Chastity Tranny Stories

8,131 results
Orientation
Length
Source
Infinite Scroll

From Dom To Sub

by ScarlettCD on Sep 14, 2017
Transsexuals & Crossdressers

Twenty minutes to go. A few days ago I had posted an ad online looking for someone to come to my place so that I could, to quote my ad, "get treated like a tranny slut by a true Dom of a man." I kept the ad low-key and photo-less to ensure none of my colleagues from work saw it of course, but more importantly, I was a Domme in my own spare time and did not w...

Sibling Revelry

by justincbenedict on Aug 14, 2018
BDSM

Lombard Londergan's wife had been christened "Peppermint Schnapps" Smythe by her drunkard parents. "Peps" for short, after she herself got sober, many assumed it was short for "Pepsi-Cola." Lombard loved Peps to distraction. She was one hell of a tease. It was so hard for Lom when Peps grabbed his cock in the changing room at the club pool. Peps was wearin...

Tough Love

by justincbenedict on Sep 14, 2017
BDSM

"So, Kearney, I called Lon, and he's coming over, honey. In about an hour?" "Lon? There's no game on tonight. We're watching the Braves game tomorrow--" "Not about that, dear. Remember? You disappointed me again." Kearney Radebaugh looked uneasily at Geneva, his wife of 12 years. But she just smiled, her eyes twinkling. Geneva had bouncing shoulder lengt...

What Now?

by justincbenedict on Dec 25, 2019
BDSM

Sigrid rubbed her nipples through her silk blouse. She thought of that morning, before she'd left for work, and how Michalina had coated Sigrid's vulva with honey, and how she'd tied her down on her verandah and released the box of fire ants. "I have to go to work, Michalina!" Sigrid had gasped, but Michalina had only laughed. "You're the big boss, you can...

Letter from Mulgrave Precinct

by justincbenedict on Aug 27, 2019
BDSM

Dear Shoeblossom-- This taped conversation between me and the corrupt Selectman I have the peculiar fortune to be wed to may titillate your readers, or make them puke. Who knows? Love, Trillian" Oh, Fritz, don't cry any more. I forgive you, honey." "I-I just--when you use that horrible--what was that thing?" "That's a sjambok. Or sometimes it's called a...

Seven Lessons Ch. 01

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

(1) - Acceptance Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it was off to another company. Talking of bi...

Chianti Cares...

by justincbenedict on Apr 9, 2019
BDSM

"I'm not even sure why I'm here." Reba said, trying to smile. In her early forties, Reba had curly dark hair and was somewhat curvaceous, but the sort that dressed sensibly to avoid the censure of her peers. Chianti had met Reba when they'd been taking an Italian cooking course together at Mallard Creek Community College, just across Buttermilk Bridge. It...

Erika's Story Ch. 04

by Quantarx on Jan 27, 2020
Transgender & Crossdressers

This is the fourth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. ************** Three months had passed, and Mary and I were at a really great place in our relationship. Ma...

Letter From Hobson Bend

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I've enjoyed the letters I've read, and I wanted to tell you of my unique relationship with my dominant wife, Beatrix, "Trix" for short. I am Doctor Lionel Lithgow, author of 20 books... University professor of physics... And president of the biggest quantum physics research facility in the Western Hemisphere... But at home I'm just a...

The Support Group

by justincbenedict on Sep 17, 2017
BDSM

"Victrola can be loving but she is also quite overbearing at times," Roger said wistfully, "And when I complain, she whips me and adds days on my chastity. I can't Galahaden ask her to go to counseling with me!" The members of the Men's Chastity group muttered sympathetically, but Rusk could tell it was all bullshit. Men didn't need to be in therapy tog...