Shemal Date Nightbdsmlr Stories

444 results
Orientation
Length
Category
Source
Infinite Scroll

A Shemale in the Office

by Bauer1 on Sep 14, 2009
Fetish

The blank computer screen in front of you is just sitting there, tormenting you. You rub your eyes and reach for your coffee mug . You're in your mid-twenties, tall and handsome. You're a hotshot Project Manager for the biggest Software Company in the country. In charge of ten of the sharpest minds in their fields from programming, to Market Research. Last y...

Blind Date

by VeniVici on Sep 16, 2017
Group Sex

"Hello, I'm supposed to be meeting a Mr. James here." The receptionist looked up from her desk and glared at Zil, seriously not smiling. "I believe you'll find him in his suite, on the first floor. The River Suite." She snapped, returning to her bookwork without giving so much as a second glance or a welcoming smile. Zil walked slowly, almost hesitantly...

Date a celebrity

by pipster2927 on Sep 24, 2019
Amateur

Please add to this story. This story takes place in an alternate universe and therefore all main characters are 18 years or older. You are John Smith. You have just received an email from Celebrity Services congratulating you on winning a date with a celebrity The email reads: Dear John Doe We are happy to announce that you have won a date with a star of you...

Date with a classmate.

by pipster2927 on Feb 3, 2021
Amateur

It is four days before Valentines day and you have wanted to ask a classmate out for some time. You decide Valentines day is good for a date. You just need to decide on who you want to ask out and just go for it. First there is Madeline James from Calculus. She is 18 years old. Her best features are her blonde hair thats always in a ponytail and her smile th...

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...

"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...

How I Met My Shemale Pt. 04

by Eroticalover1968 on Sep 25, 2017
Group Sex

Ever hear of the expression, 'Led around by the balls'? Well, it brings back visions of an epic fuck up. Whose fault? It hardly matters. Joyce peeled around the corner, cast a delirious water-eyed glance at me. She drove over a curb—our suitcases jostled around like they were fucking. "What the hell just happened? How does Cheryl have a cock? She put it in...

Jimmy Olsen Shemale Bimbo Ch. 01-02

by tawnysuede on Sep 17, 2017
Celebrities & Fan Fiction

Chapter 1 - Junior reporter on the job! Jimmy ran the brush through his shoulder length hair one more time and stepped back to admire himself in the full length mirror. The wig looked good. It was the same wig he wore each time he dressed up. He took the cap off of the lipstick tube and applied a generous coating of the scarlet wax to his lips, and then bl...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

My Girlfriend - A Shemale

by ARandomGuy on Apr 22, 2025

(hello everyone, who is reading this. so first thing, first. I'm not a first-time writer but my other account is gone. so this is my first story from this account. 2nd thing, I'm not the kind of guy who loves to jump on straight to fucking. so yeah, the story is gonna take some build-up but is not that long that you'll feel sleeping is better than this story...