Naruto Crossdressing Stories

1,244 results
Orientation
Length
Source
Infinite Scroll

Best Girl Ch. 06

by afstories on Sep 14, 2017
Transsexuals & Crossdressers

TO BE READ BY ADULTS AT LEAST 21 YEARS OF AGE ---------- Laying in bed, Todd heard someone rustling from the other side of the room. Not moving himself, he whispered out the side of his mouth. "Candy, do you hear something?" Chris woke up and said, "What?" "Shh. I think there's someone in our room." Both Chris and Todd slowly rose up and saw a figure st...

A Bend in the Road Ch. 03

by Oldguy45 on Sep 14, 2017
Transsexuals & Crossdressers

This story has been on my mind for a long time. It involves two characters from previous stories of mine: "A Bend in the Road," Chapters 1 and 2. This story is going to take a bit of a different direction from the other two. All of these stories are pure fantasy and maybe a little wishful thinking on my part. I hope you enjoy this one. * I had been out of...

Literotica

by komrad1156 on Sep 13, 2017
Mature

"Dear RomanticGuy05, I'm not sure why I feel the need to apologize for writing you, but if you knew me, you'd understand. That's just me. I suppose it's because sending you an email makes me feel like I'm intruding into your personal life, and since you don't know me, I'm sure you see me as some stranger butting in without an invitation. So I hope you'll fo...

Michele Nylons' True Stories Ch. 04

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...

Daniel and Jamie's Romantic Night Ch. 02

by lockedinsteel on Apr 17, 2019
Group Sex

Daniel woke up and realized that someone warm was pressed into his back, their arm draped over his side, their face nuzzled into his neck. As he opened his eyes he saw the clock and realized that it was later than usual, almost 10am. The events of the previous night came flooding back as his mind shook off the tendrils of sleep. He remembered submitting to...

The Lost World Ch. 04

by TheTask on Sep 26, 2017
NonHuman

Note: I've been on hiatus for a few reasons. The first was that I recently acquired a job which doesn't pay terribly well, but a job is a job. The second is that I am writing a non-erotic story which I will not be posting anywhere, I haven't really decided what I'll do with it. The third is that with me being a young man, I have certain needs, otherwise know...

Becoming Jacqueline Pt. 01

by Jacqueline_Love on Sep 12, 2018
Transsexuals & Crossdressers

Summers were always so boring. All the other kids I went to school with loved playing baseball, riding bikes, chasing girls, or going to the beach during summer break, but not me. I usually spent my time in my room playing online games or watching movies or helping with chores around the house. I did not like most sports -- I never did. It was so much effor...

Swipe Right Ch. 02

by amb_anonymous on Jul 23, 2018
Transsexuals & Crossdressers

If you haven't read part 1, I'd recommend it since that is the start of the transformation, but this story could pretty much stand on its own. This story contains interracial, dom/sub, t-girls, crossdressing/sissification and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In m...

Successful Businesswoman Ep. 02

by mattpantyhose on Jul 9, 2018
Group Sex

I would like to thank Georgia Alice for helping me with naming and dressing the characters. Somewhere by the end of this episode, during the final scene, I have made a stylistic mistake, it was done on purpose for the readers entertainment. I am curious what you think about it; please, let me know in the comments or via email. Any kind of feedback, especia...

Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...