Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

My New GF has a Dick

by DixeenormousToo on Dec 17, 2018
Transgender & Crossdressers

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog...

Naughty Neighbors Pt. 02

by pzombieson on May 11, 2020
Exhibitionist & Voyeur

Lakeside living was a treat. Every morning I was able to enjoy some great views and it was a pleasure coming home to the smell of pine, fresh air and campfires. It didn't hurt that I had some great neighbors. In part one you learned all you need to know about my developing relationship with them. To my delight our morning rituals continued. I would stand nak...

Life of Koh Ch. 01

by heavenlyKK on Jun 1, 2020
Exhibitionist & Voyeur

Authors note: This is a continuation of my story, "Houseboy Blues". Most of the characters contained herein have appeared in my previous works. * The most telling observation, as it pertained to Koh, was that he no longer kept count of the number of women with whom he had intercourse. He either lost count or else no longer thought it important. A shy cherr...

Starting from Scratch Ch. 13: R.ated P.G.

by SZENSEI on Jul 13, 2020
Exhibitionist & Voyeur

HA! PG-13!!! Henry and Tessa get to work on revising the R.P.G. game Frisque. Definitely not Rated PG-13...more XXX. ***** "Are you sure it's okay my being here in your home Henry the Ate?" Henry McKellen invited his young co-worker Tessa Harper in and watched her enter. She carrying a notepad along with a bag of art supplies were barely noticed. What wa...

Titchester Chronicles - Michelle Ch. 03

by Raazor on Jul 15, 2020
Fetish

Note: All characters are 18 years of age or older. Michelle, Mary & the 'D' Stall Girls The following events take place between 1:00 pm and 4:00 pm Friday PM Mary Tolliver looked at the split-screen showing, Selwyn Mead and Sam Warner. "The embrace was her idea?" Mary asked. Sam nodded. "I had Ben do a walk by and get her attention. The girl also embr...

Sometimes Dreams are All You Have Ch. 01

by leeagrant on Aug 24, 2020
Romance

I was laying there in a wonderful and so comfortably soft bed. The sheets felt so smooth and smelled so good. I was thinking about so long ago when I was a little boy and my mother would tuck me into my bed. The bed felt like this and smelled like this. It was what I liked to think about when I wanted to feel free. It was what I always wanted to think about...

Ash's New Career Pt. 01

by Fibaro on Jun 1, 2020
Transgender & Crossdressers

(Hey everyone, following my new schedule I'm back with another story that isn't one of my big two for the 10th. This story was commissioned by a dear Patron of mine, Julia Michelle.) Intro Ash was a regular though somewhat effeminate looking 19-year-old guy with a not so regular wish as far as guys were concerned. He had always dreamt of being a model, a s...

Cucked Up Pt. 01

by DandJ69 on Jun 1, 2020
Fetish

"I've been fucking your wife for the last three months, and she fucking loves it!" Came the shocking confession from one of my oldest friends, Steve. "Fuck you... You're lying." I replied. "Oh yeah... Then whats this?" He snarled, showing me his phone. I looked down to see several messages between him and my wife. I only read the last couple, which wer...

First Contact

by Ralphjoss on Mar 2, 2020
BDSM

Ralph tentatively hovered over the send button, this was fucking crazy. He had no idea why he was even at this point, what the hell was he doing? He didn't even know this woman. Was it a woman? Jesus, he might even been catfished! His mind was racing but he was sure of one thing, he wanted to feel the loss of control at least once in his life at the hands of...

I Once Was Lost But Now Am Found

by eviltwin52 on Oct 5, 2020
Transgender & Crossdressers

A lonely young man meets a man who becomes his Daddy I will never understand how he knew what I needed, what would make me whole. But he did know and I swore I'd always have him in my life. Leon used patience and friendship as he guided me into the life I didn't know I craved. He saw it in me. He instinctively knew I could be more than I was when we first...