Sissy Dare Stories

47,304 results
Orientation
Length
Source
Infinite Scroll

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...

A Husband Named Cathy Ch. 02

by cathynylons on Sep 18, 2017
Transsexuals & Crossdressers

When Toni had finished inserting my butt plug she turned to me and said, "There, now you'll see how much more feminine you walk. We will be going out later this afternoon so I think now would be a good time for you to go to your room and think about your behavior yesterday." I went to my room and sat at the vanity and began applying my eyeliner, eye shadow...

Dress Up For The Girls Next Door Ch. 02

by JackorJill on Jul 15, 2020
Transgender & Crossdressers

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot. “I have a few cold beers in the fridge,” she cooed. “Why don’t you take a b...

Neighbourhood Terror to Sissy Pt. 03

by Fibaro on Mar 26, 2019
Transgender & Crossdressers

(Hey, so things have been a bit busy lately, but I'm back with another part. I really hope you guys like what I have done with this and as always comments are really appreciated, enjoy.) ***** Mark woke up to the sound of his alarm with a loud groan. Taking the bus down town would take a lot of time and he had pretty much made up his mind that he couldn't...

Neighbourhood Terror to Sissy Pt. 20

by Fibaro on May 11, 2020
Transgender & Crossdressers

Chapter 22 Marcy woke up with a loud groan. Sleep had not come easy last night with how horny she had been, the fact that her butt had remained filled up, her sore throat and that chastity cage that seemed to hurt a lot more than it used to. On top of the difficulties falling asleep she was now woken up way too early. She had to since she was supposed to st...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

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...