Crossdressing

The Winemaker Chapter 1

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The Winemaker

by Theresa Black


Copyright 2020

'Mihi nomen est Calpurnia Valeria, sed cum ego natus eram dicitur Sextus, sexta vivum puerum parentes mei, et in tantum puer.' ('My name is Calpurnia Valeria, but when I was born I was called Sextus, the sixth living child of my parents and the only boy.')

I read the neat Latin script on the roll of parchment a second time. No, there was no mistake, it said 'puer' (boy) not 'puella' (girl), and 'Sextus' not 'Sexta'.



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This story is 84 words long.

Butterscotch -7- Breathless

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I’m out with my girlfriend, who happens to be a lesbian, so of course, I’m dressed as a girl. It didn’t make any sense at all, but it had a certain logic. We were just about to step off the curb when some guy stopped in front of us.

He was a bit of a blob but a big one. Six foot two or so, at least 300 pounds, with a Tony Stark beard and ‘stache and Hispanic coloring, he pointed at me. “Samantha!” he said. “You play Sam on ‘Days of Our World’!”

“I—what? No, I don’t!” I protested.

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Butterscotch

by Erin Halfelven



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This story is 108 words long.

The Big Break, Chapter 4

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The First Gig



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The Big Break, Chapter 3

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Named and Sorted

“Why do we need names?” I asked. “Because you have never seen a girl called Stuart.” I was told “Come on back to the library and we can talk about it, I think I need a drink after the relief of seeing you play as girls.” So we dropped our guitars in our rooms and went to the library where we all sat around and tried to relax.



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This story is 71 words long.

Psychotherapy

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A Deep Dive into the Back of the Closet --

A man's therapist leads him on a voyage of self-discovery.
He's not sure he likes where he's headed...

Psychotherapy

by Anonymous



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This story is 31 words long.

Butterscotch -6- Tight

“Is there an animal you think is particularly like you?”

I blinked. What an odd question. If you were a tree, what kind of tree would you be? “An animal? Uh—a chipmunk?”

She turned to grin at me. “I believe it,” she said.

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Butterscotch


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This story is 45 words long.

The Big Break, Chapter 2

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Part Two – The Old Dart

We were told that we only needed to carry our guitars on the plane as amplifiers and drums would be rented while we were there. Lesley had her keyboard packed in a case to go in the hold as well.

We tidied up our affairs and paid our various bills in advance as it was expected that we would be away for three months. Steve sold the Transit cheaply to a friend who needed to move house and the rest of us parked our old cars in Terry’s garage.



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Bridesmaid

Hello I’m Dave and this is the story of how I became my sisters friends bridesmaid... it all started a few months ago.

Chapter 1 Backup

It was my sisters wedding and she all her friends were participating in it and Kate was the flower girl, Kate told me she’d give me 200$ if I was backup flower girl and I said yes because there was no way she would miss my sisters wedding.

Chapter 2 Sick



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This story is 76 words long.

3 of 3 - The Days After

Keeping control.

grakh
 

Tales of Upper Fanir



by Julia Phillips


3 of 3 – The Days After



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Wayward Part-3

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Maddie.jpg
Wayward
Part Three

by:
Enemyoffun

 

Madison used to have this great friend Charlie, they did everything together. Then Madison moved away. Now returning home, Madison seeks him out. The only drawback, Charlie didn't know Madison was a boy.
Madison didn't know Charlie had a secret too.

 




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This story is 46 words long.

The Big Break, Chapter 1

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Part One - Quimble

My friends and I had been to school in Brisbane together, dropped out of university together, got drunk and all lost our virginity on the same night at an exceptionally memorable party. Much of that party did not feature in my own memory but I was told I was no longer a child. We all worked as shelf stackers at one of the big supermarkets in Brisbane, Australia.



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This story is 72 words long.

Butterscotch -5- Shopping

Marjorie said, “We’re dressing my baby brother up as a girl for a party tonight.”

“Not your idea?” Deirdre asked.

I shook my head. “I still don’t remember agreeing to this,” I said.

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Butterscotch


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The Excursion in Spain. Final Chapter

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The Return Trip

The following weeks flew by and my days and nights were pretty well set. Into Madrid in the morning, back via the abattoir and dairy, dropping off the empty churns; unloading the next days’ goods then cleaning out the van.



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This story is 43 words long.

Covid 19 Part 15 Small steps slowly.

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After the existence of Jessica's daughters becomes world-wide news. Terri and Jessica find themselves having to face the music without revealing Terri's gender. They re-iterate their conditions to some un-cooperative fundamentalist religious groups and they do not make themselves popular.



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Butterscotch -4- Trending

“Stop flirting with Double Johnson,” Marjorie said. “Unless you want to be dragged away by the hair.”

Double Johnson?!” I squeaked.

