Submissive Sissy Stories

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Infinite Scroll

Sissy Surprise

by silkstockingslover on Jul 18, 2018
Interracial Love

Editor's note: this story contains scenes of gay male sexual content. Summary: Wife discovers her husband is a slut for BBC and... Note 1: This is a NUDE DAY 2018 Contest Story. Note 2: Thanks to Tex Beethoven, and MesaMan for editing this story. - SISSY SURPRISE My husband hadn't been the same since he returned from a six-month military tour. There w...

Becoming Her Bitch

by HerLittlePiggy on Sep 13, 2017
BDSM

"Take it like a man you sissy bitch," Jennifer said as she thrust her big strap on into my ass. "Yes mistress," I groaned as the long life like dick pounded my prostate. "I'm not your fucking mistress you sissy pig," my wife yelled as she slapped my ass hard leaving it stinging and red. "A mistress wouldn't have her cock inside your sissy ass. From now on...

Mistress Red Fox Becoming a Devotee Pt. 03

by His_fag_wife on Nov 18, 2019
Transgender & Crossdressers

Miss Red was busy moving around the room. I wasn't sure what she was doing, but could hear her moving various bits of equipment. Then she moved the bed away from the wall. I realised that it must be on wheels. As she continued to work in the room, my mind drifted to what she'd just said. Fuck she said she understood subs, so she must be into this whole sce...

A Birthday to Remember! Ch. 05

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Decidedly put in my sissy submissive place by Mistress Leader Marta, I resolved to be much more careful and obedient. I also was aware of my excitement at her Dominance and power. When another participant sat down next to me, I was recovered enough to look up to say hello. I recognized him as one of those I had seen earlier standing around and chatting afte...

Ms. Alexandria - Interview No. 01

by gasissynora on Dec 3, 2019
Mature

I am sitting by myself in what appears to be a restaurant/bar that caters to women. I have been exchanging emails with Ms. Alexandria concerning a position she has open for a couple of weeks. She wanted to meet me here at "La Femme" to interview me about the position. I am sitting at a table in the back of the bar area waiting for Ms. Alexandria to arrive....

Heiress MMM gets Her Cuckold

by mmms_ricki on Sep 19, 2017
Loving Wives

Mary had recently inherited a rather large family fortune and become a multi-millionaire. As a result She was feeling extremely Independent and Powerful. Now that she was independently wealthy she had the urge to release Her Female Supremacy and Female Dominance side. She especially looked forward to showing off the Power She had over Her sissy submissive hu...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Letters to Michelle Ch. 01

by stevemike08066 on Oct 16, 2018
Letters & Transcripts

Dear Michelle, I hope it's ok that I email you like this, I found your email in the company database. You're a very sexy woman, and I'm not sure if you noticed me staring at you. I mean, I couldn't help it, seeing your ass in those jeans, I couldn't help it, and your breasts wrapped up in that sweater, I wouldn't mind having a couple of hours to worship...

Miss A's New Play Thing

by Pornenthusiest on Oct 8, 2019
BDSM

Chapter 1: Sexual Awakening Alex's morning ritual had changed lately. Typically he would start his day by slamming his alarm clock, getting out of bed, brewing coffee and taking a shower. But now, Alex was generally restless, always waking before his alarm could rouse him. He would rush to his computer immediately checking his messages, today was no differe...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....