Becoming A Sissy Stories

361,414 results
Orientation
Length
Source
Infinite Scroll

Sissy_World 01

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

The sun beat down on the land of Washington D.C. of the United States of America. Normally, it was cooler in the spring months, but no one in the area around the White House was going to be cool. No, they were too tightly gathered together for them not to be hot. The occasion? The inauguration of President Jessica Phoenix. Thousands upon thousands of peo...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

Neighbourhood Terror to Sissy Pt. 19

by Fibaro on Apr 13, 2020
Transgender & Crossdressers

Chapter 21 John had been looking forward to this very moment that he wasn't about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn't give away his voice while still not covering the sissy's face. A face even John had to admi...

A Natural Sissy Ch. 06

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

Dear Karen Pt. 05

by Da_Vida on Sep 16, 2017
Transsexuals & Crossdressers

06.02.09 Dear Karen, Following my successful luncheon, I was simply giddy with success. One result of this was I became man hungry. I wanted the warm, full feeling that only a hard cock could provide but I didn't want to demean myself by submitting to being fucked by my sissy husband. In fact, I could hardly imagine submitting to being used by any man for...