500 < Short Story < 7500 words

The Duality of a Transgender Teenager in the 90's

I grew up in the 1980s and early 1990s as part of Generation X. Looking back, high school was one of the most confusing periods of my life, and the effects of that confusion still influence my relationships today.

I was transgender, although I didn't have a word for it back then. The vocabulary simply wasn't part of my world. I didn't know there were other people who felt the way I did, and I certainly didn't know that what I was experiencing had a name. All I knew was that I desperately wanted to be a girl, yet every mirror reminded me that everyone else saw me as a boy.

Quarry, Chapter 5

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

Character Age: 

Permission: 

We walked out to the car, Jacinta keeping a loose hold on my right arm. She opened the back door:

“OK, sit in on the seat, then swing your legs in.”

Being a good girl, I did as I was told. Naturally, twisting around into a car pulled my skirt up; she leaned in, caught the hem, and tugged it into place.

“I’ll climb in the far side and take your handcuffs off.”

She closed the door, walked around the back of the car, got in:

Pen Pals: Cumming to Las Vegas

Pen Pals: Cumming to Las Vegas

A Pen Pal is a friend made and maintained primarily through writing. They are typically people who have never met in person and often live far apart, sharing stories, cultures, and updates via letters, emails, or messaging apps. Traditionally pen pals wrote handwritten letters or postcards using postal mail - sometimes jokingly referred to as snail mail.

Prolog

Louie, Huey and I

It was nine in the evening on December 31 and I was standing on a bridge looking down, far down, on the river where large chunks of ice floated. I was not going to jump. Not then. Actually, I was there to give me strength to go on. I was there to remind myself that there was an alternative to crime or prostitution even if things didn’t get better. Death before dishonor.

Trail Drive

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Other Keywords: 

Permission: 

Trail Drive
A Short Story

It was getting dark. The sun had already dropped below the horizon but on the plains the twilight lasts a little longer, so the stranger, drawn by the light of a fresh fire, could easily steer a horse through the low scrub.

The cattle were well settled in a basin where there was a small watercourse and some green grass alongside as well as tender tips on some of the brush. They would settle well and could be easily watched from just above the campsite where the water flowed out.

Quarry, Chapter 4.

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

Character Age: 

Permission: 

My phone rang; I was jolted awake; Janet. I answered, quite disoriented as I was in another room. I hadn’t even woken when I’d been moved.

“Hi; how you?”

“More to the point, how are you?”

“Fine. I've just woken up; what time is it?”

“7:10pm; did I wake you?”

“Yes; but I’m glad you did. I just wanted to let you know what happened.”

“You’re all over the news… and you’ve been identified from the pictures of where you tripped up the gunman. How’d you get away?”

London Cab

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Permission: 

London Cab
Two Vignettes
By Maryanne Peters

Meeting His Parents

London 1.jpg

We met again in London, two years after we had got drunk together in a Soho bar. Mark was still working for the same investment firm, and I was working for an associated one, just as I had been back then. He was more charming than I remember, but only by a fraction. I put that down to circumstance.

Jeannie Dreams

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Permission: 

Jeannie Dreams
A Short Story
By Maryanne Peters

Suvarov.jpg

It was as if I flew to the edge of space, and found heaven from there. It sounds as corny as the old TV show, but it turned out to be true, in a very strange way.

Track Ban

Track Ban
A Vignette
By Maryanne Peters

Track Ban.jpg

If you really know your horses, on track betting is the way to win. People who treat horseracing as a game of chance are fools. Why not toss a coin? That is chance and probability, but if you know horses and courses and watch the animals and their riders and the track close up and in the flesh, then it is not a gamble, it is the exercise of special skills.

Quarry, Chapter 3.

I woke Janet up with a glass of water and two more paracetamol. She wasn’t that bad; I just wanted her to be in good nick for her meeting at 11am. As usual when I was there I got breakfast; pancakes with maple syrup and bacon. We ate together and I headed off, going against the incoming traffic. I really needed to get some work out of the way so was planning to just get my head down for the day. I slowed down coming into the cul de sac which led to my apartment block and drove in, keeping an eye out for anything unusual; just what that might be, I hadn’t a clue.

Charity Auction

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Other Keywords: 

Permission: 

Charity Auction
A Short Story
By Maryanne Peters

It was a charity event. I was wholly committed to raising money for research into the treatment of myeloma, a disease that killed my dear mother.

