Crossdressing First Time Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Og's Blog Pt. 09

by oggbashan on Jul 13, 2020
Reviews & Essays

Og's Blog Pt 09 Og becomes a civil servant. Part 05 Starting in Devonport. Author's Note: Because of the Official Secrets Act, this has to be regarded as a fictionalised account and names will be omitted or changed. Any names given will not be the names of real people. Please note that Parts 01 and 02 of Og's blog are transcripts of posts made on the Auth...

Saturday Night Fever - The Sequel

by watchdwag on Sep 19, 2017
Group Sex

As the weekend approached, I became more and more anxious about what I had agreed to do. My name is Chris and last fall I was seduced by a hot blonde in her early thirties named Terry, who took me back to her apartment where her boyfriend Jim and another man introduced me to gay sex. While I did have sex with Terry as well, she encouraged me to give her boyf...

The Casting Couch

by chezshirecat on Sep 19, 2017
Interracial Love

For as long as Allison could remember, she'd wanted to get into acting. But coming from a strict, religious family, she was discouraged from pursuing it as a career. When she was 21, she married her high school sweetheart, who wrote part-time at the local newspaper and freelanced for magazines. She worked at a temp agency and made a good living. They were h...

Canada-I-O

by Isis_1 on Sep 13, 2017
Romance

Julie looked out the window of the airplane and felt both giddy and nauseous. "Am I insane?" she wondered for the fiftieth time that day. "What if he hates me? What if throws me off his verandah? What if he's indifferent, and doesn't even care that I've come?" Julie posed one absurd question after another, partly to draw out her unspoken fears, and partly to...

Next Step to Nirvana

by Lia Monde on Sep 13, 2017
Transsexuals & Crossdressers

As I sat on the bench at the mall, I tried to calm myself. I thought I had prepared myself and planned everything. But my breathing was fast, my hands were sweaty and my nerves were wired. I was home for holiday break from college and had decided to take the next step in cross-dressing. Up until now, most of my dressing had been secretly taking my older sis...

The Gynecomastia Kid Ch. 01

by Johnboy9 on Sep 14, 2017
Transsexuals & Crossdressers

This story will be told in first person narrative but this first part is written in third person narrative because the first person, or main character, is unaware of the events unfolding in this scene. ***** Inside the kitchen of her boyfriend's house Crystal makes a last ditch effort, calling his stepmom, Dr. Burns, for help: "Crystal, you're saying all...

The Lone Spring

by Native Alien on Sep 13, 2017
Erotic Couplings

Standing outside, in the cold air, looking up at the stars. Not moving, just listening to the sounds of the night. Nothing is stirring. The air is cold on my skin where the blanket that I am wrapped in doesn’t cover me. Nothing on but a pair of moccasins. The stars are bright in the night sky and the moonlight is bright. I think of the hot springs just behi...

Spring of '39

by alexcarr on Sep 16, 2017
Romance

In the Spring of 1929, Ivan Jones had regained his self esteem when, after a year of unemployment, he was taken on in a new Government incentive to find jobs for unemployed South Wales miners. It meant leaving his beloved home, his mother and father for the first time but it made a lot of sense and also gave him the opportunity for leave the nest and fend g...

Her Lessons Begin

by Genevra on Sep 13, 2017
BDSM

We've spoken on the phone, and you've told me that you want to meet me at a local hotel. "I want our first meeting to be somewhere neutral, so you're comfortable, but not TOO much so," you said. "Be there at 6pm -- sharp. There will be a key for you at the desk. Let yourself in, and follow the instructions I've left for you." I'm nervous, but I willingly a...

Furniture Store

by donaldd1963 on Sep 17, 2017
Loving Wives

We just bought a new house and my wife of 8 years is still excited. Along with the new house came promises of sex beyond a mans wildest dreams. My wife stopped at a high-end furniture store for a couch we had been looking for some time now. I was at the hardware store picking up paint when she called. "I found the couch I wanted, can you come in your pick-...