Gender Bending Stories

44,796 results
Orientation
Length
Source
Infinite Scroll

00075 NuDistrict Ch. 01

by Tarbut on Sep 16, 2017
Transsexuals & Crossdressers

Hi. My name is Israela and I am a female Jewish analytical (Jungian) psychologist. I am married with a Gentile pharmacist named Jane, and as soon as we got married, we joined the NuDistrict, a clothing-optional community. There are no stated gender restrictions, but nearly all the adult inhabitants are women -- cis or trans; male-identified people are "nudg...

Muslim Bisexuality: Roughnecks

by Samuelx on Sep 12, 2017
Interracial Love

I wish people would stop paying attention to what doesn't concern them and just mind their own damn business but that's just wishful thinking. My name is Paul Jean Renard, and I'm a young Black man of Haitian descent living in the City of Ottawa, Ontario. I attend Carleton University, where I study business administration. I also work part-time as a security...

The Project Pt. 01

by Chloecrownofthorns on Sep 16, 2017
Transsexuals & Crossdressers

Dee's bedroom lit with a dim blue glow from her smart phone. Her nailed finger swept up the screen as she scrolled the strictly platonic listings. "Boring, boring, spam, fake. Can anybody complete a sentence on here!?" she thought. She was just about to give up when she read the headline, "Mess around with gender roles..." As she read the post, she smirk...

A Better World

by timdr on Feb 18, 2021
Fetish

(Author’s Note: This is my very first story on CHYOA, thanks for reading! I’d love to hear any comments or feedback you have, and if you have any ideas for other characters to follow feel free to leave a comment or add a chapter.) This story takes place in a world where, instead of the population being about evenly split between men and women, about 70-75% o...

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The Alpha Gender Ch. 01

by Mikethe3DGuy2 on Apr 13, 2020
Fetish

One of the advantages to leaving the office late is that you don't have to fight for space on the elevators going down to the parking garage. You also don't have to worry about your car being clipped by one of your coworkers' vehicles in the crush to all reach the exit ramp to the street first. You place your neatly-folded but rumpled suit on the back seat n...

Black Journal Ch. 06

by Dhc000333 on Sep 14, 2017
Erotic Couplings

Duncan Cyrus, age 21, vs. Big Rhonda At the college, we had intramural sports. Basically sports for those who couldn't make it on the "official teams" or backyard type sports. Some of my associates on the Science and Research Academic Organization were part of this wrestling intramural team. Apparently they were doing co-ed and two team members, but a male...

Phaedra and Eliza Ch. 01

by Tarbut on Sep 16, 2017
Transsexuals & Crossdressers

The Women's Bookshop had a regular customer – a busty elderly woman named Phaedra. She weekly bought heaps of books on psychology, anthropology, foreign languages, mythology, and gender studies. She usually paid by cash, but once she told the sales clerk, "Dear Eliza, I couldn't find a working ATM. Can I pay via credit card?" "Of course, Phaedra." Phaedra...

On School Grounds

by PenanceS on Sep 14, 2017
Transsexuals & Crossdressers

It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this. I looked at myself in the mirror, just to see if my padding was well, there. I had borrowed one of my ex-girlfriends bras and stuffed it with a pair...

The Opening Party

by adalovebomb on Oct 6, 2020
Exhibitionist & Voyeur

Sarah took a step back and checked her lithographs, hanging on the walls of the small gallery. Thirty erotic fantasies made over the past year with herself as a model. Sarah gives a blowjob. Sarah mirrors her own pussy. Sarah is masturbating. Steve licks Sarah's pussy. "Do you like it?" asked Steve, who had just installed the final audio cables for his elec...

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by brit-n-birds on May 16, 2019
Science Fiction

So you sat there, staring down at the tiny little pink pill resting on the table in front of you. The half empty glass of water next to it taunted you. It wasn't full enough for anything other than swallowing the capsule before you. To put it away would be a sign of defeat. You were too nervous. You couldn't possibly go through with this. You had to go to wo...

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