Clitty Stories

3,910 results
Orientation
Length
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Infinite Scroll

Expanding Boundaries

by CanadianM on Sep 16, 2017
Transsexuals & Crossdressers

Ed awoke with a start as the flight attendant touched his shoulder and told him they were about to land. He had been in the middle of a dream about Candice and hoped his hard on was not too noticeable to her and his seatmates. His mind had been racing since he boarded the plane in Seattle, but now he was almost there and was feeling anxious about this new ex...

Dinner on Vacation

by LovingMistressT on Dec 31, 2017
BDSM

He flew 10 hours to see me. My sub, my sweet subbie, rented a nice hotel room downtown. The type of hotel that is meant for businessmen or families. The type of perso my sub way was in his regular life, his vanilla life. Not that his vanilla life was safe from ever experiencing My Dominance. He was expected to wear panties, a cock cage and sit to pee. He's...

First Time Meeting Master Gene

by sissysubTiffany on May 29, 2018
Transsexuals & Crossdressers

First off a little about myself as I am bi having been with both sexes, but lately only men. I have always it seems to have been attracted to a male cock, but not to men as weird as that may sound. For awhile now I have been going to an XXX Theater Book Store in a town about 45 minutes from me hoping no one would know me there sucking cocks and getting mine...

Helen Ch. 02

by Philippasubmaid on Sep 15, 2017
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered male. If you are offended by tales of BDSM and sex between consenting adults the read no further ......... other wise enjoy Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue... * Having withdrawn my now softening cock I g...

An Unexpected Twist

by Buildaworld on Sep 16, 2017
Transsexuals & Crossdressers

A week has passed since that event and things seem to have become steady again. Gabrielle and myself are in contact every day, Melanie has backed off and everything feels perfect. We even met yesterday for a quiet little meal, but after a meal and a few drinks, I was stretching Gabrielle's tight little pussy and she wasn't being quiet about her pleasure. B...

It Began with a Need Ch. 05

by jessikab on Aug 26, 2019
Transgender & Crossdressers

The next morning, tousled and groggy, I awoke in that disoriented state that one finds oneself when in unfamiliar surroundings. Sunlight beamed through the open curtains across my face and body and, it was only upon looking down to where my lover was draped across my lower body, still wearing his lingerie, that the events of the night before broke over me in...

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...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Caitlin and Mistress Vicky Ch. 03

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and tried to decide how to accessorize. I selected a lace choke...

Sissy Hubby Ch. 03

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

As the sleepy fog cleared my mind, I felt warm sunshine on my face. Remembering the night before, I couldn’t help but smile as I pictured my wife Stacy fucking my ass with my pink dildo. Running my hands down my slim body I felt the baby doll nightie still spread across my chest. Finding the strength to sit up and greet the day, I found I was unable to open...