Crossdressing

A First Time For Anything

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After a chance meeting with his boss's wife, Gregory and his boss share a first time experience.



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This story is 17 words long.

Wednesday Knights -- Chapter 34 and 35: Finale!

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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.

A Needed Change - Part Four

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A Needed Change - Part Four

After demonstrating ‘the kiss’ to Steph, I hung around for a bit, chatting to her mostly while Rich just channel surfed, but we ended up painting each others nails with a nude polish and I absolutely loved it. It seemed to make my fingers look longer and I ended up staying the night, sleeping on a futon in a borrowed tee shirt and shorts.



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This story is 70 words long.

Whatever Next? Chapter 24

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Whatever Next?
Chapter 24

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Phillipa Scoff Part 2

When Phillip had got home and explained to his wife what had just happened. She had just rolled her eyes and carried on getting ready for a girls dinner she had planned. Phillip had a brief conversation with his agency and they simply repeated what Stephan had outlined at the meeting. Phillip had spent his time over the next few days mentally preparing himself for just how silly he would look presenting Loose Women, and Ruth’s teleshopping shows on QVQ as a presenter who was used to being on much larger shows.



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This story is 93 words long.

Phillipa Scoff Part 1

Phillip Scoff strolled down ITB’s studios, briefly smiling at one of the members of the crew who rushed by him. He had given decades of his career in entertainment to the tv broadcaster, capturing the attention of millions of Britain’s daytime tv watchers on This Morning. Himself and his much adored co-presenter Holly Wibbly, had won the show endless awards.



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This story is 62 words long.

sissygirl’s journey 6.1

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My relationship with my auntie we where always close and loved each other she treated me like her son but when she met sissy things changed from that first weekend, it was kinda like love at first sight all over again but would definitely be going down a different path.



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This story is 50 words long.

A Needed Change - Part three

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A Needed Change - Part three

Monday at work wasn’t the first time I felt a little weird after everything had seemed to ramp up for me, but I was definitely distracted and this time it had nothing to do with being in, well, clothes that were starting to feel less natural to me. At the end of the day when I gave Steph a lift home, she told me I should probably make a doctors appointment as it’s clearly on my mind, and assign as I had changed into my sweats, I gave them a call.



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This story is 99 words long.

If It Was Your Husband 9 & 10 of 20

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9 & 10

Gaining a better look & More exposure

Alex snaps back at Carrie when she suggests that he let his hair grow longer and that he should go to her hair dresser to manage it while it does.

“You really need to let your hair grow out some more, but in the meantime, I think we should get it styled. You know different parts of your hair grow at different rates and for it to look right as it grows out, someone who knows about such things should take care of it. Just a little trim about every two weeks, to keep things growing even.”

“What!? Are you suggesting we tell someone else about our experiment? …Or did you already talk to your hairdresser?”

“No, but I was thinking I could tell her that you wanted to recapture your youth and grow your hair out, but that I put my foot down on you looking scraggly like some kind of 70’s hippy. Then I could ask her if she’d oversee your journey into the past.”

“I just don’t want to deal with another of your cronies knowing that I’m letting you feminize me.”

“Oh Alex, I’m not feminizing you. I’m guiding you as you discover your feminine side. You know all men have a feminine side, just as all women have a masculine side.”

“Yeah, yeah, we went through that before. Call it what you will, but all I know is I’m discovering a lot more of my feminine side than I could have even imagined was there.”

Alex gets the special order bras and loves the experience of wearing them and even enhances the look.

He also goes to the salon to have his hair styled and finds Janet, the hair tech, to be a really professional and friendly woman that is going to be capable managing his quest for longer hair. He comes away feeling assured that this time Carrie hasn’t betrayed his trust.



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This story is 333 words long.

Willow

Caught dressed by his best friend, what will this mean for them?



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This story is 12 words long.

A Needed Change - Part Two

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A Needed Change - Part two

On Saturday I had no plans, and knowing it would be busy out I had no desire to go out there either. I made myself some French toast for breakfast and just sat about relaxing, wearing a simple cotton dress and just hung out really. While walking from one room to another I passed the intercom which buzzed, and without thinking I picked it up, cursing myself for doing it as I said hello.