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Butterscotch

by Erin Halfelven

Part 1 - Melrose



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The Excursion in Spain. Chapter 16

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A New Direction

The following week Jordana and I drove the old van into the dealership and picked up the new one. With the number of other runs reduced by one, she was designated as my emergency driver, especially as she was also a she-male and a bit stronger than the other girls. Those churns could be a bitch to manhandle when full.



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This story is 63 words long.

Miss Judged

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Miss Judged

It’s a mistake to believe just in one god – there’s lots of them – Ahriman to Zeus – take your pick! . And it also means that people other than mere humans roam the world. Demi-gods for example. People of Power. And they have feelings. You annoy such people at risk. And with risk comes retribution, revenge and remarkable outcomes …………….. for Tim his self-centred attitude meant a risk of some big changes. And he thought it was just bad luck! Silly boy.




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This story is 83 words long.

The Experiment - Chapter 3

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The end of the summer term, what a week it’s been and so confusing. Chas and I have been fucking like the proverbial rabbits all week since the experiment. The 2nd experiment, although it worked was disastrous, from my sister finding out, to getting stuck in the device, to having to sit to pee and none of my trousers fitting me. Yes, I had to borrow Claire’s old school trousers. Ok, they fitted better but they were still tight, and it wasn’t till Thursday that Chas pointed out to me that I had VPL. Well I had to wear panties because my underpants showed too much.



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This story is 109 words long.

Wayward Part-2

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Maddie.jpg
Wayward
Part Two

by:
Enemyoffun

 

Madison used to have this great friend Charlie, they did everything together. Then Madison moved away. Now returning home, Madison seeks him out. The only drawback, Charlie didn't know Madison was a boy.
Madison didn't know Charlie had a secret too.

 




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This story is 46 words long.

The Experiment - Chapter 2

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Claire looked at me, I knew I’d pushed my luck. Well, how was I to know she’d be home early today.

“Daniel, or is it Danielle now? I’m confused, I’m not angry at how you’re dressed, but I am angry that you’re wearing my clothes without asking.”

I looked at the floor, so ashamed, I didn’t know what to do.

“You wearing panties too? My panties?”



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The Experiment

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Chas looked at me doubtfully, “I somehow don’t think it’ll work Dan” He said dismissively.

“Course it will. I’ve tested it, but I need a second opinion.” I replied.

“I’m not getting my cock out in front of you, that would be gay.” He replied.

“Oh man, sometimes you are so thick. You can take it in the bathroom and try it.”

I handed him a condom which he begrudgingly took. It was a little over 5 mins later when he returned, without the device or condom. “It’s not working for me.” He said.

“What happened?” I asked suspiciously.



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This story is 103 words long.

A Different Key - F Major

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Chrissy

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This story was originally written by Julie, sometime in the 90s and posted elsewhere. I read it and liked the premise, but the ending didn't suit me. So for my own enjoyment, I rewrote the ending. Julie's end had Chrissy transitioning, mine is more like my life. When I was finished modifying the ending, I liked it so much that I couldn’t resist posting it, so…



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This story is 67 words long.

The Excursion in Spain. Chapter 15

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I Didn’t See That Coming

I was taken aback as she had never shown any affection to me before. I asked her what was different now and she said that she could see the man in me coming back to the fore and was starting to think that she wanted to experience some genuine lovemaking for a change.



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This story is 59 words long.

Miss Taken

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Miss Taken

“Don’t steal my panties or any of my clothes.” So I stole a job Sis could have had instead. And then I had to wear panties every day. Nothing unusual about that - if you’re a girl.




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This story is 41 words long.

Miss Communicated

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Miss Communicated

Was I ever going to get inside Ivy’s panties. Chance would be a fine thing.




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This story is 18 words long.

Queen of the Masquerade Ball Chapter 2

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25 or 6 to 4



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This story is 2 words long.

The Excursion in Spain. Chapter 14

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A Country Girl Again

Friday morning dawned, as it usually did, and we had breakfast at the Vegaviana. We were all happy at having another two weeks behind us and the girls were very interested in my deputy. I told them that I had helped him sort out some internal problems and that he was a deputy for our electorate at the farm, so could be a help when it came to any problems we could have. I told them to make sure they kept his visits secret.



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This story is 88 words long.

Butterscotch -3- Salad

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She grinned. “He called you ‘miss,’ I didn’t want to confuse him.”

“You’re confusing me,” I said.

kissy-2-hat-cover.jpg

 

Butterscotch

by Erin Halfelven

Part 1 - Melrose

Chapter 3 - Salad



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This story is 29 words long.

One For The Team - Chapter 9

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Chapter Nine - Endgame

What happened to Charlotte and who did it? Will Archie and Sandra ever find love? All your questions answered and more...



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This story is 25 words long.

Miss Tress

Miss-Tress

Once in a while, a new problem comes to a head.




