Crossdressing

Dresses from Diana: A Gradual Feminization Story (Chapter Two)

He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right?

It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something unexpected: beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.

This ~50,000-word novel is available in its entirety for Kindle. This is the second of three chapters that will be shared here as samples. Hope you all enjoy! :)

-Jennifer

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This story is 153 words long.

sissygirl’s journey 5.3

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The first time mom put lipstick on me when she was tucking me in, up until then she was having me kiss my Barbie doll good night, after she kissed me good night on my cheek or forehead.

That night she said sweetie look in your purse which I usually kept on my bed at night with my Barbie doll, grabbing my purse unsnapping the clasp looking inside and there was a new lipstick tube before my very eyes, I was so excited just looking at that wonderful item of girlhood.



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This story is 91 words long.

sissygirl’s journey 5.2

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My nephew was 4 and I was 7 it’s been about 2 years now since mom and I started down my girlhood journey, I know I’m jumping ahead a little but I’ll get back to the beginning after this little side adventure.

Mom loved me and my girlhood telling me years later she did it for me seeing how I loved girl things and my girl feelings she wanted to help me also admitting she enjoyed it too, even loved having two daughters at home, I think my sister being a jock and not really being very girly had mom really enjoying my feminine side but anyway.



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This story is 107 words long.

My Clingy Little Brother

A tired academy student returns home to recharge with her favorite person: her clingy little brother who also happens to love crossdressing!



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This story is 22 words long.

Wednesday Knights -- Chapter 29: Three's a Crowd

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Wednesday Knights

By Melanie E.

A group of friends streams their gaming on Wednesday nights. But not all the action is on the dining room table.



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This story is 26 words long.

sissygirl’s journey 5.1

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I just wanted to say two things.



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This story is 7 words long.

sissygirl’s journey 5

Most of mom’s girl talk with me was when she was tucking me into bed and also a good time to introducing me to other girly things too.

Mom started out being somewhat curious about my interests of girly things and it grew from there, seeing what else I liked and seeing how far she could take it, I think at that point she was really enjoying it.

I always had that girl gene deep inside me and mom pushing me towards girlhood it was more than not a little emotional and embarrassing to say the least but I survived and of course I loved it too.



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This story is 108 words long.

Dresses from Diana: A Gradual Feminization Story (Chapter One)

He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right?

It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something unexpected: beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.

This ~50,000-word novel is available in its entirety for Kindle. The first few chapters will be shared here as samples. Hope you all enjoy! :)

-Jennifer

DFD_V1_3 (FINAL).jpg



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This story is 149 words long.

Whatever Next? Chapter 18

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Whatever Next?
Chapter 18

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Dark Light

I was a teenage girl pop star.



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This story is 7 words long.

Wednesday Knights -- Chapter 28: Mic'd Up

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Wednesday Knights

By Melanie E.

A group of friends streams their gaming on Wednesday nights. But not all the action is on the dining room table.



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This story is 26 words long.

Driven from Normal. (Chapter 34)

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This story is 0 words long.

Whatever Next? Chapter 17

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Whatever Next?
Chapter 17

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Halloween Romance (6)

Halloween Romance
Sequel to
Mischief Night Magic
Part Six: A Lesson on the Perils of Womanhood

Gwendoline took a deep breath as she closed the heavy wooden doors of the girls bathroom behind her. She then started to walk around every square foot of the bathroom. Once she was sure we were along she turned toward me and heaved another long, drawn out sigh.



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This story is 64 words long.

sissygirl’s journey 4

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As I handed mom her purse she always gave me that cute little smile as with her eyes too, she knew I loved her purses while giving me purse time and still being nonchalant about it, a few times she would quietly say you love it, I knew she was just having a little fun I just stood there and didn’t say a thing but yes I did.



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This story is 69 words long.

sissygirl’s journey 3

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So mom really didn’t get upset or mad about anything but she did let you know if she was not happy and her personal lipstick collection was one of them.

