Diaper Sissy Chastity Stories

13,981 results
Orientation
Length
Source
Infinite Scroll

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

Ms. Marca Ch. 63

by Ms. Marca on Sep 15, 2017
Loving Wives

My name is Marca. I am mid 30’s, 5'10", thick dark hair and a very womanly figure, with 40D breasts (for those of you who need to know, big round nipples silver dollar size) and 38, but very firm, athletic hips. I have been told that I have a perfect complexion. Large dark nipples cap my very creamy gold brown breasts and I have a shaved pubic area. I have a...

The Nemesess Ch. 02

by ProfessorPlums on Sep 15, 2017
Fetish

Correspondence from older (50-70), dominant ladies most welcome. * The next few weeks passed slowly for Chris. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spice...

Katie the Whore Ch. 03

by Mixedwritings1993 on Sep 25, 2017
Fetish

Katie was having a wild meaningless dream. She saw she was standing naked around a bunch of people. All of them were either her family member or her adult life friends. She suddenly noticed her mom crying at a corner hiding from the rest of the crowd. She walked past the group of people to her surprise nobody tried to grope her or abuse her in anyway. Sh...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

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...