First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Swinging Bi

by Nemasis Enforcer on Sep 14, 2017
Loving Wives

"How about it?" Liz said to her husband as they sat at the computer and read the page she had brought up to read "Are you sure this is what you want?" Eddy said as he read on "Oh god yes after 20 years of marriage I think we need to spice things up a little don't you? And this seems perfect as long as you are ok with it" she said with a smile as she massag...

In The Beginning Ch. 07

by Tall_cool_one on Aug 31, 2017
Erotic Couplings

When Louise says she is going to give you a bath, consider it to be a complete bath. She scrubbed me from head to toe and then some. She then proceeded to dry me with the red towel until my skin was almost bright red. "Enough, already," I howled, "There won't be any skin left." She whacked me on the butt with her hand and said, "To bed with you, tomorrow's a...

The Heat of the Sun and of Passion

by lustingwanderer on Sep 13, 2017
Exhibitionist & Voyeur

This story is pure fantasy, written by a male, from a female point of view (I hope). * Isn't it funny how you go on holiday and wake up at the normal workday time? I used to think it was unbelievably annoying until one holiday a couple of years ago. One thing that gets me horny is warm sunshine, in winter I still enjoy sex, but as the spring sun warms the...

The Unsuspecting Candidate Ch. 01

by missvicky53 on Sep 11, 2017
Fetish

I had been told what to expect and there he was, my next candidate! Even if I hadn't been told about this one, I would have recognized the potential he exhibited. How did I know this? I can't really explain it in mere words. All I can tell you is I knew this one would be susceptible to what I had in mind. I had been watching him watch me for more than ten mi...

Cyndy Decides to Stray

by User666 on Sep 13, 2017
Loving Wives

Toby was sitting at the kitchen table, finishing his morning coffee, slurping the last remnants at the bottom of the cup. It made a rude noise that always annoyed his new wife. She glanced at him, exasperated. Like her mother, she was a stickler for propriety. Manners and decorum were important. In fact, she took almost three hours the first day of their hon...

Joan Gets a Surprise Ch. 01

by JustALittleCrazy on Sep 14, 2017
Novels and Novellas

Author's note: This is a short sequel to Joan's Story and the fourth installment of The Dirty Old Man but this is from Vanessa's point of view. This is a fantasy and all characters are fictional. Any resemblance to persons living or dead is purely accidental. Every character that has sex in this story is over the age of 18. I do suggest you read the "Dirty O...

A Birthday Party for Maria

by exjock on Sep 16, 2017
Loving Wives

Note to readers: I want to thank my wonderful editor LazyDays1221 for helping turn this story into a living adventure. Without her help, the story would not be nearly as interesting nor would it be as erotically charged. Thanks LazyDays1221! **************** Adriana and I have an extraordinary life together. We've always tried our best to think first of...

My First Time Ever

by Cromagnonman on Sep 14, 2017
First Time

I was eighteen when I met Sean for the first time. I had just finished high school and was preparing to begin my first year at university when my father invited him home to have dinner with us. The 'us' in this case being my father, Robert Francis who worked in the same office as Sean, my mother Marjorie and me, Natalie. My father had started with the compan...

Reunion (the Horror)

by BillandKate on Sep 25, 2017
Loving Wives

No sex in this one (and yes, I know it's Literotica); just a cautionary tale about the realities of adultery. You've been warned. +++++++++++++ Who would have thought that the birth of my first grandchild would lead to the possible destruction of my 24-year marriage to Jane? I'm sitting in the back of this rented utility van, just up the street from my d...

A Taste of Innocence

by Mason_Hess on Mar 27, 2019
Romance

All characters are 18+ ***** ————————Prologue———————— The five girls sat on the floor, a huge bowl of popcorn and cups of various drinks spread between them as they chatted. It was the last week of school, the last week before they graduated and became, allegedly, adults. They were separating soon. Josie was heading to Vancouver, intent on becoming a mar...