Chastity Crossdressing Stories

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The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Your Waitresses

by weluvhose on Sep 15, 2017
Transsexuals & Crossdressers

We have not submitted anything for almost a year as daily life as certainly been in the way for ALL of us. My wife and I decided this one would be a slight change to the previous submissions. It is all fantasy but we both would enjoy bringing this one to "true" life if ever possible. Enjoy and we always welcome any comments!...

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

Just This Once Ch. 02

by SecretRaptor on Apr 3, 2019
Transgender & Crossdressers

Being in my senior year, the thought of summer should be my own personal wet dream. Freedom from school, from my family, from my social torment. And maybe 4 months ago it would've been. But I've never been so directionless in my life. And now that I stand on the precipice of escaping and enjoying my adulthood, I'm more miserable than I've ever been. The cro...

Stephanie's Toy Ch. 03

by cuckoldwishes on Sep 25, 2017
Transsexuals & Crossdressers

THIS STORY CONTAINS THEMES OF FEMINIZATION, CROSSDRESSING AND FEMDOM. IF YOU DO NOT LIKE THESE TOPICS THEN PLEASE DO NOT READ THIS STORY. I APPRECIATE ALL CONSTRUCTIVE CRITICISM BUT RUDE COMMENTS WILL BE DELETED. THANK YOU AND ENJOY ;) I stared at myself in the mirror. Over the past few months my body had changed a lot. I had never been fat but I did have...

Shooting The Moon Ch. 04

by SEVERUSMAX on Nov 8, 2017
BDSM

"So, that's it. The new contract for Robert and me in our new life of bondage to you. I rather like it, in fact. It's making me wet, just thinking of how much we're both your sluts now. My hubby and I. We belong to you for life, by our own agreement. We will gladly serve you, as this contract stipulates, Master," Lindsay assured me, her silky hands caressing...

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

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...