by
komrad1156
on Sep 12, 2017
Transsexuals & Crossdressers
"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes.
Ky had sandy blond hair so Kyleigh could easily b...
- 67,011 Views
- 44 Favorites
- 12 Comments
- 8,116 Words
- www.literotica.com
by
Tomsparty
on Sep 16, 2017
Transsexuals & Crossdressers
Imagine your sister asking you to chaperone her on a date. Would you? Debatable - Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal.
This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and b...
- 121,954 Views
- 26 Favorites
- 3,090 Words
- www.literotica.com
Miscellaneous
Who do we follow?What's next?
A boy
A girl
What's next?
A boy
A girl...
- 3,558,385 Views
- 1,221 Favorites
- 6,985 Likes
- 84,200 Words
- chyoa.com
- Interactive
Open in SmutMD Reader
by
GreenGale
on Sep 11, 2017
Transsexuals & Crossdressers
There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection.
"Hey son we're home from our trip to Hawaii!" she beamed.
"Oh...
- 132,293 Views
- 71 Favorites
- 11 Comments
- 2,352 Words
- www.literotica.com
by
chloevargas
on Jul 15, 2020
Transgender & Crossdressers
"If this is what you want," she said, her tone even and controlled. I could tell she was disappointed. Perhaps she'd dreamed of a relationship or she'd fantasized of an emotional connection with me.
She'd never hinted or remotely seemed interested. I thought she was happy with being friends. My few fumbling attempts to offer something more were rebuffed po...
- 1,546 Views
- 1 Favorites
- 2 Comments
- 2,076 Words
- www.literotica.com
by
sissy_janice
on Jul 6, 2020
Fetish
I was uncertain which category I should post this story under. I love the crossdressing stories most, and this would certainly fit there. But the main action really is about cuckolding, so I've put it in the Fetish section.
***
I had thought that my wife was unaware of my crossdressing. Not only was I wrong but, as it turns out, I was the one unaware - -o...
- 11,598 Views
- 18 Favorites
- 5 Comments
- 1,945 Words
- www.literotica.com
by
lynntg0444
on Mar 18, 2020
Transgender & Crossdressers
I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...
- 4,516 Views
- 3 Favorites
- 1 Comments
- 1,920 Words
- www.literotica.com
by
Haley_Hazel
on Sep 26, 2017
Fetish
You are John Doe
An average man, not too young, not too old. You have zero money, no car, no girlfriend... Basically a real loser.
You live in a dive apartment downtown. It's not a great place to live, but it's home. Everything you need is right nearby. Groceries, Bar, Restaurants, it's near a park, and there's even a porno shop down the road.
Because it's d...
- 174,399 Views
- 192 Favorites
- 404 Likes
- 6,800 Words
- chyoa.com
- Interactive
Open in SmutMD Reader
by
Katnaace
on Nov 25, 2019
Fetish
Having logged in, you get to the biggest question of all - who are you going to play?
It's not like this is a big deal. You can just create your character and be on your way.What's next?
Danny Hopkins - Dude with a sister
Lydia Onava - Widow waking up in an unknown place
Claude Rogers - On his way to visit his Aunt
Henry Wells - Protesting H20
What's next...
- 223,297 Views
- 228 Favorites
- 715 Likes
- 19,400 Words
- chyoa.com
- Interactive
Open in SmutMD Reader
by
Domestic
on Sep 24, 2019
BDSM
Your name is John Doe.
Where this story takes you is up for your decision. You can choose your gender, you can choose your significant other.
But after that, you will lose the ability to choose.
You will become obedient, like you know deep down you should be.
Ready?
Pick one, and begin.
NOTE: {[email protected]}It is highly recommended that you play thi...
- 42,300 Views
- 33 Favorites
- 32 Likes
- 7,000 Words
- chyoa.com
- Interactive
Open in SmutMD Reader