Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

Maid to Order Ch. 03

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele lay on her bed sobbing. She felt confused and defiled. Michele's alter ego Mick had spent many years in the army, he knew how to fight and would never allow himself to be coerced or forced into doing anything he didn't want to. But when he transformed into Michele, all of his resilience training and self-defence mechanisms seemed to have disappeared...

Kasey's Legs Ch. 02

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Darcy and I were having breakfast and talking about my first experience going down on a man. I had been dressed up in my sexiest girl clothes with my makeup and hair giving me an almost passable look. Darcy had brought me out to a club that hosted a "drag night" and I had been a hit. I kept explaining to men I was straight and I crossdressed f...

Piece of Cake

by Nils Huim on Nov 26, 2017
Transsexuals & Crossdressers

Will asked if I'd be willing to show him my naked body after I put my wig and makeup on but before I got fully dressed. I said sure—my only other fem adornments being my cherry-red toenails and a matching bead anklet above my left foot. With all the security and body scans and what-not at airports these days, I hadn't even worn panties under my street clothe...

Jimmy Olsen Shemale Bimbo Ch. 00

by tawnysuede on Sep 17, 2017
Celebrities & Fan Fiction

Prologue.... Six Months Later In the back of her dim witted mind, she knew that something was not quite right. In the back of her throat, she knew that Steve Lombard's long hard cock felt so very very good.. If her mouth had been empty... if his balls had not been slapping her chin, Gemmy would have squealed in delight. "Oh Stevie... feed me your dick! Cr...

Big Daddy

by latexcd69 on Sep 12, 2017
Transsexuals & Crossdressers

BASED ON ACTUAL EVENTS As is the case with most hard drug users, you start off small and end up making your way up. Since I was 15 I had been smoking weed. One of my friends had introduced me to some other drugs like meth or coke a few years later. The weed was still a big influence but it all seemed so tempting. It was a different high and on a much higher...

Caught in the Toilet

by Dennis_St_John on Sep 14, 2017
Transsexuals & Crossdressers

Kneeling on the floor beside the toilet, dressed in lingerie and wearing pink lipstick waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it. I remembered sitting on the toilet earlier today looking at my bright pink nylon and white lace panties, resisting the...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

The Wedding Ch. 01

by kinglem on Sep 16, 2017
Transsexuals & Crossdressers

The characters in this story were introduced in another series "Cancelled Date Night". This story is designed to be self-contained so it is not essential to have read that series first. However, if you care to get a more rounded view of the characters and see what led to the events of this series then you should read that story first. ***** Dave was start...

Lady In The House Ch. 04

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

From Part III Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve stepped back and looked down at me, on my knees, may face covered in come, my clothes a mess and makeup mixed with semen, caking my...