Caught Crossdressing By Wife Stories

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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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Tales of Feminization

by AnonWriter on Jun 11, 2014
Fetish

In a seemingly normal town, a new social movement is taking place. White boys are encouraged to act, dress, and be feminine. You are a student at this school, and this is story of how you become a dirty sissy slut. Choose a boy to play as and be feminized. (All characters in this story are of legal age) (I'm only working on Mark's story right now, but feel f...

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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...

Blackmail

by thosearemysecret on Mar 15, 2013
Miscellaneous

To the average person, your life is fairly mundane. You have a steady job, a decent home in a lovely suburb, a fairly attractive wife (although her age is starting show), and a daughter about to head off to college. Some would probably say that you're fairly ordinary. Many might even say behind your back "Boy, John Doe is boring." It wouldn't surpr...

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The Awakening Ch. 03

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part Three - The Cost of Doing Business The woman is slim. Mauve satin blouse, navy-blue skirt, black high-heeled pumps. The hem of her skirt teases the backs of her knees. Taupe stockings with black seams. She's attractive; heavily madeup and her black bob is obviously a wig but of good quality. She falls to her knees and smiles. A faceless man approaches...

Obey Thy Neighbor Ch. 02

by jealouscuck on Sep 25, 2018
Transsexuals & Crossdressers

In the first few weeks after Li had discovered my crossdressing fetish, I worried constantly about her changing her mind and telling my wife about my activities. However, the more time I spent with her, the more confident I became that she was genuine. Since Li's husband, Ronald, was hardly ever around we were in very little danger. Even if my wife, Chelsea,...

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...

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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The Door to Door Stocking Salesman

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

In 1959 Brian Macklin was in his mid forties and was making just enough money to get along; his dreams of affluence were ruined when his marriage failed. He used to be a sales executive for an affluent London based firm but all of that came to an end when his wife left him; his father-in-law owned the firm where he worked; say no more. To make matters worse...