“Beck, is that you?”



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This story is 84 words long.

Wednesday Knights -- Chapter 33: Man Down

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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.

Relevant Dress Code

As soon as I woke up I knew that this would be another scorching hot June day. It also meant that the boys’ decision to stage a skirt-protest against the dress code not allowing shorts would be implemented that day. I smiled. I had the most dashing skirt I was planning to wear. I decided to really girly up. Instead of having my long blonde hair in a low ponytail I decided to let it flow down to my shoulders over my ears. I picked my favourite white blouse and some thin tights. The tights somewhat negated the purpose of the protest but I couldn’t resist.



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This story is 107 words long.

sissygirl’s journey 6 lipstick girl

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Yes I’am a lipstick girl, from the very beginning I was mesmerized by my mom’s lipsticks and at that time all the magazines had pretty women with amazing makeup and of course amazing lipstick lips, this is a little embarrassing but as a very young boy 5 or so I would find myself kissing those pretty models in the magazines and enjoying it very much so I guess that was one of my fetishes to be forever in my life, lipstick kisses that is lol.



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This story is 86 words long.

Whatever Next? Chapter 23

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Whatever Next?
Chapter 23

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

A Needed Change - Part One

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A needed change - Part 1

I sat there and looked at the surprise on her face. I think she was expecting me to be nervous, not do what I just did, but I wanted to show her I was serious and it was the easiest way I could think of to prove it. I took hold of the end, pulling it back and looked at her, then I did it again, taking my hands away and waggling my eyebrows at her. I hoped she could see I was smiling, but instead I saw the door open and her boyfriend, Rich stand there looking at me.



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This story is 105 words long.

Pete's Vagina -41- Game Face

Pete needs a makeover....

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Pete's Vagina
41. Game Face
Erin Halfelven


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This story is 10 words long.

Gina’s Unexpected Adventure, part the third.

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Gina’s Unexpected Adventure, part the third.

“Yes please, tea or white wine.”

Melissa looked at her and waggled her eyebrows, “aren’t you underage to be drinking….”

Gina looked affronted, “no I am….” And then tailed off as she looked down to remind herself how she was dressed, she blushed a little, and then grinned.

“Well you could always spank me for it….”

Melissa grinned back. “And of course, I should be spanked for subverting a minor….” And grinned broadly.

“One moment I have just the thing,” She added as she went into the kitchen.



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This story is 96 words long.

If It Was Your Husband 7 & 8 of 20

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If It Was Your Husband
By Patricia Marie Allen

7 & 8

Exploring my feelings & On the fast track

Alex’s curiosity gets the best of him and he decides to explore women’s androgynous out in public without Carrie prompting him or having her along. He doesn’t quite have the guts to include a small bust line, so his bra cups lay fallow. On returning home, he tells Carrie where he’s been and how he’d dressed on purpose almost bragging about what he’s done.

Carrie notices that he’s not put anything in the bra cups and corrects the deficit. She then proves to him that he should have gone with the enhancement because not even people who casually know them notice anything. Carrie spring boards the incident and Alex finds himself in a lingerie shop. This leads to a whole new definition of “out and about.”

From there things get a little out of hand.



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This story is 160 words long.

Wednesday Knights -- Chapter 32: Bwahaha!

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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.

The Cutest Girl(y Boy)

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I twirl and strike a pose. A dozen different cameras go off, capturing me from every possible angle. I smile the sweetest smile you could ever imagine, and blow a kiss to the camera. The cameraman nearly passes out from the excitement.

My name is Candy. Well, that’s my stage name, anyhow. I’m a 12 year old boy, but I’ve been modeling girl’s clothing for about a year now, and I’ve made quite a name for myself. Everyone wants “The Cutest Girl(y Boy)” in their magazine! I even do fashion shows for big companies, and my youtube videos get tens of thousands of views.



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This story is 109 words long.

Whatever Next? Chapter 22

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Whatever Next?
Chapter 22

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Orphan Petal 4

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Orphan Petal

May 2023 - Part 4

Shirley is bitter and mad at the world. His new life will change him in ways he never knew possible. Can he find himself and be happy? What does he not want to tell the world... it himself?

