Sissy Stories

6,529 results
Orientation
Length
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Infinite Scroll

Transformation Ch. 02

by Grey Eagle 286 on Sep 17, 2017
Loving Wives

My life was perfect. I had a beautiful young loving wife, two tiny beautiful little girls. Enough money so we lived very comfortably. We really enjoyed our life. Then we were invited by our best friends to help them put on a benefit program to help raise money for a Foundation. Our friends, Savanna and Jonas Lambert, had a foundation that provided plastic s...

The Business Trip

by WRJames on Sep 13, 2017
Anal

"I can't believe I let you talk me into this." Eileen was starting to sweat seriously now. It had been chilly in New York, even colder on the plane. Her little white ribbed turtleneck had been just right. But now, in the middle of the Arizona desert, she was dying. "I thought it was your idea," Tom countered. Actually, it had been the two of them. They had...

Wife's Sexual Awakening Ch. 02

by MILF4black on Jan 21, 2020
Interracial Love

Editor's note: this story contains scenes of non-consensual or reluctant sex. *** The four of us; Carl, Sarah, Andre, and I got into Carl's car. Carl drove as Sarah got into the passenger side front seat and I climbed in the back and Andre got in behind me. Once Carl started the car the music blasted through the speakers. I slid my body to the far side of...

Slaves and Studs Pt. 01

by AmethystMare on Jun 1, 2020
NonHuman

This is a short work of erotic fiction containing furry, or anthropomorphic, characters, which are animals that either demonstrate human intelligence or walk on two legs, for the purposes of these tales. It is a thriving and growing fandom in which creators are prevalent in art and writing especially. All characters in all of my stories are over eighteen an...

American Vacation

by hyperpress on Dec 24, 2019
Transgender & Crossdressers

After picking up my luggage I walked out where all the taxis and buses and family members queued up to pick up passengers arriving from around the world. Miami Dade. You waved from your little SUV. You were smiling. I smiled back and hugged you before you could get all the way out of the driver's seat. You opened the back, I threw my suitcase in and hugged y...

Hung Trans Lesbians Fuck Two Ladyboys

by mrstanley on Jul 15, 2020
Transgender & Crossdressers

I haven't written a Trans story this year. In this story I try to describe more intimate intense scenarios with a wider variety of details. If you enjoy the story please vote and comment. Feel free to read my Fetish and Mature stories as well. Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, A...

The Rose Diaries Ch. 16

by RoseB on Apr 10, 2019
Transgender & Crossdressers

Disclaimer and Notes: The Rose Diaries is an incredibly dark story focusing on forced (heavy emphasis on "forced") feminization of a completely non-compliant individual. There are elements of non-consent, violence, and dark subject matters. In addition, this story depicts dysphoria, dissociation, and general depression. I hope you do enjoy this chapter if...

My Friend's Daughter: Kristin Pt. 02

by timetravhippie on Jun 24, 2019
Erotic Couplings

Continued from Part 1. Please read that first then come on back! Kristin and I had slept together for the first time yesterday, meaning we'd fucked. We had slept in the same bed a few times but yesterday was the first time I'd really had her. And when we were done, I had her again. I woke up bright and early the next day and the sunlight was streaming into...

God of Whores Ch. 07

by SizeQueenSupreme on Jun 12, 2019
Fetish

Hey everybody, sorry I've been quiet, work got absolutely insane, and then, just for bonus fun I was sick for a while. Now I'm somewhat better I'm getting back to it. All questions and comments should be sent via the e-mail in my profile page. Enjoy the chapter! ***** It was another month of his rigorous workout before he re-evaluated himself. During that...

Be My Guest Ch. 03: CASUAL sEX

by SZENSEI on Nov 12, 2019
Exhibitionist & Voyeur

As daylight filtered overhead Heidi Baker woke up on top of her blanket. Her ass was sticky making her frown and rub her cheeks. Dawning on her who to blame she lay there staring at herself in her upright mirror. "What the hell are you doing?" She pondered her near miss night. Zach had her exactly where he wanted her, but didn't follow through. All it would...