Crossdressing

Dumb Bet


Dumb Bet


By Patricia Marie Allen


Edited by alys9

Author’s Note: While Alys9 did edit this for me,
I didn’t necessarily use all of her suggestions.
Any errors remaining in the text are mine.

“I don’t know why you can’t dress like a girl. I mean, I’ve never seen you in a dress and you’ve lived next door for five years,” I told Susie, the tomboy that lived next door. She was my sister’s age, two years older than me, and I was starting to notice girls and she was one I noticed. Under her jeans (boys) and loose shirt, there was a good looking body. The only time you could tell was when she put on a swimsuit. “And you should do something with your hair and maybe wear some nail polish or somethin’,” I continued.

“Leave her alone Frank. She can dress how ever she wants. I don’t blame her. I like to wear jeans and sweatshirts too,” my sister defended.

“Yeah, you’re nearly as bad as she is. You only wear dresses sometimes, when there’s some kind of special occasion. You’ve got a drawer full of nice nighties and all you ever wear to bed is flannel pajamas. The only difference between you and Susie is you polish your nails. Susie never wears dresses,” I complained.

“I don’t always wear flannel pajamas.”

“Oh yeah; I forgot. During the summer, you wear Dad’s old T-shirt and Boxers. Real girlie. I’ll bet Susie wears that kind of thing year round.”

Susie whispered something to Karen, who nodded. “I’ll tell you what,” Susie said. “Let’s have a contest. I’ll bet that I can do everything you do and that you can’t do everything I can do. If you win, I’ll wear whatever you say for a whole week and fix my hair all girlie. I’ll even let you go first.”

“What if I lose?”

“Well then,” she grinned, “you’ll have to wear whatever I say all week.”

“What ever we say… I’ll even do it too. And you’ll have to do something with the sorry mop you call hair to make it look better. I don’t know where you get off talking about Susie’s hair. At least she washes hers,” my sister Karen insisted.

The Tale of Two Girls part 10

The Tale of Two Girls part 10

Dear readers,

I have included a list of the characters which will help you keep track
of all the people in my story. It's basically in order of appearance.

New readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize.

Please enjoy my writings; it gives me such great pleasure to write about
a subject that is so close to my heart

List of Characters

Chrissy's new life
------------------

The Tale of Two Girls Part 9

The Tale of Two Girls Part 9

Dear readers,

I have included a list of the characters which will help you keep track
of all the people in my story. It's basically in order of appearance.

New readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize.

Please enjoy my writings; it gives me such great pleasure to write about
a subject that is so close to my heart

List of Characters

Chrissy's new life
------------------

The Tale of Two Girls Part 8

The Tale of Two Girls Part 8

Dear readers,

I have included a list of the characters which will help you keep track of
all the people in my story. It's basically in order of appearance.

New readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize.

Please enjoy my writings; it gives me such great pleasure to write about a
subject that is so close to my heart

List of Characters

Chrissy's new life
------------------

The Tale of Two Girls Part 7

The Tale of Two Girls Part 7

Dear readers,

I have included a list of the characters which will help you keep track of
all the people in my story. It's basically in order of appearance.

New readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize.

Please enjoy my writings; it gives me such great pleasure to write about a
subject that is so close to my heart

List of Characters

Marley for the Win Part 11

The look on his sister’s face was a complex mix of emotions, amusement, anger, surprise, such a wide range of human feeling can be broadcast with a simple glance. Marley froze then quickly tried to cover himself with his hands, which he realized was kind of useless, he wasn’t exactly naked anyway. “You’re supposed to be at scholar bowl,” he spit out.

“Yeah, I wish I was, it was canceled, So, what’s going on?” Ann asked with a wicked smile. Marley was trapped, his sister blocked the door, he made a useless glance at the window and thought about jumping through it.

Twin Set

Twin Set

© 2016 by Nom de Plume

“Set point!”

