Feminized Sissy Stories

6,870 results
Orientation
Length
Source
Infinite Scroll

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

From Husband to Castrated Sissy

by meeah on Sep 25, 2017
Transsexuals & Crossdressers

"Oh my god!" My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?" "Kelli what the fuck's going on here?!" At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old...

A New Toy

by keptsissy on Sep 13, 2017
Fetish

I love this view. It never gets old. I watch the top of his head. I see his tasseled brown hair as his mouth moves back and forth on cock. I see the curve of his perfectly rounded baby smooth cheeks, ever so slightly spread by way he arches his back, his butt perched up on top of his heels, his toes dug into the carpet as he kneels in front of me. I hear him...

Jenny Plays with the Big Girls Ch. 06

by Johnboy9 on Sep 12, 2017
Transsexuals & Crossdressers

The following is part 6 of the continuing saga of Jenny, our newly feminized sissy boy once my brother Jimmy, as he continues his trials and tribulations to learn to play with the big girls, as it were. I want to again thank all those who write and/or vote their continued support to me as I keep up with my attempts to produce this, hopefully, well-written fi...

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...

Jenny Plays with the Big Girls Ch. 05

by Johnboy9 on Sep 12, 2017
Transsexuals & Crossdressers

Well, that was one fine mess we got our Jenny out of that last story, wasn't it? Whew! This story is a lot calmer and yet a promise of more to come. I again want to thank all supporters and interested ones who have urged me to continue this tale of our Jenny to see what will happen to her in the end of her journey through this unfortunate (?) web in which sh...

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...

Dressing Room Punishment

by bluesbirds on Jun 1, 2020
Transgender & Crossdressers

I immediately knew I wanted the plain black sweater on the closest rack to the left. It was cut off at the belly button, but it looked warm and cozy. It clung tightly to the mannequin, the breasts noticeably perky under the fuzzy fabric and highlighting the curves inward to the hips. Tight sleeves came down about halfway to the elbow. It wasn't particularly...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

Pillow Fight

by AmberFemXD on Sep 16, 2017
Transsexuals & Crossdressers

Five little Sissies laughing and giggling like goofy teenage girls exchanging recipes, sharing makeup tips, Omigawshing about everything, and who knows what else. Wandering around in the gossip garden . . . Planting new seeds, indeed. A night, tonight together. Funzies. Sissies only. No! Men! Allowed! Grrrrrrrrr. Purrrrrrrrr. SPLAT! And the slumber party b...