Sissy Wedgie Stories

7,074 results
Orientation
Length
Source
Infinite Scroll

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...

Officer Down Ch. 01

by Alucarda on Feb 6, 2018
Exhibitionist & Voyeur

Panic upon waking was only dulled by the bastard headache behind her eyes. Dehydrated. Dizzy. Disoriented. Dirty? Then the punishing recollection. Shame quickly crowded out even the most severe symptoms of her mammoth hangover. Abby felt bare yet smothered. A clammy sheen of perspiration clung to her pale white flesh. Others still slept alongside her in th...

Hot Donna Ch. 07

by baremetal on Sep 14, 2017
Loving Wives

We fall into our hotel room moving directly to the bed, Rob is as hard as I have ever known him to be and I am so aroused if he can't satisfy me I going right back to Luke's room and ride his cock till morning. I mount his stiff member and moan with pleasure, the ache between my legs subsides a little. "Oh God Rob it feels so good to have a nice fat cock bu...

Please Play with Me

by pangolin on Aug 19, 2017
Exhibitionist & Voyeur

I was the girl in high school that everyone fucked with. Somehow, word got out amongst my schoolmates that I was the school slut. It wasn't true. Well, not entirely true anyway. I didn't make out with everybody. I gave it up more than most of my friends, but what I really wanted was to be the center of attention. Being "that girl," after all, had its privile...

The Gym

by estragon on Aug 19, 2017
Exhibitionist & Voyeur

This story is racist and sexist...just what you'd expect from a porn site. But since Lit is a higher-class site, the writing is better than you'd find on most porn sites, if I say so myself (because no one else will). Needless to say (but I'll say it anyway), I am not the narrator, although much of this story, if you can call it that, is derived from actual...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...