Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

Slave Ch. 11

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: I have no idea if a resort like the one in this chapter actually exists, but damn I'd love to go if it did! If you haven't read the previous chapters, I'd suggest you do, as it would help to understand the characters better. This story is about a bisexual man who has completely submitted to his Mistress. It contains scenes where he has sex with...

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...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

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...

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...

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...