Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

The Sibling Diaries Ch. 03

by Intimate Confessions on Sep 11, 2017
Chain Stories

Full chain & introduction can be found at this link. UNITED AIRLINES FLIGHT 2069 FROM DENVER TO SAN FRANCISCO Now here it is four years later and Gretta has moved in with me. She’s been here for a few months and she’s started to settle in. I find it ironic that I’m sitting in coach on a flight returning to San Francisco as I take this story up. After a...

A Happy Trouple

by Dennis_Kiros on Sep 14, 2017
Fetish

You should probably skip this story, if you don't like to read about men engaging in sexual activities with other men. ***** 1 Breaking up is never easy, but sometimes it's inevitable and absolutely necessary. I wasn't happy when Brit and I broke up, but I think both of us were relieved that our one-year-long relationship had finally come to an end. We w...

Trojan Whores

by Wholemanz on Sep 19, 2017
Transsexuals & Crossdressers

Proofed by Maggie Finson DECLARATION: This story is an original literary work. I wrote a story just to stretch my creative muscles. All characters, Sirens, and rapists in this work are fictional. Any resemblance to anyone living, dead, or born in the future, is purely coincidental. WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence,...

Letting Go

by Iread2relax on Sep 12, 2017
Romance

Hi everyone. This is a story that I worked on towards the end of my break. I just had a chance to polish it up and post it. I'm placing it under romance. I hope you enjoy. I want to thank Andi for checking behind me. Any errors found are not because of this wonderful person. I'm not perfect so I'm sure you will spot a few mistakes. Please don't let them ru...

The Bearing

by SecondCircle on Aug 29, 2017
Erotic Horror

This is an entry for the 2013 Halloween Contest. Be sure to place your vote and check out other entries. Thanks. **** "It's that offensive line, man," Gary said. "You can't do anything with a line that's in shambles." I took a drink of my beer and nodded. "I wish they would've spent some money on that instead of those puny running backs and receivers t...

Not Drunk - Plastered

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

I was to marry on Saturday week and didn't want a stag night. The very idea of getting blindingly drunk with a loud, raucous bunch of mates unpalatable. I told my best man it wasn't required and to say nothing to my fiancé, Lily. Over the years I made many girlfriends and still secretly saw them on a platonic basis. I preferred their company to guys. One ni...

Red Wine On Her Yellow Dress

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to snowbear for the editing of this story. * ROBIN'S STORY It was a bad day. It really was a very bad day for me, indeed. I had lost my job and I had lost my apartment. Though none of these matters were my fault, they happened with the worst possible timing. Only one week ago my girlfriend of one and a half years and I had agreed that we wer...

Daddies New Girlfriend Ch. 02

by LilLindaMelons on Oct 8, 2019
Transgender & Crossdressers

Part 2 AKA A walk in the park After the torrid love making session he had enjoyed with his Father just over a week ago, Jerry knew his life would never be the same. That night Doug had tenderly held his special Gurl against his chest and had warned his son that if he ever caught him dressed up as Cynthia again he would not be able to control himself becau...

Guarded Ep. 03

by GCStargazer on Dec 23, 2019
NonHuman

Leo strode over to the check-in desk of the hotel lobby. He was still in his leather pants, his jacket open and plainly exposing his sculpted muscles for all to see. The front desk girl gave a polite bow to him not seeming the slightest bit surprised by the display. "Good evening Mr. Montone, your room is ready for you already. The penthouse suite on the top...

Decorating Her Dainties Ch. 03

by wordyone on Oct 3, 2018
Fetish

Back at work in the new year, I was missing Sophia's horny body. A sight for sore eyes amongst the chaotic views of site work. She turned up all overalls and paint rags one lunchtime at the end of the first week. I was mortified when she took her bag of used nylons away with her. I had missed her naughty little body and her cheeky ways but to have a little...