Transgender & Crossdressers Stories

12,569 results
Orientation
Length
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Infinite Scroll

Sarah had to Show Off her Panties

by SarahCD on Dec 3, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more detail and corrected some mistakes. ---------------------------------- My girlfriend and I had a relaxing lunch and then got ready for our dinner party that night; we were having our...

Surprised

by Submissivelatinlover on Jan 23, 2019
Transgender & Crossdressers

My best friend in college had called me and told me he needed to talk to me. I had noticed he had been different with me and was worried that something was going on. We decided that we would hang in his apartment. He was a Junior and had a nice loft. It was a great one bedroom apartment that we would go to hang out whenever we wanted to get away from the col...

The Fort

by hydrangealawrence on Dec 24, 2019
Transgender & Crossdressers

I ring the doorbell of the brownstone and rub my gloved hands together. Aaliyah opens the door with a warm smile. "Hey Millie!" She gives me a big hug. "Come in, come in." I take off my coat in the foyer and look around. "Wow, this place is gorgeous! How do you know these people?" "I baby-sit the kids sometimes. They're all at Disney World until Friday."...

Two and a half hours

by lynntg0444 on Mar 2, 2020
Transgender & Crossdressers

That is how long I spent at Mack's apartment today. I hadn't seen him since before Christmas, and we were already into February. I had tried Craigslist to get laid, but didn't find anyone that was worth the effort. About half the guys that answer want me to fuck them. I don't shave my legs, go to yoga, and get facials so I can fuck some dude with a hairy ass...

Delilah

by jezzaz on Mar 18, 2020
Transgender & Crossdressers

So, this was supposed to be for the 750 word project, but a) I was traveling and just didn't get time to edit and refine it and b) I couldn't get it down to 750 words anyway, no matter how I tried. So, 862 words instead. Just something that came up and I had to dash down. * What kind of author is late for his own challenge? Tsk tsk. Hi. I'm Delilah. Hope...

Promise

by MichaelFitzgerald on Jul 15, 2020
Transgender & Crossdressers

Promise By Michael Fitzgerald (Years ago, I wrote this for a friend who was going through hard times. He called me just now and asked me to post it here to celebrate the Supreme Court's ruling. Hope you like it.) Alone upstairs, Belinda adjusted her veil. The quiet noise of family and friends drifted up the steps. The ceremony would be in the garden behin...

Birth of a Slut Pt. 02

by Njcdslutgina on Oct 6, 2020
Transgender & Crossdressers

I had enjoyed sucking Denny's cock so much I couldn't wait till the next night to do it again. I had played by myself and had put a broom handle in my ass but it came out with shit on it. I decided to give myself an enema and that worked much better. Since I had the entire day to myself I decided to experiment. I decided to try adding alcohol to my enema. I...

The Shemale Possession

by SexyKate69 on Dec 12, 2018
Transgender & Crossdressers

I was in another day in the laboratory, arranging the experimental machines. It would be an ordinary day if it were not for one of the machines that went into overload and exploded, after the explosion I opened my eyes and I was scared to see myself stretched out on the floor. How could that be? There was only one explanation, I was dead, that's when I notic...

Shock

by acylote45 on Sep 16, 2017
Transsexuals & Crossdressers

Please note that the characters in this story are fictional and are not children. If you do not like to read about transgender and/or homosexual people then this is not the story for you. Please do not post my story anywhere without my permission. You may have heard the story of Jack and Jill, and how they went up the hill to get water. Well actually...

Exotic Employment

by LadyDaisy on Sep 16, 2017
Transsexuals & Crossdressers

Elliott and Abby had been married for over ten years. They were in their thirties now, with good jobs, a nice house, and two lovely young children. As most couples often do at one point or another, they had begun to go through a rough patch in their marriage. Neither was satisfying each other that much, especially sexually. For their sake and the sake of the...