Crossdresser Marriage Stories

54,168 results
Orientation
Length
Source
Infinite Scroll

The Agreement Ch. 02

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Neither Sarah nor I spoke of "The Agreement" the next day. However, the following evening Sarah poured us both a glass of red wine and after a few sips said, "So.... Are we going to discuss this anytime soon?" I could tell by the playful enthusiasm in her voice she was definitely interested in talking and quite possibly following through. "Sure," I said in...

The Panty Raider

by ValoryG on Oct 30, 2018
Transgender & Crossdressers

There, I did it again. Filching another pair of delicious panties from an unsuspecting girl - well, young woman. I'm a sophomore at a conservative Christian college in Tennessee (Robb Relertson College) and I'm having problems balancing studies and women. You see, the word seems to have gotten around that I'm a great kisser and well, great beyond that 'ol fi...

Kerri's Costume Party

by CorsetCutie69 on Sep 12, 2017
Transsexuals & Crossdressers

Let me start by saying that I have been a closet crossdresser since I was quite young. I have kept it a close secret for over 20 years now. I consider myself to be a semi-normal straight heterosexual married male with a liking for the softer side. I let my wife discover my secret about 3 years ago, after over 7 years of marriage. She was very supportive of m...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

The Secret is Out Ch. 01

by erinssilence on Sep 16, 2017
Transsexuals & Crossdressers

This story is not based off a true story. It is about a crossdresser who chooses to go to a conservative christian college only to be found out by their roommate. The story is a bit slow going at first but is necessary to set up the remaining chapters that are to come. **************** My name is Kelsey. Well, actually the name I was born with is Kevin but...

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

Dressed for Disaster: The Prequel

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

Dressed for Disaster: The Prequel Pat Summers put his suitcases on the bed, and made a quick survey of his room. He noted with approval the full-length mirror on the back of the closet door, and he poked his head into the bathroom to inspect the bathtub and vanity. Not overly luxurious, but they would do. First things first. He opened his computer case and...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....