Being a very curious little boy and mesmerized by her lipstick I would always find myself looking through her lipstick collection.

Little boy’s can never put anything back correctly or organized we’re just too focused on the prize and her lipsticks being in a pretty tube I would twist those amazing lipsticks out of their tube and spend my time enjoying all the different and wonderful colors and scents.



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This story is 102 words long.

Halloween Romance (5)

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Halloween Romance
Sequel to
Mischief Night Magic
Part Five: A Cup Of Poison

I felt my hips starting to sway this way and that, all in tune with the music the dj was playing as I waited for my vampire to return with my requested cup of spiked punch. As I waited, I felt small beads of sweat starting to roll down my body, making my costume sticking to me. And I could feel the effects of the alcohol taking hold of me. I was sure I was starting to catch the first rising curls of a buzz.



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This story is 98 words long.

sissygirl’s journey attachment

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I love little girls patent Mary Janes.



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This story is 7 words long.

sissygirl’s journey 2

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Hi everyone, before I continue I would like to give a little view into my life at that time.

Mom, what can I say she was a wonderful mother very supportive of everything my sister and I did with all the love she had.

My sis was 3 years older than me and being a real jock she had her own group of friends and from what vibe I got from her she wanted nothing to do with me especially when mom and I were exploring my other side, of course mom always tried to kept it out of sight so nobody got uncomfortable to a certain point as you will see, she was a great mom.



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This story is 116 words long.

sissygirl’s journey

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Being about 5 or 6 I was mesmerized by my mother’s black patent purses and her lipsticks also my sister’s black patent Mary Janes, any chance I had I would go into her closet and reacquaint myself with those beautiful patent little girl shoes.

I would pick them up to get a closer look feeling the shiny smooth patent leather and playing with the buckle just in amazement of how pretty they were, if time allowed I would take them back to my bedroom to wear them.



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This story is 87 words long.

My Roommate's Cat Revealed My Secret

When a nerdy crossdresser’s female college roommate gets a cat, it drags his deepest secret out before her, and she responds far more positively than he could have ever imagined!



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This story is 31 words long.

Wednesday Knights -- Chapter 27: Rings

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Wednesday Knights

By Melanie E.

A group of friends streams their gaming on Wednesday nights. But not all the action is on the dining room table.



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This story is 26 words long.

Halloween Romance (4)

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Halloween Romance 
Sequel to 
Mischief Night Magic
Part Four: Kiss of the Vampire



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This story is 13 words long.

Whatever Next? Chapter 16

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Whatever Next?
Chapter 16

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Family Therapy

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A father and son in crisis reach out to an online therapist who, unbeknownst to them, is actually an artificial intelligence. But after the machine mistakenly deduces that one of them must be transgender—and bound by its programming to maintain its patients' privacy—it ends up feminizing both father and son. When the truth finally comes to light, will this bring the two of them closer together, or tear them hopelessly apart?



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This story is 73 words long.

Halloween Romance (3)

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Halloween Romance
Sequel to
Mischief Night Magic
Part Three: A Cup of Spiked Punch



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This story is 14 words long.

Just Do What The Nice Man Says Honey

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Alex lives with his mother Julie and refuses to get a job or to help Julie pay the rent and household bills. When Julie sees pictures of Alex dressed as a girl she sees that Alex has potential for meaningful employment, even though Alex might not want the job.



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This story is 49 words long.

Driven from Normal. (Chapter 30)

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Driven from Normal .

(Chapter 30)

Simon McKenzie started his week normal enough, but after a series of events he now finds himself standing in a bar wearing a cocktail dress. Chapter 30.



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This story is 30 words long.

Wednesday Knights -- Chapter 26: Skimpies

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Wednesday Knights

By Melanie E.

A group of friends streams their gaming on Wednesday nights. But not all the action is on the dining room table.



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This story is 26 words long.

One to love - Part 3

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"What is my babygirl upto",Ankita had written.
The bulge in my panties increased on reading this.



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This story is 17 words long.

Whatever Next? Chapter 15

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Whatever Next?
Chapter 15

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Driven from Normal. (Chapter 29)

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Driven from Normal .

(Chapter 29)

Simon McKenzie started his week normal enough, but after a series of events he found himself standing in a bar wearing a cocktail dress. Chapter 29.



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This story is 29 words long.

Pink Bear Romance - Part 18

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Pink Bear Romance - Part 18
by Melanie Brown
Copyright  © 2023 Melanie Brown



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This story is 11 words long.

Driven from Normal. (Chapter 28)

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Driven from Normal .

(Chapter 28)

Simon McKenzie started his week normal enough, but after a series of events he found himself standing in a bar wearing a cocktail dress. Chapter 28.



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This story is 29 words long.

Wednesday Knights -- Chapter 25: Bolster

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Wednesday Knights

By Melanie E.

A group of friends streams their gaming on Wednesday nights. But not all the action is on the dining room table.



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This story is 26 words long.

My Time as a Wife

This is a continuation of "Life's Lottery". Steve is delving deeper into his Sarah persona.
This story contains sexual scenes.

I bit the bullet and took some pictures of myself as Sarah. Nothing
outrageous, mainly just myself in various wigs and underwear. Then I
posted them on a few contact sites. I really did not know what to expect,
and to be honest I really don't know why I did it. I think I was seeking
affirmation that I was acceptable as a woman by men.



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This story is 86 words long.

Love Story - Chapter 9.5

The next morning, my wife woke up before me, full of energy. She got up, turned around and climbed on me, while I was still asleep. She gave be a hug, body touching body, her head on my shoulder.

I could smell her hair and feel her softness and warmth, like a blanket on a very cold morning.

"Mmmm", I woke up and yawned, hugging her back, tightly. I placed kisses along the side of her neck, stroking her hair with one hand.



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This story is 83 words long.

Driven from Normal. (Chapter 27)

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Driven from Normal .

(Chapter 27)

Simon McKenzie started his week normal enough, but after a series of events he found himself standing in a bar wearing a cocktail dress. Chapter 27.



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This story is 29 words long.

Whatever Next? Chapter 14

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Whatever Next?
Chapter 14

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Interview

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Sorry for the bad English, but I wanted to get the story out of my head as quickly as possible.



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This story is 20 words long.

Love Story - Chapter 9.4

The next morning, I woke up earlier than my wife. I had freshened up, put my hair in a messy high ponytail and then made us a pot of coffee. I sat on the couch, sipping from a cup. Waiting.

She eventually woke up and sauntered over to where I was sitting, "Last night was something magical. I didn't know we could do that"

"Mm-mmm, yes, it was great", I said, giving her a side ways glance. She was in her night wear, with bed head, hair tousled this way and that. She gave a yawn.



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This story is 96 words long.

Some final notes

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Allie - The teenage years of Alexander Horten

Some final notes



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This story is 11 words long.

June 5- June 11, 2016

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Allie - The teenage years of Alexander Horten

June 5- June 11, 2016



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This story is 11 words long.

Driven from Normal. (Chapter 26)

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Driven from Normal .

(Chapter 26)

Simon McKenzie started his week normal enough, but after a series of events he found himself standing in a bar wearing a cocktail dress. Chapter 26.



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This story is 29 words long.

May 29- June 4, 2016

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Allie - The teenage years of Alexander Horten

May 29- June 4, 2016



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This story is 11 words long.

What Mrs. Pritchard Wrought

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Mrs. Pritchard has a solution for boys who disrupt class. Funny the after-effects a punishment can have...



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This story is 17 words long.

May 22- 28, 2016

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Allie - The teenage years of Alexander Horten

May 22- 28, 2016



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This story is 10 words long.

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