Shemale College Stories

702 results
Orientation
Length
Category
Source
Infinite Scroll

2 Bodies, 1 Mind

by ReallyCoolDude on Apr 22, 2025

As you wake up you see your bedroom. And your bathroom. They’re almost overlayed on top of each other, like if you put your hand between your eyes and tried to look at two different pictures. You try looking to the right and both views shift, showing both the shower and the poster on your bedroom wall. After a second you immediately get dizzy trying to under...

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...

My First Bottom Experience

by NoLongerCurious on Jun 4, 2019
First Time

I never thought of being with a man until I was 45. It was the internet that sparked my curiosity. I first discovered shemales on the internet and was very aroused by men sucking shemale cock. I realized that cock was really hot and I wondered if it might be fun to suck one. That lead to a nervous craigslist encounter with a very nice guy who lead me patie...

Leather Shemale & Leather Wife

by LeatherKev on Sep 19, 2017
Fetish

I have always loved seeing others wear leather. I, too, love to wear leather and have a growing collection. I can't remember when it started but it seems I have always had this fetish for leather. During my first job out of college, I met a lovely young woman named Mikky. She was beautiful. Long dark hair, blue eyes, and long legs. All I could think of was s...

Christian College Sex Comedy Ch. 18

by FinalStand on Sep 25, 2017
Erotic Couplings

*If you make one person happy, you save the World. Make a million people happy and you become a politician* (Thanks for Fortima's presence fixing so many of my mistaks (Oddly there is no sex in this chapter; just prepping for the next rollercoaster) (Yes, this tale is supposed to be somewhat humorous and outrageous too. While not always comedic, I'd lik...

The Missing Link and it's Yummy!

by 7yearsitched on Sep 13, 2017
First Time

I was now riding my various length dildos in the shower at least once, usually twice a day and was now very comfortable with taking them past the second threshold. As a young adult I shaved my arms and kept my upper body clipped but I was now clipping my legs to blend in with my now daily shaved ass and cock, much like the Transgenders in the videos which...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

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...

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...