Crossdressing Wife Stories

121,758 results
Orientation
Length
Source
Infinite Scroll

The Glass Door

by JackOLantern on Oct 16, 2018
Fantasy

((Author's note: I have made this story open to the public. I encourage people to post their own chapters and threads. If you are a potential writer want an idea of how the mirror works, read the first handful of chapters in my main thread to get an idea. You are under no obligation to make it function in the same way unless you want to, however. Have fun wi...

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Crossing over

by twizted77 on Nov 14, 2019
Transsexual

In the year's that you've been married, you and your wife have rarely spent a night apart, so you'd be telling a lie if you said you weren't somewhat thrilled about her week long business trip outnof town. You already had mental plans to drink too much, sit around in your boxers, maybe smoke a cigar or two and watch porn on the big television in the living r...

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The Fairer Sex

by PrinceCai on Aug 13, 2020
Fetish

What might the world look like if women were usually stronger and more aggressive than men? Perhaps a society existing very much like the one we know, but with almost every gender role reversed. Not only that, but what if the ideas about the sexes that evolved in such a world were far stricter, enforced through every aspect of society and any deviation looke...

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Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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It Had Been Far Too Long

by lynntg0444 on Nov 26, 2018
Transgender & Crossdressers

For me, the ultimate feeling of femininity happens when a man is inside me, and It had been far too long. Over the last few years, my wife had effectively shut down my indulgence in the hobby of crossdressing in public - mainly at bars frequented by the transgendered and their admirers. She only suspected how far I had taken it. My opportunity arose when she...

Cruising for a Bruisin' Ch. 01

by komrad1156 on Sep 16, 2017
Transsexuals & Crossdressers

*Note to readers: After writing The Agreement, I had several people email me and ask why I don't go full time. The answer is very simple: I like being a guy. I only want to be a girl part-time. I've never had any interest in being a woman, and any thoughts along that line were completely dispelled after going on a cruise with a former boyfriend. Whenever I...

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...

A Night of Surprises

by StephaniePlayland on Oct 16, 2018
Transgender & Crossdressers

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy the friendship and no judgements about a...

Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...