Sex Sissy Fantasies 436 Literotica Discussion Board Stories

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Casey's Submissive Journey Pt. 01

by corduroysissy on Dec 14, 2017
BDSM

Karen walked into the bedroom and Casey thought he would have a heart attack. He was reading a book in the corner chair and looked up at his lovely wife. She was wearing a pair of dark red, mid-wale corduroy jeans. Casey had a corduroy fetish, corduroy turned him on a lot. He'd purchased many pairs of corduroys for her over the years and she knew the red o...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Sometimes That's All You Need

by Hungry4aman on May 12, 2020
Erotic Couplings

This morning's headlines are not grabbing me. Typically, I wake up, fix coffee, and read the news. I am, typically, horny, and sex fantasies swirl through my mind like the steam swirling from my coffee. Like, how it feels to kiss and hug and grope a man's back and hips and ass and cock fully dressed. And how a man's ass can be so round and heavy with sex...

Learning

by Adanaliyik on Oct 12, 2017
Group Sex

This is the story about how, when I was trying to teach my wife how to make all my fantasies come true, by embracing her inner slut, she taught me how to please us both, by getting me to embrace fantasies that I never knew I had. I suppose that when I went looking for someone new in my life, after my second divorce, I could have chosen a girl who was already...

Fantasy Weekend

by DWornock on Sep 24, 2019
BDSM

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain. The youngest person in this story is a 19 year old receptionist. 4Play has given me permission to make modifications and additions to his story "Date Night." I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted...

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...

The Entertainment Ch. 04

by econut on Sep 26, 2017
Fetish

Steve sat back and wiped his mouth with the back of his hand. It dawned on him that he had just crossed a line that he would never be able to deny. He had just sucked another man's load of cum from his own wife's pussy. He knew then that his life would never be the same. Steve's wife, Tracy sat on the sofa in front of him, her legs splayed lewdly. Her face...

Blackmailed

by AfroerotiK on Sep 17, 2017
Loving Wives

Ronald Waterman had the perfect life. He was an annuities manager at an investment firm on Wall Street making more money than most people could ever dream of making. He'd made a few sound investments and done some trading that wasn't really above board but he didn't get caught and he made a bundle in the process so debt wasn't a huge issue. He and his wife w...