Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Panty Husband Fulfills a Fantasy

by DrLit on Sep 12, 2017
Fetish

My wife is one of the rare sexually free women on this earth. She loves sex and loves fulfilling my fantasies with a zest for the unique and special. She delivered my first strapon fucking in the wildest of ways and I loved every second. She uncovered my love of panties and makes sure I wear them as much as possible and for sure every date night. She buys me...

Jeff Explores His Fantasies Pt. 04

by majorpayne_1342 on Apr 13, 2020
Transgender & Crossdressers

For most of my life, I was always the shy kid. I barely had any friends. So experiencing everything I had this past week filled the void I had inside. I spent most of my birthdays alone and hardly received any gifts. This year, however, was going to be different. I never expected to receive the gifts I was given that year. First, taking things further with R...

Mistress Kim

by couldbeyours on Sep 17, 2017
BDSM

This story is completely fictional and is intended for mature readers, the characters names and situations do not represent anyone real and are completely chosen at random. This all started about a month ago when I was getting bored with all the wannabe Mistress's I'd been encountering online for the past year, finally I had found a women who sounded for re...

Happy Shavesgiving

by 9volt on Dec 24, 2019
Fetish

I woke up, to the most wonderful feeling in the world, as Brandi's lips were wrapped around my cock. She smiled and winked at me as I opened my eyes. She released my cock and caressed my balls with her talented tongue before returning to the head of my cock and slowly, teasingly, gently engulfing the head of my cock. I was close and she knew it. Suddenly s...

Night at Amber's Ch. 03

by simple_jack on Sep 14, 2017
Anal

The Finale The bedroom lights were dimmed when the three submissives entered. Their mistress, Amber, was lying on the bed completely nude, drinking a glass of wine. Seeing her slaves, Amber stood and fastened her pride and joy, a 14-inch strapon, to her slim hips. She motioned for the three to kneel in child's pose on the bed with their hands behind their b...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

My Girlfriend's Sex Slave Ch. 02

by subboy4821 on Sep 11, 2017
Transsexuals & Crossdressers

"Don't look at me like you're surprised, I know how much of a cock whore you are," she says. "Why don't you get over here and suck my strapon you skanky little bitch." I refuse, knowing there was no way I was going to give her a blow job. However, she comes over and grabs me firmly by the hair and yanks me over. "On your knees bitch!" She forces me down to m...

A Strapon Tale Pt. 01

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex and chastity play. Alex (29) and I (36) had been seeing each other for about a year now. During our first date I immediately sensed that she had kinky potential. There was simply something about her looks and attitud...

Multiple Melia Ch. 06

by realityischoice on Sep 26, 2017
Fetish

I heard the crunch of tires on stone as the car pulled in front of the house; my pulse quickened a bit, knowing who and what the car was carrying. Melia and I had made it to her bedroom by this time and had been standing together, kissing passionately; she picked up on my excitement and smiled through the kiss. "This is going to be a night you will never wa...