Crossdressing Bet Stories

66,523 results
Orientation
Length
Source
Infinite Scroll

Roland and Susan

by saddletramp1956 on Dec 23, 2019
Loving Wives

Many thanks to those who offered comments and constructive criticism on my previous stories. For those who want to say this or that would never happen, remember this is my universe, a place where nearly anything can, and often does, happen. At least on paper... Please refer to my profile for more on my personal policy regarding comments, feedback, follo...

My Halloween Fantasy - Eva

by BigMadStork on Nov 4, 2019
Erotic Couplings

Everyone having sex is at least 18. This story is a work of fiction. I made it all up. Check reality at the door and enjoy it for what it is. Special thanks to goducks111 for his help and making this a better story. ***** Chapter 1 -- Dinner with Eva I push the doorbell and hear, "Dingggggg, Dongggggg." I am standing in front of Chloe's house. Chloe is t...

Mom Pt. 01

by Asperger27 on Nov 20, 2018
Loving Wives

The weekends were the only times I can get away from my school life. I get to sleep in til 10 and mom makes chocolate chip pancakes when I wake up. I take my time eating them, enjoying my morning. Afterwards, I would return to my room and play on my game console til lunch. Then mom would go shopping for dinner and I'd tag along. She always sweetens the tri...

Louise Submits Ch. 15

by bydasea on Oct 9, 2018
Exhibitionist & Voyeur

Greetings all, I again wish to thank all who have read, voted, and commented on this series. This story is a work of fiction and fantasy. The events depicted did not and should not happen in real life. Any similarities to real persons are strictly coincidental. I also need to state that everyone in this chapter is above the age of 18. I also wish to thank...

Star Wars: Zoloz Sluts

by HandcuffGirl on Nov 19, 2018
Celebrities & Fan Fiction

Authoress' note: The following story is a hypothetical sequel to Transformations, where Tahiri is kidnapped by outlaw swoop-bikers and turned into a biker slut. If I continue this storyline though, I'll probably disavow this story, and have Tahiri either not return to the Zoloz, or kill them. Feedback is always appreciated, public or private. Zoloz Sluts...

The Gunfighter

by gordo12 on Apr 3, 2019
Loving Wives

Foreword: The first profitable mass literature in America arrived in 1860 when the dime novel (AKA Penny Dreadfuls in England) appeared.. With America's and indeed much of the world's attention focused on the Wild, Wild West, and the Civil War, these cheap books became a sensation very quickly. Popular authors were Buntline, Ellis, Ingraham and Wheeler. With...

Jessica

by Floydman1 on Apr 9, 2019
Transgender & Crossdressers

Author's note: This is mostly vanilla first-date stuff. The story starts out fairly extreme with BDSM, squirting, and fisting that's all SSC (Safe, Sane, and Consensual) but it turned out that her story was much more of a traditional "figuring things out" story of a transwoman, albeit an involuntary one. On that note, I am a cisgender male so if I got any of...

Partner Games Ch. 01: The Neighbor

by m_storyman_x on Jun 4, 2019
Loving Wives

It sucks to get old. When the old calendar ticked to the sixty mark this year it was almost terrifying. Not that I look that old. Most people that see us often guess we're in our late forties at most. My wife still looks every bit as good to me as the day we got married. Well shaped, a bit more sag in the fun bags, but almost no gray in her short cropped bro...

Housekeeper Pt. 03

by CrazyDaveTrucker60 on Jun 11, 2019
Loving Wives

You may wish to read parts 1 and 2 first, so things make sense... Or not, hey it's a free country. Nobody under age eighteen is in here, please remember it's a piece of fiction, not reality, any resemblance to persons living or dead is completely ridiculous. Try to be civil in your comments, please. Especially you Mr. Anonymous! ************ My soon-to-be-...

The She-Shed Ch. 02

by Brittni4u on Mar 25, 2019
Group Sex

When I awoke early on December 31st, I was careful not to wake my boyfriend Shane who slept soundly beside me. We were guests at Nancy and Joe's villa near Phoenix and had been there the last four days. I was happy that I had convinced Shane to loosen up and have sex with Nancy even though he was unaware of my total sexcapades the previous three days or with...