Crossdressers Chastity Stories

18,166 results
Orientation
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Addicted to Candy

by MistressCheyenne on Sep 16, 2017
Transsexuals & Crossdressers

Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to Candy and lusting for him constantly. After deciding that te...

Justin's Secret

by ameliawrites1 on Sep 19, 2017
Transsexuals & Crossdressers

"Shit." the first word of the surprisingly cold morning pierced the quiet bedroom, almost punishing the speaker already for sleeping in just underwear. He pushed his covers away as fast as he could while still feeling sound asleep, and was soon at his room mate's and also best friend's side, shaking him awake. "Justin." The room mate grumbled as a way of wa...

The Suitcase Ch. 02

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Part 2 is here! Hope you enjoy. More to follow ASAP. ***** I couldn't quite believe my situation. I was standing in my boss' office, wearing a camisole, a pair of pretty pink panties, suspender belt and stockings and he'd just cuffed my hands behind my back. I thought my clitty was going to explode, it was so hard! He ordered me to spin slowly and I compli...

The Suitcase Ch. 01

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Enjoy the story, more to come, as soon as I'm able. It all started when I was 25. After graduating with a 2:2 degree in English from Plymouth University, I'd moved to London and gotten a job as a journalist for the Evening Standard. The pay wasn't great, and I was making next to nothing after paying off my rent, travel and living costs. I certainly didn't...

The Intersexed Blues Ch. 01

by Akito01 on Sep 12, 2017
Transsexuals & Crossdressers

Having specialized in the field of sexual dysfunction for a solid decade, Dr Fastow thought she’d heard and seen nearly everything. That was until she met Andi Tate. From the referral, Dr Fastow knew the patient was a young woman suffering from problems of sexual identity and a physical non-conformity. Issues of orientation where certainly not uncommon, but...

Ashley's Wrath

by dysfunctionaldreams on Sep 16, 2017
Transsexuals & Crossdressers

It was Friday night and I was at my friend Ashley's house. A bunch of us had gone over for some beer pong. Ashley was a twenty-three year old blonde with long legs and perky little breasts. She was as tall as I was with a nice ass. I had gotten partnered up with her and we were winning, but with each round, I felt myself getting more and more drunk. I had fo...

Sex Change for Black Boyfriend

by watersoda on Sep 14, 2017
Transsexuals & Crossdressers

I have an interesting story. I am now 26 years old. I was born a male but at the age of 23 I had a full sex change at the request of my boyfriend. Here is how and why it happened. I knew I liked men from an early age. I was interested to talk with girls and be their friend but I wanted men. I looked at men in the street, at their muscles and their penile bu...

Magic Panties Ch. 04

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Shall I do another recap? For some reason a magical pair of panties fell into my possession, me, bein...

Magic Panties Ch. 02

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. Any inaccuracies between stories, accept the changes. You may reprint this as needed, just give credit to the author. Oh, and enjoy! Chapter 2: Discovery Let me recap for all of you. Two nights ago, I was stood up at a bar, and the next morning a box arrived...

An Alternate Reality

by rik581 on Sep 12, 2018
Transsexuals & Crossdressers

"Kevin, get up. Breakfast is almost ready," his father called out. "Wake up." Kevin slowly got out of bed. Today was the first day after high school graduation and he was looking forward to sleeping in. It had been a long night. He looked at the clock. 7:00 AM. "Kevin," his father called out again, "let's go honey." Honey? His dad never called him honey...