Chastity Anal Stories

51,359 results
Orientation
Length
Source
Infinite Scroll

A Trip to Remember Ch. 04

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I made some weak statement about changing my clothes but she would have none of that. During her earlier search of my room she came across my two purses and she told me that I should pick one to maintain the proper illusion. I chose my red fake Louis Vuitton purse and Judy exclaimed "That purse actually has style." I certainly agreed. How can you go wrong...

Innocence Lost Ch. 17

by bradley_stoke on Sep 16, 2017
Novels and Novellas

In Which Gryphon purchases affection and gains a little satisfaction; the provision of Chastity to those willing to pay; and Gryphon's discovery of the hidden virtues of Innocence. Despite the rewards of her affair with Chastity, Gryphon still didn't feel that her sex-life was wholly satisfactory. She acutely felt the insecurity of having a relationship wit...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

Out of Control

by AlinaX on Jul 24, 2018
Loving Wives

I love my husband, Eric, but I am a highly sexed woman who finds it very difficult to say 'No' to interesting propositions. Eric knows this, but at least during the early years of our relationship he was more than able to keep me well satisfied. He has a kinky side too, and loves to see me in high heels and short skirts. He guards me possessively in public,...

Husband in Training Ch. 02

by Freakboy80 on Sep 15, 2017
BDSM

The next morning, before she left for work, she left a list of chores for him to complete before she got home. The list included doing the laundry and picking up the dry cleaning. "I expect these done when I get home from work!" She put at the bottom of the note. When she arrived home, she saw him sitting on the couch as usual, but this time he wasn't watch...

Girls only costume party

by latexdoll on Oct 31, 2008
Science Fiction

"This Halloween we will be hosting the first ever "All Whores Eve." No one will be admitted to the party unless they come in their best sexy, slutty, costume. The cover is only $20 which gets you in the door, entered in the costume contest, and see a special live performance by pop sensation Gwen Stefani starting at 8 pm, and she has promised...

Open in Reader

A Trip to Remember Ch. 01

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk. I packed two bags, one with my b...

Black Bulls in Chastity!

by Samuelx on Oct 3, 2018
Interracial Love

Meet Bartholomew "Bart" Jones, a big and tall young Black man living in the City of Ottawa, Ontario. Born in the City of New Orleans, Louisiana, Bart moved to the Canadian Capital to expand his horizons and explore new things. He had a Business Management degree from Louisiana Tech University, and felt like giving life in Canada try. Life in Canada had alway...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

Open in Reader

Innocence Lost Ch. 11

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Mouse appreciates Innocence and her thespian ambitions in equal measure; her performances help Kedi otherwise wedded to Chastity; but she affirms greater affection for the virtues of Innocence than those of Chastity. Mouse was passionately in love with Innocence, with a passion that burst through her tee-shirt and swelled her breasts. She could har...