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The Excursion in Spain. Chapter 13

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A Turning



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This story is 2 words long.

GLOOteus Maximiss Part 3 - Grody to the Max

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GLOOteus Maximiss
Part 3 - Grody to the Max

It was literally a slap heard round the kingdom. Reginald's family did not look happy and neither did the King and Queen. They saw their potential new tourist attraction going up in flames due to their hot-headed replacement daughter.



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This story is 47 words long.

One For The Team - Chapter 8

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Chapter Eight -- The First Fifteen

Archie and Sandra arrive home to find that their marriages, hanging together by a thread, are in dire jeopardy. We learn more about Charlotte's relationship with Quinn and what happened at the cottage that Charlotte liked to call 'One for the Boys' gentleman's club.



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Princess School 2

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Princess School
II. Freshman Fall Orientation
by Jennifer Brock

Kayden Winne’s family is poor so when he gets a scholarship to a prestigious private high school, he is at first happy about it. Then he realizes he knows just enough French to translate the name of the school, L’École pour les Dauphines, to English: School for Princesses. (story squib by Erin)


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This story is 62 words long.

One For The Team - Chapter 7

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Chapter Seven - A Change of Management

May 1986

Charlotte takes over management of the gentlemen's club and turns blackmail into an art form. Archie and Sandra take a trip to Brighton to find out exactly what happened to Charlotte.



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This story is 39 words long.

The Excursion in Spain. Chapter 12

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Strolling Along



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One For The Team - Chapter 6

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Chapter Six -- Smells Like Poison

As the search for her killer commences we find out how Charlotte became enmeshed in the web of prostitution and how she and Wendy created their 'Gentleman's Club'. We also learn that the two detectives assigned to the case are amorously involved with each other.



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This story is 51 words long.

Princess School 1

purchased with standard license from depositphotos.com
     
Princess School
I. Preliminary Interview
by Jennifer Brock

Kayden Winne’s family is poor so when he gets a scholarship to a prestigious private high school, he is at first happy about it. Then he realizes he knows just enough French to translate the name of the school, L’École pour les Dauphines, to English: School for Princesses. (story squib by Erin)


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This story is 61 words long.

"How dare you! I'm NOT Gay!"

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How dare you. I’m not gay!!

I knew at school that I was different. I was called ‘gay’ just for being different – cruel, ugly, untrue. Although I’d admit to being a bit puzzled about, erm, some aspects of life – yeah, alright, sex. Then things really got strange when I was at college and stayed with Aunt Maddie. And I learnt more than I ever expected about girls – in a new and different way. A story in two distinct sections.




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This story is 81 words long.

Butterscotch -2- Traffic

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She watched me with sideways glances as she drove. “I like your hat,” she said with dimples. “It suits you. Not many guys would have the nerve to wear it.”

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Butterscotch

by Erin Halfelven

Part 1 - Melrose



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This story is 37 words long.

One For The Team - Chapter 5

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Chapter Five - The Cottage

Charlotte's story takes a dramatic and life changing twist as her relationship with Robert begins to sour and her trans-friend Wendy makes a proposal that Charlotte accepts. The whole of Chelmsford Private Boarding School is thrown into turmoil with the consequences.



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This story is 46 words long.

Where there's a will ....

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Where there’s a will ….

You can never be sure how changes will happen …. but where there's a will, there may be a way.



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This story is 24 words long.

A Different Key - D Minor

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One For The Team - Chapter 4

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Chapter Four -- Wendy Takes Charge

Charlotte hands over her regular 'house-keeping' duties to William who she transforms into Wendy whilst she and Robert continue to become romantically entangled. They go away for a week so that Charlotte can be herself outside of the confines of Chelmsford College.



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This story is 48 words long.

Hatter’s South American Safari Chap. 4

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The Excursion in Spain. Chapter 11

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More Circles?



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Susie Mondays

I've read through this once, with some slight editing, but it's mostly un-proofread.
Another day in Susie's life, see Saturdays and Sundays before this.


David yawned as he stepped into the kitchen, and gave his mum a sleepy hug.

"I thought you might sleep in a bit today?" Georgie asked her slowly waking son.

"Bad habit this waking up stuff." David replied with a touch of cheek, as he dropped some bread in the toaster and continued, "My alarm doesn't seem to understand pupil free days. Maybe I'll have a nap later to make up for it."



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This story is 97 words long.

Wayward Part-1

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Maddie.jpg
Wayward
Part One

by:
Enemyoffun

 

Madison used to have this great friend Charlie, they did everything together. Then Madison moved away. Now returning home, Madison seeks him out. The only drawback, Charlie didn't know Madison was a boy.
Madison didn't know Charlie had a secret too.

 




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This story is 46 words long.

The Excursion in Spain. Chapter 10

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Going Around in Circles



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This story is 4 words long.

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