Gay Sissy Stories

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Infinite Scroll

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Master Gene's Email Response

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Back at home that night I kept thinking of what had transpired that morning with Master Gene while still wearing my cum stained panties as Master had told me I could only remove them to shower. Otherwise the pink thong panties that had been soaked in cum would remain on at all times until I was told I could switch to other panties of mine. Was this a sign Ma...

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...

Euphoria Resort

by sissyashley4bbc on May 4, 2020
Transgender & Crossdressers

"Welcome to Euphoria!" a good looking black man said as he greeted my wife, Jess, and I. I couldn't help but notice two scantily clad maids getting our bags for us. "Come right thus way to check-in with your specialist," he directed us. We clutched each others hands and hurried in, we were giddy to get started. Euphoria was no ordinary resort, it was cou...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

Mindy's Moving Day - CFNM Ch. 02

by BuckyDuckman on Sep 25, 2017
Interracial Love

Author's note: I think this works as a stand-alone. I get my lily white ass reamed by a big black bull in front of my wife, her friend and my swim team. Delicious humiliation! Mindy's moving day signaled a huge change in her life and the relationship I have with my wife, Debbie. That was the day we put on a real life show of me offering up my sissy ass wh...

Scorned Bitch

by lyzunchik on Sep 16, 2017
Transsexuals & Crossdressers

"I'm assuming this is not entirely business," I asked Rod when I meet him for drinks after work. He's a fellow businessperson and we collaborate on some projects. I provide technical and consulting services that augment his contracts with various businesses and government agencies. "No, not really, but I thought it an appropriate segue to get you here fo...

A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

Caught Erect in the Greek Shop

by SissyChazzy on May 1, 2018
Fetish

My wife and I took a vacation from Canada to Greece one summer. It was really lovely. Nude beaches and beautiful waters. On one of the Islands, we headed into town to do some shopping. And here's where it happened. I was standing in the Greek souvenir shop, looking at the little figurines, when I came across the naked section. Greek men with hard dicks were...