Crossdressing First Time Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Things Can Change Quickly Ch. 02

by mrnoname93 on Sep 13, 2017
Erotic Couplings

There's not too much sex but I hope to introduce a few characters and give a feel of where this story could possibly go in referenced to those other characters and also between Sam and Damian. Please give any feedback you think I need or deserve! - MisterNoName _ "Dude, seriously, help me," I almost screamed down the phone as I jumped onto my bed, exhauste...

Melissa's Story Ch. 05

by iraussieguy on Sep 13, 2017
BDSM

Chapter 5: The Training Continues As I closed the door after the last client of the day Melissa padded on bare feet from the living room, an open can of VB in her hand. "Here you are Sir, I thought you may like a cold beer after a hard day of spanking." She giggled as she passed the drink to me. "Thank you my subbie, I love it when you read my mind," I lau...

The Winner Gets Everything

by Winterfrog on Sep 16, 2017
Loving Wives

Many thanks to Renee and Kent for the editing of this story. * When this story began about five years ago I, Sebastian Sandell, ought to been the happiest guy in my small Scandinavian hometown because I had most of what most young men wanted to have. I had many good friends, a good job, nice apartment, almost new car and a very beautiful girlfriend. Who,...

Pond Life

by risgrynsfisk on Sep 16, 2017
Romance

We sat in our ravens nest surveying our domains with the pond and the sunlight glittering upon it, singing a soft harmony to the birds chattering and declaring our domains to be theirs and that was fine since we didn´t mind sharing, not with them. Sharing with Them was more problematic, since They like ants wanted to fill the world and the constant moronic...

Mara Servatis Ch. 01

by Reil on Sep 14, 2017
Novels and Novellas

Author's Note: This is my first submission so any and all feedback is more than welcome. My main goal here is to improve. The story is set in one of my alternate histories so don't go looking up any of the terms or peoples, though as you'll see, everything is heavily based on Roman culture and language, so if you have any suggestions about how I can be more...

Twenty Dirty Dates Group Pt. 04

by Ratamaquee on Jun 9, 2020
Romance

Date Sixteen, First Time—Ginny "My first time was with one of my hand job buddies. We developed serious hots for each other at the beginning of my first year in college. I gave him hand jobs, and blow jobs. He would rub me off with his fingers and eat my pussy. We got in on pretty good but I would never let him stick it in me, I told him I was afraid I woul...

Natural Beauty Pt. 03

by sarobah on Nov 6, 2018
Exhibitionist & Voyeur

I was awake half an hour before dawn, and went out onto the balcony to sit and think and watch the shadows of the ridge behind the hotel retreat off the bay and up the beach. It was very peaceful. Nobody was congregating on the lawn this morning. No voices were coming from the adjacent deck. Rain had chased away the songbirds but had since dispersed. The sil...

Chasing the Dragon Ch. 02

by AwkwardMD on Sep 12, 2017
Sci-Fi & Fantasy

"Man, you devoured that!" Roxie was only halfway through her plate, even though she'd started first. "D'ya want more?" "Yes!" She slid her plate to him and turned back to the stove. Beez had stopped caring what it might be as soon as he realized it was good. It was funny how, not that long ago, he would have turned up his nose at even off-brand foods. Hi...

Femdom Island Ch. 03

by JackBro on Sep 11, 2017
Exhibitionist & Voyeur

Warning: The following is a sexually explicit story intended for mature audiences. If you are offended by stories of such nature, do not read it. All characters are fictional and not intended to resemble any real people. Comments welcomed. * * * * * The next morning Lori decided on a cultural adventure - or at least that was what she told me. It might have...

Finding a Lost Puppy Ch. 15

by PoeticallyChivalrous on Sep 14, 2017
BDSM

I would have said Monday morning rolled around too quickly but that isn't what happened at all. I suddenly set up straight from a dream that woke me. You know the kind where you are actually portraying a character in the dream and acting it out for real til it wakes you up. This was one of those dreams and it pertained to Jill with the dream still lingering...