Sissy Wedding Stories

39,844 results
Orientation
Length
Source
Infinite Scroll

The Sweetest Husband in the World

by donaldelliott11 on Sep 15, 2017
Loving Wives

My husband, Sandy, is one of the nicest people on Earth. He doesn't have a single enemy. He cheerfully helps anyone he knows, anytime he is asked. His basement workshop has always been a friendly neighborhood hangout for the other husbands on our street. Sandy is also a failure at everything, including our marriage. He has no particular talents, never learn...

The Virgin Tranny & the Bride Ch. 03

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta continues her true tale of transformation and dominance from her bisexual neighbours' as she becomes a form of sex slave both in the privacy of their home and also on the streets. Initially attracted to Margaret and her sexy underwear Roberts' secret was discovered by sex starved Margaret. She dressed in her bridal gown for hi...

Roommate Dress-Up

by silkstockingslover on Oct 26, 2020
Transgender & Crossdressers

Summary: Straight guy is feminized by female beauty. Note 1: This story is dedicated to the real Mike who requested this story. Note 2: This is a 2020 Halloween Contest Story so please vote. Note 3: Thanks to Tex Beethoven and Robert for editing this story. Roommate Dress-Up "Shit," I sighed, as I saw my outfit for the wedding... I should have guessed s...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

A Sissy Saga Ch. 21

by Snurge on Sep 15, 2017
Novels and Novellas

The next morning Jennifer Hancock went down the stairs with her hair piled on top of her head and wearing a crumpled pale-blue linen overall to be amazed when Lulabelle said she looked as fresh as a daisy. Her mother was talking on the telephone, and when Jennifer appeared in the sitting-room she clapped her hand across the mouthpiece. "I've been negotiatin...

Quarantine Slave Ch. 01

by grizzley123 on Jun 9, 2020
Fetish

I was lonely. Only 4 days into the quarantine I was assigned to after testing positive for COVID-19. I was barely ill, but I didn't want to infect the world, and the world certainly didn't want me to share. I was supposed to stay out of the world and already I was going nuts. I was also horny as all hell. And then I got a text. Need Anything? I didn't kn...

Blushing Bride Ch. 02

by britneyfan on Sep 25, 2017
Transsexuals & Crossdressers

`I stood there, with my hand on the doorknob, waiting to go into the living room where all my friends sat drinking to celebrate my upcoming marriage. I hesitated there for a moment, not quite sure what their reaction would be upon seeing me dolled up like this, my fiancee's beautiful strapless wedding dress worn over sensual white lingerie, my face covered b...

Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supporti...

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...