. One day just as term was about to finish my mum said that I was going to spend the summer holiday with my auntie Dee. She said that as I...

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Getting Spanked by Mom (part 1)

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Let me first start describing my family. It's just Mom and me. Dad cheated on Mom just after I was born, and Mom threw him out. He disappeared, and I guess he did not care about me. The feeling is mutual. I never recall Mom dating anyone, but always wondered why. I was too shy to ask girls out and my Mom kept pestering my about it. However, I enjoyed being just the two of us. I was always the man of the house, but Mom always treated me like her little boy not wanting me to grow up. For...

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The Start of My Panties Punishment

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A lot of boys seem to have drifted into a regime of punishment at the hands of their mother, aunt or perhaps a dominant wife or girlfriend. For them it’s perhaps hard to identify the moment their lives changed and they became either a sissy. Not so for me. Looking back I can identify the precise incident which lead to me being what I am today – a submissive sissy, meekly accepting his wife’s every whim. It was around the end of the Christmas term in my final year of junior school, so I would have been ten years old....

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Jamie and Mrs. Gray

5/5 - (1 vote)

I'd been renting a room from Mrs. Gray for almost 4 months. She was an older lady, a divorcee who looked similar to my mother in many ways. They were both tall, almost a full head taller than I stood. They were both sturdily built with broad shoulders, big boobs, wide hips, and thick thighs. And like my mother, they were both kind, but strict at the same time and could become firm if the need arose. Affectionate is not a word I'd choose to describe either of them. Even more, Mrs. Gray never liked to repeat herself or be...

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Aunt Mary’s Fun Day

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  I got my first enema one summer when I was visiting my Aunt Mary. It was a hot September day and I spent the morning working outside for my Aunt. I was having a hard time concentrating as I had been constipated for a week now. I knew my Aunt Mary would be the only one that could make me feel better. After lunch, Aunt Mary asked me if I'd had a bowel movement today. She told me I had to have one today, period. I knew I needed something to help me but had no idea what was...

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An Indecent Aunt

3/5 - (2 votes)

Tommy Parks could barely believe his eyes: as his Aunt Jennie stooped over in her garden, Tommy could see her butt. Not just the shape of it; his aunt's cut-off jeans shorts were on so loosely Tommy could see from her mostly bare back all the way down her crack. The more she bent over in front of him, the more creamy white ass flesh he could see. Tommy tried not to let his aunt see him sneak furtive glances down her smoothly shaped backside; as he peered he could see, much to his surprise, that his aunt wasn't wearing...

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12th Birthday Medical Exam (part 8)

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In Chapter 1, we met Family Practice Doctor Marcy Harris. The 54-year-old woman with two grown sons of her own was a respected Doctor who gave thorough exams. In the first six chapters, she examines several boys of varying ages, and in Chapter 7, she hosts a charitable day in an underprivileged neighborhood and uses one of her nurses" sons to demonstrate how to properly examine and spank a young boy to a group of moms and guardians. Erica Jimenez was one of the women attending Dr. Harris"s presentation that day after seeing a flyer on her college campus. While...

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12th Birthday Medical Exam (part 5)

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In chapter 1, we met Family Practice Doctor Marcy Harris. The 52 year old woman with two grown children of her own was a respected Doctor that gave thorough exams. In the first four chapters, she examines two boys, Kyle Roberts and a new patient Michael Sanchez, 11. Our story continues with Dr. Harris seeing a patient, Wayne Andrews, a boy that she has known since he was one year old. Wayne Andrews had very mixed emotions this summer morning. On one hand, the boy was excited to be on summer vacation and it was his 14th birthday. On the...

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Slutty Best Friends

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There are three things I must tell you about Martin. First, he's a tall, gangly youth, lean and fidgety, with a shock of black hair, earnest brown eyes and cute button nose. Second, he's a perfect brat, mucky minded and insolent with it, and third, I had the misfortune to be his aunt. He usually stayed with me for a week or two during the summer holidays, to give his mother a break. She had younger children to cope with, and Martin's slovenly ways and cheek were a constant source of anguish to her. I lived alone, and was better...

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You Have No Idea (memoirs of a panty thief)

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I have previously chronicled in these pages how my wicked little addiction began in my Mother's closet and quickly graduated into my first panty theft. I have also shared the sweet memories I have of Susan, the panty heiress, and my delicious descent into nylon delirium with her massive collection of confections. Perhaps the time has come for another installment. What follows here is a random collection of memories, philosophical musings, and (mostly true) stories. My bliss at securing my first sacred pair from the perfectly twiggy Sheila was absolute. I worshiped at their altar, day and night. I studied...

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Wearing Mom’s Panties & Slips at 6

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Wearing Mom’s Panties & Slips at 6 I  began masturbating at the age of 5, often lying on my stomach and rubbing the front of my cotton briefs with my palms.  The feeling was very good but always made me feel very quilty and shameful afterward. I discovered sis' panties at 6 just bcfore she married and moved out. I don't know what it was but the very sight of panties just commanded my attention and gave me a funny feeling in the bottom of my stomach. I'll never forget seeing panties for the first time. My sister was putting laundry away...

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Witches Panties (or How I got my Tits)

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By Ginger I had been married for about a year before my wife, Nichole, discovered my little secret.  Initially I thought she suspected that I only loved her panties, but the reality was that I loved all feminine under-things.  Yes, I love her panties, especially her used panties, but I also had a pretty extensive collection of my own, and not just panties.  My stash included bras, pantyhose, a corset, stockings, high heeled shoes, breast forms, and of course lots of panties.  I had kept this hidden from her while we were dating, but it would be harder once we...

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Trick or Treat

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Henry felt like an idiot. Here it was, Halloween. All his friends were out egging people's doors, throwing water balloons at cars, and just generally causing trouble -- exactly what every 14 year-old boy SHOULD be doing on this day in a small town ... exactly what he should be doing. Instead, thanks to his mom, who had to work an extra shift tonight, he got stuck walking his little sister Trish around for trick-or-treat. It just wasn't fair. He loved his sister and all, and she wasn't nearly as much of a pain in the ass as some 8...

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Tutor Tits

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My wife, Judy, and I have been engaging lately in exposing her naked body to all sorts of men as foreplay to great times of sex between us that she likes to use as her excuse to do it. She has long been an "innocent" exhibitionist that enjoys being braless and can fluster even good friends or neighbors when we're out working in the yard where she will tease them with close-up views of her nipples poking into the thin tops that she deliberately chooses to wear when she knows she might get caught. Our intentions have always been that...

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Understanding Auntie

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    Synopsis: While spending his summer vacation with his aunt Madge, Timmy gets caught in the embarrassing situation of being discovered wearing her lingerie! She knows he probably won't quit his little "hobby" but comes up with a unique plan to keep him out of her things for the rest of the summer! "So that's why the lingerie in my dresser drawers always seem like somebody's been rummaging through my things!" My aunt said as she undid my pants and pulled them down to reveal I was wearing a pair of her lace trimmed, pink satin panties!  She then...

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Unexpected Exam

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Wednesday 2:00 PM. I was 16 at the time. Sitting in my 7th. period Civics class. My girlfriend Misty Jones was in the desk beside me. I sat there undressing her with my eyes. Just one more hour and the two of us would be on our way to her house. And I’d be undressing her for real. Her mom is single and usually works late. And gives us hours of quality time to do as we please. Of course she doesn’t know, but does have her suspicions. Motherly instinct I suppose. Or that’s what I thought. Unfortunately things went...

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