Sissy Gangbang Stories

10,687 results
Orientation
Length
Source
Infinite Scroll

House Party

by xaggothe on Sep 14, 2017
Loving Wives

Please note that this is a cuckold/bull story. If that is not your FANTASY, please do not read this. This story is a FANTASY. The people are not real. The situation is not real. It is a FANTASY. * The part of town that we were driving in was new to me. I was concerned about getting lost on all of the winding streets. I could only hope that the GPS had all...

The Only Constant is Change Ch. 07

by Minstrel_Blue on Sep 12, 2018
Novels and Novellas

Author's Note: I said in the comments to Ch. 06 that there would only be one more chapter until Jeremy left for the Navy. Turns out, I lied. There are just too many story threads that I want to tie up before we make the jump into the next phase of his life, and this chapter started getting a little more complicated than I anticipated. But I will make you a...

Becoming Jacqueline Pt. 01

by Jacqueline_Love on Sep 12, 2018
Transsexuals & Crossdressers

Summers were always so boring. All the other kids I went to school with loved playing baseball, riding bikes, chasing girls, or going to the beach during summer break, but not me. I usually spent my time in my room playing online games or watching movies or helping with chores around the house. I did not like most sports -- I never did. It was so much effor...

Mike & Karen Ch. 08

by BiscuitHammer on Aug 27, 2018
Romance

Disclaimer: All characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. As always, many thanks and gratuitous panty shots from Freja and Jeanie to my long-suffering editor and beta-reader for their assistance in polishing up and improving this work. Rev...

From Russia with Love Part DVA 02

by pellucidbard on Jul 17, 2018
Loving Wives

Author's ed. notes: This story is part 2 of 3 and does not stand alone. Please read part 1, "From Russia with Love, Part Dva, 1 of 3." For the best read, go back to the first story in this series, "From Russia with Love." I strongly recommend you read that first. The primary characters and story theme are developed there. This is one of my longest stories...

Jake and Audrey Ch. 02

by jsmangis on Mar 6, 2018
Loving Wives

In this Chapter, the story of the young couple's exploits continue, as they share their love and passion with a whole new group of 'friends'. * Chapter Two, More Friends and Lovers. When Audrey and Kaci pulled up in front of the beach house, they saw Jake and Staci relaxing in the spa. They each grabbed a bag of groceries, and as they reached the top of t...

Private Eye

by PastPresentFuture on Oct 15, 2017
First Time

Part One: Virgins Need Not Apply Kimi sent me the Craigslist ad over Facebook. 'Photographer needed for private investigation firm. Must own camera and working car. Virgins need not apply.' I wrote her back after checking out the ad and the rather generous hourly wage. -Ha ha, looks like just the job for me.- -Are you going to apply Matt? You have a camer...

The Man Inside Her

by tre34harr on Sep 16, 2017
Transsexuals & Crossdressers

"I had finally done it, completed what I had first started all those months ago... I had done it through the power of mere suggestion; making her see, making her feel that this is something that she alone had wanted all the time... I had made her take and welcome every last change. Yes it was a slow and steady process, but in the end it all work and oh how w...

Five Into Three Does Not Go

by scribbledehobble on Sep 14, 2017
Transsexuals & Crossdressers

Note to reader – This story has both transgendered and lesbian themes. It arose from an extraordinary story I once heard that quite illustrated the difference between smut and erotica. There are two groups of lovers, one group makes love, the other has wild sex. Not for the faint hearted! Note – The story is told from the perspective of five people – Jim...

Chance Encounter Ch. 09

by Miguel59 on Sep 13, 2017
Loving Wives

C sat all alone. He took a sip of his cappuccino thinking it was the best he ever tasted. He immediately wondered if its delicious taste was because of its link to their unique marriage and the very enjoyable evening he was having with his queen, Jean. He muttered aloud, "For a cuckold, it doesn't get any better than this." Each time he moved, no matter...