crossdressing sex stories

Tale of a Sissy Named Janie

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Part One – How It All Began Johnny’s father was an inventor who worked covertly with the CIA, but he died tragically in a car accident when Johnny was only six years old. Somehow, Johnny inherited the same love of inventing and tinkering that his dad had, and he was great at installing gadgets around the family home. Johnny’s friends and classmates thought he was great as he would help them fix broke gadgets or help them build projects they were working on. Many people in his neighborhood felt he might become the next Thomas Edison or Elon Musk. But...

The Day I Wore My First Pair of Panties

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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...

Knickers Seduction

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(The story of Peter and Brenda, and their first adventure in directoire knickers) I was on my knees weeding the driveway at Miss E’s house. It was one of the more boring jobs that I had to do, but better than weeding the flower beds. My thoughts were on the new bike I was saving up to buy, and I was trying to work out just how much more money I would have to save when I became aware that Miss E had driven into the drive and stopped a few feet away from me. In those days the front...

Sissie’s Ordeal

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On my fourteenth birthday my mother and I went to my Aunt Cheryl's new house. It was my first time to go there, usually I meet my aunt at my house. I had been dressed for the occasion in my pink dress, the one with the very short skirt, pink slip, pink socks, black Mary Janes, and as usual, I had my pink panties on, the ones with the lace in the back. My mother made me wear a collar around my neck so she could attach a leash, and with that, she led me into the house. Mother said,...

My Start with Auntie’s Things

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My auntie kept her underwear in a drawer in her bedroom. I used to sneak in and pull it open, and run my hands over the neat piles of white slips, bras and panties. The sight of them aroused me greatly. My heart would pound as I imagined myself slipping into them. One day when we were alone in the house she caught me with the drawer open, running my hands over her undies. I was about sixteen at the time. She asked me sharply what I was doing. I mumbled shamefaced that I wanted to dress in her clothes....

My Love of Panties

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I'm a 47 year-old panty-perv from Australia and I've been wearing and jerking off into women's and girls’ silky panties, bras, slips and nighties etc since I was 10. And I'm proud to say I've creamed 100's if not 1,000's of them over the years. I started off by taking my mum's and sister’s worn silkies from the washing hamper and putting them on in bed at night and jerking off like crazy, reveling in the incredible feeling of the silky nylon against my cock and body until I blew my cum all over them. I did this at least...

My Mum Caught Me

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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 usually wait for her to go out to...

My Obsession with Panties

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I've been obsessed with panties from a very early age; probably the first time I noticed the difference between my sisters' silky, lacy undies and my own boring cotton "Tidy Whities." I should probably add here that I have three older sisters, one more beautiful than the other. Mom is rather attractive too; that's where they get it from! Dad left early on, when I was about 10 or 11. When my parents divorced, Mom gathered my sisters and myself and told us things would be different from now on. She said she got a new job and that we...

My Favorite Aunt Fantasy

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This is a pure fantasy that I developed many years ago and concerns what some might consider incest… this fantasy helped to produce many loads of hand-pumped cum in my early 20’s, and actually came about as the result of a real-life experience. Through high school and my early college years I did some part-time work for an uncle who was in the home remodeling business. During Christmas break of my sophomore year of college he was working on the home of his sister. Since he was my uncle through marriage to my dad’s sister, his sister wasn’t actually my...

Mother’s Sexy Clothes

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It was a typical Saturday night in our household. I was preparing for another night in front of the television, while my Mother was getting ready for a night on the town. There was only the two of us in the house since my Father left us when I was about four years old. I was eighteen years old, but due to being skinny and boyish looking people took me for being about fifteen. I was also very shy, especially around girls. I longed to have a girlfriend, but I just did not have the confidence to ask anyone out....

Mother/Step-Mother

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It was just Mom and me. Dad split several when I was twelve. It was hard at first, for both of us. But, even though we never saw or spoke to Dad, he was pretty generous and sent money at least once a month. Mom tried hard to be the father figure, but it really never worked out. She was just too darn motherly with no trace of a masculine side. Because of being constantly in her presence, I adopted some of her mannerisms and speaking traits. Nothing overtly female, but enough to be noticed. Now Mom loved clothes. She...

Milli’s First Lesson

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Janice pulled the Lexus into the driveway, and noticed her bedroom light on. She was positive she turned it off before she left this morning. If her wayward Nephew was nosing around in her room there would be hell to pay. She was already extremely ticked off at having to attend a meeting with his Principal this morning. A meeting which ran on too long, causing her to miss her flight to Chicago. Thank goodness she was able to assure the Principal that Bill would be on his best behavior for the next few days, until graduation. Janice closed the...

Mom and Her Drawers

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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...

Mom Got Me Addicted

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Thanks to a stupid play I was in back in 8th grade, I have had a major fetish for panties. I was playing a role of an Aussie detective who went undercover as a woman to solve a case. It was a lame part and at first the idea of having to wear a dress did not thrill me, but the night before the dress rehearsal my mom, who was a slightly plump small breasted woman was ironing my costumes. She asked me to try on the dress and I obliged. I went into the bathroom and came out...

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Tags: crossdressing, mother-son, panty-fetish

I Made my Son Crossdress in my Nightie and Panties

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Hi friends, my name is Bani. I am a 45 years old woman working in a Govt Bank. My husband works in a top IT company and thus he mostly stays outside the country. I have a daughter who is studying engineering in New Delhi. I have a son who is in high school and is 17 years old. About me, I am a good looking woman who is very traditional and loves to wear sarees while on work. My height is 5.2 feet and my vital stats are 38-34-36. Yes I am a plump woman or you can say...

Girl Time 2

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Amy opened the envelope addressed to her. "Oh mom, it's so great." "What is, Amy?" "Debbie's pool party. It's next Saturday and she invited me to the sleepover afterwards." "Aren't you forgetting something?" Amy screwed up her 11-year-old face and then it hit her. "It's Girl Time!" Girl Time started when her grandmother caught her Cousin Greg going through his sister's panties drawer. Greg was sent for the summer to live with Amy and his Aunt Kay to learn how to be a girl. When his mom got back from Europe she noticed the change...

Forced to Serve at my Aunt’s Tea Party

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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...

First Time in Girly Clothes

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I had to spend two weeks with my aunt while my mom was away on business, and I flew into the airport. My aunt picked me up, but my luggage was lost. The Airline said it could be a couple days before it turns up. So I had no clothes. We got to my aunts house about 2pm, my aunt had to be at work at three, and would not be home till 11. She told me that her ex boyfriend and his teen daughter lived with her a year ago, and the daughters clothes were upstairs in the spare...

Dressing Memory

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In the 1950,'s when I was 12 years old, I grew up in a family of all women, so it wasn't unusual to wander by an open bedroom door and catch one of them dressing up for a date. I always admired the clothes that girls and women got to wear. Such a variety of pretty things, from delicate undergarments to soft, sensuous outerwear. For a guy it was pull on a pair of Jockey shorts and a pair of pants or jeans, top it off with a white shirt and bowtie and you were dressed. A young girl dressing...

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...