Chastity Tranny Stories

8,131 results
Orientation
Length
Source
Infinite Scroll

Valentina of the Colfax Inn

by justincbenedict on Feb 25, 2019
BDSM

SUPERBOWL SUNDAY AT THE COLFAX INN Valentina was toying with her husband's scrotum. Normally Val wore snug but dignified cashmere sweaters, but today she was clad in a belly tee shirt and what the longshoremen at Buttermilk Pier referred to as "whore shorts". Nibs, Val's loyal and faithful husband was bound to the narrow coffee table in his back office. Hi...

Lulu Exposed

by lulu_dools on Apr 25, 2018
Transsexuals & Crossdressers

My name is Louis and i'm 35 years old. I am just a normal guy with an average build and really long brown curly hair. I like a beer on the weekends when i am watching the footy, used to smoke weed but have grown out of that except for the odd occasion. Every once in a while i also like to have a line of speed and this is where my problem started. You see, w...

Laughter in Buttermilk Falls

by justincbenedict on Sep 17, 2017
BDSM

Darrel came into his outer office, passing Thelma's desk. Usually she would give him an exuberant smile, have brought him a latte from Starbucks, but not today of course. This was the Day After. "Good morning, Thelma," he said with a halting smile. Thelma's eyes narrowed, and her lip curled with obvious revulsion. "Uh, good morning, Mr. Plunkett." Darrell w...

Letter from Grimalkin Canals

by justincbenedict on Nov 11, 2019
BDSM

Dear Shoeblossom I am a partner at Prescott & Briggs, and I suppose I should be looked up to, but most of the men employed under me, from junior brokers to mail clerks and elevator operators laugh at me behind my back. I have a "hotwife" as they say in BDSM and cuckold literature; and she demands that I find her attractive young men (loves, LOVES blacks an...

My Master was a Matchmaker

by justincbenedict on Aug 8, 2018
BDSM

SAID THE SPIDER TO THE FLY JULY 2018 STORIES THE MAN FROM MOUNT EIDERDOWN Cheverus Glass knelt before Specs, looking a little ill at ease out of his gray suit from Rogers Peet. Cheverus began stroking his penis slowly, biting his tongue as he did it. "Haven't touched this in a long time." Cheverus said, looking up at Specs, who was a little bored. Chever...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

The Hairdresser

by justincbenedict on Sep 17, 2017
BDSM

JULY 2001 "Can't I cum, just once, Jenise...it's been 139 days and counting!" But Seifert knew what would happen to him if he bugged his wife again! THWACK! Jenise Quynlan thwacked her husband in the side of the neck as he scurried to the back of the Buttermilk Beauty Bazaar. Yes, and then she tugged on the chains that were locked through the hoops on his...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...