This is a spin-off to the story "The Teenage Years of Alexander Horten"



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This story is 56 words long.

Orphan Petal 3

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Orphan Petal

May 2023 - Part 3

This is the story of an 11-year-old who loses his parents and is now an orphan. He is bitter and mad at the world. His new life will change him in ways he never knew possible. Can he find himself and be happy?

This is a spin-off to the story "The Teenage Years of Alexander Horten"



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This story is 61 words long.

Family Therapy: Nonbinary Reflections

Bonus scene! Bonus artwork! Bonus--well, it’s just those two things, actually. But that’s still pretty cool! After Fraylim got inspired to do some additional artwork for “Family Therapy,” I wanted a way to share it with you. So, to avoid undercutting the original story, I’m offering this as an “alternate ending.” Here, we see a young trans woman on the verge of an important decision as she muses on the unusual road that her life has taken, and the role that her father-turned-mother played in it...and may yet play in the future.



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This story is 96 words long.

Pink Bear Romance - Part 19

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Pink Bear Romance - Part 19 - FINAL
by Melanie Brown
Copyright  © 2023 Melanie Brown



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This story is 13 words long.

If It Was Your Husband 5 & 6 of 20

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5 & 6

Happy New Year and Putting it to the test

Christmas has come and gone. Alex spent four glorious days wearing the soft luxurious fabric and deliciously feeling lingerie. Getting ready for work he almost doesn’t think about it as he reaches in the lingerie drawer. As a result, he has to admit to himself that this thing is growing on him. He tries to fight it and finds that he regrets his decision to abstain.



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This story is 77 words long.

Being Beatrice, Chapter One: An Excess of Spirits

A theatrical performance goes off the rails. Can it be saved?



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This story is 11 words long.

Orphan Petal 2

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Orphan Petal

May 2023 - Part 2

This is the story of an 11-year-old who loses his parents and is now an orphan. He is bitter and mad at the world. His new life will change him in ways he never knew possible. Can he find himself and be happy?

This is a spin-off to the story "The Teenage Years of Alexander Horten"



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This story is 61 words long.

Wednesday Knights -- Chapter 31: Pillow Talk

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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.

Orphan Petal 1

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Orphan Petal 1

May 2023 - Part 1

This is the story of an 11-year-old who loses his parents and is now an orphan. He is bitter and mad at the world. His new life will change him in ways he never knew possible. Can he find himself and be happy?

This is a spin-off to the story "The Teenage Years of Alexander Horten"



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This story is 61 words long.

Whatever Next? Chapter 21

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Whatever Next?
Chapter 21

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

Daisy and the Phantom Nurse (4)

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Once I entered the cafeteria I paused and looked around. I  then closed my eyes and slowly opened them. I was ready for a nap, but food had to come first. So shrugging my shoulders I walked over and joined the line for the hot food. The other doctors and nurses in line only peered at me, none of them said a signal word. I guess most of them wanted to eat and go home. Which suited me just fine. Or on the other side of the coin they wanted to get a quick bite of breakfast before starting their day.



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This story is 101 words long.

My Mom, My Cousin, and Me: Part 2

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*** AUTHOR'S NOTE *** Hello, I'm Hibari and thank you for all the wonderful reception on my first story! I saw a lot of comments to continue the story, and that's exactly what I've done here. I have a lot of great ideas where I can take this story in future installments, but in order to explore a more interesting narrative I will have to delve into some more mature topics. For this particular entry I wanted to give a CONTENT WARNING in regards to some of the topics that you will read. Please let me know what you girls think, I hope to continue this soon!



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This story is 105 words long.

sissygirl’s journey girl names

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I just want to talk for a minute on girl names and sissy’s kinda scolding, kinda.



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This story is 17 words long.

Daisy and the Phantom Nurse (3)

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Daisy and the Phantom Nurse
Act III



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This story is 7 words long.

Telling Her

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Consequences of telling her about the "hobby."



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This story is 7 words long.

If It Was Your Husband 3 & 4 of 20

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If It Was Your Husband
By Patricia Marie Allen

Blurring the Edges and Santa Claus is Coming to Town

Carrie is off and running. Alex wrestles with his feelings about underdressing and wearing lingerie, and his alter ego gets Christmas presents. Meanwhile, Alex gets a look at just how feminine he can look when Carrie blurs the edges of his masculine face with makeup. Oh, and pictures



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This story is 67 words long.

