Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Fall of '69 Ch. 03

by wilderness on Sep 14, 2017
Novels and Novellas

Becky was made for moonlight. I woke up and watched her sleep -- so peaceful, so radiant. I worried about her. I prayed for her -- something I hadn't done since I was a child tucked in at night. Becky slept on her stomach, her hands underneath the pillow. Her hair had fallen across her face and I brushed it back to see her clearly. She mumbled incoherently...

Emma

by marriedbuthoping on Sep 18, 2018
Romance

This is partly, well almost entirely, true (However the names have been changed). l will leave you to speculate what is true or not. It is written as we would both speak the words and sentences so if the grammar or vernacular seems wrong, i assure you it is not. That's how we talk...Any feedback is always appreciated. Thank you. ***** Chapter One: Let me...

Railroad Club

by craigool on Sep 15, 2017
Group Sex

Judy is a strange woman. My eyes rake over all the potential targets in the club, locking onto her 34C-24-34 figure, taller than most of the women at 5'8", slim, maybe 120 lbs soaking wet. Great as all that is, it isn't what holds my gaze. Her hair looks like it is living fire, moving around her head as she stands in the breeze of one of the fans aimed at th...

Cindy's Creative Imagination Ch. 02

by walterio on Sep 17, 2017
Mature

INTRODUCTION In chapter one you met Jim and Cindy and learned about Cindy's games and role playing. She always acted innocent and behaved as if she was the one being seduced. The first costume that Cindy wore was a private school girl uniform. Cindy acted as the innocent school girl and Jim was incredibly turned on by her looks and behavior. In this chapter...

Terry Ch. 01: Losing Virginity

by Harvey_32 on Sep 12, 2017
First Time

This is the story of Terry unexpectedly losing his virginity to a mature lady many years his senior, certainly not in the way he wished. My grateful thanks for the help I have received with the editing of this story. -o-o- I was in foster care from the age of eleven to seventeen and stayed on paying rent to my foster parents till I was nineteen. I kept i...

My First Cock... BBC Ch. 04

by peter49parker on Sep 14, 2020
First Time

Opening Acknowledgment: I want to make sure that my friend, Apple-Of-Eden, gets the proper credit for these stories of mine. The experiences are mine, but without her encouragement to write them, they would remain just memories in my mind. She not only encourages me to write more, she helps by pre-editing them for me. She unscrambles my sometimes disjointed...

Cuckold Couple Ch. 05: First Stranger

by CuckoldingCouple on Jul 3, 2019
Loving Wives

Hi, Please read Cuckold Couple Chapters 1-4 for the complete journey so far. *** Angela says our sex life has got even better since her involvement with Pete and she still wants new experiences. She wants to spice it up even more by trying sex with other men as well as with myself and Pete. We have checked all kinds of websites and dating apps to find pos...

Tatiana's Choice

by Fredsowner on Feb 25, 2019
First Time

In the third week after her 18th birthday, Tatiana and her mother Svetlana sat down to review all the offers. Tatiana had had the idea that the best way to secure her future was to sell her virginity. She discussed the idea with her mother Svetlana who agreed. She could see that her father, who was a drunken sot, and spent all the money on vodka, would never...

Vivian Laaning Ch. 19

by Bodington on Jul 10, 2018
Novels and Novellas

On the Saturday morning of Vivian's Messalina Weekend, Michael Hennessy was the first to wake up. He thereupon fixed a hearty breakfast consisting of bacon, eggs, hash browns and pancakes. Vivian took care to eat an ample amount since in the next twenty-four hours she would only have the opportunity to eat an occasional cheeseburger here and there. Then she...

Forgiveness vs. Permission

by Skippy47 on Nov 19, 2018
Loving Wives

Carleigh and her husband had just finished a session of sex. As had been usual lately, the session ended after Ian had an ejaculation, but Carleigh had not. There had not been any orgasms for Carleigh in a long time. As they lay back in bed, a nervous Carleigh asked, "Was it good for you?" Ian was tired of answering the question that his wife had now asked...