Becoming A Sissy Stories

361,414 results
Orientation
Length
Source
Infinite Scroll

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...

Becoming Marc's Sissy

by grizzley123 on Jun 19, 2018
Transsexuals & Crossdressers

This is a story with themes some may not like. If that is you, read it, don't read it, your call. But if you are going to comment, keep in mind that no one required you to read it, and no one requires you to like the themes. Writing nasty comments only makes you look foolish. For others, I would love to hear your comments. And I hope you enjoy the story....

Sissy Pills Pt. 01

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

Some say it was some sort of experiment gone wrong. But it hit the streets and it changed everything. A pill a drug that you took that made you sexually submissive and made you especially sexually submissive to men. Semen made it worse apparently. And there were addicts that ended up not just being gay or fags but entirely sissies and that was fastly bec...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

Becoming Her Whore

by ecdilettante on Sep 19, 2017
BDSM

Last time we parted, you told me that you were going to fuck me when we next met. You loved the fact that I've never been taken with a strapon and you promised to be gentle, in the beginning. It sent a shiver of excitement and fear through me, which made you smile. I can imagine heading to your small apartment, anxious and excited. I haven't cum for days a...

Natalie Finally Begins to Learn

by natalieukcd on Oct 6, 2020
Transgender & Crossdressers

Background I am a long-haired man in my forties. I have been married, divorced and married again. I have children from both relationships. I do plenty of manly things. Yet, behind all of this is the overwhelming desire to be a sissy. I cannot explain it to myself never mind to anyone else. I fight against it mostly as it does not fit in to my everyday life...

A Day Alone with My Inner Sissy

by Abitinsecure on Jan 21, 2020
Transgender & Crossdressers

It started off like any other of the rare days I have the house to myself. I woke up early at sunrise and slipped out of bed and headed for the shower to cleanse myself for the fun I was preparing myself for, something I always make sure to do as my mind starts flooding with my sissy fantasies and curiosity. I would consider myself a straight guy, work a la...