Daisy and the Phantom Nurse (2)

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Daisy And the Phantom Nurse
Act II

Night has now fallen, the hallway outside my door is as quiet as the grave. The harsh white light from the light bulbs above that somehow filters through the crack of the doorway into my room is the only  hint of any sign of life. Outside my window, I can hear the wind starting to howl, big, fat raindrops the size of pennies are falling down by the trillions. I can hear those fat, drops of rain splashing upon the window.



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This story is 88 words long.

Driven from Normal. (Extra A.I. Images)

Precision driver Simon McKenzie’s work week started reasonably normal with a job in Queenstown, New Zealand, driving a vehicle for a new TV ad being filmed there.

After only a few days, and a series of events that seemed to quickly snowball, the 23 year old found himself standing in a bar waiting for his new girlfriend to arrive… But, what wasn’t normal, is that it's him wearing who's little black cocktail dress…

Driven from Normal. (Extra A.I. Images)



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This story is 81 words long.

Daisy and the Phantom Nurse

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Daisy and the Phantom Nurse



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This story is 5 words long.

Whatever Next? Chapter 20

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Whatever Next?
Chapter 20

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

My Mom, My Cousin, and Me: Part 1

It was a scorching June day when this all took place. I was 13 and living alone with my single mom. I was homeschooled, but not sheltered from the world. My mom was my hero - my dad was gone before I was even born, so she raised me solo without any help, all while owning and operating her own successful salon. We did well for ourselves, had a nice house with a pool. Despite her busy schedule she always made time for me, and even though I was homeschooled I never felt coddled or alone with her parenting. I based a lot of my personality and work ethic off of her.



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This story is 111 words long.

If It Was Your Husband 1 & 2 of 20

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Authors Note: This story is complete and sitting on my hard drive. The novel is 49,188 words long in twenty chapters. I will be posting two chapters per week, roughly 5,000 words per post, on Fridays.


Synopsis

Alex comes home one day and his wife, Carrie, tells him of a problem in Mike and Lisa's marriage. Mike is his best friend since middle school. It seems that Lisa caught Mike cross-dressing and came unglued. She had come to Carrie looking for solace and support for divorcing Mike. But Carrie told her about a Phil Donahue show she'd seen as a teenager featuring married cross-dressers and said that cross-dressing really was no big deal.

Lisa was offended that Carrie wouldn't back her up and said, "If it was your husband, you wouldn’t think it was so cool," and left in a snit; part of her anger now directed at Carrie.

Carrie, on the fly, hatches a plan to help Lisa see that if it was her husband, she'd still think it was no big deal. Alex somewhat reluctantly goes along with it and discovers things about himself that he never knew existed.



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This story is 190 words long.

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

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 third of three chapters that will be shared here as a sample. Hope you all enjoy! :)

-Jennifer

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This story is 154 words long.

Wednesday Knights -- Chapter 30: Aftermath

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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 36) - the Final.

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Driven from Normal .

(Chapter 36)

Simon McKenzie started his week normal enough, but after a series of events he found himself standing in a bar wearing a cocktail dress and the weeks that followed didn't return to normal.



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This story is 37 words long.

sissygirl’s journey 5.5

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It’s funny how being a little mortified and days later looking forward to the same thing, isn’t it crazy how human emotions can play little games in your head, that’s how I felt about sissy meeting my auntie one minute thinking one way and now really looking forward to it, mom really didn’t say too much just mentioning sissy that would be nice to give our guests a hello kiss just to make them feel welcome.



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This story is 80 words long.

Whatever Next? Chapter 19

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Whatever Next?
Chapter 19

by Angharad

Copyright© 2022 Angharad

  
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This story is 7 words long.

sissygirl’s journey 5.4

Mom having me kiss my Barbie doll with my freshly applied lipstick I think was just a way to have me start wearing lipstick because she knew i was fascinated with her lipstick and it wouldn’t take much to have me fall in love with wearing lipstick.



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This story is 48 words long.

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