Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Do I Know The Woman I Married?

by The Wanderer on Sep 15, 2017
Loving Wives

I thank my LadyCibelle and Techsan for their patience, proof reading, editing skills and of course encouragement they always give me. As I've been known to fiddle with stories, after they've seen it. I take full responsibility for the content and any cock-ups in this story. While I'm at it, I think from now on I'm going to thank all my friends out there, w...

A Sorcerer in Downtown Atlanta Ch. 07

by auguy86 on Mar 19, 2018
Sci-Fi & Fantasy

Chapter 7 – An English Honeymoon Maddie squealed in delight as the plane lifted into the air. Even with Dave explaining the concept of flight to her, it was still the most surreal experience she had ever felt in her life. Though Dave could have simply teleported them to England, he didn't want to rob Maddie of the exhilaration of her first flight. It was t...

Sex in the Office and Beyond Ch. 02

by walterio on Sep 13, 2017
Novels and Novellas

ANAL IN THE OFFICE After breakfast and my morning constitution on Monday I douched my pussy and ass as Walt had instructed. I dressed in dark brown cotton sweater and one of the wrap around skirts he had bought for me. Of course I was still wearing thigh high hose and silk panties. The sweater was dark enough and I braved going without a bra. The feeling on...

Suzanne Comes Again Ch. 05

by yowser on Sep 18, 2017
Group Sex

Best enjoyed if you begin with Part One. ***** Sometimes thinking about upcoming sex is half the fun. Well, not half actually, things are always best when it is your own nerve-endings exploding right now in real time, and your legs are quivering and your heart-rate is up, and little moans are coming out of your mouth. And your lover is taking you to the li...

Getting to Know You

by deinde on Apr 15, 2020
BDSM

You're kneeling on the bed, waiting for me, when I enter the room. I'm barefoot, of course, and moving quietly, so with the blindfold on you don't know that I'm here yet, and I can take my time to examine you. I think I've seen you before. We haven't met, but you look familiar. Someone I've seen at parties, I think, maybe a friend of a friend. You of cours...

Isabel, The Beauty Next Door Pt. 01

by Bamo68 on Dec 14, 2020
Novels and Novellas

Hi, welcome to my first ever story. This story is based in the UK. Be warned, there is no sex in this episode. Please enjoy, but be kind. Episode 1 Letting out a grown as the bright morning sunshine blinds me through my bedroom window. It's Saturday morning, and like most other Saturdays my morning is taken up with my dad working. Now I have finished coll...

Kip and Salina Ch. 02

by rmlooker on Aug 30, 2017
Fetish

Starting with the first chapter will help understand this one better. Strong sexual content! * Kip and Salina had been home from their vacation for almost two weeks. They enjoyed their jobs so were glad to be back to work. Kip was an electrical engineer and Salina was a translator for a government agency. She had just gone back to work two to three days a...

Wifely Duties

by PTWinters on Sep 26, 2017
Humor & Satire

This is the first chapter of the adventures of a 1950s housewife. I'd love to read any feedback you may have after you've read it ***** Jane looked around her home. It was a nice middle-class home that contained all the state of the art appliances a 1950s housewife could want. She had a husband she loved very much and practically everything she could ask...

Nympho Wife Ch. 01

by Sam1888 on Sep 19, 2017
Loving Wives

My name is Sam and I am married to a beautiful woman called Jane. She has shoulder length dyed blonde hair, blue eyes that sparkle with devilment and luscious red pouting lips that beg to be kissed. She has a fantastic body. Her breasts are firm and perfectly shaped not to big but by no means small. Her nipples are a dark brown colour in contrast to her ligh...

Dark Redemption Ch. 02

by BarbraNovac on Sep 14, 2017
Romance

Peter and I met at my first job. He's a lawyer and I was tax accountant appointed to his case by my firm. His office back in those days was huge and sophisticated, unusually but tastefully decorated. Peter was an enigma. Everyone knew about him. Young Brilliant no want for clients. Everone clamoured to get hold of him. He was successful,. Ruthless divorce l...