Cum In Chastity Stories

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Orientation
Length
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Infinite Scroll

Race to the Bottom

by jujou2006 on Nov 27, 2017
Fetish

The bump was totally unexpected. Jujou had been running round the track for some time and had fallen into that trance state so well known to the long distance runner. She hadn't even noticed that another runner had joined her on the track and when the contact came she lost her balance and spilled on the ground. "Watch out slow poke!" The taunting words dri...

The Twelve Horny Princesses

by Lady Malachite on Sep 15, 2017
Humor & Satire

There was a king who had twelve beautiful daughters. They lived in a tower in the castle, in a room occupied entirely by one gigantic beautiful bed, which the king had commissioned a great sorceress to construct. When they went to bed, the doors were shut and locked up, and they were all placed securely in their chastity belts, but still, each time the king...

Chastity's Lessons Ch. 01

by Goldeniangel on Sep 19, 2017
Interracial Love

Chastity giggled as she hurried down to the gardens, thrilled that her father was leaving for the day... whenever he left she would rush down to the extremely attractive 29 year old black man that worked in their garden. At the young age of 18 she found him fascinating, not in the least because her parents kept her so sheltered. She'd been in the outside wor...

Secrets of the Deep Ch. 01

by Lady Malachite on Sep 14, 2017
Sci-Fi & Fantasy

Once upon a time, when magic was everywhere and wishes still came true, there was a tribe of women of such distinguished beauty and insatiable lust, that the sun itself stared open-mouthed at them, and the corals turned their heads to listen to their sinful moaning. And because they seldom were seen in anything resembling clothing, they were known in the hea...

Lucky Me Ch. 01

by live2beloved on Sep 15, 2017
BDSM

Please... Mistress... Please it's... been... so many... days... please let... me... cum... and again I was smothered by her pussy. I was breathless, my balls were aching and my cock wanted to break through that chastity. I was never aroused so much in my life, I was helpless and the bondage was cutting through my veins, I just wanted to cum. I wanted to cum...

A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...

Letter from Boston

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I have read with interest your letters from chastity belt couples. I really thought I was an enthusiast, but now I think it may have gone too far. My love affair with chastity and denial began, I think, in my early twenties. In the summer after my junior year at Harvard, I wrecked Dad's BMW while drunk on the Montauk Highway, near our vaca...

Chasing Chastity Ch. 01

by Bibliophile on Jun 8, 2020
BDSM

Author Note: This arc begins with "A Cure for Loneliness" where our heroine gets her guy. It continues with "Helping a Friend's Loneliness" where she makes things better for herself and for a friend she meets along the way. For some reason, there's more in my mind to write for pun'kin, so here we go for anyone that might still interested... ================...

Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...