Chastity Tranny Stories

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Orientation
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Infinite Scroll

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Mistress Di

by justincbenedict on Sep 14, 2017
BDSM

Di gently stroked Trent's dick with her red nails. "You like that, Trina, you little bitch?" she whispered softly in Trent's ear. "Mama may want you to go suck some dicks for her later worthless little tranny-bitch." She lay next to Trent in her low cut blue velvet embossed chemise and scalloped lace trim. Trent, for his part was wearing pink stockings and...

Mistress Vavi

by justincbenedict on Sep 19, 2017
BDSM

Desmond Carne looked worshipfully at Mistress Vavasour across the table at the Paincafe, Buttermilk Falls's restaurant that served the kinky set. Vavi was so delicious, her impudent curls bouncing around in the close crop on her head...She grinned at Desmond as she speared her last asparagus. "What's on your mind, Desmond?" Mistress Vavasour asked. "Rememb...

Panzer's Last Stand

by justincbenedict on Jul 3, 2018
BDSM

EVERYONE IN THIS STORY IS OVER 18. *** "It's just so weird how I've changed." Panzer grinned at his buddy Stetson Tyll. "Yeah, I heard you even went off the Prozac." Stet guided his 20011 Nissan Altima into the parking lot in front of the Grangerford's house. "I never could get why you turned twenty-one and didn't drink 'cause your mom preferred you n...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Letter FROM MEMPHIS

by justincbenedict on Aug 6, 2019
BDSM

LETTER FROM MEMPHIS Dear Shoeblossom: I always thought I was just an ordinary Tennessee farm girl until I graduated from secretarial school and went to Memphis, the big city. My life now is unbelievable! Just yesterday, I was in my short-shorts and high heels, watching poor Aleron scrubbing my floor. She kept looking up at my long legs as she pushed close...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

Cruel Master Zigfield

by justincbenedict on Aug 6, 2019
BDSM

I was once Reverend Zigfield Quinn, but then I had an awareness of my true role, and I decided to give it up to be a male Master. I have some interesting clients, that is to be sure. I keep telling Hollander that he can't stop being a natural submissive. Hollander is due to wed a sweet girl, a nice little creature with a flower shop or something, and he's t...