I suppose that myeloma is not a disease that people think demands immediate attention. Some people live with it, and some, like my mother, die – there is no known cure.

Quarry, Chapter 2.

I woke early. At this time of the year it is getting bright around 4:30 and I had not slept well. What had started out as a good day two days ago had developed into a bit of a nightmare all due to an impulsive act involving me in something that wasn’t really my business. On top of that, I had possibly endangered Janet, and maybe my family. I hadn’t called home yet and was a little surprised that they hadn’t made contact with me. I would do it later; first things first.

Sundress & Sunlight

Author: 

Audience Rating: 

Publication: 

Genre: 

Character Age: 

Permission: 


He went to work for a dare. She left a different person: alive, luminous, hunted.
Click to discover Evan’s transformation and the enemy who already knows her name.


Sundress & Sunlight


People are Complicated

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Permission: 

People are Complicated
A Short Story
By Maryanne Peters

I was an experienced transvestite. I had been closeted for years. I denied it to myself and did not tell my wife the full extent of my need to dress. She was open to “kinky sex”, but she drew the line at anything more than that. I decided that I would lie to her as well as myself.

Issues

Drew Balor was at 1st fairway of Three Rivers Country Club in a tux pacing back and forth while taking a long drag from his cigarette. He wished he could calm down but knew he would not. His nervousness has been building up for the last year so how he felt has been par for the course for him. This state of mind all started by him asking Becky Stewart to be his wife. All the groom wanted was for this day to be perfect for who he saw as his perfect mate.

Sky Fall

I found out on Friday the 22 of May in 2026 that E.E. Nally, one of our prolific writers in the Whateley Academy stories, passed away on April 30th, 2026. It’s with great sorrow that I bring this news to you all. I had chatted with him almost every day or two for quite a while but he had fallen silent somewhere in the middle of February. I thought maybe he was in the hospital and unable to communicate with me but, as I feared in my imagination, he had gotten worse and eventually passed away.

Victim

Victim
A Short Story
By Maryanne Peters

Every crime scene is different, even though they all look the same after a while. They even smell the same, when you walk past the uniformed cop on the door and smell the iron in the blood, and maybe a trace of feces from the fear or a pierced gut.

The Shadow Theatre

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

Character Age: 

Permission: 

Tracy Lane, 2026.
Released into the public domain.

The Shadow Theatre

A Day For A Night

It was a night of shadows and flickering light, the television humming softly in the corner. Just another listless evening in with my folks watching some faded Hollywood musical, a tale of "The Olden Days," when trains ran on steam and streets bustled with carriages; no different from a dozen others I'd seen over the past year or two. Or so I thought...

One Froggy Morning

This is a fanfic based on Dorin Naga's webcomic, Murry and Lewy: https://murryandlewy.com/

One Froggy Morning
by Erin Halfelven and Suzan Donamas

Copyright ©2026 by Dorin Naga

A story set in the world of Murry and Lewy

Characters by Dorin Naga — Story by Joyce Melton

An Occurrence at Owen Craig’s Bridge

Author: 

Caution: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Other Keywords: 

Permission: 

With apologies to Ambrose Bierce author of the famous American Civil War story. There was no redemption in that story, nor is there any in this.

Only read on when you have read the Cautions.

This story reflects the attitudes of the time in which it’s set.

The groups involved are not important. The story is about attitudes, not politics.

******************************************************************************************************************

The Devil Wears (Charity Store Shoes)

Author: 

Audience Rating: 

Publication: 

Character Age: 

Permission: 

{This is a very short story by my standards}
The art of the window dresser is easy to understand. Their goal is to grab passersby's attention, then entice them to come into the store and, hopefully, persuade them to spend a lot of money. That is the theory… In practice, it only works sometimes.

There's Something About Mary

In sophomore year there was a new girl in school. There was nothing special about Mary. Well, that was what everyone else but me thought. I always felt she was special. Ok, so she was not beautiful. Cute perhaps in the girl-next-door way. Not one of the popular girls. While smart far from the top ten students in our class. Not an athlete. Actually, she was prone to various illnesses so she didn’t take PE and was she was away from school for a long time in after Christmas. Not a recluse either . Just one of the girls. But for some reason she was the girl of my dreams.

