Sissy Dare Stories

47,304 results
Orientation
Length
Source
Infinite Scroll

Opening Him Up Ch. 03

by humbleboy on Sep 12, 2017
BDSM

Amy laid down next to Tim exhausted. “Tim, now I want you to suck on ALL that cum you just shot in my pussy.” Tim without a word placed his mouth on her trimmed pussy and began to suck and lick her hot organ. “That's good. You love this pussy, don't you?” Amy had always liked the way her husband eat her out, but now it was the power trip getting her off. “D...

Sissy Arlene's Soul Mate Ch. 02

by SissyArlene on Jul 10, 2019
Transgender & Crossdressers

Note to reader; This is part of the ongoing story of sissy Arlene. To get a full sense of this Saga, you need to read the 3 parts of "SIssy Wants Her Wife's Boyfriend," and then read "Sissy Arlene's Soul Mate." And now, "Sissy Arlene's Soul Mate chapter 2." ***** I awoke to the smell of coffee and bacon. My first thought was that my wife had slipped out...

Truth or Dare Takes a Turn Pt. 05

by Cutiepie183 on Oct 19, 2020
Transgender & Crossdressers

The rest of the week flew by in a blur of pure bliss. I really settled into my new role as Luke's little sissy slave. I would wake him up each morning with a hot, passionate, sloppy blowjob and give him breakfast. After that we would shower together and I would wash Luke's whole body for him and Luke would give me a golden shower in return before letting me...

A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

A Well Groomed Sissy Boy

by keptsissy on May 15, 2018
Transsexuals & Crossdressers

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?" He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard. "Please, Daddy, no. Don't do that to me, please...I'll be good...please..." I stammer through sincere tears. "Well then, all you have...

Surprise

by cwsissy on Sep 13, 2017
Fetish

Yesterday my wife called on my cell phone and told me to get home because she needed me. Having an inkling that there might be some fun in it I rushed home. When I got there the bedroom door was closed and there was a note stuck to it telling me to have a shower and make sure I was shaved clean - face and pubes. I obeyed as fast as I could. Then I went into...

Mother Dear Pt. 01

by keptsissy on Sep 13, 2017
Fetish

"Let's say for instance that I had son that was a sissy boy. A son that not only was a sissy boy that did very dirty and naughty things while he still lived in my house, dirty things for our next door neighbor, but a naughty little boy that liked to dress up in his mother's underpants too. I think a boy like that would need guidance. Don't you? I remember wh...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Francis Meets a Black Stud Ch. 02

by FrancisAlba on Sep 14, 2017
Transsexuals & Crossdressers

The first story was easy and this one went by pretty well. If you have any thoughts or suggestions for where Francis should go in installment #3 email me. I will respond to your email and sometimes I will send out previews of what I am working on if you treat me right. Thanks. As I was walking to get the key to my camper I wanted to cum so badly and really...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...