Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Isabella's Reversion Pt. 03

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have...

The Craigslist Killer Pt. 03

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

I lay there in stunned silence, my death sentence ringing in my ears. "I have H.I.V," Ron just told me. How many times had I warned myself about the dangers of dating on Craigslist? How many guys had I blown off because of the teeniest suspicion that they might not be safe? How much time did I have? I bolted out of bed and raced into the bathroom. There w...

T Ladies Orgy

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

(T minus three weeks) Mike Harris called it 'The Quickening'. He had borrowed the term from the film 'The Highlander' where the quickening refers to the awakening of special powers that lay dormant in certain people until they are triggered by a significant event. Mike applied dramatic licence to the feelings that regularly overwhelmed him and called these...

Restitution Pt. 02

by MoniqueSinclair on Sep 15, 2017
BDSM

Carl wiped at his face and pulled himself away from Kelly's bosom. His head ducked and he hurriedly pulled his pants up from his ankles. His cock was still wet as he stuffed it into his briefs. He made no attempt to button his trousers but rather held them together with his hand and turned away from his wife. He paused as if he was about to say something, Ke...

The Lingerie Catalog

by JuanSeiszFitzHall on Jan 28, 2020
Mature

(All characters in this story are at least 18 years old when they engage in sex acts. This is an entry in the Valentine's Day Contest. Please read and vote. Thanks.) * This is 2020, the e-commerce era, but the postal service still delivers catalogs. One showed up in my mail several days ago. Glossy paper, bright colors, sharp photography. Women in skimpy l...

Bailey Ch. 02

by WhiskeyIsGood on Aug 6, 2019
Transgender & Crossdressers

All characters in this story are 18 years old or older. Sorry for the wait. Still wrestling with this whole writers block thing. I got a lot of good feedback on Chapter 1 and I'm very thankful for everyone's comments. So, here's chapter 2. Hope you all enjoy as much as the first one. There's some slight violence and a bit of drama in this one, so if you're...

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...

Cunt! Ch. 08

by chandler831 on Dec 2, 2019
Transgender & Crossdressers

Around six in the morning I awoke snuggled up against Mark, his arm draped over my body and my ass pressed against his crotch. I was wearing only my bikini top. Realizing how incredibly incriminating this might look if his parents happened to wander into our room, I scooted out from under his arm, got up, took off the bikini, and threw on some athletic short...

Creating Ginger Ch. 05

by Ms_Allison on Jun 8, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consistent in referr...