Feminizing First Step Stories

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Orientation
Length
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Infinite Scroll

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Reminiscing about Her Deliciousness

by my_slut_mouth on Jan 22, 2019
First Time

I am typically a shy guy, with very little to say, typically in public. Since my teenage years, I've enjoyed using my mouth in the sexual department more than not. I'm picky when it comes to my sexual partner. There needs to be some kind of connection. And besides, I like to know what I am getting in too. One night I decided to join one of those BDSM feti...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Nudist Resort Feminizing Ch. 02

by exhibitor on Sep 16, 2017
Transsexuals & Crossdressers

On my way to their RV, I stopped in the clubhouse and took a very thorough shower in anticipation of what the next hour might bring. All eyes were on me as I boldly walked through the pool area towards the campground. When Jill greeted me at the door of the RV, she looked quite different. She had on black fishnet thigh-high stockings and black patent leather...

A Feminizing Fuck

by lynntg0444 on Jun 5, 2019
Transgender & Crossdressers

The last conversation with John ended with the line no tranny wants to hear. "Lets take a break for a while, I want to date some women". I was devastated, but knew that day would eventually come. He is a good looking man that fucks good. So what does a girl do, but join a dating site. I used my usual moniker of "Horny Mature will do everything your wife won'...

The Molly Virus Ch. 02

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

There this absolutely hot girl at the frat party called Cherry. She came with a bunch of hot chicks, but she, she is something else the classic blonde with these huge tits that have to be implants, they're too big, too firm for her to be going braless but those nipples are poking through amazingly. I dance with her and she has me so turned on my balls hur...

Ems' Dating Tits

by Timjob on Sep 28, 2020
Transgender & Crossdressers

I checked my phone again. She was five minutes late. I sighed but tried to be patient; not all girls are as anal about punctuality as I am. Plus, I suspected, she was a virus girl so she almost certainly had more to worry about than me. I wondered idly which strain she had. The cafe's door chimed, and I looked up. The biggest pair of tits I'd ever seen in...

The Engagement Ch. 04

by Compliant1 on Sep 26, 2017
BDSM

Once Louis was standing in his corner, I picked up the stereo remote and put on some soft jazz. "He's standing too close to the speaker to hear us, if we speak softly." "Della, he must have been excited, being treated that way. Why else would he allow you to humiliate him, unless he enjoys being dominated?" I turned to face Stephie. I reached out and gent...

Feminized at Thirty-Three

by Borntolust on Sep 16, 2017
Transsexuals & Crossdressers

This is the story of a man who never realized the strength of his inner woman until he was in his thirties. It is a story of loving feminization and incest. The story is fiction. Everyone is eighteen, or older. I would normally post this story under the incest category, but I thought it would fit just as well under crossdressers. ***** I was thirty-three...