Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

Dark Rescue Ch. 01

by TheKeith on Feb 6, 2018
Loving Wives

Standing outside the private diagnostic clinic, the rain came down in buckets. The kind of rain, in big drops, so closely spaced, that if you looked up and opened your mouth, you'd drown. That kind of rain. Standing there, just under the overhang, I was still mostly dry. The girl—well, woman—standing next to me wearing a thin cotton dress, bare shoulders,...

Classmate Crush

by DanielBrown on Mar 27, 2018
Toys & Masturbation

There had always been a thread of tension between us, the natural result of two people with similar personalities and interests, two people that would have been a couple by now if she wasn't already dating someone else. All throughout class we held a whispered commentary under the lecture, laughing quietly at our professor's odd mannerisms. After class ended...

Studying Hard at Magic University

by superbutt on Mar 28, 2018
Erotic Couplings

The soft grey stones of Craven's first Magical University soaked in the summer heat. They were rough, but Larry couldn't help but feel joy at brushing his fingers across them. This was his second year, and he was quietly confident about his chances with the presentation. High marks here would set him up for a better class next year. Talent was a responsibili...

The Event Pt. 02 (A Spin-Off)

by AnonymousPerv on Feb 6, 2018
Fetish

Hi folks. This is one I wrote super fast, so I hope it isn't too noticeable. It's a take on The Event, but with a different set of "mechanics." Also, the original series is under Incest, while this is Fetish. No incest in this very short tale, and I can't think where best this belongs. Maybe exhibitionism. I suck at choosing categories. What is the same: an...

Tanya Lets Go

by andrezagato on Mar 5, 2018
Loving Wives

Tanya and I have a rich fantasy life together in bed, but at the time of this story, we had yet to explore the fantasies involving other men in real life. In our day to day lives, Tanya is a successful executive and is very much in charge of her life. In bed, she can play many roles and encourages me to push her submissiveness. Our fantasies often include he...

Staying Warm

by Reddragon5002 on Mar 5, 2018
Loving Wives

It was early spring, and we had decided to go to Breckenridge, Colorado, just the four of us. Our Punta Cana trip was a resounding success and over time we had found a sense of comfort around each other. At this point, Kathy and Tyler had been dating for almost a year, the divorce now finally in their rear view, and their future with us ahead. We had been fl...

Ms. Jiggles Ch. 03

by Cappadonna on Sep 25, 2017
Mature

She found herself to be a bit overwhelmed when she walked out in public, yet loved it. People gawked over the extra weight she was carrying behind her, as many have not seen an ass so large in size. Whenever Ms. Johnson wanted a break from the constant harassments, she wore a pair of baggy grey sweat pants, and a long t-shirt, but the idea failed miserably....

Sandra and Stevie Ch. 06

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixth installment in a series entitled "Sandra and Stevie". If you have not read the previous five episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongly recomme...

Transformation of a Husband Ch. 02

by Karenkay on Sep 12, 2017
Interracial Love

"Damn it Terry. How could you do this to me? I'm your wife Damn It! How dare you bring that little slut into our house. What were you thinking mister?" "Momma. I'm sorry. Please forgive me. I promise it will never happen again." "I'm going to call a good divorce lawyer in the morning. Do you think I'm going to stay around here and work my ass off and come...

Ben & Jerry's Halloween Surprise

by Schwingprose on Sep 14, 2017
Exhibitionist & Voyeur

I screwed up. I screwed up and I got caught. I don't really regret the screwing up part because I got to fuck the neighbor I'd been lusting for since I first laid eyes on her a few years ago. Let me start at the beginning. My name's Ben. My wife Barb and I have been living next door to Pam and her now twenty year-old son Jerry for the past five years. They m...