Naruto Crossdressing Stories

1,244 results
Orientation
Length
Source
Infinite Scroll

A Sissy is Forged

by KassiSmart7 on Oct 15, 2017
Transsexuals & Crossdressers

This is my first go at writing. I've had a lot of fun writing this, I'm publishing this to see if other people enjoy it as I have. If it's a success, I'll continue the story. Hopefully, more chapters to come :) ***** When I told my girlfriend, whom at that point I'd been with about two years, that I was interested in exploring my sexuality, she was more th...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

Nathalie's Makeover

by Cagivagurl on Dec 2, 2019
Transgender & Crossdressers

Where to start? My name is Nathan and I am a married man, wed to my beautiful wife Vivian for three years. I work as a software engineer for a local manufacturing plant. Vivian works as an office administrator at a local paint distributor and in a word she hates it. Vivian has always been obsessed with fashion and everything there is to do with it. All sh...

Tai's Story Ch. 05

by Cagivagurl on Nov 4, 2019
Transgender & Crossdressers

So back at work and it was hot and sticky 300 KM from anywhere. The daily temperature on site was close to 45 degrees Celsius and I had never seen rain in all the time I had been there. It was hot dry and arid. Work was becoming more and more of a chore. When I started here initially it was amazing. It was good to get away but now it was becoming a drag. The...

Born to Be Ch. 07

by DamienDeath20 on Jun 8, 2020
Transgender & Crossdressers

A.N. Return to the strap on! If this isn't my favorite chapter so far, it's definitely one of my favorites x))) Buuuut chapter 8 is preeeetty awesome too ;D I know I'm a whore. The Following Contains: Interracial between a tall black lady and a crossdressing femboy. Which in conclusion creates a formula of strap on penis being inserted into femboy bott...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

A Problem in Russel Hall

by typical_boy on Sep 14, 2017
Erotic Horror

It was 4:22 in the morning, and I couldn't sleep. I knew it had been a mistake to do a Thirsty Thursday the day before a test. Ricky, down the hall, had brought in some friends from home, the chemistry boys had played flip cups, and of course I'd done shots with everyone else. Ricky's friend from high school, Kayla, had been super-hot, with a super-curvy bod...

The Photographers Assistant Pt. 01

by panty_wearing_sissy on Feb 5, 2018
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and only suitable for persons over the age of 18, mature enough to understand and distinguish the difference between fantasy fiction and real-life. All character in the story are ove...

Unextpected Change.. Pt. 02

by whydidyou1992 on Sep 15, 2017
Transsexuals & Crossdressers

Note* thank you all for the great comments and the bad ones it has help me a lot sorry for taking so long to get the rest out. I apologise ahead of time for the poor grammar and spelling I suck at both but if you can bear through it I do believe you will enjoy the story. Everyone in the story is 18 or older.* ***** It takes me a while to snap out of my tr...

Misstaken Identity

by thrillerauthor on Sep 11, 2017
Transsexuals & Crossdressers

As I write these memoirs, my deeply tanned legs are stretched out before me on a lounge chair on my lanai. My pink toenails provide a nice contrast to the aquamarine sea visible in the distance, framed by swaying palm trees on golden sands. I brush a strand of hair from my forehead, and tug my sundress a few inches towards my knees. Looking back, it's hard...