Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

Holiday in Paris

by SEVERUSMAX on Jul 31, 2018
Group Sex

"Do you like what you see? You've been admiring the Seine for several minutes now, just like every new tourist in Paris, if you ask me. Never been to France before?" the voice startled me out of my thoughts. "Actually, I was thinking of the history of this city. Hard to believe that this was once a provincial village in the Roman province of Gaul, not to me...

Ashley's Tail Ch. 01

by SEVERUSMAX on Dec 17, 2017
Exhibitionist & Voyeur

I was thankfully in a very relaxed mood that Halloween, probably due to not having to deal with trick or treaters this time around. My twins were spending Halloween with their mother. Although I missed them and enjoyed their company, I wanted to kick back and have some beer, not spend the evening answering doors when I was alone. I much preferred to do somet...

Crystal Clear Ch. 10

by Romantic1 on Sep 12, 2017
Group Sex

This story is part of a continuation of my Road Trip series (see the end of 'Road Trip -- California' for a list of the chapters of that series, in order to be read). You need not read that series to enjoy this series. Although real places and celebrity names are used for realism, this story is fiction. Please 'read, enjoy, vote, and comment.' This chapter...

State Rally Ch. 02

by Ollegio on Sep 1, 2017
Group Sex

In which Tony returns to his biker rally motel room after a hot threesome with Karen and Cole. "Sooooo, how did it go," Donna asked with a smirk and more than a tinge of sarcasm in her voice. Donna and I were sharing as room for financial reasons. Although there has been plenty of sexual tension, flirting, and innuendo between us for the past few years we...

Passion & Perspective Ch. 10-11

by adamgunn on Sep 14, 2017
Mature

This is a novel of twenty-five chapters. I suggest you begin reading at Chapter 1. The novel deals with hotwifeing and cuckoldry. If those are subjects you aren't interested in, you may reconsider reading this.

 Please read my statement regarding anonymous comments in my biography. Chapter 10 It was dark, I was in bed having a dream about flying an airpl...

Isolated Love Ch. 04 Pt. 2

by GiveMeLove on Sep 13, 2017
Interracial Love

Alright peeps, let me let this be known.. YES, Arabeth is an idiot. She's so naïve, she's so gullible and it makes me sick... but THAT is her character. And the more you guys complain about how stupid she is and how much you hate the story because it, the more agitated I become. Honestly, I'm not writing this to purposefully piss people off but there are som...

Genie Chronicles - Make a Wish 03

by BebopJet on Sep 19, 2017
Sci-Fi & Fantasy

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. Thanks to Ultrafem, Stickymon, NinjaKitty, and Anasheya for drawing pictures that inspired these stories. Milla Jov...

Oddball Ch. 07b

by JimBob44 on Sep 12, 2017
First Time

Chapter 1 Mary looked at the photograph on her desk. It was a digital photograph; Tiffany had taken it at their Halloween party. Mary, in man's suit, long brown hair stuffed into a fedora, plastic machine gun tucked under one arm, stood next to Thomas, dressed in his police uniform. On the other side of Thomas, dressed in man's suit, blonde hair stuffed in...

The Runt of the Litter... Pt. 03

by Kent100 on Sep 12, 2017
Transsexuals & Crossdressers

This story originally only dealt with the topics of gay sex and incest, mostly suited for a long jack off story. As the story has taken a twist, while it's still man on man sex, it also involves cross dressing. So I am entering this in Transsexual and Crossdressers catgory. If these topics offend you, please avoid it. If there is any interest in it, let me k...

The Prize

by Pattie1007 on Aug 31, 2017
Exhibitionist & Voyeur

I couldn't believe it! I'd just been notified that I was the winner of the 1st Prize in a competition I hadn't remembered entering? However, this wasn't unusual in itself. A bit sad really but I loved entering competitions – small or large, I was hooked. I entered so many I'd lost count, so I didn't question the fact that I had no recollection of this one....