Sissy Trap Stories

19,529 results
Orientation
Length
Source
Infinite Scroll

The Slave and the Sissy

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or h...

Caretaker Joe

by CarrieQ on Dec 2, 2019
Transgender & Crossdressers

It was my first time living on my own. I was 18, and enrolled at a college to study art and photography, in a town far from home, in fact close to London. I took a room in a hostel, popular with students. It was halfway down an ill-lit corridor, and no one seemed to bother me, which suited me just fine; I liked the solitude. I was confused about my gender i...

Sissy Sidney and Sister

by FemFreak on Apr 17, 2019
Transgender & Crossdressers

Summary: Sidney is reluctantly persuaded into submitting to Ellen's humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity. All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest. ~~~~~ Angie loved to bully her little brother Si...

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

You Knew

by TwistedPanties on Mar 18, 2020
Transgender & Crossdressers

You had willingly searched and jerked off to sissy porn for years. You regularly read Literotica fiction and would love to stroke yourself for hours. It was not uncommon for you to chat or flirt with other bloggers or online friends. You sought out a deeper role. The hypnosis of online flirts and short sissy skirts led to cravings, stronger and stronger with...

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Sarah Goes to College Ch. 04

by Sarahcheer on Sep 19, 2017
BDSM

Chapter 4: Sarah before the Court Sarah was utterly beaten, and she knew it. Brian, her owner, had been keeping her locked in a cage at his dorm room for the last week, only letting her out to use the bathtub restroom and to fuck her pussy when he was in the mood. Otherwise, she had been left locked in the cage, forced to wear a VR helmet that had continual...

Sissy Fantasy to Nightmare

by Anon729 on Sep 16, 2017
Transsexuals & Crossdressers

My first ever story here so I would appreciate any feedback. Hope you enjoy it! ***** Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me. "Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag." It was just 3 days until our wedding and the...

Trapped! Pt. 01

by TheEroticProspero on Jul 6, 2020
Transgender & Crossdressers

Trapped Part 1: A Trap Is Sprung As a teacher, I shouldn't admit this. But sometimes you have students you just hate. And for almost a year I had hated Jessica Dane. I was only 25, fresh out of university, straight into a job teaching English. For all my life I was poor, short, thin, and pale. My only saving grace appearance wise was my long, rocker...

Man Disciplines Sissy Ch. 03

by LanaBehave on Aug 20, 2018
Transsexuals & Crossdressers

I watched Daddy walk to the door of the hotel suite, and I watched him open the door, and then I watched him step into the hallway. He was gone. The door closed behind him. I stood there, in my dress. In my heels and wig. I felt a shiver run through me, and I thought about Daddy, and what had just happened. I went to long mirror on the bedroom door, and I...