My twin sister stuck out her tongue as she crept in front of the baseline. We had played against each other countless times, and it always seemed to come down to this, a long deuce or a tiebreaker at the end of a tense, competitive match. Although I was a boy and she was a girl, we were evenly matched, and I sometimes felt that the only edge I had over her was that she had to wear a tennis dress or skirt at the uber-conservative club that our parents belonged to.

The Tale of Two Girls Part 6

The Tale of Two Girls Part 6

Dear readers,

I have included a list of the characters which will help you keep track of
all the people in my story. It's basically in order of appearance.

New readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize.

Please enjoy my writings; it gives me such great pleasure to write about a
subject that is so close to my heart

List of Characters

Chrissy's new life

------------------

Just Let Me Do Your Hair…Part 4: What to Wear?

Sam's sister, Jenna, has dreams of working as a hair stylist. But with Jenna's hair too short to do much with, Sam reluctantly lets his older sister put his own long hair into girlish style. But just this once... right?

Here are 5 teaser chapters for my 33 chapter novel cleaned up, re-edited, and available on my Kindle page. If you've already read, thank you! If you haven't yet, I hope you enjoy! :)

KDP1_V2.png

The tale of two girls Part 5

The tale of two girls Part 5

Dear readers,

I have included a list of the characters which will help you keep track of
all the people in my story. It's basically in order of appearance. New
readers please read the preceding chapters of this story and the two
preceding stories, Chrissy's new life and Chris's surprise prize. Please
enjoy my writings; it gives me such great pleasure to write about a subject
that is so close to my heart.

List of Characters

Chrissy's new life
------------------

Just Let Me Do Your Hair…Part 3: The Fashion Expo

Sam's sister, Jenna, has dreams of working as a hair stylist. But with Jenna's hair too short to do much with, Sam reluctantly lets his older sister put his own long hair into girlish style. But just this once... right?

Here are 5 teaser chapters for my 33 chapter novel cleaned up, re-edited, and available on my Kindle page. If you've already read, thank you! If you haven't yet, I hope you enjoy! :)

KDP1_V2.png

In Too Deep - Ch 35-39

  • A morning news flurry while Dana and Sloan each contemplate their future.
  • Marco and Dave also make some new plans.
  • Danielle gets a bit more controlling while Thomas Dern and friends visit the hospital.
  • News at Eleven, Dana and Sloan make some choices, and Thomas Dern contemplates the past.
  • Sloan and Dana hit the Spa, then head to the party house to get ready for Sloan's big night.

My dreams coming true

I'm finally getting my own place. I've been waiting for this moment it feels like forever. Since i made the decision to finally live my life as a woman. I will be taking my hormones and getting my huge breast implants what is gonna take a while longer is getting srs. I'm tired of looking at my small cock., i want a beautiful tight wet pussy i can play with all day and night. I cant wait to have my first cock fuck my pussy, everywhere i go im gonna fuck everyone. Always wearing short dresses and skirts with no panties for easy access.

Catfish Part 3

catfish, noun: a person who sets up a false personal profile on a social networking site for fraudulent or deceptive purposes
Merriam-Webster.com

So apparently things could get more awkward between Mark and Jason.


In Too Deep - Ch 30-34

  • Dana and Sloan have a heart to heart chat.
  • Thomas Dern learns about Sloan's upcoming audition.
  • Taylor Sloane earns a reward from Ms. Sharp.
  • Miss Taylor Sloane has an exciting day of shopping.
  • Thomas calls in his dogs and Danielle gets nervous, while Brandin Sleeps In.

Just Let Me Do Your Hair…Part 2: A Bit More Feminine

Sam's sister, Jenna, has dreams of working as a hair stylist. But with Jenna's hair too short to do much with, Sam reluctantly lets his older sister put his own long hair into girlish style. But just this once... right?

