Sissy Cocksucker Stories

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Orientation
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Infinite Scroll

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Brandi's Turn Pt. 02

by 9volt on Mar 3, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** So we woke up with my sister looking, mouth agape, at my husband in his torn panties, garter belt stockings and bra and me with a 6-inch strapon cock jutting from my otherwise naked body. There wasn't even a blanket handy to pull over ourselves. There was a pretty awkward silence...

Subliminal Obsessions Ch. 05

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

Sarah's right they'll watch anything. Including me sleeping. I don't feel different sleeping with the videos going and listening to everything but that's going to take awhile if at all. I do feel my jaw though and my bum. Sarah and I paid a lot of guys yesterday to let us suck all those gorgeous cocks and then fuck us blissful. I had so much cock in me...

My First Visit

by gbr2004 on Jan 1, 2019
BDSM

This is fiction. Do not read if gay action and discipline aren't your thing. ***** I was nervous as I drove through Tucson on my way to meet a man I had met online. I saw his ad on Craigslist and he said he was into dominating other men. I emailed him telling him my interests in this but also told him about my lack of experience with other men. I had been...

More Than I Wanted Ch. 03

by gbr2004 on Sep 16, 2017
Fetish

This story continues the saga of Steve and how his life is changed from one meeting with Mike, the man who is now in control of Steve's life. Mike has pictures that will he is threatening to send to his employer if Steve doesn't do as told. Worse yet, he threatens to send the pictures to his parents and brothers and this is not an acceptable option for Steve...

Kasey's Confession Ch. 02

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

After Mike left, I stood in front of my big mirror and stared at myself. I kept thinking of all the excuses I had given myself, and other people, about why I shaved my legs and liked wearing short shorts, skirts, high heels and stockings. All that had changed in a single afternoon, although the writing had been on the wall for a long time. Even before I had...

How Far Would He Go

by stories55 on Dec 29, 2017
BDSM

This story was inspired by a Domme that wanted me to write a story about being with a man. It was at first just a few paragraphs. She then wanted more and suggested I add various elements. She knew it embarrassed the hell out of me to write it. But then she knew how much I was a victim of my own sensuality and more would follow. She knew she just need to giv...

The Sissy Diaries Ch. 1

by colettegrrl on Aug 18, 2017
Fetish

This is a story about my new life, my new way of being. I wanted to share my story so I started to record my events. I figured the best place to start was, well the beginning. Here's how it all started. * * * * * I come home to find you sitting at the dining room table, laughing and drinking with a tall, dark, well-built and handsome black man. You introdu...

Mistress Sharon Pt. 01

by corduroysissy on Sep 5, 2018
Transsexuals & Crossdressers

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses...

The Lawn Rangers Ch. 14

by texaswade on Sep 14, 2017
Group Sex

My girlfriend Claudia and her twin sister, Monique, had just watched John fuck my ass. We had all spent the evening at a costume party. I was still wearing part of my costume as a Victoria's Secret angel in fact. I had collapsed onto one of the two beds in our hotel rooms. "Oh my god Bobby...," Monique said. "Your ass is gaping open!" I moaned a confirma...