Dilator Stories

92 results
Orientation
Length
Source
Infinite Scroll

A Slave's Love

by MountainWillow on Sep 13, 2017
BDSM

I'm bent at the waist, my torso resting comfortably on a padded pedestal, my breasts dangling. My hands bound behind my back with thick leather cuffs, a length of rope connecting my wrists to the leather collar adorning my neck, forcing me to arch my back. You reach down and grasp my right ankle bringing it up to hook to my wrist restraints, leaving me per...

The Boss Ch. 01

by lordodie on Sep 16, 2017
Anal

I tried to ignore my lingering headache and focus my attention at the task at hand. Following my usual morning routine, I was making the final adjustments to the large butt plug that would work Mandy's veteran asshole for the rest of the day. Mandy was my personal secretary. She was a cute, mousy, little blond in her early 30's. You know the type: Bubbly per...

Sex Change for Black Boyfriend

by watersoda on Sep 14, 2017
Transsexuals & Crossdressers

I have an interesting story. I am now 26 years old. I was born a male but at the age of 23 I had a full sex change at the request of my boyfriend. Here is how and why it happened. I knew I liked men from an early age. I was interested to talk with girls and be their friend but I wanted men. I looked at men in the street, at their muscles and their penile bu...

John Tames Me

by theorinwinter on Sep 15, 2017
Transsexuals & Crossdressers

I met John through some friends at a party in college, I was in my second year, he had just graduated. That first night I ended up drunk and alone in a room with him blabbing my mouth about some of my deepest trans fantasies and I don't quite remember how but I ended up blowing my first cock that night. John was a big guy, a football player body and just th...

Tormenting Rose

by slutty_jannelle on Sep 17, 2017
BDSM

Note: This is a chapter of a projected consensual S and M novel. * It was her second day at the Institute. She was stiff, sore, and sticky from yesterday's 'orientation.' After a light breakfast and her normal enema, douche and shower routine, Rose was ordered into her tightest girdle. This wasn't unusual, but her Trainer seemed to be tense, and more abrup...

A Proper Young Woman's Guide to Anal Etiquette Ch. 03

by lordodie on Sep 12, 2017
Anal

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is...

Allison's Anal Adventure

by Wet_dream_maker on Sep 13, 2017
Anal

Not all people can honestly claim that they love their job. Not everyone is really excited to be at work each morning. You see I enjoy every bit of mine. I am Dr. Joseph Scott, MD in Proctology. In short I am an ass doctor. And that is what makes my occupation exciting. Different women, different asses, different issues. No two women are the same, and as f...

Rose in Training

by slutty_jannelle on Sep 17, 2017
BDSM

Note: This is a chapter of a projected consensual S and M novel. * It was her second day at the Institute. She was stiff, sore, and sticky from yesterday's 'orientation.' After a light breakfast and her normal enema, douche and shower routine, Rose was ordered into her tightest girdle. This wasn't unusual, but her Trainer seemed to be tense, and more abrup...

Girl with Something Extra Ch. 09

by JonThomas_ on Jan 31, 2018
Transsexuals & Crossdressers

Dear readers, tis I, your ever so humble omniscient narrator, with the latest news and events in the life of the girl with something extra. ~ It was the first holiday season Daisy was spending alone. Her parents had decided to take a Christmas cruise. The new friends who'd recently come into her life since she'd become a post-op transgender woman, weren'...

A Proper Young Woman's Guide to Anal Etiquette Ch. 10

by lordodie on Sep 18, 2017
Anal

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is...