Sissy Cuckold Gangbang Stories

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Orientation
Length
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Infinite Scroll

Aunt Margo - The Family Slut Ch. 07

by Kalimaxos on Mar 10, 2020
Loving Wives

This story is the property of the writer Kalimaxos. In memory of my aunt. A slut of epic levels and magnitude. And a heart of gold. *** WARNING! WARNING! *** A warning to all. This is a CUCKOLD stroke story of the first time Margo and George had an experience with another man. It is as graphic as cuckold stories get. If you have problems with this, DO...

Man-up, Pussy!

by laptopwriter on Sep 14, 2017
Loving Wives

This story is a little different than my usual but I certainly hope you still enjoy it...and as always, I love to hear back from you. ***** Of all the gin joints in all the towns in all the world, he had to walk into mine. Okay, it's not really my gin joint, but I did stop in after work from time to time. It was called Plato's Place. It was my refuge and I...

The Descending of Jessica Ch. 16

by Jessie92 on Sep 19, 2017
Novels and Novellas

Sorry it took so long to get this chapter out, life has been overwhelming. The Amber series is about to start, and I may sporadically add to the Jessica series as well. So, here's the thing; if you haven't read any of the previous chapters, you are bound to be totally lost. The story thus far is too long to explain, so I would urge you to read them first,...

Daniel and Jamie's Romantic Night Ch. 03

by lockedinsteel on Apr 24, 2019
Fetish

Daniel woke with his arm under someone. As the fog of sleep lifted, he remembered vividly the day before. His wife taking complete and total control over him. His ass being turned cherry red by the spanking to end all spankings in order to teach him his place. His lips on his wife's girlfriend's pussy to suck out his boyfriend's cum. Two hours on his knees e...

Money Shot

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

All persons depicted in nude/sexual situations are 18 and up. This work is entirely fictitious. Any relationship to persons living or dead is unintentional and entirely coincidental. Shy nerdy virgin Danny is gets a project of a lifetime: photographing his shemale classmate in the nude which leads to new sexual experiences and a new lease on his formerly se...

No Greater Love

by saddletramp1956 on Jun 25, 2019
Loving Wives

This story is a spin-off of my ongoing "Snugglebunny" series about the life and love of Chris and Chloe Weber. To understand all of the background and context, you will need to check that series out. As the stories are posted under different areas of Literotica, I suggest you check out my profile for links to those. To fit the timeline of those stories, this...

Consequences of My Porno

by JBEdwards on Dec 10, 2018
Exhibitionist & Voyeur

It can be a slippery slope from porn into submission Warning: This story contains elements of video sex, threesomes (MMF and FFM), group sex, nonconsent/reluctance, and even a gangbang. ************************ I caught my boyfriend Brad watching some porn on his computer. It was gross, but really, it was not surprising. Most men watch porn on their comp...

Audition Ch. 05: Nanette

by craigool on Jul 13, 2020
BDSM

"Audition 05: Nanette" by CraigOOL BDSM -- A wanton virgin spy in the house of love [Author's notes: Warning! This is a BDSM sex story. There are strong Dominance and Submission themes in this story. There are some interracial themes in this story. This story has substantial male/female, female/female, MFM, FFM and group sex sexual contact. This hopefully...

Girlfriend with Testing Device Ch. 19

by Razmagurk on Dec 2, 2019
Transgender & Crossdressers

Warning: This chapter features especially jiggly tits, Basketball, Homework, Cute waiters, Red Lipstick, Evening dresses, Boob pride, Body language, Not-body language, Dick swaps, Guy-on-girl blowjobs, Facials, Talent swaps, Height Swaps, Toxic masculinity, Simmering Rage, Boring lectures, Sissy Professors, Fancy restaurants, and an assortment of climaxes, m...

Kidnapped (A One Week Chronicles)

by Louise69 on Oct 15, 2017
Transsexuals & Crossdressers

Prologue Crystal checked the address on her phone as she walked through the bustling crowds of Leicester Square. She had a few minutes before she'd be missed, so hurried quickly, her tall heels and tight fitting dress making the task difficult. The pub was just around the corner and she ignored the lustful looks she received from a drunken crowd outside th...