Milf Sissy Stories

11,621 results
Orientation
Length
Source
Infinite Scroll

Descent into the Abyss

by Twisted_Fellow on Apr 27, 2019
Science Fiction

This is before the true beginning. Descending into the world that is the Abyss. A dangerous place where the uncommon and rare are common place! In this tale Gaia has opened the door to the protagonists abilities to awaken. The world becoming that of a game for them in more ways than one. Illusion barriers separate our normalcy from direct confrontation of th...

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The Ultimate Cuck Experience

by Joggles44 on Mar 12, 2021
Cheating Spouses

(UPDATE: Custom names for all main characters have been successfully added! Enjoy!) (Note from the author: Hello! Hope you enjoy my story. Before you start reading let me clarify that this story is set to "private", meaning no one can edit it or add chapters but me. I'd like to keep the writing to myself while the project is developing. HOWEVER, I...

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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...

Somali Hijabi MILF Doctor

by Samuelx on Sep 12, 2017
Erotic Couplings

Alright, I might as well confess at this point. I've got a thing for "mature" Somali women I see walking around wearing the Hijab and those traditional long skirts they wear. Every time I see one I get an instant boner. There, I said it. So why don't I feel better? As I sat inside Dr. Fawzia Hassan's office in downtown Ottawa, Ontario, I felt frustrated like...

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

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Die Mädchenschule für Jungen

by Redboom on Feb 12, 2020
Transsexual

In einem kleinen Café: Verträumt blick Leon in den großen Spiegel auf der anderen Seite des Raumes. Das Spiegelbild zeigt zwei Damen in den Enddreißigern, eine junge Dame Anfang zwanzig und ein hübsches Mädchen gerade achtzehn Jahre alt geworden. Zumindest sieht sie aus wie ein hübsches Mädchen: Eng anliegendes dunkelblaues Chiffonkleid mit locker über die S...

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Sissyhood of Travelling Panties Ch. 03

by daddyslittlebitch on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3: Carl Blake's mind could not shake the image of the pair of sexy red panties hidden in his room. As he ran down the stairs to answer his mom's call that Carl, his best friend, was here, all he could think about was the sensual scarlet satin of the boyshort panties with their red lace details. His mind could not help dwelling on how he had rubbed h...

Changes: One Spell at a Time

by Guy_Faux on Aug 31, 2017
Fetish

Author's note: This story involves themes of incest, mind-control, the abuse of magic, and transgender. If these don't appeal to you then don't read it. Otherwise please enjoy. * I was still young when I lost my virginity. She was older than me, a high school girl in fact, but she was so impressed by how large my dick was that she gave me a shot. I imagin...