Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

Bitch Maker Ch. 03

by YANKEE DAN on Sep 12, 2017
Transsexuals & Crossdressers

Author's Note: A lot of people have requested that I continue this series, and finally I have gotten around to it. Enjoy! * "Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay t...

The Bradfords Ch. 01

by Erotictales4u on Oct 13, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and transsexual/cross-dressers niche, it is focused on humiliation. This is the first of a new series. I would love your feedback. ***** "What the fuck is the meaning of this Tim!" screamed Tim's wife Jane as she ran her hand through her lo...

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...

The Sexy Cuckold Couple Pt. 05

by cuckcpl4play on Sep 19, 2017
Fetish

Ceremony Preparation Continues as Does slave's New Life at Work (Day One) part 5 Background: we are a cuckold couple and one of our past Bulls ordered cucky to write a long story that included creative ideas that he could employ with us as a couple. As such, much of what is written here is based on fantasy and we would not live out many of the situations he...

You're Like a Little Boy at Times Ch. 02

by Myneed on Sep 13, 2017
Fetish

This is the continuation of a slightly twisted femdom love story that make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** It was a long week for me. I wasn't surprised when Mel didn't call. It made sense that we needed some t...

Subliminal Obsessions Ch. 04

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

*Before... I open my mouth and pump the last bits out of him and show him and Sarah's sort of become invisible as she recorded all of this. Alberta's standing and staring from the doorway and I show her too and her wide eyes widen more and then I swallow it. I rise up to standing and deeply kiss Leon. "That was perfect, worth all those years working for...

The Handyman

by sammysamson4 on Jun 25, 2019
Transgender & Crossdressers

My DIY skills were limited and my new apartment needed a bit of work to freshen it up, so I decided to get a builder in. I had known Tim for a few years after going to school with him and he had a good reputation as a handyman. He also had a reputation with the girls with his good looks, lean body and, from seeing him in the showers at school, a rather larg...

Ms. Marca Ch. 63

by Ms. Marca on Sep 15, 2017
Loving Wives

My name is Marca. I am mid 30’s, 5'10", thick dark hair and a very womanly figure, with 40D breasts (for those of you who need to know, big round nipples silver dollar size) and 38, but very firm, athletic hips. I have been told that I have a perfect complexion. Large dark nipples cap my very creamy gold brown breasts and I have a shaved pubic area. I have a...

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...