Caught Dressed As A Girl Stories

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Just This Once Ch. 02

by SecretRaptor on Apr 3, 2019
Transgender & Crossdressers

Being in my senior year, the thought of summer should be my own personal wet dream. Freedom from school, from my family, from my social torment. And maybe 4 months ago it would've been. But I've never been so directionless in my life. And now that I stand on the precipice of escaping and enjoying my adulthood, I'm more miserable than I've ever been. The cro...

Riding the Train

by Agnol on Sep 1, 2017
Group Sex

Just a quickie I tossed off. Everyone is over 18 * Cold rain whipped at the platform, umbrellas held low almost like shields to protect the passengers who waited in the shifting lines to board the train cars. Elizabeth Reynolds, sandwiched between two large men tried to maintain some semblance of propriety but the surging crowd made it impossible not to cr...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Choose Own Piss Adventure Ch. 01

by kingshogi on Jul 3, 2018
Fetish

All characters are 18+. Chapter 1 At Home The alarm clock started its irritating buzzing; Sarah yawns and rolls over to stop the clock. As she does her right breast is exposed to the chilly air, instantly erecting her brown nipple. "Damn it's cold," she thinks to herself. She wants to just bundle up in the sheets but her body is screaming at her that...

Fake Memories of a Desert Rave 02 - Darcie Pt. 02

by HalfAsleep on Sep 14, 2017
Exhibitionist & Voyeur

That morning found us at our most tender, and most raw. Darcie woke up with the memory of the risk she had taken, the risk of destroying our relationship over her desire to suck a strange boy's cock. I found that my love for her was not lessened by the act, that instead we had grown closer. In some weird way we were both freer to be ourselves in front of eac...

Rich has an Adventure

by jackie_em on Aug 7, 2018
Transsexuals & Crossdressers

This has some sex, but not a lot. It includes cross dressing, and sex with both male and female, along with reluctance in the cross dressing. ***** It started when my neighbors took a long winter vacation to Florida. They had a condo down there and kind of felt like they wanted a break from the chilly northern weather. I am Rich, a 20 year old guy who live...

Stepmom Sent Back to School Ch. 03

by redwolf555 on Mar 11, 2019
Fetish

Chapter Three: "The next few weeks" The next morning, Monday, all was well. Jessie drove Jenny to school. Before she left her, Jessie said to Jenny, "Remember, you are to delay as long as you can until Silva shows up." "Yes mom." Jessie drove to work and had a great day. First, her immediate boss thanked her for her hard work. Then the CEO sent her a pe...

Caught in the Act

by darrkmysticrayvn on Sep 14, 2017
Erotic Couplings

There is an old saying "Appearances can be deceiving." This could not have been more true for Randy Davis, an average red blooded American male 23 year old college grad student. At first glance, most people would have him pegged as a nerdy geeky Poindexter type, with his short black hair cut like Joe Friday from the 1960's Dragnet Television series, and the...

I Married a Pervert Ch. 03: Wing

by IMarriedAPerv on Aug 27, 2018
Loving Wives

I was getting ready to go up and see Rick and was a little worried. I had been getting to know his housemates, Dustin and Sammy, and they mentioned Rick didn't like going out much anymore. I told them they could be someone else's Wingman. They laughed. I asked them what was so funny and Dustin said, "He had a different Wing...man." I asked again, but they...

Foolishness & Humiliation Ch. 06

by Sabineteas on Sep 26, 2017
Exhibitionist & Voyeur

Marianne made me sit on that hateful cock, stuffed, while we ate. The thing in my bottom made the cock seem so much larger than it ever had before. I was truly stuffed, both front and back. And of course I was naked. Naked as I always was for Marianne, it seemed. Clothes for me were an afterthought for Marianne. It was hard to sit and eat as though there wa...