Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

Cattle and the Creeping Things

by JukeboxEMCSA on Dec 2, 2019
Erotic Horror

It's a hell of a thing, knowing the Creeping Things are out there. Really knowing, I mean. Everyone knows that there are times when they're alone in a room, but they're not really alone. Everyone knows that sometimes they do things that don't really make any sense and they can't really tell you why. Everyone knows that sometimes they feel nervous or sad or a...

Search for a Lactating Relationship

by Leeaz383 on Dec 3, 2019
Fetish

Thanks for stopping by to read my story. This story is based on mostly facts, with names changed and details left out, to protect everyone involved. And of course: everyone in this story is way older than 18 years. No infringement is intended where some facets of this story reference materials I found on the Internet. If you are squeamish about having affa...

I Never Should Have Taught Her

by Just_Words on Oct 8, 2019
Romance

I suppose that my only excuse for this is that I've read too many Loving Wives stories. Parts of this are true, although it was a friend who taught my fiancé the lesson. While my wife sometimes threatens me with it when she is annoyed, she has never actually done it. >>> >>> >>> I was lying on our living room floor, dazed and rub...

Checkmate Ch. 01

by Kitty9Tail on Oct 8, 2019
BDSM

This is part of a long story which is mostly already written. The series will contain BDSM, humiliation and high stakes. This story was written in collaboration with my friend J - thanks! -- PROLOGUE At the prestigious Notre Dame d'Excellence, a simmering rivalry is soon to turn to flourishing anger, with dire consequences for all involved. All may be f...

Princess, Enraptured

by bogjelly on Jan 20, 2020
BDSM

"Take it, Princess," he moaned against my ear, hips rocking against me. He felt so big inside of me. I gasped and whimpered against him. He held me so tightly, as tightly as my pussy held him. I felt so small in his arms, overwhelmed by the waves of pleasure roaring through me with each thrust. I was all his. "Yes," I gasped agreed moaned Ellie sig...

The Gangbang

by hydrangealawrence on Jan 20, 2020
Group Sex

My fiancé and I were together 11 years before I found out who he really was. Eleven bullshit, wasted years. We started dating in high school. We were each other's first everything. But somewhere along the line he became another person, and I couldn't let go of the memory of the man he used to be. He cheated on me. Constantly. I don't know exactly when it...

He's Got The World On A String

by Westward on Mar 17, 2015
Science Fiction

Faded text like this are just notes, primarily - but not limited to - things I want in the story but have yet to smoothly work into the narrative. I apologize if they break your immersion, though I’m sure my bad writing will do that first. Format Key: - Plain Italics are thoughts. - Bold text is written. - Bold Italics are memories. [CHAPTER ONE - Awakening...

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Lily Finds Happiness Ch. 03

by shivery on Mar 9, 2020
Mature

"Hold on - say that again?!" I was having coffee with Kim, my oldest and best friend. She was in town for a conference. It was the first time we'd seen each other since I'd moved in with Cathy and Steve many months earlier. Kim had asked about whether I was dating anyone, and I decided at the last minute to be honest with her. I hadn't been sure whether I...

Libertine Adventures Ch. 13

by a_libertine on Mar 3, 2020
Group Sex

All the people are over the age of 18. Please vote in the end, using the stars. Any comments are more than welcome as well. Thanks, and enjoy it. This one is a departure from my norm, so here's hoping it doesn't suck. It is an MMF story, so if that isn't your thing please skip this one. Thanks A_L ******** I woke up Sunday morning with my left side coo...

An A&A Weekend

by exploral on Mar 31, 2020
First Time

Beth was a friend of my fiancé Olivia. She was a very attractive woman in her mid-forties, she had a pretty face, she was fit and she had a great pair of fake tits. Beth was always a bit envious of my fiancé, not that I was the perfect guy, I was far from it. Beth just wanted to have someone in her life, someone she could do couples stuff with. Beth seemed...