Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Daniel and Jamie's Romantic Night

by lockedinsteel on Nov 8, 2017
Group Sex

Jamie stepped out of the cold up to the hostess desk at the chic, trendy, new restaurant. It was the first time that she had been out with her husband, without the kids, in she couldn't remember how long. It was a weird feeling, she thought to herself. Not to have to worry about anyone making it inside or helping kids off with their jackets. It was liberat...

Caffeine and Miss Forgetful

by mindingutter on Sep 14, 2017
Transsexuals & Crossdressers

"It's really nice of you to do this, Trent," my twenty-two year old little brother said as we sat in the kitchen sipping morning blend amongst several moving boxes He smiled, a rarity, at least until a couple weeks ago. The coffee maker was the about the first thing unpacked, and we had already fired it up. "C'mon, we better go," I said, "not sure how the t...

My Seduction into CD'ing & Gay Sex

by pantycladlad on Sep 18, 2017
Transsexuals & Crossdressers

MY SEDUCTION INTO CROSSDRESSING & GAY SEX It all started out easily enough. Mr. and Mrs. Ferguson had been our neighbors for many years. Their backyard abutted our backyard, a bit at the side of the end, so contact was frequent but not too much so. They socialized with different friends, maybe because my parents were younger, but were certainly nice neighbo...

Know Thyself Ch. 09

by Bethesda on Sep 25, 2017
Sci-Fi & Fantasy

Thank you everyone for following through on the journey of this story. I'm sorry for how long it took to get this final chapter out. I found it hard to end my adventures in this world and wanted to make sure it was just right. If you put up with the length of time between the last chapter to this one, I honestly can't thank you enough. And if you've read the...

Becoming Abby Ch. 08

by Abby_Hart on Sep 24, 2018
Transsexuals & Crossdressers

We had laid together for about an hour, but my mind would not shut off. Not to mention my belly was growling non-stop. I slipped out from under Missy's arm gently, and she rolled onto her back. I padded across the room, and grabbed my silk dressing gown from the back of the door. I looked back at Missy one last time, before pulling it on and heading down the...

Julia, Ben and Lisa Ch. 07

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 07: Monday A few quick notes: 1. this is the seventh chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned I got up at 9 a.m. and had the house to myself. It was Memorial Day a...

One for the Team Ch. 04

by MicheleNylons on May 19, 2020
Transgender & Crossdressers

Chapter Four -- Wendy Takes Charge November 1984 Robert wanted Charlotte to stay the night but they both knew it was fanciful and a downright dangerous idea. Robert Fellows may be the housemaster of Bridge House but he was still a student at Chelmsford College and would be subject to expulsion if they were caught. "Do that thing to me again and then I'll...

Finally a Princess Pt. 04

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Finally a Princess (Part 4) Part 4 of a Disney loving crossdresser who has come out to his wife on a Disney Cruise. With a lot of help, and some Pixie Dust, dreams do come true. For the third morning in a row I woke up and saw just a little light streaming into our stateroom. My wife Sarah was sleeping on the bed and I could hear her lightly snoring. One...

The Square Peg Ch. 08

by icedragonmo3 on Apr 15, 2020
Transgender & Crossdressers

Disclaimer: Welcome to chapter 8 of The Square Peg. This story contains a relationship between a mtf and a ftm. Things don't always go perfectly. If you haven't read the previous chapters, much of this won't make sense. Vonnie goes by the name Kevin at school and at home, and by Veronica at work. Drew goes by Andrea at school, and his dad sometimes calls him...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...