Crossdressing Interactive Stories

1,783 results
Orientation
Length
Source
Infinite Scroll

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Bedtime Story for My Pet #07: Bound

by zenmackie on Feb 3, 2020
Text With Audio

This is another interactive audio in the 'Bedtime Story' series, which allows the listener to follow instructions from an imaginary Sir and verbally respond to his questions and commands. Here is the scenario: Sir has ordered you to stand before him and strip naked. And now he has tied you to the bed, spreadeagled and blindfolded, for his enjoyment. PREP...

Shrinking Around Humanoid Pokemon!

by TGA666 on Oct 5, 2020
Fetish

Welcome to the world of humanoid Pokemon! This idea originally comes from several interactive stories from writing.com, but CHYOA has much better tools to avoid requiring 20 chapters just to choose your pokemon. You can be either a trainer, being shrunk by one of your Pokemon or a Pokemon you are trying to catch, or an average citizen in the pokemon world. Y...

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Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...

Fast Fap: Fairy Tail

by dirty1992 on Oct 11, 2019
Fan Fiction

Welcome John to fast fap, the interactive where you get to the sweet sexual action with you favourite fairy tail character without having to read about how it came to be. So if your ready let's start this fap train all I need to know is your gender and sexual orientation then your off to pick you fairy tail character and get to fapping! Ps be sure to check...

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Sexbot

by ElOle on Jul 27, 2008
Erotic Couplings

While checking your email's spam folder, you see an interesting advertisement . . . FREE TRIAL! New sexdoll robot, so real you'll never go back. 100% Satisfaction guarantee!!1! Intrigued, you read more. It seems the sextoy company HUMPCO is ready to do some market testing on a new sex doll, the SexBot6900. It is supposedly very realistic and includes some ad...

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A Master PC Tale

by radiedwa on Dec 31, 2010
Science Fiction

Welcome John Doe to the Master PC Universe. Don't know what that is well you are in for a wonderful treat. To get started just select your sex below. Or if you wish to read more for background and history... I suggest a word from JR Parz himself... http://www.asstr.org/~JR_Parz/MasterPCUniverseWriters.htm Also, all the stories he found to his liking, along...

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Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Erika's Story Ch. 03

by Quantarx on Jan 22, 2020
Transgender & Crossdressers

This is the third part in Erika and Mary's widening exploration of crossdressing, if you have not read the first couple chapters I encourage you to go back and read those first. also, thanks for the feedback I have received and please continue to rate and leave feedback and comments so I can continue to evolve as a writer. *** I lay in bed with my loving...