Caught Crossdressing By Wife Stories

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From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

A temporary wedding

by Amira on Apr 22, 2025

Amira was fiddling with her niqab, which was constantly getting caught by the wind. She still didn't like to wear it, as the black garment blocked her vision. She could see only through a tiny slit, unlike the hijab she more preferred. But she was forgetting more and more that she wore it after some minutes. Now outside, Ahmed pointed out that she had to use...

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Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Crossdressing Stories

by Dayeandknight on Apr 29, 2025

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...

Secret Lives Pt. 02

by WildDaisy85 on Dec 16, 2017
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 1. I highly suggest reading that first as it sets the stage for this. As requested by a reader on Pt 1, I have combined two chapters into this one to provide more length. I appreciate the feedback and please keep it coming. *********** I laid in my bed, dressed in women's lingerie and completely bound, as my siste...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

By the Grace of Guile

by komrad1156 on Sep 14, 2017
Transsexuals & Crossdressers

*Author's note: Several years ago, I read an interesting book by author Loyal Rue, a professor of Religion and Philosophy at Luther College, called By the Grace of Guile. An excerpt from one review says this: "For people who are troubled by a world increasingly filled with the sweet-talking duplicity of politicians, preachers, advertisers, and sundry huckste...