Crossdressing

High School Failure

The principal’s office at Henrietta Orville High School for girls. The Principal and a mother have a conversation. In the background some girls sing the Snow White inspired school song.

- I’m sorry Mrs Anderson but I did warn you when you enrolled your son here at Henrietta Orville High School for girls that he most likely wouldn’t be able to graduate.

- But he so desperately wanted to attend and he really applied himself.

Butterscotch -9- Smiles

“Rescue time, girls,” Marjorie said. “Baby sister Kissy here just graduated from being a tomboy, and she has a hot date tonight!”

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Butterscotch

by Erin Halfelven

The Big Break, Chapter 6

The Tour Proceeds To the Conclusion

The first set of gigs went well; we travelled to the venue in the bus, did our show, and came back again. Cambridge was full of drunken students and Colchester was full of drunken soldiers but the others were good. It was when we went up to Birmingham that things went strange.

The Big Break, Chapter 5

Saturday Sensation

Next morning we all slept in. After I had showered and shaved I opted for my black jeans with the boots and a black tee shirt. I would have not picked the tee shirt if I actually was a girl as it showed the outline of my corset at the bust line and I got a lot of interested looks from all of the fellows. Lesley told me I was brazen and Tess said I was hot. Sven and his band had already eaten their breakfast and left, as they had a gig in Holland tonight. That was, I thought a real slice of good luck. The sisters were happier about that as well.

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'.

Butterscotch -7- Breathless

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

The Big Break, Chapter 3

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.

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

The Big Break, Chapter 2

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.

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

Wayward Part-3

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.

 


The Big Break, Chapter 1

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.

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

The Excursion in Spain. Final Chapter

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.

Covid 19 Part 15 Small steps slowly.

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.

The Excursion in Spain. Chapter 16

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.

Miss Judged

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.


The Experiment - Chapter 3

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.

Wayward Part-2

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.

 


The Experiment - Chapter 2

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?”

The Experiment

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.

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…

The Excursion in Spain. Chapter 15

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.

The Excursion in Spain. Chapter 14

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.

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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