Chastity Surprise Stories

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Orientation
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Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

Indolent Ivan

by justincbenedict on Aug 27, 2018
BDSM

February 24 From JosephineMiller To: Wrenjohnson Wren, this is great. I couldn't believe it. Ivan proposed last night. He presented me with a diamond engagement ring. I was kind of like "I hope this isn't a bribe, you're still not getting to orgasm till the end of next month." Although for a ring like that, I might have given up the whole Mistress/Slave t...

Black Wife Cuckolds Black Hubby

by Samuelx on Sep 12, 2017
Group Sex

Watching my Somali Muslim husband Omar Suleiman's soulful brown eyes, I smiled as I began sucking on Tyson Jacobsen's long and thick Caribbean dick. Omar Suleiman, a short, slender yet muscular, forty-something Black man of Somali descent with light brown skin and a cool bald pate, watches as I, his darling Somali-American wife, suck off another man. That's...

Relentless Teasing

by Iwanowitz2002 on Sep 11, 2017
BDSM

So, here I am, on a Friday morning, sitting behind my laptop writing down the recent and current experiences as instructed by my beloved wife. Just so you know, as I write this, my dick is enclosed and locked in a chastity cage (guess who has the keys) with a pulsating, vibrating cock ring over the penis tube of the device, hugging my balls at the same time....

Enslaved by Myself Ch. 05

by Lausunaht on Sep 14, 2020
Fetish

I had fully accepted my place as my clone's personal slutty sex slave and did anything he asked. I became his cum bucket and fleshlight and secretly became addicted to being his. I was still attracted to girls more than guys, but I hadn't seen a girl in months, in fact I hadn't seen anyone in person for months, except for my master. I had no choice but to...

Meghan's Revenge Pt. 02

by AnonymousHoppingBunny on Apr 28, 2020
BDSM

Mike had felt nothing but anger toward Meghan after being left handcuffed to the chair, denied, and in chastity. It had taken him hours of struggling to free himself from the chair and finally negotiate the key from the melting puddle of ice. Yet in addition to his murderous anger and desire to get back at Meghan, his sexual denial had left him with her body...

Slave Immigrant Ch. 22

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and webs...

The Next Step

by Robert_Anthony on Sep 25, 2017
BDSM

Matt sat on the edge of the bed looking down at the steel tube which encased his cock. He'd waited so long for this moment, but still he was tremendously nervous. As he looked down he caught sight of his face, reflected in the highly polished surface of the chastity device. Could he really go through with this? He steeled himself and pushed the small padlock...

A Wife's Night Out

by amaleSwitch on Aug 18, 2017
Fetish

Kirsty Aitkens was once again contemplating if she and her husband Graham were crazy. What they had planned for tonight certainly wasn't normal behaviour for a married couple. A slow, measured breath steadied her nerve and she returned to her self-appointed task: driving her husband mad with lust. Adjusting her stance over the bathroom sink so her husband c...