Crossdressing First Time Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Panther Tales Ch. 02

by Snowkemper on Sep 14, 2017
Sci-Fi & Fantasy

Any character engaging in any kind of sexual activity in this or any of my stories is over the age of 18. ***** Panther Tales II-Snow's Story Part One 'At least it's finally over,' Sally thought as she walked awkwardly toward the sleen pens. A guard held each of her biceps, towering over her small frame, making sure she didn't fall. Her hands were cuffed...

The Student

by Eros con Pollo on Sep 12, 2017
First Time

"I don't know," Penney sighed, setting her tray on the table. "Sometimes I think these boys are coming on to me." "Of course they are," replied the older man seated across from her. "When you've taught as long as I have, you'll be used to it." "Really?" He laughed at the tone in her voice. "Don't sound so astonished, Miss Clarke. Even fat, balding fellows...

Rob and Susie

by SlamDuncan on Sep 13, 2017
First Time

The summer over, Rob pulled into the Quinn family driveway in his new Mustang convertible, top down. He saw his friend and next-door neighbor, Susie Baker, sitting on her front porch swing. He tooted his horn and waved at her. He had spent the last three months working for his Aunt Peggy at her home, a two hour drive away. They were both going to enter thei...

Derailed Ch. 04

by Uncle South Loop on Sep 14, 2017
Erotic Couplings

Thursday, I woke at 5:30 refreshed and eager to get to work where I could stop thinking about Amelia. By the time I reached the office, Iā€™d ratcheted my work mode up to a new height and attacked my work. I went non-stop to 7:30 before calling it a day. Having purposely worn myself out, I retired early and was asleep immediately. Friday was a repeat of Thurs...

Island Adventures Ch. 03 - Changing Currents

by Saltysooner on Jul 29, 2019
Romance

Chapter 1 introduced the main characters, Mike, Monica, and Cheryl. Mike ends up leaving his bartending job with Monica to work as a mate on Cheryl's charter sailboat. In Chapter 2, Mike's relationship with Monica suddenly changes from one of casual sex to something much deeper. In this chapter, his relationship with Monica ends before it barely begins and...

Lisa's Second Chance Pt. 03

by Lisa_Sweety on Oct 31, 2017
NonHuman

Introduction Lisa is an attractive, blonde 25 year old human living and working on earth. Alien life had been found over 100 years ago and various shady governments existed but were kept secret from the population. Space travel had become affordable and a growing industry blossomed. Fresh from a broken relationship and with no prospects, she meets a new fri...

Waiting Up for Michelle

by Kinky Writer on Sep 13, 2017
BDSM

"Going out dancing tonight ā€“ wait up for me." Matthew's heart began to race as he saw the text message from his wife Michelle pop up on his iPhone. The last time he waited up for his wife, his ass had been sore for a week... Of course, in reality he loved every minute of it, but much like her seemingly-innocent text message, it was something that was kept...

Evie's Promise

by AdamZasse on Sep 12, 2017
First Time

By Adam and Evie Lyn Zasse The authors of this story are real. The event described actually happened. It occurred on a quiet, peaceful afternoon several months ago. The experience initiated a new friend into the exciting and world of womanly pleasures. The authors welcome your comments. * Chapter one, Initiation Evie Lyn quickly set the lunch dishes i...

Debutante Sex

by SchoenazX on Aug 12, 2019
Exhibitionist & Voyeur

I have certain visual memories that cycle through my dreams. I hope they never go away. One of these recurring visuals is about a lover who liked to be naked wherever and whenever she could be. Our first "date" lasted just less than a week and the location was a luxurious suite in a five-star hotel in Boca Raton. The bathroom was big enough to hold a band...

Calabasas Moms Ch. 02

by Fanta_Story on Jul 13, 2020
Erotic Couplings

Chapter 2 (of three): Make sure you find the correct hole, the wet one "You are welcome to stay. I prefer to fuck in the morning." He murmured his agreement or some kind of approval, she could not determine. She snuggled back against his chest. "Kurt?" "Mmm" "Do you ever wake up the middle of the night with an erection?" "Mmmm some times, why?" "If you...