Husband Sissy Stories

110,093 results
Orientation
Length
Source
Infinite Scroll

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...

Mistake

by magmaman on Sep 13, 2017
Loving Wives

{This story has sex outside of marriage in it, so if you will be outraged, then be forewarned.} +++ Sissy lay there in the soft bed, her mind in a whirl. She could hear the soft snores of the man who lay beside her. The room kept blinking to a reddish hue, right outside were the motel's large neon lights. She remembered seeing those, the red portion was...

Sissy_World 02

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

John Maxwell hummed under his breath as he wiped down the counter tops of the kitchen, cleaning up before his Husband got home. Dinner was ready and waiting on the stove for her whenever she got home from work. He was petite, standing at four foot five, and slender though lightly toned. He had long ash blond hair that fell past his well rounded, juicy ass a...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Miss Guided Pt. 04

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

The next morning I went to Dr. Emily's office for my appointment and reuniting with Charles. When I arrived There were two people talking to the receptionist and I couldn't see her face. Then, I realized that the receptionist was Charles! I heard one of the patients address him as "Charlene." He looked just like a woman. Dressed in a conservative skirt s...

Humiliated Sissy Husband Ch. 02

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Max was very busy hand washing all of Tonya's underwear and lingerie in the kitchen sink. He dipped a pair of her panties in the clean rinse water dunking them several times before twisting them and squeezing out the excess water. He then placed them in the clothes basket on the counter. Tonya insisted he wear 6" heels around the house especially when doing...

Sissy_World 01

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

The sun beat down on the land of Washington D.C. of the United States of America. Normally, it was cooler in the spring months, but no one in the area around the White House was going to be cool. No, they were too tightly gathered together for them not to be hot. The occasion? The inauguration of President Jessica Phoenix. Thousands upon thousands of peo...