Clitty Stories

3,910 results
Orientation
Length
Source
Infinite Scroll

Humiliated by Wonder Woman

by littleerection on Sep 17, 2017
BDSM

So it's a nice day today. I decide to go outside to get some fresh air and go for a walk. I wanna soak in the early spring cool breeze. I find myself going through the woods. Eventually I end up near the end and I see her past the trees standing alone on the cliff: The one and only Wonder Woman, looking out over the town! I couldn't believe my eyes! I've alw...

The Office Sissy XX Ch. 02

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

CHAPTER 3 The smell of Dannie's pheromones was making me giddy. It had been so long since I had last tastes sissy clitty; too long. My mind flashes back to boarding school, Gloucestershire. I was young, under age by English law. It was just after the summer play, and James had decided we should change costumes; boys wear the Shakespearean dresses of the gir...

I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

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Discovering Amber Ch. 02

by Ms_Allison on Sep 25, 2017
Transsexuals & Crossdressers

Mistress's Note: I would like to thank you all for your kind words regarding Amber's tale. Amber has now been My sissy for 7 years and lives like a true sissy should. Yes she does sit when she urinates at home and at work and yes she will eventually be with a man. She's been with quite a few over the years but you'll find out about those later. Your feedback...

My Awakening Ch. 02

by doonie on Aug 31, 2017
Exhibitionist & Voyeur

I walked down to the station feeling extremely excited and rather moist between the legs and caught a train into town to meet my boyfriend. The bay in my carriage was empty and with my hands resting loosely in my lap I could feel the outline of my engorged pussy lips. I nearly forgot to tell you that I'd completely shaved that area after my morning shower ex...

Playing Alone

by lustyem on Sep 12, 2017
Toys & Masturbation

This is my story of how I play and use my toys when alone. I guess it depends on my cycle and or my mood, sometimes I can't seem to get enough even with a regular boyfriend. It all begins in my mind, I might see a cute guy or think of something from the past. Once my mind takes over I just get more and more horny till I do something about it. Sometimes I ge...

Sissy Slave Fantasy

by tinkerslut on Sep 13, 2017
Transsexuals & Crossdressers

A fantasy written to my mistress.. Sissy kneels before you, her eyes down, waiting on your pleasure. Sissy is wearing frilly panties with a matching bra, thigh high black lace stockings encase my legs. The red dress barely covers her smooth bottom. The high heel shoes, locked on my ankles, crossed behind me. I can't speak because of the ball gag in my mouth...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Daddy's Babydoll

by songman60 on Sep 19, 2017
BDSM

The air was cool, as she slipped her dress from her slender shoulders. She looked towards the window and walked over, carefully shutting it then drawing the curtains. There was no need for her neighbors to see her private life, even though they barely know her and she barely knows them. She had recently moved into the area two months ago after leaving the se...

Lauri's First Adventure Pt. 01

by stockingsofsilk4me on Feb 12, 2019
Transgender & Crossdressers

Micha and I met in the early days of Yahoo chat, when finding explicit chat rooms was easy and there were plenty of fun people online. I'm Lauri, or more formally, Lauren Carruthers, a name I chose to match my desired feminine persona. Now in my mid-40's, I've been crossdressing since my early teens. Micha and I met online and chatted for almost a year and...