Boys Become Sissy Brides Stories Stories

188,913 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

Payson's Wedding

by fantaseeboy on Jun 5, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Very early on in our relationship, Becky learned how much I enjoyed anal play. While lying naked across her lap, she was giving me one of her mind-blowing handjobs when she suddenly slipped a finger between my cheeks and touched my wrinkled hole! I obviously wasn't expecting it an...

Boy Brides Ch. 3

by yano on Sep 14, 2017
Fetish

Chapter 3: A Lesson in Loyalty Having just driven to Tulle Towers Wood, I got out of the 'Dark Secret' as Mandy issued instructions to the three kinky boys. Darren continues his memories. "O.K, you lovely kinky people, it's time to get out. We've got a wedding to get prepared for and you gorgeous clitlickers have got lots to do," Mandy announced as we ste...

Halloween Seduction Ch. 02: The Brides

by Templar_Writer on Nov 18, 2019
Erotic Horror

This is not the end of this story, but first a small story as a breather before continuing this one and a few from the past that I have left uncompleted. This includes the recent Haunted Incest as well as Wishing for a Domme and Becoming a Pet. Possibly I will be continuing others, but for now that is my plan at this time. After the amazing experiences of...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

My Cuckold Wedding

by CuckinChastity on Sep 16, 2017
Fetish

Note - this is a piece of fiction. The characters are not real. The scenario is purely a fantasy and does not describe any actual relationship. Laurel is not my actual wife. Enjoy! ***** I stood at the altar alone with Rev. Carl, the minister, looking out at the wedding guests. It wasn't a large wedding, still to me it seemed there were a lot of people l...

Mistress Chantel, Tranny Dominatrix Ch. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Wedding Plans, Shopping, Men's Stag and Girl's Stagette. The girls all get into Kerri's Ford Expedition. Who are they? Gillian, Penny, Jessica and her girlfriend Linda along of course with me and Kerri at the wheel driving. We are all dressed casually chic of course Kerri and I tend to sex it up the most, as t-girls often tend to do. We a...

Kinky Bride Confessions Ch. 8

by yano on Sep 16, 2017
Interracial Love

Wedding Day Preparations - Part One My girlfriend Emma continues to describe her first porno wedding and her first day at the Kinky Brides Group. "The morning of my kinky wedding I met Bree at 10am and then went to the appointed meeting place to be collected by Mr. Belston. Bree and I carried an overnight bag, each of us telling our parents that we were st...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...