Feminized Sissy Stories

6,870 results
Orientation
Length
Source
Infinite Scroll

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

At Their Mercy

by Subserver on Nov 9, 2017
BDSM

Miss Erin and Miss Erika giggled and teased, pinched and fondled me as they made me into their feminized plaything. When they had finished I was wearing a short blonde wig, eye and face makeup, red lip gloss, red nail polish on my fingers and toes, small hoop earrings, perfume and black satin panties with lace insets, a matching bra that was filled with fal...

Sissy Watches Her Wife Get Fucked

by tiffanyfoxe on Sep 19, 2017
Transsexuals & Crossdressers

I was dressed in my favorite maid's uniform, hot pink with white lace ruffles around the neckline, the cuffs of the sleeves, and the hem of the skirt with a wonderfully feminine full ruffled petticoat that made my skirt stand out almost straight. As a proper maid should, I also had on a white satin and lace maid's apron, white lace wristlets and a white lace...

The Sissymaiden's Tale Ch. 01

by ppeaks42 on Mar 7, 2018
Transsexuals & Crossdressers

The world was not always this way. Though few remember it, and even fewer choose to speak of it, there was a time when things were different. Before disease ravaged the land. Before the great feminization. Before the influx. Before the Femocracy. It was whispered that once white men had been just that: men. It was nearly impossible to believe, seeming more t...

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

FMDM Inc - Jerry's Story

by satinmarabana on Sep 13, 2017
Transsexuals & Crossdressers

"I just want him to get what he needs without destroying my family or our marriage," said Mrs. Farrett quietly. She was sitting in a corporate office speaking to Amber Giles, a woman half her age and twice her breast size. Approaching this mysterious FMDM, Inc. had been her last resort to saving her marriage. "I understand, Mrs. Farrett," said the FMDM repr...

Melody the Maid

by nohbdy88 on Sep 14, 2017
Transsexuals & Crossdressers

Melvin had been out of work for six months now. After being let go from his previous job, he had promised his wife Susan he'd find new work soon, but soon fell into lazily living off of Susan's income. At her request, Melvin had started helping out with the housework even more. One day, a package arrived in the mail for Susan. "Honey, I have a gift for you...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...