Crossdressing Bet Stories

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Orientation
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Infinite Scroll

Sweet Alice

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

It is typical in these sorts of confessional stories to change names to protect the innocent, but in this case the concept of 'innocence' barely applies. That said, I will refer to my friend here as Sweet. If you're old enough to remember the singer Matthew Sweet, then hopefully it won't seem too odd to call him that. I think the gender ambiguity of that nam...

A Fantasy Night Exposed Ch. 01

by tfrah on Sep 12, 2017
Fetish

This is the first part in a story based on my fantasies which my wife has long been encouraging me to finish writing and publish. In my defence this is also my first ever submission and the first time I've tried to properly finish a fantasy story so I'm also very curious to see its comes out purely self indulgent or if it actually works as an erotic story. I...

Obey Thy Neighbor Ch. 04

by jealouscuck on Oct 24, 2018
Transgender & Crossdressers

After I had witnessed Cecil and Li fucking I began worrying about what Chelsea might be missing out on. After all my cock was less than four inches long when erect. Seeing his massive cock penetrate Li's pussy and seeing her pussy afterward I was feeling so inferior that I almost wished Chelsea could have that type of experience. One of the reasons why I was...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...

Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...

Crossdressed by Hot Girls

by tgirlchrissy on Sep 16, 2017
Transsexuals & Crossdressers

While I was a senior in high school I had an experience I would never forget. I had a group of girls that I called my "Ladies" and I was always close with them, I even hooked up with 2 of the 6. One summer night there was going to be a party and they were all going so me and a couple of my friends were going to go too. Earlier that day I was hanging out with...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...