Crossdress Chastity Stories

7,038 results
Orientation
Length
Source
Infinite Scroll

Forbidden Codex

by TheCanadian on Aug 30, 2018
BDSM

You’ve got a freind named Denise, with a strong interest in the supernatural--something you have in common. At times, it seems she has a crush on you, but you’ve been friends for years. Besides, Denise was just older than you by enough that you figured she didn’t think of you that way. One afternoon, you knocked on Denise’s front door. When the door opened,...

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Disgruntled Curves

by TheCanadian on Aug 26, 2018
Miscellaneous

I'm not a big enough creep to stare and drool or follow a nice booty around...but if it happens to be in front of me, of course I'm going to look. But on this fateful day, I happened to be on an elliptical behind the wrong booty (or, I suppose, the right one, depending on your penchant for being objectified by objects). I watch her in her black leggings, ste...

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Secret Lives Pt. 03

by WildDaisy85 on Jun 19, 2018
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 2. I highly suggest reading the previous chapters as they set the stage for this part. This part is more of a development chapter and some readers may find it lacking in the sex department, but I feel it is important to the overall tone of the series. I appreciate the feedback and please keep it coming. I am also lo...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Sissy Truth or Dare

by BimboBarbie on Dec 23, 2017
Transsexual

You wait nervously outside the front door of Samantha's house, your heart pumping as you still can't quite believe your luck. Just a small, nerdy guy like you being invited over to the most popular girl at school's house! Finally gathering up the courage as you tentatively press the doorbell, hearing the sing song chime through the door. A whole minute passi...

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Dreambox

by Hanna on Aug 11, 2020
Transsexual

“Boring dreams? Fragmented dreams? No more, try Dreambox, where your inner dreams come alive”. The radio had boomed this for a long time, and my curiosity was intrigued. What is Dreambox? I walked down to the mall and after some shopping did I find that my favourite restaurant was closing, with a sign “Dreambox is coming”. Two months later Dreambox had opene...

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Barrack Room Betty Ch. 03

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three -- Michele's Story The four Wrens of Collins Division woke at 'call the hands' at 0640. Doris had got out of bed at 0600 to prepare breakfast and was in the galley. She'd tried her best to do her makeup and dress like a Wren but she still looked like a 'scranbag'; not that it mattered, in the steam filled, greasy kitchen. Her hair was matted...

Learning to Crossdress Pt. 02

by crossdressme70 on Sep 15, 2017
First Time

Since relating my "First Experience" to you, I have been re-playing it over and over, in my head, and realise how fortunate I was to meet a lady who wanted to indulge her fetishes with me, and established my desire to crossdress. As I left off, she had me wearing her silk panties, with her kneeling across me, my hands sliding up and down under her half slip...

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...

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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