Crossdressing First Time Stories

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Orientation
Length
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Infinite Scroll

The Chronicles of Miss-chief

by vanillathunder on Feb 21, 2020
Transsexual

These are just some prompts to get started, feel free to add threads for new ones! Salon-the-Job Training: When a young man gets a job sweeping up at a salon, his co-workers decide to teach him about the various treatments they do there. Spell-ing Error: Two friends get more than they bargained for when they try to conjure up a woman with a stolen spell book...

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All Inclusive Resort

by Dayeandknight on Sep 26, 2015
Transsexual

Tracy fell back onto the bed, finally able to rest after his ordeal. He worked in an office and he dearly needed a break from the monotony of it all. Cancun, Mexico would be his escape from his life. He worked with a travel agent and got a travel package to his liking and saved what he could for the trip. The airport was a nightmare he thought would never en...

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CD Stacy's First Adventure

by CDStacy on Sep 18, 2017
Transsexuals & Crossdressers

I've enjoyed crossdressing for most of my life, but it has been only in the past few years that I have discovered that there is a Stacy inside of me, and have allowed myself the joy of complete transformation: clothes, wig, makeup...the full package. Crossdressing has always been an erotic turn-on for me, and even more so when I am dressed up and completely...

the corporation

by davidigor on Oct 21, 2014
Transsexual

you arrive to the building, you've been requested to come here to sign a contract for working here the call didn't give you too much information and you can't remember having asked for a job here... but you need the money so you decided to come here the building is a big one in an important neighbourhood... but strangely, the door is in a small alley in a si...

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Arabian Nights Pt. 01

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Michele felt the huge member buried in her anus begin to pulsate; hot, creamy semen flooded her back passage. She was lying face down on the huge bed; pressed down into the satin sheets and soft mattress, her own penis trapped in her satin panties was also hard and leaking pre-seminal fluid. She lay still as Ahmed, the man lying on top of her, emptied himsel...

Summer Plans

by Weebwithkinks on Feb 21, 2020
Transsexual

Finally summer is here you've been waiting for this for a long time after a gruelling 1st year of university, you can relax for the next 5 months without any deadlines or assignments. You're heading back home for the summer to spend it with your family, nothing special but a much needed change of pace. Last time you spoke to your parents they said nothing mu...

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Lick The Vamp

by SPARTAN047 on Sep 15, 2017
NonHuman

On request by an unnamed Literotica user. Fetishes: femdom, footjob, foot worship, crossdressing, maid outfit, slavery, humiliation Tags: Monster Girl Encyclopedia, monster girl, vampire, vampire hunter NOTE: If you're not into crossdressing fantasies, press the 'close' button on your browser, or keyboard-ninja your way out of here using ⌃-W or ⌘-W. I'm n...

Ash's Metamorphosis

by Katnaace on Aug 6, 2019
Fan Fiction

Ash took a deep breath. For as good as life had been for the trainer, things were starting to become... stale. It felt as if he was stuck in a loop of sorts, unable to break free no matter what he did. "I just want a change." he thought, laying down in his bed. Sleep came quickly, with him unaware of what would await him come tomorrow.What's next?...

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Sissy Constructs for the Manly Man

by _Rinaldo on Nov 16, 2019
Fetish

Alpha males all have an image to uphold. They spend decades, perhaps even their entire lives honing their bodies and personalities to achieve a higher standing in society: to be viewed as the perfect example of what the ideal male should be. Handsome, strong, muscular, confident, etc. The perfect breeding candidate, in essence: desired by all women, and envi...

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An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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