First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

From Virgin to Stud, My Evolution

by NerdySex on Apr 17, 2018
First Time

In the summer between my Freshman and Sophomore college years I lost my virginity. I know, a little later than most. But I was an exceedingly shy guy. In high school I was fairly short and wore thick glasses. And a nerd, great at math, not so good with girls. I put on some additional height my last year of high school and first year of college. Also got rid...

We Need to Separate... 04

by mikoli5763 on Sep 19, 2017
Loving Wives

The last eight months had been the most stressful of my entire life. Having to take Angie with me everywhere I went to keep her away from Mary during the two weeks it took to get everything squared away in Tennessee had been a nightmare that I didn't think would ever be topped. I had to threaten to put my half of our farm out on the open market to get Aaron...

Baseball Annie

by SweetPrettyAss on Sep 11, 2017
Group Sex

This is my entry in the Literotica Summer Lovin' Contest. I hope you read it and enjoy it and vote accordingly. It is a story of one aspect of Baseball, the great American summer pastime, and I believe it fits perfectly in the theme of this contest. * It was a Friday night in August as Sylvia Jones shuffled her feet impatiently while waiting outside the d...

In a World of Black and White Ch. 02

by komrad1156 on Sep 15, 2017
Interracial Love

*Author's note: If you haven't read the original story, please do so before reading the sequel. I often get requests to write additional chapters and rarely ever do so. However, I got so many on this story I decided to give in and write a follow-on story. You guys win, okay? ********* He didn't sleep well all night and found himself wide awake at 4am and...

Melinda's Fishy Discharge Ch. 02

by Paradiggler on Sep 26, 2017
Fetish

I had been masturbating vigorously for many weeks following my encounter at Melinda's place. The thoughts of what I experienced that evening were a wonderful source for some very dirty and beautiful fantasies about her for some time afterwards. What I had experienced was direct contact with several pairs of her soiled, smelly panties. Those deep, brown di...

Business Before Pleasure

by DeepBlueC on Sep 3, 2017
First Time

I wish to thank my editor who requested to remain unnamed but without whose efforts, insight, sensitivity and perception this story would surely be less than it is. I hope you enjoy reading it. * * * "Ah, I'm so glad this is finally done," Camila breathed with a flood of relief. She was so relieved to be done with this project, she actually put her arms a...

The Sunlight Episodes Ch. 05

by BlueNotes on Sep 13, 2017
Erotic Couplings

Amber ran back up the stairs with a handful of ice cubes wrapped in paper towels, told me to hold it against my lip, then hurried back down the stairs, saying she had a midnight snack cooking on the stove. When she came back five minutes later she had a plate of grilled cheese sandwiches in one hand and two glasses of a red table wine in the other. She sat o...

The Dating Scene

by DG Hear on Sep 13, 2017
Romance

Thank you to my two favorite editors, LadyCibelle and Techsan, for making my story a much better read. * Chapter 1 There are many men out there; they are all sizes and shapes, tall, short, heavy, trim. Some have a full head of hair while others are nearly bald. Women have a tendency to look at the young, good-looking ones with a body with six-pack abs and...

Mattei: A Nation's Father Ch. 02

by AuthorMommy on Jan 27, 2020
Sci-Fi & Fantasy

Copyright Pending -------------------------------------------------------------- On the other side of the door, Mattei found a line of women who appeared to be waiting for the men as they came through the door. The woman at the very front walked towards him. "Hello," she said, her voice firm with authority, but yet friendly. "I'm Dr. Lura Izaki, but you ca...

The Eighth Warden Ch. 011-012

by Ivy_Veritas on Aug 5, 2019
Sci-Fi & Fantasy

Chapter 11 The morning after leaving the forest, Corec woke to find the elf girl—Shavala—calmly sitting on a large rock in the middle of the camp, near the remains of the fire. She waved at him and smiled brightly. He pushed aside his blanket and stood. "What are you doing here?" he asked, before his mind woke up enough to realize how rude he sounded. "It...