Sissy Bride Stories

17,340 results
Orientation
Length
Source
Infinite Scroll

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

The Virgin Tranny & the Bride Ch. 04

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Continuing the story of young transvestite Roberta and her adventures with Margaret and John. I have also received the following letter which is a little worrying. Dear Yano, I'm very sorry it has taken me so long to send the next part of my story, things have been very strained over the past few months and particularly between me and Margaret since I got...

Slip-n-Slide Bride

by scatwoman on Sep 15, 2017
Illustrated

When Chet and Trisha got married, he thought their wedding night would be a night to remember! They booked the most expensive suite at the fanciest hotel on the most romantic island in the Caribbean. Little did he know that the big, black priest at the wedding was Luke Powers, a black stud his fiancée had been fucking behind his back since they got engaged!...

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...

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...

The Journey Pt. 01

by MissYellowPanties on Sep 13, 2017
Transsexuals & Crossdressers

Part 1 The Journey. I sat in the back seat of the car, my legs stretched in front of me and crossed at the ankles, the short skirt I wore barley covered my panties, and I could feel the cool leather of the seat press against my legs. I smiled at the reflection of the drivers hungry eyes in the rear view mirror, longing, lust, and power, mixed together in...

Joining the Ranks of Lady Bois

by eviltwin52 on Sep 14, 2020
Transgender & Crossdressers

This is a story about one man's transformation from loving husband to lady boi. His evolution began with a colleague leading him to an aggressive indoctrination. The journey takes him from the safe confines of a married Caucasian heterosexual male to celebrating his new life as Black cock loving lady boi. On a side note I have chosen to turn off the anonymo...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

Dry Valley Ch. 20

by RedHairedandFriendly on Sep 18, 2017
Chain Stories

Finishing Touches Three days had gone by since the break-in and attack on Jessica and Bailey. The women had been moved to the Walker Ranch, much to Missus O's soft muttering. But she knew the ranch was the place the girls needed to be to recuperate, she was however out there every day just to ease the burden on her friend Sissy, though Sissy didn't find it...

A Sissy Saga Ch. 24

by Snurge on Sep 13, 2017
Novels and Novellas

The early morning sun made the windows of the great house sparkle, and the ancient, dappled walls of Fairyfield Grange looked like they'd been daubed with gold. Abigail swept across the back patio and admired the recent changes. The large windows facing onto the terrace had been taken out and replaced with French doors. It was a facet of his mother's ultima...