Sissy Humiliated Stories

21,486 results
Orientation
Length
Source
Infinite Scroll

Her Friend Came To Visit

by Dewmyne on Oct 13, 2020
Transgender & Crossdressers

Chapter One A few years ago we had an old friend of my wife's visit us when he was in town. She invited him to stay with us and I didn't know at the time they had been an item 25 years ago. We had dinner and quite a few drinks and were sitting around visiting. She was snuggled up to him on the sofa laughing about old times. She went to fix more drinks and h...

My Beloved

by quotidian01 on Aug 30, 2017
Fetish

"My Beloved, I am your dedicated lover and I will do anything for you. I thank you for letting me make this web site, where I can feel the whole world watching me. Everything I do here is for you, Beloved. And in pleasing you, I am pleased." My voice sounded a bit tinny in the cheap computer speakers. I knew I was displayed while the voice spoke: sometimes i...

Sarah was Made into a Sissy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place and wait for my things when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed t...

Sissy Comes Clean

by Cuckyboy3 on Oct 6, 2020
Fetish

Reflections after Mystic: On the scenic drive back home from a fall getaway vacation with my lovely wife, I pondered quietly how the excursion would be remembered as a first of a kind. I had begun the trip with the expectation of a quick and routine spanking followed the next day by an epic sex experience. Three days later, however, I emerged having not onl...

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...

Sissy Awakening Ch. 01

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sex Shop Glory Hole - "Hey baby, when are you coming home?" the text message buzzed quietly. Pulling the phone discreetly from my pocket, I type out, "Same time as usual, just after 5, why... what's up?" It's my lover Sarah, my best friend, and woman I'd known for over 10 years. We were dating and quite a serious item within months of meeting. Everythin...

Sarah Shows Off Her New Panties

by SarahCD on Dec 12, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was posting a picture of me wearing black ruffled panties on a "Men in Panties" website when I remembered something naughty th...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

A Dream Come True Ch. 01

by searic on Sep 17, 2017
BDSM

Arriving at the hotel you had selected after a not-unpleasant drive up, I had plenty of time to obey my instructions. Carefully unpacking, I hung up and put in drawers my few vanilla clothes and all the sissy things you had selected for me to bring. How relieved I was to find myself able to be prepared and in position in advance of the time you had set for...

Hung like a Grape Ch. 02

by sissysherry2 on Apr 10, 2018
Transsexuals & Crossdressers

The story of our sissy heroine continues... We left things in the last chapter where a female coworker uncovered "Sherry's little secret" and proceeded to humiliate and dominate her. This is part two of three. Thank you to those who reached out for suggestions and hope you enjoy this chapter. I am still new at this and appreciate any guidance either below or...