Strapon Pegging Stories

2,794 results
Orientation
Length
Source
Infinite Scroll

A Dickgirl's Birthday Present

by sajukno on Sep 19, 2017
Transsexuals & Crossdressers

"Happy birthday, Ann!" Charlene presented her long-time girlfriend, Ann, with a beautifully wrapped present. The two had been together since they were both freshmen in college. Ann was drawn to Charlene's beautiful smile and her wit. At first, Charlene hadn't been very receptive of Ann's overtures, but after a spontaneous drunken fling, Charlene had fallen...

Silver Linings Ch. 02

by tdallyn on Apr 17, 2018
Group Sex

This is part two of what could be a multi-part story. Although one can read this independently, the reader will get a better feel for the characters and what's going on by reading part one first. If there's an interest, more chapters are just waiting to be written I hope you enjoy! ***** "Good morning sweetie," my wife Samantha kissed me and sat down at ou...

Grace Under Fire Star Does Blacks

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

Brett Butler looked at herself in the mirror. At the age of fifty three, she still looked good. Blonde-haired, blue-eyed and curvy. Blessed with Irish good looks that simply refused to fade. Unlike her star in the upside down world of Hollywood. That one faded so damn fast she went from being a household name to a nobody in no time. It had been so long since...

Black On Black Pegging: True Love

by Samuelx on Sep 11, 2017
Fetish

I don't know why he thought I wouldn't be able to handle it. I really hope he'll stop hiding stuff from me after this experience. Female on male strap-on domination, Afro-Caribbean style. Seriously. I honestly wish he told me about this really hot fetish of his sooner. My name is Malinda Lexington and I'm a short-haired, green-eyed and kind of chubby young B...

An Anal Beginning Ch. 01

by caffinated on Sep 16, 2017
Anal

This is the beginning of a longer story. It is the first piece I am publishing in this format. Your feedback is welcome. John's deepest desires left him lost. He longed for something that went against every fiber of his being. John's girlfriend Heather had opened a door to his sexual exploration, and now John longed for more. His deepest desire was hard en...

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...

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...

Kylie Minogue - Equilibrium Ch. 02

by Noj on May 4, 2020
Celebrities & Fan Fiction

This story is entirely fictional and is in no way connected with the subject. This story contains adult material and is only suitable for people over the age of 18. If you are under 18 please stop reading now. All characters appearing in this work are fictitious. Any resemblance to real persons, living, dead, or undead, is purely coincidental. All characters...

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...

All Black Men Love Strapons

by Samuelx on Dec 12, 2018
BDSM

My name is Elisabeth MacLeod and I'm a sex therapist. I don't look like it, though. I'm a six-foot-six, bodacious dame with long blonde hair, pale green eyes and alabaster skin. Yeah, I'm a tall woman. One of the tallest in the Boston Area. And I am proud of it too. Just call me the Scottish Giantess. People come to me to help them solve their problems. Espe...