Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

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...

Tranny Chasers: Shirley and Chrissy

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Shirley looked around as she entered Cavalier d'Eon, hoping to spot Ron and Bernie. She had promised that she would be there, and fully expected them to be waiting for her. Her survey caught the eye of many a hopeful tranny chaser. She had not known of the breed a week earlier, now she could spot them with ease. And there easily were over a dozen or two at t...

Summer Bucks the Trend Pt. 03 - End

by xerox2 on Jun 11, 2019
NonHuman

WARNING: The following story contains erotic transformation. Please read parts one and two before this concluding section! ***** Summer put her headgear back on and locked her room behind her. Cynthia lived in a studio just across campus. She hurried over and took the back roads so that no one would see her. It didn't really matter at this point. Her entir...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...