Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Last Minute Crossdressed Sex

by Lovinhose on Sep 14, 2017
Transsexuals & Crossdressers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Al...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

A Crossdresser's Night In The Park

by cdtiffanymd on Oct 5, 2020
Transgender & Crossdressers

A Crossdresser's Night in the Park cd, bdsm, con, mm, anal, oral, toy Last night I was online in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with...

My Name is Raquel Ch. 01

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

Chapter 1 All characters in this story, involved in sexual situations, are 18 or older and are fictional. ******** My name is Raquel and I'm a crossdresser. I didn't become Raquel until later, but this is where I came from. At this point my interests lied only in panties. I wore them as often as I could get away with, as long as I could change out of the...

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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sissy's life

by cdbaby on Apr 20, 2018
Fetish

INTRODUCTION: (sorry the way it was originally seemed unclear) Sissies, they're all over the world, and beyond. Discover their origins, their fears, their lusts.What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy? What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy?...

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Forced to Dress

by married40scouple on May 11, 2020
Transgender & Crossdressers

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "I don't want to talk about it." He replied in a husky voice. "At least you look real good." I smiled at him. "She dressed me up. I have...