Stories

Sandra the Babysitter

Beginning when I was seven, my mom hired a babysitter, Sandra, a pretty girl, in her 20s, who laughed and giggled a lot and worked part time at the bank, to watch me after school at her house. I was usually there 3- 4 evenings per week, while my mom waited tables as a second job. Sandra began to grooming me pretty much right away, insisting that she be present when I took my bath. Which was unusual, because by that time I could bathe and wash myself all over very well, but she claimed all little boys say that,

Tags: babysitter, bath, woman-boy

April 15, 2025 No Comments

Young Awakenings

Chapter 1 I was only 12 when it first happened It was pouring down hard and the field was muddy and wet. I had watched the other boys leave one by one. Most of them had parents who stayed and watched the game. The only thing keeping me from mother nature was a thin soccer jersey with my favorite number on the back. I made my way to a wooden picnic table I used to sit under to wait for my mom when I was younger. I crawled under and wondered how I

Tags: aunt-nephew, doctor, jerking-off-with-panties, medical, nylon, older-woman, woman-boy

September 18, 2024 No Comments

Trouble for Toby (part 1)

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

Tags: anal, anus, aunt-nephew, big-breasts, femdom, huge-tits, lingerie, masturbation, panties, punishment, rectal, rectum, seamed-stockings, spank, stockings, woman-boy

September 18, 2024 No Comments

Trouble for Toby (part 2)

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

Tags: aunt-nephew, big-breasts, femdom, masturbation, nightgown, nightgowns, nightie, punishment, stockings, viagra, woman-boy

September 18, 2024 No Comments

Tommy Gets Taught

Little Tommy Turnell wasn’t so little anymore. At least that’s what his Aunt Susie said every time she saw him at Christmas. Except now that he had recently turned fourteen, there had been some definate changes. The sandy brown haired youth was filling out in some areas. Muscles, teeth, hair. All getting strong and more mature. But it was those other areas he didn’t need to worry about before that were really giving him worries. Tommy was concerned when he found weird hairs growing out of his armpits, and even worse, around his private

Tags: big-boobs, femdom, first-time, teacher-student, voyeurism, woman-boy

September 18, 2024 No Comments

Showering with Mom

When I was a child, I had this problem: Every morning, I would argue with my mom over who would use the bathroom first. We were always in a hurry. I had to go to school; she had to go to work. When I was going first, she was always complaining that I was hogging it, and vice versa. So one day, we got in the shower together. OK, actually she got there first and I kind of crashed. Stubborn as a mule I refused to leave, so we ended up sharing it. But

Tags: exhibitionism, incest, masturbating, masturbation, mother-son, naked, showering, voyeurism, woman-boy

September 18, 2024 No Comments

Shower Check by Mom

This happened when I was much younger, and I have masturbated to this experience many, many times. I grew up in a normal, loving, everyday family with two siblings, older brother and sister. Both my older brother and I have foreskin, which is not that common in the USA where we live. Growing up, mom always told us to pay special attention to keeping our privates clean during baths as she bathed us, inspecting the cleaning job herself. As we got older and took baths ourselves, she did not do inspections that often, but

Tags: bathing, exhibitionism, masturbating, masturbation, mother-son, voyeurism, woman-boy

September 18, 2024 No Comments

Panty Drawer Spanking

I was at my friend Linda’s house. Linda was a year older than me but we were very good friends for many years. Linda and I were going to go swimming that evening, but first she had to baby-sit a couple of neighborhood kids for a couple of hours. Instead of going home, we decided I should just wait at Linda’s house. Her Mom was at work and I could watch TV for a while. When Linda left I waited for 15 minutes to make sure the coast was clear. Deciding

Tags: caught, femdom, masturbation, nylon, older-woman, panty-fetish, panty-wearing, punished, spank, spanking, woman-boy

September 18, 2024 No Comments

Panty Mom

This story is of my most shameful, darkest secret, of how I have seduced my only son and become his lover. Although the attraction between us is mutual, it was my inability to control my own lust that has brought us together. I know it is shameful and wrong, but I don’t know how I could ever stop sleeping with my son now. It all started when I arrived home a little earlier than usual one day, after closing a sale at the real estate office where I work. After letting myself in and

Tags: caught, exhibitionism, first-time, incest, jerking-off-with-panties, masturbating, masturbating-with-panties, masturbation, mom, mommy, mother, mother-son, nightgown, nightie, older-woman, panties, panty-fetish, punishment, spank, spanking, stockings, tease, woman-boy

September 18, 2024 No Comments

Penis Cream

(Editor’s Note: We often tend to overlook the physical harm that the practice of self-abuse causes. Although we are no longer concerned that masturbation leads to vision loss, hair growth, or dermatological abnormalities, we forget that habitual and excessive indulgence often causes penile abrasions and other motion stress injuries. The health-care professional should always be on the look out for the physical effects of masturbatory addiction and be prepared to apply appropriate treatment. – Dr. Margaret Wilson, Registered Genital Therapist) The maddening itch grew worse each day, and Peter was finally

Tags: cfnm, hand-job, humiliation, masturbating, masturbation, medical, nurse, woman-boy

September 18, 2024 No Comments

My Mom’s Boobs

First of all, I love boobs, the bigger the better. I always jerk off to busty women on the internet. My parents know I jerk off, and they don’t mind, and have caught me many times. In my home, it is normal to see anyone one, including me and my little 12-year-old sister, walking around naked after a shower to go and hang the towel up or something like that. One day, when my sister was away on a trip with her friends, I was jerking off in my room looking at

