Sissy Wedding Stories

39,844 results
Orientation
Length
Source
Infinite Scroll

Siss the Bride Ch. 02

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Anyone who tells you that married life is hard must be part of a straight couple that survives on vanilla sex once every two months or so. I love being married, I get to live out all my wildest fantasies and adventures with the man I love; just over a year ago I married my brother (I could explain why right now but that's a whole other story), but because I...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Sara becomes The Bride

by Sexy_SaraCD on Sep 14, 2017
Transsexuals & Crossdressers

Becoming Sara has been the most amazing experience I have ever had in my life. Between the clothes and living as her all the time, to becoming the thing men fantasize, it has been an amazing transition. While I had some good friends, girls like myself that I met at one of the trans bars in town, I did lack male friends. I was never a sociable person, very...

Julie's Collaring Ceremony Pt. 01

by julieaugust72 on Dec 24, 2019
Transgender & Crossdressers

Please allow me to introduce myself. My name is Julie and I am a very submissive older sissy. I am 5-9, with a soft feminine body. I have been taking fem pills for years now. They have given me a feminine shape with a nice soft arse and 36C tits. I work out very hard in the gym to keep my body tight. But I still have a bit of a belly which people that the me...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Sissy Wants Her Wife's Boyfriend Ch. 01

by SissyArlene on Aug 21, 2018
Transsexuals & Crossdressers

I knew that my secret sissy life was about to be exposed. Cindy, my wife, had been dating real men since my hormone therapy had rendered my sissy clit useless to her, but she was still trying to keep our "unique" marriage hidden from friends and family. Two months ago, Cindy said, "I'm tired of trying to keep your transition a secret Arlene. I'm not going...

Controlling Sissy Janice Pt. 01

by sissy_janice on Jul 6, 2020
Fetish

I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I've put it in the Fetish section. *** I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware - -o...

Sissy Fantasy to Nightmare

by Anon729 on Sep 16, 2017
Transsexuals & Crossdressers

My first ever story here so I would appreciate any feedback. Hope you enjoy it! ***** Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me. "Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag." It was just 3 days until our wedding and the...

Owned

by NoFearGenderqueer on Jan 22, 2019
BDSM

Content Warning: Non-consent, substance use (poppers), Blackmail (implied), feminisation, misandry, transmisogny, mind control/hypnosis, sissy [If you would like to see more of this story, please let me know. I have a habit of never getting past the first section of a story, but would be interested in continuing this. Comment and let me know your thoughts a...