Sissy Bride Stories

17,340 results
Orientation
Length
Source
Infinite Scroll

Cuckold Chronicles: Todd

by deltonaman2man on Sep 15, 2017
BDSM

Lord, how I hate Monday mornings! A wise man once said," Monday morning is a shitty way to spend one seventh of your life". I believe it. Of course I feel that way about the other 4 days of the work week as well. It's not like I have to get dressed and go to work, mind you. It's just that after getting to sleep in for 2 days, I don't want to leave that warm...

The Chief Pt. 01

by Aunt_Joanne on Sep 14, 2017
Transsexuals & Crossdressers

When I was 19, I was still trying to figure out what I wanted to do with my life. I had just dropped out of college and was working construction in my home town. Construction work was hard, but I liked it. The guys I worked with were cool. It was honest work and it paid enough for me to keep my head above water. It was also a "manly" pursuit, and that was im...

Kitty Ch. 01

by ts_candi on Sep 15, 2017
Transsexuals & Crossdressers

Hi, my name is Kitty. I live in a small town in China, which is more like a large village, with my mistress - Madam Kia. I used to be a man, but I changed. The story of my change is complicated, but I will try to tell it as clearly as I can. I never lived in china, to start with. I was a happy man, all of 24 years old. I loved my women, and I had a fair sha...

Jacki's Journey into Sissyhood

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like...

Neighbors Delight Ch. 04

by gummidurango60 on Mar 25, 2019
Transgender & Crossdressers

Coastal Retreat Aaron woke me early and told me we were taking a two day vacation up the coastal highway all the way to San Francisco and that I should dress in something sexy; something showing my mid-section and something short; preferably a skirt. He also added that I should bring sneakers or hiking shoes to change into just in case we wanted to survey t...

Cuckold Striptease Game

by Iftheshoefits on Sep 12, 2017
Fetish

I'd forgotten my damn key again. And my wife was taking forever to answer the door. What was she doing in there? I was mildly irritated by the time she finally opened up, but before my lips could even form the words to some smart-assed remark about how long I'd been standing there, my senses were overloaded with the sight before me. I gave her a once ove...

Jaclyn and Her Bitch Go Out

by lusty Vamp on Sep 12, 2017
Transsexuals & Crossdressers

Greg was kneeling at the door as usual when Jaclyn walked in. Without even a glance downward she handed him her briefcase and her jacket' "Good evening my love." Greg said. She ignored him and began shuffling through the mail. Greg hung her coat on the rack and set her brief case on the floor next to the rack. He hurriedly caught up to Jaclyn as she enter...

The Making of a Mistress Pt. 03

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This fictional series about a character first introduced in my "Coming Home; Coming Out" serial continues with Marie, now engaged, is going to meet Charles's parents. She also takes Charles to meet her mentor, Dr Sara Walters and her sissy cuckold, Paula. As in all of my work, every character is over 18 years of age, and all sexual practices a...

Mamma J Ch. 01

by Transbabe55 on May 4, 2020
Transgender & Crossdressers

"Mom, what am I going to do about Jason?" My daughter sat facing me seated at my kitchen island with a troubled yet familiar look upon her face. It was the same look I'd seen when she was doing poorly in a class or when one of her friends slighted her. The circumstances were quite different this time, however. She was thirty years old and had just found...

Dan's dreams come True Ch. 02

by JenniferTaylorTV on Jan 20, 2020
Transgender & Crossdressers

Caroline giggled with delight at the look on Jennifer's face. "She never had any idea, Suzanne. She thought you were a real girl!" Jennifer felt like crying. She was so excited, so turned on by the beautiful Suzanne, she couldn't believe what she was seeing. But there in her delicate silky panties was a hardening cock. Bigger than Jennifer's own not tiny ef...