Crossdressing Wife Stories

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Orientation
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Infinite Scroll

How Marissa Became a Woman

by CDSean on Sep 19, 2017
Transsexuals & Crossdressers

This is a work of pure fiction. It deals with adult subject matter including crossdressing, and consensual male on male sex. If any of this offends you, please stop reading now. This is my first story for others so any feedback would be appreciated. ***** Henry and Lisa have been married for many years. During that, time both of them made many little pe...

Obey Thy Neighbor Ch. 05

by jealouscuck on Oct 29, 2018
Transgender & Crossdressers

I had gotten better results from my task than I expected. Li had instructed me to somehow include my wife in my panty fetish. By this time, fetish seemed a pretty tame word. My fetish had progressed to dressing totally as a woman and attending Li's fuck sessions. The last one she had me clean up her lover's cum from her pussy. The next step was to call me ov...

In For a Penny... Ch. 02

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: Thank you for all the positive feedback and encouragement to write Part Two. I apologize for taking so long. However, I didn't want to submit a story that contained any clichés, so I had to take my time to think through how this next installment was going to play out. Let me know how I did. This chapter picks up immediately after Part One. I...

In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

True-Life Confessions of a CD

by Nils Huim on Nov 25, 2017
Transsexuals & Crossdressers

November 3 My hole is sore. But it's a good kind of sore. It feels s-t-r-e-t-c-h-e-d. More on the reason for this in a minute. Sex-wise I had a good day yesterday—one of the best ever. I invited three guys over to my house and two showed. (The third emailed me later saying he'd fallen asleep. "Are you available tomorrow?" "NO!") For fickle Craigslist, espe...

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,...

Pretty in Pink Ch. 02

by jealouscuck on Sep 18, 2017
Transsexuals & Crossdressers

I could not believe my good fortune. Not only had Jessica accepted my crossdressing, she had changed her whole attitude toward my fetish. We talked about it afterwards and she told me she was continuing to research the topic. In the meantime she made me promise that we would have no more secrets between us. Over time, she got me to tell her the full extent o...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

Feminine Fate Fulfilled

by mattpantyhose on Jun 15, 2020
Transsexual

Like all of my other stories this one had been already published on Literotica. You can find it here: https://www.literotica.com/s/feminine-fate-fulfilled__ For whatever reason Chyoa doesn't include Crossdressing in the category of Transsexual and doesn't have a separate category for that theme. This story does not include any transsexuals, but I considered...

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