Tags: big-breasts, bras, huge-tits, incest, jerking-off-with-panties, masturbation, mother-son, woman-boy

September 18, 2024 No Comments

My Mom’s Underwear

Life at 14 is not exactly the easiest time in a young person’s life. Especially if there is nothing special about you whatsoever. My name is Alex, and I am pretty much one of the most average teenagers you would ever meet. I’m 5’4″, weigh 125 lbs, and have red hair, and blue eyes. I’m not ugly but I’m far from good-looking. Pretty skinny as well. I make mostly B’s in all my classes, don’t play sports, and I’m in one club. So, I’m pretty much an average typical student. My parents are divorced. My

Tags: caught, incest, jerking-off-with-panties, masturbating, masturbating-with-panties, masturbation, mom, mommy, mother, mother-son, oral-sex, panties, panty-fetish, woman-boy

September 18, 2024 No Comments

My Mum Caught Me

I thought I would share one of the times my mum caught me. Although she did catch me a few times, this is the most memorable. I was 15 and my parents had separated. My mum had a couple of jobs. At her day job she worked in an office and would always wear a skirt and blouse or a dress with heels and tights. Her second job was working in a bar 3 nights a week. It was on these nights that I had my chance to dress up. I would

Tags: caught, crossdressing, humiliation, mother-son, nylon, woman-boy

September 18, 2024 No Comments

My Neighbor Peg

I was the oldest in a family situation that was unique to families of the WWII era. There were four of us but I was seven years older than my next youngest brother. My three younger brothers were born after the war and I happened earlier before my father left for military service during the war. I was a toddler when he left and a big kid when he returned, we never did connect as father and son. I can’t say that my parents didn’t love me for they always were there to give me a word of encouragement when

Tags: doctor, first-time, medical, older-woman, romance, woman-boy

September 18, 2024 No Comments

My Crazy Life

Hello, my name is Michelle. My life has done a crazy flip in the past few weeks. If I don’t write it all down I think I will lose my mind. I feel safe putting it down here because I have changed all the names to protect the (not so) innocent, and no one here would know me anyway. I am 38 years old and in my second marriage. I have kept myself in shape and work out four times a week or more. I brought two kids into this marriage and

Tags: caught, jerking-off-with-panties, lingerie-fetish, masturbating, masturbating-with-panties, mom, mommy, mother, mother-son, nightgown, nightie, nylon, stockings, woman-boy

September 18, 2024 No Comments

My First Exposure (part 2)

“Maybe I can help him get a better look,” I thought as I reached for a napkin on the table and “accidentally” dropped it. “I’ll get it for you Mrs. Tyler,” he said as he bent over to retrieve it. I pretended to look away while he was bent over but saw him turn his head and look up my skirt as he was leaning over. For that moment, I parted my legs and left them open a little longer to give him a clear view of my moist

Tags: downblouse, exhibitionism, older-woman, tease, upskirt, voyeurism, woman-boy

September 18, 2024 No Comments

My First Exposure (part 3)

You’re looking at my panties again Jimmy. Still curious about what it looks like under there?” “I sure am. Gee, you’re almost naked now any way. You might as well let me see you completely naked. Come on Mrs. Tyler, let me see a naked woman for the first time!” He was getting smarter for an innocent kid. Here I was, a 40+ year old woman almost naked in front of a teenage boy and loving every minute of it. But hey, why not. I was enjoying it as much as

Tags: exhibitionism, masturbation, medical, nurse, older-woman, tease, voyeurism, woman-boy

September 18, 2024 No Comments

Mom and Her Drawers

Part I It was kind of a dull rainy Saturday and Mom announced that she would be going out to do some shopping for the afternoon. She asked if I would like to accompany her but up to that point I found her shopping quite boring – and besides, I had other things in mind. But first some background. I was then about 10 years old and by some crazy fluke had recently discovered a unexplainable fascination with my mother’s lingerie and of all things – her shoes. Mom was in her late 20s and although not beautiful, was a

Tags: caught, crossdressing, high-heels, humiliation, lingerie-fetish, mom, mommy, mother, mother-son, nylon, panty-fetish, punished, punishment, spank, spanking, stockings, woman-boy

September 18, 2024 No Comments

Mommy And Billy (and Mrs. Schwartz)

Carol had Billy, her 14 year old son, when she was in her early 20s and so she was still young, healthy, playful and uninhibited and loved having sex with her husband. Recently however, she realized there was now another man in the house, as Billy was growing up and fast. And she’d been noticing that Billy was starting to look at her differently than he used to. And he’d ‘accidentally’ walked in on her recently when she was sitting on the toilet, with her shorts and panties down around her ankles.

Tags: anal, anus, forced-nudity, jerking-off-with-panties, masturbate, masturbation, mom, mommy, mother, mother-son, panties, rectal, rectum, spank, spanking, voyeurism, woman-boy

September 18, 2024 No Comments

Mommy’s Boy

It was bound to happen, 100% inevitable, and now that it did I am much more free mentally welcoming whatever happens next. This story started not too long ago, but the background did as for my formative years revolved mostly around just my Mother and I. Never knew my real dad, my aunt told me that my mother got pregnant on homecoming night her sophomore year in college when she was twenty years old. My aunt thinks that the football team captain is the donor, but thought that my mother probably had

Tags: aunt-nephew, big-breasts, exhibitionism, first-time, huge-tits, incest, masturbate, masturbation, mom, mommy, mother, mother-son, older-woman, punishment, voyeurism, woman-boy

September 18, 2024 No Comments

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