Sissy Quest Stories

12,616 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Clitty Transformation - One Month In

by DivinaTellsAll on Jan 1, 2019
BDSM

Exactly one month ago, on a cold Saturday night in Dallas, Madame Vega and Goddess Kimberly evaluated what I had previously referred to (my entire life), as my cock. This evaluation revealed what I already knew at heart. It was far too tiny and small to be used as a cock, or even considered a cock. I begged them to allow me to embark on a quest that would...

Desiree's Cock Quest

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

It had only been a month or so since Suzie discovered my secret stash of letters between my alter ego Desiree and another transvestite. In them she read how we both love to suck big black cocks and our bragging on the longest cock we'd ever sucked. Needless to say, it put quite the strain on our marriage. With the fact my love for long hard cocks was all o...

Daddy's Sissy Staircase Ch. 01

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

I've cleared my calendar for the afternoon and going to be spending this time with my fwb Daddy. On the drive over to his place, it got me thinking, he and I have been FWBs for a long time, and this story is an attempt to chronicle how I went from being a newbie sissy wannabe to his addicted, shameless cock slut. This is my first submission ever here; I hope...

Uurf Ch. 01

by Beatnic_jazzman on Sep 16, 2017
Sci-Fi & Fantasy

The Dragon Ring Book Two. Uurf 01 The fork was half way to my mouth with the breakfast sausage when the ring began to tingle. I could feel the warmth in my finger as the green stone glowed softly. Just as sudden and unexpected was the man who walked through the wall. I sprang defensively to my feet, knocking my chair down. "Greetings," said the stranger....

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Suspected Affair - Confirmed

by 69Jance on Jun 1, 2020
Transgender & Crossdressers

Second Part of Suspected Affair After confirming my suspicions, I was looking forward to seeing what was next with a hot wife and a pair of handsome twins. Actually though, from what Maxwell said, they all were looking forward to bringing me out of the proverbial closet and see what is next for their new sissy. Maxwell had said "We should go meet Heather a...

Aphrodite's Curse Ch. 066

by Gaius8666 on Sep 15, 2017
BDSM

Orion was the only passenger on the ship now speeding towards Arcadia. Ever since Artemis had returned from Olympus, angry and obsessed with the capture of Demetrius, not only had her blessings ceased, but so had the stream of young female initiates to her wild isolated island, so new arrangements needed to be made for his passage. Being on a mission from bo...

Domme-in-Law Ch. 03

by bartleby_prefers on Sep 14, 2017
Transsexuals & Crossdressers

This is the third chapter in a series. All characters are fictional. Previously: Discovered masturbating by his Mother-in-Law, Jim is made to be her sissy slave. Now, having discovered his wife's complicity in the affair and the depths of incestuous depravity in her family, he prepares to meet the patriarch of this lustful clan. ______ Much to my surpris...

Game Monster

by Cantalope on May 11, 2015
Science Fiction

As the world loads in you rise up, drawing up your power... before unceremoniously flopping onto the ground. What's the point? The heroes would just waltz through and kill you 20 minutes from now. You didn't even get the satisfaction of killing them over and over again like the bosses did. You were just a creep put here so the heroes could farm XP. The more...

Open in Reader

Foxfire Stables

by centaur mare on Sep 16, 2017
BDSM

I was silently fuming as Marina worked the kinks from my lower back. Her oil slick palms and roughly digging fingertips worked the tension out slowly. The room was scented a deeply, rich with lavender and dragons breath from the incense burner cradled on a low bench in front of the massage table. I expelled a short “ugh” as Marina continued deeply stroking m...