Here are 5 teaser chapters for my 33 chapter novel cleaned up, re-edited, and available on my Kindle page. If you've already read, thank you! If you haven't yet, I hope you enjoy! :)

KDP1_V2.png

Xdresser to transexual

I've been crossdressing since i was 12 yrs old. Im 46 now, so it's been a crazy journey. But now I'm ready to take it to the next level. I have no family left no tires to where I'm at now. I'm just waiting on a big settlement check, this is going to change my life forever. Once i get paid, im gonna get laser hair removal, see my doctor for hrt, get huge beat implants and a little minor surgery. I'm gonna buy all brand new panties and lingerie, dresses, skirts, blouses, shoes, makeup,jewelery, wigs, once i start to look good in gonna turn into the biggest slut.

In Too Deep - Ch 25-29

Thomas and Brandin come up with a new plan to get the role. Dana is being run ragged in her new job as Matt Sharp's PA. She has a long talk with Gabi about the Sharps' lifestyle. Meanwhile, Sloan is being personally tutored by Danielle Sharp. She is painfully blunt about their sexual proclivities. Sloan struggles to impress Danielle with his femininity. Dana works late and Sloan worries that she is spending time alone with Matt. Dana drags in late, and shares a tearful confession with Sloan.

Just Let Me Do Your Hair…Part 1

Sam's sister, Jenna, has dreams of working as a hair stylist. But with Jenna's hair too short to do much with, Sam reluctantly lets his older sister put his own long hair into girlish style. But just this once... right?

Here are 5 teaser chapters for my 33 chapter novel cleaned up, re-edited, and available on my Kindle page. If you've already read, thank you! If you haven't yet, I hope you enjoy! :)

KDP1_V2.png

Calum, meet Cassie - Part 3

"Morning mom" Sarah announced her and Cassie's presence.

"Good morning... dears" She smiled a reassuring smile, hoping her slight hesitation wasn't noticed. She knew it would be a little awkward, a new experience for everyone, and will need getting used to.

"Morning auntie"

"You look lovely Cassie"

"Thank you" Cassie said, smiling nervously

Boy, was this new. For Anne and Cassie, and Sarah felt it too, but things became more relaxed and 'normal' after a little while chit-chatting over breakfast.

The BIG Adventure - I'm ready now.

The BIG adventure – I’m ready now.

Even when you go out filled with confidence - there are nasties offering endless pain. For first-timers, the risk may be more than they can bear.


In Too Deep - Ch 23-24

Sloan and Dana arrive at the studio. Dana delivers Sloan to Danielle for his interview, then begins learning her new role as Matt Sharp's Personal Assistant. Both of them begin to learn their new role in the production company.

Calum, meet Cassie - Part 2

I wish to mention. I know there are matters that would arise in real life that I'm not dealing with. It's by design, I'm calling it artistic licence. It is fiction after all, and I want to keep it 'sweet and sentimental'.

Ages... undetermined, I don't know myself, early teens maybe. Calum/Cassie 12 to 14, Sarah 14 to 16. Perhaps. I've left that up to the reader to call, if you choose.

**********

Tuesday came around.

Art Project – 2 Possibilities Become Problems


Andrew has attention deficit problems and is a little use to getting his way…
He has moved and registered late for the new school he’s in. He insisted on taking an Advanced Art class. He has taken on a project of designing a prom gown…
The instructions that he didn’t hear would lead to a problem…

Catfish Part 2

catfish, noun: a person who sets up a false personal profile on a social networking site for fraudulent or deceptive purposes
—Merriam-Webster.com

Jason's prank doesn't go as planned, and he finds himself dragged deeper into things than expected.


Daddy Will Be Here Soon

A gender-questioning child is apprehensive about meeting with Father after a long separation. The last time they saw each other it was as troubled father and closeted preteen son. How will they relate now?

Calum, meet Cassie - Part 1

Calum, meet Cassie:

It was a rainy Saturday afternoon, and Calum was daydreaming on the bus. Gazing absentmindedly out the window at the passing scenery, taking in it all and none of it.

