Sissy Fired Stories

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The Virgin Tranny & the Bride Ch. 02

by yano on Sep 25, 2017
Transsexuals & Crossdressers

This is part two of a confession related to me by my transvestite friend Roberta, and like the first part, is so sexy without any further elaboration by me. Having seen some of the photographs, I can only say that she strays very little from the truth. Meantime I am trying to convince her to let me publish a few on the Internet. Watch this space. Exactly tw...

Discovering Amber Ch. 09

by Ms_Allison on May 6, 2019
Transgender & Crossdressers

Mistress Notes: My intentions with amber were simple at first, but became more complex over time. Our roles seemed to continuously evolve with her becoming more and more submissive and femme and my becoming more Dominant. After a year I really couldn't see her as anything but amber, even when we went to her company's holiday party (which she wore a suit and...

Jesse's Journey Down a Rabbit Hole Ch. 08

by Rebeccasm on Sep 25, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

Dan's dreams come True Ch. 02

by JenniferTaylorTV on Jan 20, 2020
Transgender & Crossdressers

Caroline giggled with delight at the look on Jennifer's face. "She never had any idea, Suzanne. She thought you were a real girl!" Jennifer felt like crying. She was so excited, so turned on by the beautiful Suzanne, she couldn't believe what she was seeing. But there in her delicate silky panties was a hardening cock. Bigger than Jennifer's own not tiny ef...

Road Dog

by TwistedPanties on Mar 3, 2020
Erotic Horror

It all started with a bit of fun on his road trip. Bryan was en route to San Francisco to hang out with an old female work colleague, as "friends". She was a couple years older than him, 32 to his 29, and she had a great apartment downtown. Of course Bryan had wondered if she would let him put the moves on. It didn't matter if he got to hookup with her or n...

A Better Life through Chastity

by chlomo on Aug 31, 2020
Transgender & Crossdressers

I wrapped my arms around Sophie and squeezed her tight as I shot my load inside her. She was perfect; large breasts a peachy rear all in a pale curvy frame, her long brown hair framed her big welcoming eyes gleamed up at me. I didn't deserve her. I sighed heavily and sank into her as she smiled and gently stroked my hair. I had failed her again, I knew it,...

Making of a Porn Queen Ch. 02

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

I had set my alarm to wake me up early on Friday. Mark would be back from his trip by Ten AM and I wanted everything to be perfect when he got there. Tracy also got up early as she wanted be ready for when her husband arrived. I had to wear my house boy uniform as Tracy didn't want Mark to know what we had been up to for the last week. Even though I still wo...

Sissy Awakening Ch. 02

by Torbjornson on Sep 28, 2020
Transgender & Crossdressers

Sissy Awakening Ch. 2 The drive home was quiet, and I was glad for it to be quiet. I'd done some things that I probably shouldn't have but I was so caught up in the evening that I'd done them anyway. I didn't feel bad for having done them but I wasn't ready to talk about it yet either. Pulling in to the driveway just as the sun started coming over the hor...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

A Slut. An Insatiable Slut.

by hunter_gatherer on Sep 12, 2017
Loving Wives

"Mr. Jenkins and Mrs. Jenkins, I have seen enough over these last few months and will recommend an amicable divorce. It's the best for both of you. You will have joint custody of your four year old daughter, on terms you both can work out on," said our counselor. I was heartbroken. I had tried to make everything work. I wanted to be together as a family. A...