The Black Valley Study Club, Chapter 10

Author: 

Caution: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Permission: 

“Hurry up, I’m ready to go.”

Why did I need to pee again? After all, I had nothing to be nervous about; I was just going to divulge a secret to my mother that could mean the end of all the things that I most enjoyed about last year: Cheerleading practice, Cailíní Canadh Ghleann Dhubh, dressing, being one of the girls. What could possibly go wrong?

The Volvo pulled out of the driveway; I waited until we were well on our way so my mother wouldn’t be tempted to turn back. Past Ballymore, now on the Ballyhowan Road.

“Mom, I have something to tell you.”

Mothers in Law

Mothers in Law
A Short Story
By Maryanne Peters

Some say that if you want to know what your wife will be like in 20 years time, meet your mother in law. But for me, I have two mothers in law. Which one would she be like?

Altered Fates: The Legacy of David - Part 1

Altered Fates: The Legacy of David - Part 1

By Marie7342231

The Black Valley Study Club, Chapter 9

Noise; lots of it. I’m cold: I must have shivered as someone wrapped a warm blanket around me. Drift away again…

Noise again, light… My mother’s voice:

“I think he’s coming around.”

“Let’s have a look.”

Male, foreign, heavily accented.

“Ah; you back to us, yes?”

“Grunt”

“Whatyouname?”

“Huh?”

“He’s asking you for your name.”

Mother’s voice again.

“Name… Aisling…”

“It’s his stage name…”

Opening eyes, lights on ceiling, a man standing over me, white coat, stethoscope.

First Time Out

This is a story about a trans woman taking her first steps into the big bad world. ( not my usual sex stuff )

street.png

I looked out of the window of my small bedsit one last time as I steeled myself to face the world. I held my breath and nearly scrambled out of my front door and the main door. I forced myself not to run up the path. I had been watching to make sure my neighbours were not approaching or leaving. A few steps and I was on the street.

The Black Valley Study Club, Chapter 8

The sun was warm, even at 10AM. I collected the oars of the rowing boat from the machinery shed where we kept two pairs hung carefully on the wall. This was my first time using the boat this year, the first time I had felt able to bring it out. I walked the 200 yards to the lake and waded in. The boat, fastened by its painter to a post on the shore, was deliberately left some way out to stop the cows causing damage by scratching themselves against it.

Correspondence

Author: 

Audience Rating: 

Publication: 

Genre: 

Character Age: 

Permission: 

Tracy Lane, 2026.

Correspondence

Following the publication of our earlier articles on The Jane Doe Mystery, Sightings has learned that Dr. Nathan Ralston and his team at the British Center for Paranormal Research have begun a preliminary investigation into rumors of anomalous activity in and around Brixton. While Ralston cautions that many of the more recent reports may be little more than reactions to our coverage, he admits that the sheer volume of testimony cannot be ignored...

Prayer Group Tale

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Other Keywords: 

Permission: 

Prayer Group Tale
A Short Story for BJ
By Maryanne Peter

I was one of those sinners who had real doubts about Christian Feminization. I knew that my desire to have sex with other men was wrong, but it seemed to me that cutting away part of my body was going too far to fix that. I was counselled to attend a prayer meeting of feminized Christians. The expected dress was “feminine, conservative and comfortable”. Although I was not a crossdresser, I did my best to meet expectations.

The Comfort Gurl Part 4

In this part our "victim" agrees to transition and is surprised by what is possible.

I couldn't sleep when I got back. It was the first time I had experienced actual pleasure since this all started. I just couldn't reconcile feeling pleasure having sex as a woman.

I was a guy. sex with men was shear humiliation most of the time. At best is was a chore. A chore that I learned to mentally block out.

"Ohh, yes baby. Do me, You're so big" etc. All this to encourage them to finish so I could leave. At worse, it was mental torture. When they would say things like.

Plumbing

Author: 

Audience Rating: 

Publication: 

Genre: 

TG Themes: 

TG Elements: 

Character Age: 

Permission: 

Plumbing
A Vignette
By Maryanne Peters

Plumbing.jpg

My roommate had given him a key as she was out of town that Friday. She told me that she had. He was expected, but somehow in all the excitement, I just forgot.

Pages

Subscribe to 500 &lt; Short Story &lt; 7500 words