Husband Sissy Stories

110,093 results
Orientation
Length
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Infinite Scroll

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Second Sight

by sr71plt on Sep 17, 2017
Non-Erotic

"But don't you find it just a tad bit strange?" Cliff Clayton asked his wife, Susan. Even though they were sitting knee to knee on rickety kitchen chairs, they barely could see each other through the decorated and lit pine branches. Two bushy Christmas trees, enveloping the room in a strong, eerily light, were positioned in the small living room, in opposite...

The Doll's House

by Velvety on Sep 14, 2017
BDSM

He stopped the car on a deserted country road, calmly turned the ignition off, then turned to look at her. His eyes trawled over her. She was wringing wet, and her dress clung to her skin, clearly outlining the shape of her slim, shivering thighs. Push-starting a car in the dead of night was not her idea of fun. 'I'm cold,' Sissy said, wrapping her arms aro...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Husband, Drop to Thy Knees! Immediately! Ch. 01

by Ashesh9 on Mar 7, 2018
BDSM

"Husband drop to thy knees!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!! The vast assemblage watched the spectacle appreciatively: male phalli th...

Sissy Cuckold & The Old Bull Ch. 01

by DirtyDaddyHunter on Sep 19, 2017
Loving Wives

He waited on the bed as instructed. He had dressed exactly as he was asked: A pair of lavender lace trimmed panties stretched tightly over the young man's small cock; a matching bra covered his hard brown nipples too. He also had on a garter belt and some high heels. Too top in off he had on some coral lipstick and he had painted his nails perfectly. There...

May Ch. 01

by Jack1107 on Oct 31, 2018
Mature

Jack was in his last term at University before his finals at the end of May. Easter had been early this year. His mum, Jean, had asked her friend May if Jack could stay with her Monday to Friday for the last term as her Town House was a two-minute walk from the University. Jack had a fifty-minute drive to it then another fifty-minute drive home in the evenin...

Sissy Gets Punished on His Birthday

by NSEW1 on Jul 3, 2019
Fetish

My lovely goddess of a wife had promised me a memorable treat for my birthday. I stayed on my best behavior that week, in anticipation of an exciting climatic night of pleasure. During the day she texted me 'hope u are ready for treats.' I wrote back to confirm and then told her I was doubly thrilled to get not just one but multiple treats. She responded bac...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...