Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

My Sissy Boss

by newbie88 on Sep 24, 2019
Transgender & Crossdressers

I knew this is why you'd hired me. I knew it from the start but had wanted to be sure before I actioned any of the dirty thoughts that filled my head on a daily basis. I had watched you watch me, had seen the desire in your eyes. I knew you wanted me, knew what you wanted and I could not wait to give it to you. I chose my outfit carefully that day. A loose...

The Settlement

by cathynylons on Sep 12, 2017
Transsexuals & Crossdressers

While my wife was away visiting her mother for a week I had a wild fling with Kate, the sexy new secretary at my office. A young tart about 22 yrs. old in tight skirts and spike heels. She drove me crazy and before I knew it we were doing it on my desk with our clothes mostly on. Then, at her place near the beach and then, on the beach at night. Wild times....

Mistress Chronicles Ch. 04

by MistressMtoyou on Sep 25, 2017
Fetish

Background: The next three stories involve my only long-term on-line subject who I have named Nancy. This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets. We agreed to continue training...

Trip to LA

by gbr2004 on Sep 15, 2017
Fetish

The bar at the Hyatt in LA was about half full, mostly businessmen with a few couples scattered around. I found myself a seat at the bar and started looking over the crowd. Look like it was going to be a tough place to meet a babe in, probably would have to go out somewhere else later. I'm married but that hasn't been going to smooth lately so thought the tr...

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...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

Jacks Awakening Ch. 01

by Surreallemming on Sep 15, 2017
Toys & Masturbation

This is my first story! Please CnC :x Chapter 1: The Mistake Another hard day at work, finishing late yet again because my boss needs me to do her work for her and saying no is harder than you first think. I dump my keys into the bowl near the door and waddle into the kitchen. My boots fall off my feet on the way and I reach up into the top cupboard and gr...

Begging for a Pegging Pt. 02

by Cirkle7 on Oct 12, 2020
Fetish

This story is dedicated to the muse who inspired it. I think she would most certainly enjoy taking the reins in the bedroom. In fact, I think she may have pleasured herself while she read the last story. Thanks again I'm speechless, but I love your dirty mind! All characters are above the age of eighteen, please this story may not be for you, but don't read...