Chastity Tranny Stories

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Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

Letter from Sherier Place

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I am a member and Substitute Treasurer of the Keeplock Club, a select group of women who keep their husbands and significant others in chastity belts. Our oldest member is seventy-eight, the youngest, a college junior. It's a constant vigilance, and I thought you might find it interesting, as your column discusses much of this. On Wednesd...

Bibbit Smithers's Ordeals

by justincbenedict on Jul 11, 2018
BDSM

The Colonel's Chastity Tales June 2018 Stories BIBBS JUST CAN'T GET A BREAK Bibbit Smithers, Senior wondered why he was spending an expensive week at the Thumbscrew Lodge. Bibbs had had his ass kicked by his older brother, "Smitty" which you would think would have been bullying enough, right? And, Bibbs, no jock, had been charged with handing out towels t...

How I Met My Wife

by Godscountry on Sep 13, 2017
Transsexuals & Crossdressers

When they ask, I tell people that I met my wife on the internet. I'm sure they assume it was on a dating site. But the full story is much more interesting, how she came to own me and how I came to worship her as my wife. I'd been single off-and-on for a long time. 28 years old. I had a decent job in engineering. I've had a few good girl friends, but nothin...

Limbo's First Day

by justincbenedict on Jun 19, 2018
BDSM

"I'm so happy you're investing in the Paincafe and our subsidiary, the Dungeonopolis Gift Shop, Liggins." said Seneca Smorthwaite. She was so happy that some money was being pumped in here. The master/slave scene was so online these days. "Yes, it's great. I do have one condition, though. I have a relative, ah, Limbo Lawrence, who needs-needs work." Senec...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Letter from Hartford

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Miguel awaits me, as he and his assistants prepare the cocaine with baking soda. Mig gives orders mostly, and the fellows chop and mix the drugs, and suddenly, there I am in my snug little Hello Kitty top and cargo pants. I've been out shopping with Miguel's Platinum Visa, and I grin at him loopily. "Remy, honey how are you?" Mig smil...

Always Read Before You Sign Ch. 11

by Reaver90 on Jul 13, 2020
Transgender & Crossdressers

"Wakey wakey sweetie!" Paula beamed. "What is it?" Samantha mumbled, half asleep. "What do you mean what is it? It's Christmas!" Samantha's eyes lit up and slowly got up only for her to be tackled back down by Paula with the latter's boobs in the former's face. "Merry Christmas Sammy!" Paula cheered. She let go of the young woman. "Your boobs in my face...

Bookstore Bound

by shawnavinyltv on Sep 13, 2017
Transsexuals & Crossdressers

My Master, ever the gentleman, held the car door open for me. I smiled at him as I turned to get out of the car. I made sure to spread my legs in a very unladylike manner, giving him a good peek up my short dress. He simply shook his head and took my arm. We made our way over to the entrance to the adult bookstore. A small bell jingled as we came in, making...