Sissy Dare Stories

47,304 results
Orientation
Length
Source
Infinite Scroll

The Darkness

by littlemissnaughtygal on Sep 12, 2017
BDSM

Kim was always the good girl, even when Darnell and Kim were into their Domination nights, Kim always submitted to Darnell, she had worked with him for so long little by little trying to pull his dominant side out in him, she knew it was there, she could see it in his eyes, and she had seen it in her dreams so many times. Each night they did this, he becam...

Another Submissive Slut - Ms Shawna

by Stillherer on Sep 19, 2017
Fetish

Ms Shawna had rung. I had been summoned. As expected I was dressed as ordered and waiting nervously in front of the building when her taxi arrived, late. Ms Shawna was excessively infusive in greeting me as I climbed awkwardly into the back of the cab with her. The driver was a leering foreigner, with a manic smile who was far more interested in sneaking a l...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

Sissy Truth or Dare

by BimboBarbie on Dec 23, 2017
Transsexual

You wait nervously outside the front door of Samantha's house, your heart pumping as you still can't quite believe your luck. Just a small, nerdy guy like you being invited over to the most popular girl at school's house! Finally gathering up the courage as you tentatively press the doorbell, hearing the sing song chime through the door. A whole minute passi...

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X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

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Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Power of Panties - The Beginning

by satinmarabana on Sep 12, 2017
Transsexuals & Crossdressers

When I was growing up, underwear was just one of those details of life. Always wear a clean pair in case you get in an accident! Sure it was nice to get sexy pairs as I got older. I still remember my first satin bra and panty set from Victoria's Secret, a gift from my older sister who delighted in showing me the ways of the world. But I never understood wha...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...