Chastity Tranny Stories

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Transsexual Treasures

by dirtyjoe69 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Steve and I am a thirty seven year old divorced male. I am considered good looking. I am very tall standing six foot seven and have a good build for my size. My marriage didn't work for many reasons money, being too young were a couple of them but the biggest reason was sex. I wanted it and she didn't. It always seemed to be a chore for her and wh...

A Sissy's Wish List

by slutty_lucy on Sep 16, 2017
Transsexuals & Crossdressers

Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how to best share my desires. I want to be a perfect little slu...

I Wanna Both His Balls

by enfantterrible on Sep 14, 2017
Humor & Satire

The Brooklyn mob boss Joe Slow is sitting in Carlito's slurping on a bulging bowl of meatballs. The restaurant is dark and empty, just the way Joe Slow demands it everyday at the same time. A mobster with a habit like this is a Hitman's dream, but that's another story. So we see the scene and tomato sauce is smeared all around Joe Slow's fat chops, which fla...

Trailer Trash Tranny Ch. 03

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 03: Strip Club Jeannie, a blonde tranny living in a trailer park outside of Omaha, Nebraska, was working as a hooker to try and make enough money to get a boob job and move to New York City. She was working the parking lot of the truck stop just down the highway from her trailer. After an initial night where Jeannie made a good amount of money, thin...

A Glory Hole for Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each days, growing into text messages each day, and more. No idea...

Recruiting of a Sissy Maid Ch. 04

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel, Fitting Into Her New Lifestyle. Master Holt says, as the two of them walk out from the elevator on the 2nd floor, "This will be the floor that you will begin your life in servitude to us Chantel. Lets go find your head maid Penny and then get you to your room." Chantel grows more and more resigned to this new life as she see's a very...

Trailer Trash Tranny Ch. 02

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 02: Truck Stop Jeannie grew up poor in a trailer park just outside Omaha. That made it tough at school. So did being born with the wrong gender. She was a girl trapped in a boy's body. Even though as a kid she only dressed up as a girl in private (what little there was of that in the small trailer she shared with her mother), it was obvious to every...

The Virgin Tranny & the Bride Ch. 08

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta writes to tell me that recent surrender of her boy pussy to her Master was, sadly, not for love but as a means of gaining embarrassing video footage to use as sexual blackmail. Master John is now teasing Roberta and she is about to embark on a new career as a call girl and prostitute. She writes: With the lining removed and m...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Twenty Questions

by DrLuverotica on Sep 19, 2017
Transsexuals & Crossdressers

THURSDAY I was just settling down to watch a movie when my wife arrived home after a night out with her girlfriend's. "You're home early," I said. "Lucia had to be back by ten. She's on the early shift." "Meet anyone else?" "Just a couple of hunks - they're coming over for supper later." "Very funny." "Actually I wanted to come home because I was feel...