Shemale Milf Stories

702 results
Orientation
Length
Category
Source
Infinite Scroll

Becoming a Masturbation Fantasy

by TransforMaster on Sep 26, 2017
Humor & Satire

In this story people become any person's jerk-off fantasy. Figuratively or literally. Fantasy or reality. Willingly or not. Let the cum games begin!What's next? [Reserved] Matthew's father becomes a masturbation fantasy! Help, I'm jerk-off material! Mike, malfunctioning transformation app. What's next? [Reserved] Matthew's father becomes a...

Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Babysitter Cupcake: MILF Cuckqueaned

by silkstockingslover on Feb 26, 2019
Fetish

Summary: College girl seduces wife and then fucks husband. Note 1: I have been asked by a number of people for a couple of years to write a cuckquean story (which made me look up what cuckquean means). I had begun attempts on one a couple of times over the past couple of years, but I set them aside when the plots didn't work. Then after a few more requests...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

Futa Fight League!

by Sex-Shooter on Oct 26, 2019
Fan Fiction

"So we're doing this?" A thing asked in a monotone conveying exasperation. Two figures stood in some gray and black plane covered in white robes that hid their features. The other being spoke with conviction. "Yes. We need to know." "Do we honestly or are you just too prideful to admit you're just a nasty pervert?" The other bei...

Life for Futa

by GCStarnen on Jul 22, 2018
Fetish

Disclaimer: This story is the story "Living in a Futanari society"/Shemale Worldo but kind of reborn, somethings in the story have been edited here and there and some characters names and traits they have might also change from the original. (Such as the mothers name being changed). Also this story is hugely inspired by Futanari World/Shemale World...

A Transforming Invention

by TransforMaster on Jun 1, 2016
Humor & Satire

In this story, somebody comes across a transformation device. This device allows the user to transform themselves or anybody else into anybody and everything. First choice is... What situation does this story start out with?What's next? Sara, a 24-year old student Sexy girl on a sofa! Two naked women(?) in bed Kate and Her Iffy Shapeshifting Chamber You are...

Goblin breeding slave

by kire5613 on Feb 16, 2014
Fantasy

Kazex was a tribal goblin who lived in the enchanted forest far from civilized society. He lived in a cave with tribal decor, an alchemy lab, and a large sleeping mat. He left his tribe almost a year ago. He felt that he could run the tribe a lot better than the current chief and he spoke his mind off it. That got him exiled but didn't mind. He made a plan t...

My Speciality

by jazz4bj on May 11, 2020
Exhibitionist & Voyeur

I turned 19 and was pretty sure I was hot enough as a female to get hired by the porn industry and continue working till I am considered a milf. Why specifically? I would love to suck the biggest dicks and swallow the entire thick cum loads. My favorite thing in the world and here is how it went.. Pretty, teen sexy and a nice tanned and toned body with perk...