Sissy Quest Stories

12,616 results
Orientation
Length
Source
Infinite Scroll

The Cause

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Often I've wondered why the only thought to stir my sissy cock, some 40 years into life, is the vision of a hard, throbbing, blue veined cock arched just before my eager lips. Was it the spiked heels I pranced around the house in younger years or perhaps the love for the pale yellow slip I stole from my sister and wore secretly under my jeans and shirt while...

A Date with Destiny

by StarrOftheNite on Aug 20, 2018
Transsexuals & Crossdressers

Most people like to have a mind's eye picture of what the narrator of a first person story looks like, and since this is a true autobiographical story about my personal quest for gender identification, sexual orientation and self-realization, it's probably important to the narrative, too. Physically, then and now, I'm almost six feet tall, broad shoulders, n...

My BBW Cuckold Latina Wife

by cuckytoher on Sep 17, 2017
Loving Wives

I lay between my beautiful BBW Latina wife's Jasmine's legs and pounded furiously. My futile attempts were met with her laying there snickering, remote control in her hand channel surfing. You see, I'm Jasmine's cuckold husband and she is my world. She is a very curvy Latina woman with long, wavy dark hair, pouty lips, hips, legs and an ass to die for and br...

The Dragon Ring Ch. 04

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

The first days travel was wholly uneventful. We stopped to rest the equinininys mid morn; some people had brought snacks to eat while others including us took the air. My mistress declared that eating was bad for the digestion when one was thrown around on the track, which had turned to bare earth outside of the town. We stopped at an inn at lunch time t...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

Uurf Ch. 05A

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

We had breakfast with them, an assortment of dried fruit and honeyed seeds, compacted into a bar. And more of the cookies from the barrel, one for now and one for later. We said goodbye to the girls, and Davina, she gave Martin a long lingering kiss as they parted Alice turned and beamed at me as we left, a radiant toothy smile. Like the duchess's cat, on...

Auntie's Panties Ch. 03

by EasilyConfused on Sep 14, 2017
Transsexuals & Crossdressers

The air in the lounge was filled with both aromatic and visual sexual pleasures as Phoebe continued to enjoy the skill with which Anna ploughed her Mistress's slit with her tongue. Phoebe's hands were on Anna's head ensuring that the penetrations from the latest addition to her brood were deep and long. Anna made muffled sounds as she battled for air whilst...

How Low Can You Go?

by Compliant1 on Sep 16, 2017
Transsexuals & Crossdressers

Be careful what you wish for; that's a popular phrase in these Literotica stories. I found out the hard way the import of this message. I have always had a submissive streak a mile wide, but in my twenty-eight years I'd never experienced the feeling of completely surrendering to another person. With the Internet and its free personals web sites, I decided t...

Who I Am Ch. 02

by AngelSand on Sep 16, 2017
Novels and Novellas

Hello Again Friends, I want to say thank you to everyone who voted for Who I Am chapter 1. For everyone who left a comment, THANK YOU, THANK YOU, THANK YOU to each of you. I am so grateful that you took the time. Please don't stop!! Did I already say I was grateful? :) FYI Session: New Readers: Each chapter is a continuation of the previous. It is highly...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...