Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

Behavior Modification Institute Ch. 12

by NancyPan on Sep 12, 2017
Fetish

I was back in my room after an exhausting day of training. The prostate stimulating butt plug had been removed. I longed for the sensations it had provided me, and I had asked Madam Christina to leave it in. She had only smiled and said, "So easy, so easy; but no I will not leave it in. You will have to earn the pleasure you have learned that your ass can pr...

Barbara's Cuckold Story Ch. 11

by HOTMOM_BARB on Sep 12, 2017
Interracial Love

This is a true story by a drop-dead gorgeous mid-thirties housewife (so I've been told) who has been proudly black owned for the past three years. Many of the details may not be as graphic as you would like, but I am putting this together from three years of memories. James came by the next night, and we spent the week-end fucking, sucking and talking. He...

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

My Little Husband Ch. 2

by Wimp46 on Sep 19, 2017
BDSM

Author’s note: This is the second part in this series. Your warm response has encouraged me to continue writing. This is a fictional story. It did not really happen, although it might. If you take offense or do not care for stories where a wife completely dominates her husband, please pass this one by. This series is copyrighted by the author. It may no...

My New Friend Amy Ch. 02

by DRobbie06 on Dec 10, 2019
Fetish

"Hey Rick, can you meet at the coffee shop across from my work tomorrow at about 3:30?" Amy's text read. It was the morning after I had stopped in her store. "I sure can." I quickly replied. "Couple quick questions though. What is off limits to you sexually?" Amy asked. I texted back, "I'm can't stand anything that has to do with poop or blood. And no p...

Sissyhood of Travelling Panties Ch. 03

by daddyslittlebitch on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3: Carl Blake's mind could not shake the image of the pair of sexy red panties hidden in his room. As he ran down the stairs to answer his mom's call that Carl, his best friend, was here, all he could think about was the sensual scarlet satin of the boyshort panties with their red lace details. His mind could not help dwelling on how he had rubbed h...

The Locksmith

by cdbrittany4bbc on Jul 18, 2018
Transsexuals & Crossdressers

I wish to thank thewinedarksea for editing this beast. Summary: Fantasy night goes awry. Let me start off by saying my wife Amy and I have been married eight years now. I must admit our love life has been waning, and sex — when and if we have it — is plain vanilla. Our anniversary weekend was coming up. I told her we needed to do something to reignite our...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...