Illustrated Milf Bondage Sotries Stories

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Literotica Monthly Awards 2020: March

by Literotica on Jul 14, 2020
Exhibitionist & Voyeur

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of March Reader's Choice Awards. First Place ($150 Cash Prize Winner):When Angels Cum Ch. 19 by CapDragon121Second Place ($100 Cash Prize Winner):Chasing The Last Roa...

Snowball Hypnosis Story

by CelebMaster69 on Apr 29, 2025

This is a collaborative story, based off Snowball Story Writing (credit to Whatsa) and Snowball Blowjob Story (credit to street0) except these stories are based purely on hypnosis/mind control. All sotries must have either a) an image that shows the women hypnotized or b) an image that a hypnosis based story can be written around. Someone posts a pic. Then s...

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Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Bondage Sex Training

by Bobrt on Nov 9, 2016
BDSM

8 sets of eyes are suddenly assaulted with light. They were once in a dark Room, but now they can see. Unfortunately, what they see is a Facility full of bondage implements, sex toys and other BDSM paraphernalia. They struggle, but find no relief. All of them are naked as the day they were born, bound in tight ropes and gagged. There is no escape. They look...

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The Panty Perils of Me 01

by HarleyFatboy1 on Sep 13, 2017
Illustrated

It has been 4 weeks since my embarrassing exposure to the neighborhood hormonal charged 18 year olds at my daughter's high school and as a constant reminder I have a group of them lurking outside my home to get glimpses of me. Normally I guess that I should be flattered, however it has become a bit unnerving for me and I have found that I have purposely alte...

Sarah's Sexcapades 01

by TommyTells on Sep 15, 2017
Illustrated

Sarah the Sexy Secretary The Sexual Awakening of a 40 Something MILF Sex with my wife, Sarah has always fun...but was pretty vanilla for many, many years. Then in her early 40's Sarah started to loosen up, big time. Not sure exactly why? Perhaps a combination of factors: a change in hormones, a more relaxed attitude in general (and willingness to have a co...

The Bondage Forest

by Bobrt on Apr 29, 2025

Everyone in the Country knows about The Bondage Forest. It is a place where women end up being left there bound and often gagged. The State has no protections for Women and anything goes there. Officially, it is a crime to take Women to the Forest. Unofficially, nobody can stop it from happening! People deposit unwanted Ladies into the Forest and they become...

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Hotwife Iris Goes to Party w/Jack

by Aynsley on Sep 26, 2017
Loving Wives

"Are you sure you're okay with this?," queried my beautiful 45yo wife. "Heck, yes," I said. "I am a little nervous…but in a good way. I think this is kind of exciting. I'm surprised YOU are not more nervous." "Oh, I am. But Jack is such a darling. And I think it's so cute that he wants to show me off to his friends," said Iris, as she continued to...

The Photo Album Ch. 03

by IdeeFixee on Sep 15, 2017
BDSM

The Photo Album Ch. 03 Please read Chapters 1 and 2 before this next section. Dinner Photo 1 The wall clock says 7 pm. The chair holds a large black penis gag with leather straps. How did S. spend the afternoon? Did she rest in bed as thick pieces of dried spunk on her face, tits and belly cracked and fell onto the expensive sheets. Did she relive the d...