Master Sissy Stories

61,161 results
Orientation
Length
Source
Infinite Scroll

Amy's Coming Out Party

by Cyndi44 on Sep 16, 2017
Transsexuals & Crossdressers

"What are you going to be for my Halloween party?" A simple question, really, but one I had been avoiding. My friend and co-worker, Jackie stared at me as she waited for the answer. "You know, when I was a kid, I loved dressing up for Halloween. Free candy and all that. Now. I am a 35-year-old man. Who wants to see me dressed up as Superman or Batman. No...

Kara Calls Bill for Rod

by PinkDelphi on Sep 2, 2017
Fetish

Kara Arranges a Special Visit For Rod Rod gets a toy So by now, after reading my two earlier stories, The Leather Couch, and Lingerie For Rod, you probably have a fairly good idea of what my boyfriend likes. He has some intense, unusual, desires at times. I get really turned on sometimes, just listening to him during sex. He really knows how to express hi...

From a Husband to a Dutiful Sissy Ch. 15

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fifteen: A Big Decision and Telling Mikel. Helen and I are dressed and ready to go to the ladies gym for a morning workout. I love this and dressing in my girlie workout clothes. Today I am going all black, a black leotard, black tights and black ladies shorts. I am going to contrast with my bright pink trainers. My now comfy long, just below my sho...

It Started with a Chocolate Biscuit Ch. 02

by Lion24655 on Sep 16, 2017
BDSM

Judy opened the door and led Christine into her favourite tea-shop. Not only did the shop make first class tea and scones, it was also perfectly laid out for Judy's plan, and the owner was an old friend. Since the morning she had confronted Christine about what had happened with Bill, she had been waiting for the perfect time for the next step. Today wasn'...

Susan Helps Me Get Promotion Ch. 02

by Quietoldie on Sep 17, 2017
Loving Wives

Nigel takes up the story; The three pictures sent from his mobile show Susan in a very sexy outfit, the skirt barely hiding her panties. I realised at this that she was enjoying all this despite herself. That strange mixture of jealousy and lust engulfed me and I spurted for the second time that day. She came home at around 9.30 the next morning. I was hop...

Green Figs for My Honey

by Rain_Lover on Sep 1, 2017
Group Sex

We started the last day of our holiday with a fight on the beach. It was all Animal's fault, really it was. He hated the navy blue one-piece Gucci swimsuit I bought in Mykonos the day before. "Not sexy, babe. Buy a chastity belt and be done with it!" I rolled over in the sand, took off my sunglasses and glared at him. "Covering up can be very sexy. This...

Trick or Treating a Witch

by nvioxos on Sep 1, 2017
Group Sex

In her usual indolent way, Eve crawled right on me. I could see her hips move left and right as she was getting closer. She kissed me knowing I loved the taste and smell of her cum-covered, puckered lips; this was our ritual after a blowjob. She was a woman who loved giving head and swallowing more than she loved anything else; you could say she lived to suc...

The Awful Minute

by clinton09 on Sep 15, 2017
Loving Wives

[©2010 BY CLINTON09; ALL CHARACTERS OVER THE AGE OF 18; NO EVENTS DESCRIBED ARE TRUE] [Warning: this story contains cuckolding, male humiliation, suicide, sex, violence, golden showers, parody, and any other plot device I could think of. It is the ultimate dark vision and is intended as such. All events are presented with the subtlety of a ball peen hammer....

To Satisfy a Man

by MrWhiteTiger on Sep 13, 2017
Erotic Couplings

The wind blew that night as Kitty drove along the winding country road through forests and farmlands. Her headlights shone against clouds of leaves funnelling across the asphalt and she had to drive slowly to stay on the road and avoid slamming into a tree when rounding a bend. Why had she taken this route when she could have driven to a major highway? Partl...

The Mistress Ball Pt. 01

by mrbrightside88 on Sep 17, 2017
BDSM

I heard the crunching of gravel as the van stopped. My body swayed, I had to re position my knees on the hard floor of the van. I could hear voices as the van doors opened and closed, footsteps on the gravel. I felt so groggy, how long had I been out? How long had we driven? How far? My head hurt, my hands hurt. I was fixed to the side of the van somehow, my...