Sissy Humiliated Stories

21,486 results
Orientation
Length
Source
Infinite Scroll

Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

Auntie Jean Drummond Lloyd Ch. 4

by Sissy Adele Howells on Aug 31, 2017
Fetish

The final humiliation by Auntie Jean Drummond Lloyd was reaching its very kinky conclusion. I was looking really cute in Karen Lloyd's pink pyjamas. I could smell Karen's perfume and bodily juices on them. Karen had even left her shit stains in the ass part. I was now paraded in Auntie Jean's bedroom. Kimberley Holmes, laughed at my blushing face. Her black,...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Caught Erect in the Greek Shop

by SissyChazzy on May 1, 2018
Fetish

My wife and I took a vacation from Canada to Greece one summer. It was really lovely. Nude beaches and beautiful waters. On one of the Islands, we headed into town to do some shopping. And here's where it happened. I was standing in the Greek souvenir shop, looking at the little figurines, when I came across the naked section. Greek men with hard dicks were...

Behavior Modification Institute Ch. 06

by NancyPan on Sep 12, 2017
Fetish

Ms. Panington screamed and pushed me from her lap. The arousal monitor alarm was blaring. Ms. Jensen leaped to her feet and ran to Ms. Panington's side. Upon seeing the mess, she shouted, "Naughty sissy! Didn't you hear the alarm?" I lay on the floor ashamed and humiliated. I had heard the alarm begin to sound, but I so much wanted to cum I had thrust my co...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Appointment by Card Only Ch. 01

by Sputnik57 on Sep 17, 2017
BDSM

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The...

John Meets Sandra Ch. 5

by eeric on Sep 16, 2017
Interracial Love

If you have the time you can e-mail me and tell me what you thought. ***************************************** It has been a few months since I asked Sandra to marry me and she said yes. It was late in the afternoon and Sandra was getting ready to go to her bacholarette party. I didn't have that many friends so I wasn't having a stag party. When Sandra c...