Crossdressing Sissy Stories

7,212 results
Orientation
Length
Source
Infinite Scroll

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Mom's Big Black Hobby Ch. 03

by MiddleKoala on Jun 15, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is fiction as are all characters....

Sicily's Lesbian Son Pt. 02

by SubtleDeviance on Jan 29, 2020
Transgender & Crossdressers

Story contains themes of crossdressing, feminization, incest, and anal play Dante awoke with a little tent in his white lace panties, excited about the day to come. He smiled to himself and stretched across the clean white sheets, wearing one of the babydolls his mother bought for him, sheer, white and sexy. His bed had been the only place he could safely...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

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...

A Weekend Away Ch. 01

by SluttyChrissy on Sep 21, 2020
Transgender & Crossdressers

My wife Tiffany had been hinting for a while about my birthday surprise. She wasn't great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long week...

My First Time as Sara... Pt. 04

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki p...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Sarah Visits Chicago

by SarahCD on Sep 19, 2017
Transsexuals & Crossdressers

I was on a business trip to Chicago and I was staying at a nice downtown hotel. I decided to go out for the evening dressed as Sarah. Well, what did I have to lose? No one knew me there and I would never see anyone that I met again. I put on blue lace panties and a matching bra. It was a warm summer evening and so just I wore an ankle length blue strappy su...

Becoming a Sissy Slave

by mikhaylacumme on Sep 16, 2017
Transsexuals & Crossdressers

He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You might be scratching your head saying 'what choice?' Let me start...