He stirred to life as the bus drove into the outskirts of the town he was vacationing in with his Aunt, Anne 'auntie Anne' and his cousin Sarah. 'My stop soon' he reminded himself, cautious of the stop he was to get off at.

On arrival he alighted from the bus with a bounce, he was looking forward to seeing his Aunt again, and Sarah.

Marley for the Win Part 9

Returning to school is never fun, especially after the weekend that Marley had. At least he got to relax most of Sunday after doing some homework and getting a short ride. His morning classes had flown by and now Marley sat down to lunch with his friends. Bent Fork School was small, the middle school was attached to the High School and shared most of the same facilities, including the cafeteria. The 7th graders were all eating now and there were less than 40 of them. Small classes like these tended to be tighter, everyone knows everyone, but social groups still form.

Marley for the Win Part 8

Marley for the Win Part 8

Paul’s thoughts were suddenly thrust to his past. We never did it, I mean not that I didn’t try, there was that one time we kissed but it ended awkwardly. Everything makes so much more sense now, he thought. “So that’s why we never could get things going,” he said.

“Not that you didn’t try, how many times did I have to slap your hand away from my…” Lisa said.

“That’s not fair you led me on,” Paul laughed.

“When did being friendly and spending time together becoming leading someone on?” Lisa asked.

Catfish Part 1

catfish, noun: a person who sets up a false personal profile on a social networking site for fraudulent or deceptive purposes
Merriam-Webster.com

Jason's prank on his roommate goes terribly wrong... or terribly right.


Marley for the Win Part 7

Marley in his sister's clothes
Marley and his Mom walked across the school parking lot and across the school’s front lawn until they reached a bench, Lisa double checked to make sure no one was around then said, “OK, so Marley, I’m going to ask you something, why do you want to go to dinner with Paul and his family so bad?”

Art Project


Art Project



Andrew"s attention deficit and is often used to get his way…
He has moved and registered late for the new school he’s in. The result is he insists on taking an Advanced Art class.
He has taken on a project in designing a new outfit…
The instructions that he didn’t hear could lead to a problem…

Marley for the Win Part 5

Marley for the Win Part 5

“Yeah Mom, your new boyfriend thinks you have two daughters,”

Marley stopped and just stood there, his sister was laughing, but his Mom looked seriously upset. That guy Mom knows thinks I’m a girl, God this is messed up, Marley thought. Oh and she likes him, and now I’ve screwed that up, Marley’s embarrassment bubbled over and he yelled “Damn it this isn’t funny!”

“Yeah knock it off Ann,” Lisa said. “I’m so sorry Marley, this was such a stupid idea, listen let’s just get you back to normal and go home.”

In Too Deep - Ch 14

Gabriel, Matt, and Danielle receive a visit from Brandin Jessup's agent, Thomas Dern. The agent is pushing to get his client back into the film project, while Matt and Danielle have already decided to use Sloan. In Hollywood power plays between producers, directors, and agents, who's will is stronger?

In Too Deep - Ch 13

Sloan has a chance to get the role of a lifetime in Matt Sharp's new Hollywood blockbuster...all he has to do is convince them that he can play the part; however, Matt and his wife Danielle are looking for much more than an actor to play a trans-gendered hit man. They are looking for a submissive to replace Gabriel/Gabi-girl, who is finishing his internship and returning to University.

In this chapter, Sloan and Dana start working out some issues as they discuss their plan for the upcoming costume party at which they hope to convince the Sharps that Sloan's acting talent will make him a perfect fit in their new film.

For acting like a Boy

Dennis thought by messing up his dress clothes, he'd get to stay home and play with friends... He insisted that he was not sweet and nice... Mom didn't get too angry so he thought he won... Unfortunately, every time he acted up she crushed his bad boy spirit a little more. Until he began to like what he saw.

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