Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

A Twisted Wedding Night

by FrostShard on Sep 18, 2017
BDSM

"Did you really think that you were going to consummate this marriage, my dear?" giggled my newlywed wife. "I know we're married now, honey, but that doesn't mean I'm a different person now. I still have the same needs." Alicia was absolutely gorgeous in her bridal wear. The very picture of innocence. If people only knew. "But, Alicia, it's our wedding nig...

A Different Relationship Ch. 04

by Newbottombitch on Sep 14, 2017
Fetish

Chapter 4: There's someone else in my bed "To be honest honey, I really thought you would say you want another nipple piercing. You kind of surprised me with the navel. However, my mind was made up so I decided to go through with it. I hope you're not mad at me?" "No never. I was just... surprised that's all. And the navel piercing looks kind of girly don'...

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...

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...

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

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...

Another Submissive Slut Ch. 06

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

As I stared transfixed as Ms Shawna rose off of Mr Lennie's drug rigid cock. His dick was shiny slick with a mixture of their cum, the goo thick about the folds of Her twat. "Oh god Lennie," She gasped breathlessly, "where do You get all Your beautiful cum from." I groaned involuntarily as a cum gushed from within Her to slip down Her inner thigh, while Mr...

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...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...

Hugo From Pode Hole

by egmontgrigor2010 on Sep 13, 2017
Romance

CHAPTER 1 The ruggedly handsome guy with long black hair and very pale complexion leaned back on the chair in the half-empty Starbucks and wished he'd chosen a coffee that tasted like coffee. Idly he studied three under thirties women at a table who were dressed like businesswomen. He winked at one and she turned away embarrassed and their heads went togeth...