Crossdressing Friend Stories

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Orientation
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Infinite Scroll

Sarah Was Caught Masturbating

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

After collage, my girlfriend's best friend and I found ourselves working in the same town and so we decided to share an apartment. Her boyfriend had another year to go in college and my girlfriend worked in a different city. I loved living with her; we became the best of friends; just friends but very close. We cooked together every evening and watched TV....

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Life's What You Make It

by HYjaCK on Jun 7, 2020
Amateur

The first thing I see as I wake up is the blinding light coming through my curtains. Sadly, I couldn't afford blackout curtains due to my poorly-paying job that barely covered the bills, but I've slowly gotten used to it. I sit up and get off the sofa, stretching my back and neck. I also couldn't afford a large flat, so I had to make do with a single-room wi...

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Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

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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Kasey's Legs Ch. 02

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Darcy and I were having breakfast and talking about my first experience going down on a man. I had been dressed up in my sexiest girl clothes with my makeup and hair giving me an almost passable look. Darcy had brought me out to a club that hosted a "drag night" and I had been a hit. I kept explaining to men I was straight and I crossdressed f...

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...

Boy to Bride Pt. 01 Ch. 01

by sissyscarlet on Jun 19, 2018
Transsexuals & Crossdressers

Part 1: Adam MacDonald Chapter 1: Ms. Alice the Widow Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam...