Crossdressing Dare Stories

42,978 results
Orientation
Length
Source
Infinite Scroll

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

Lacy Dreams

by Starrberry on Sep 16, 2017
Transsexuals & Crossdressers

Tate nervously walked towards the self-checkout station, giving a glance to the pile of clothes in his shopping cart. He looked around, making sure nobody saw him, and when he was sure nobody would know, he sighed. It wasn't easy, buying sexy lingerie and clothes for himself and his fantasies. Moving as quickly as possible, he scanned tens of lacy and racy...

Serving the Dark Lady Ch. 07

by Certeis on May 27, 2019
Sci-Fi & Fantasy

"Twenty gold for the engagement ring." Karee looked up with a start at the Tiefling who ran the jewelry stand. "You were staring at it, cutie pie. Hoping to get one from a special someone?" She smirked at him coyly. Karee laughed nervously, and then blushed when that didn't work. "No... just daydreaming." "About your future..." She paused, letting the word...

Crossdressing Days 03: Sendoff Day

by cdtycoon on Mar 17, 2020
Transgender & Crossdressers

First, all the characters in this story are above 18. Second, it is the third story in this series as well as where the first one was mild and the second one was medium, this will be the hot one, at least from my perspective and I hope you will also think the same, thank you and enjoy the story. ---------------- Before going to the actual day, let me tell...

Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

Cocksucker: Crossdressing

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is forced to cross dress and suck cock. You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series: Chris, a married straight man, is stuck at t...

Master Walt's Homecoming

by tommibottom on Sep 15, 2017
Transsexuals & Crossdressers

Walt had been talking for months about taking me with him on one of his river trips. He was the skipper of a river tugboat and would be gone on trips for about a week at a time. When he finished a run, another captain would take his place and he would be home for a week. In the year and a half ,or so, that I had lived with Walt and Ellen, I lived as a femal...

Sucking It for Karen

by BuckyDuckman on Sep 11, 2017
Transsexuals & Crossdressers

For Karen, Brad would do anything, including posing naked for her camera. Not just naked. Naked, hard, and standing absolutely still while he received a blow job. The way she talked to her models made it more fun. Karen's mouth didn't have filter. Her constant patter kept your head in the moment. "Suck it," Karen purred with a happy grin on her face. "That'...