Mature Crossdressing Stories

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Pretty in Pink Ch. 06

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

My wife, Jessica, not only found out about my crossdressing, she researched and accepted my fetish as part of our sex life. Our adventures had escalated from going out as "girlfriends" to some light exhibitionism and finally to a "lesbian encounter" with a pretty girl. Never in my most intimate moments would I have thought of anything like we now found so...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

The Perils of Young Guys

by Etaindarcy on Aug 7, 2019
Transgender & Crossdressers

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up. I met Jack and Kyle in...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

Serving the Dark Lady Ch. 07

by Certeis on May 27, 2019
Sci-Fi & Fantasy

"Twenty gold for the engagement ring." Karee looked up with a start at the Tiefling who ran the jewelry stand. "You were staring at it, cutie pie. Hoping to get one from a special someone?" She smirked at him coyly. Karee laughed nervously, and then blushed when that didn't work. "No... just daydreaming." "About your future..." She paused, letting the word...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

The Devil You Know Ch. 02

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat at his desk struggling with his conscience as he remembered what had occurred the previous evening at Mike Harris' house. He didn't think of Mike as a man in drag; he thought of Mike as the uber-sexy transvestite Michele Nylons. But the outcome of his visit to Michele's had not turned out as he planned it; he had taken liberties with Michele...

The Futa next door

by Abusedbyfuta on Jan 11, 2019
BDSM

You have lived in the same l cul de sacyour entire life. It's not a bad place to life, very much a part of suburban America. It's just not very exciting. You live in a large White House that looks the same as all the others on the street, probably a ploy by the developer to keep costs down. Every day you see the same boring neighbors, have the same boring ro...

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