Sissy Truth Or Dare Stories

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So Many Poles, So Many Holes!

by dirtyjoe69 on Aug 29, 2017
Group Sex

The room was dark and humid; all the bodies raised the temperature to that of a steam room. If one was to stand back from the group we would look like a pile of garter snakes coming out of hibernation. Limbs were everywhere, flailing and twisting in the throes of passion. I didn't even think it possible to have that many people on one bed. Five men and five...

Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

Truth or Dare Takes a Turn Pt. 06

by Cutiepie183 on Nov 2, 2020
BDSM

I wake up in a small strange concrete room, still wearing the pink latex that Master Brent bought for me but this time without the hood or the gag. I look down and see masters foot on the concrete floor tapping. As I look further up I see his tall muscular body dressed in tight leather and the big smirk on his face as he says "well looks like our little bitc...

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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Slut for All Pt. 07

by Knightofround on Sep 26, 2017
BDSM

It has been over a month since the night I crossdressed and got fucked by Anthony, a large black man with a massive cock. Vikki and I have gone back to our normal sex routine. The rules of wearing my collar and panties are still there, but she hasn't used a strap on or any toys in my ass for the first two weeks. I guess she wanted to make sure I recovered ni...

Truth or Dare with Sisters

by sissyboy_stacey on Sep 18, 2017
Fetish

Ringgggggg... Ringgggggg... "Sean, can you get that?" "Hello? Hey Gina... what's wrong? Ok, hold on, I'll get her..." "Katie, your sister is on the phone. She seems really upset and said she needs to talk with you." When I heard my wife Katie pick up the phone in our bedroom, I pretended to hang up, but instead, I put my phone on mute so that I could eav...

Truth or Dare Takes a Turn Pt. 02

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

Morning rises and I must have eventually fallen asleep during the night as I am awoken by a swift and stubborn kick to the stomach. "Rise and shine sissy boy, you've got a lot to do today" sprooked Luke as he looked down at my filthy curled up body. I peel myself off the hard cold concrete of the patio and instantly feel the pain of my cock being squeezed...

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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The Babysitter Takes Over Ch. 02

by sissysherry2 on Mar 20, 2018
BDSM

Chapter 2: The party "Ok bitch, I'm going to invite my friends over tonight for a party. I'm going to text them an invite and I want you to do it. Now go over there and start talking. And you better make it good or I'll post the pictures on my Facebook page." I went over to the corner and started talking while Teri got her phone out again and pointed it at...