Chastity Bra Stories

145,642 results
Orientation
Length
Source
Infinite Scroll

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Decent into Debauchery Pt. 01

by LucidlyConfused on Sep 12, 2017
Exhibitionist & Voyeur

Edited by Slavegirl70 ***** I woke up early for a run in the crisp air before the sun came up; it was the only way I could clear my head. I got dressed in a pair of tight shorts that were a bit small and a sports bra. Sure, the outfit was a bit revealing, but it was four thirty in the morning—who was up besides me? I began to stretch in the front yard as...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

Becoming His Ch. 11

by mrdomdavis on Jan 22, 2020
BDSM

Chapter 11: Chastity Part 11 of 14 at this point. Many thanks to lovesexandmore for helping to edit this story. "Your work outfit is set out for you, Pet," he says, "make sure to stop in my office for an inspection before you leave." She quickly runs up the stairs, excited to see what her Master has laid out for her. "Make sure to use the bathroom before...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Our True Marriage Life

by SlaveJ on Sep 25, 2017
Fetish

I fell in love and married Julie, my beautiful wife who is now 31, and who is beautiful and charming in every way. She has a very sexy body, great legs and long reddish-brown hair. Our sex life has always been good as Julie is very passionate. After a year of marriage, I rekindled my intense fascination in chastity belts. The idea of being locked up sexually...

Hannah Ch. 02

by AndreaJordan on Sep 18, 2017
BDSM

Later that night they arrived at the restaurant and were shown to a table at the back. Tom had obviously been there before and seemed to know most of the waiting staff. Hannah looked at the attractive guy sitting opposite her. "Did you really like what I did earlier, I mean was I OK?" "It was great, you were great," Tom smiled. "Wasn't it a bit scary fo...

The Devil's Mystery Box

by bbcummings on Jan 30, 2019
Fantasy

Author's note: My idea is for the stories to mostly be 3rd person. However, this section basically has to be second person, so bear with me. *** The box you found was peculiar. Usually, a box didn't come with strange markings. It wasn't made out of exotic materials that seemed to defy normal physical behavior. Boxes were usually cardboard or wood. They held...

Open in Reader

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...