Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Riddle of the Copper Coin

by Bramblethorn on Sep 12, 2017
Sci-Fi & Fantasy

Mix of modern-day and fantasy adventure with F/F romance, poetry, and eventually some smut. Hope you enjoy it! * * * * * Rafi and I had been friends for years, but there were still a few things I hadn't figured out about her. I knew she was a fellow nerd—we'd been playing Dungeons and Dragons together for five years—and I knew she liked cats and sci-fi, an...

Just a Weekend

by Emmie8111 on Mar 13, 2019
Group Sex

Chapter 1: I stood at the bar, checked my phone for the 10th time in as many minutes. Where was she? I felt a warm breath against my ear, hands slid discreetly slightly under my shirt. "Wanna come out back with me baby?" "Please remove your hands, before I scream." The man dropped his hands and peered over at my face. "God, sorry. I thought you were som...

Looking Out for a Friend

by nylonsart on Mar 25, 2019
Group Sex

Note from the author. This is the first adult story I've ever written I hope you all enjoy it as much as I enjoyed writing it. ***** Charlotte and I had been together for over 17 years, married for 15 of those. We met in university and both felt lucky to have each other. We had similar interests, same taste in music and films, we both loved food most impor...

A Learning Experience Ch. 05

by Joscelyn2tg on Sep 19, 2017
Transsexuals & Crossdressers

--- *** Warning: This chapter has several sections which contain rape, violence and physical abuse as major parts of the story. If these things would bother you, please don't read this and wait for chapter 06, it will be along soon. However if you wish to understand all of my transition and what was behind the many hard decisions I made... then it becomes i...

Stupid Sexy Smartphone

by Axelotl on Sep 13, 2017
Humor & Satire

Alex poured the pancake batter into the frying pan. He normally didn't go to too much trouble cooking breakfast, but today was a special occasion. He took a sip of his instant coffee as the pancake cooked in the pan. Then the hairs on the back of his neck stood up. He got the feeling that the ghost was going to make an appearance again. It wasn't an actual...

A Very Hard Working Girl

by keptsissy on Sep 12, 2017
Transsexuals & Crossdressers

I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things I've done and continue to do. And I love to think back and r...

Planet of the Asses

by MawrGorshin on Nov 24, 2017
Celebrities & Fan Fiction

[Jizz was fucking Phlatyllis doggie-style when they received the distress signal, from far away, on another planet. Waves, vibrations, emitted through space to where they were. He pulled out of her, and she moved aside. "Fuck!" he growled, his head then swaying back and forth. "Do you sense that?" "Yes, I do," she said. "From a...Peter Balls?" "With a nam...

Explanation to the Sorority

by escriterra on Sep 12, 2017
Fetish

"I think we all know what's going to happen here this evening," said the woman who had been teasing me online for two months. That this night was the first time I had met her in person punctuated my obsession with experiencing what I knew beyond all doubt would be the most exciting sexual experience of my life. "Ladies, this is the gentleman I was telling y...

The Friend Zone

by Humpdee84 on Sep 13, 2017
Erotic Couplings

Joshua was shy. He could barely speak to women and yet, he yearned for them, longed for them, and desperately needed them. He had plenty of women friends, there was no question of that, they LOVED Josh, and yet, he got the impression that they considered him their 'gay' friend, as straight as he was, and they seemed to sense that, yet, dismissed it. Josh was...

Show & Tell Ch. 26

by murphtsurf on Sep 14, 2017
Erotic Couplings

What happens when the laws of propriety no longer matter? When you're free, not from your primary responsibilities, but free from the normal bounds of society? In one word... "Shameless." As you know, after a half dozen trysts with strangers from the "Friend Finder" (FF) site and hook ups at both "Options" and "Eden Redux" there wasn't much that Elle would...