Small Penis Chastity Stories

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Infinite Scroll

The Prisoner Pt. 04

by Jamie77917 on Mar 3, 2020
BDSM

Martin is in trouble! Left naked and bound spread eagle on top of a table in a dark room, he can do nothing but await the return of Warden. Left there by Warden naked on the table, exposed and vulnerable, Martin just couldn't help it... he was getting hard. Martin tried desperately to think of other things. Anything other than his current situation. He was...

Cuckolding Gets Moist Ch. 02

by Imgoingallnatural2 on Oct 19, 2020
Loving Wives

I never wear deodorant. Having smelly, all-natural armpits has health benefits, but it also helps me easily separate the men from the boys, or the Bulls from the cuckolds. Last week, I went to the local gym. I was wearing my usual: a cotton sports bra and shorts. I noticed the air conditioning was off. After about half an hour, I was drenched. The creases u...

The Proposal

by PamperedDiva on Sep 17, 2017
Loving Wives

When I started this journey, all those weeks ago, I stated that I had no intention of locking my husband in a chastity device, no intention of caning or spanking him, and so on. Well, it hasn't turned out like that, and for the most part, hubby has been accepting of our changed roles, and of his loss of control over his life. His acceptance came to an abrup...

Watch the Receptionist

by justincbenedict on Oct 7, 2019
BDSM

When Aram got back from lunch, he saw Holt, his new assistant, sitting in his chair, her long legs crossed, and she did look smashing in her cream muslin dress. Really, it was a bit beyond the office code, as the dress was more of a mini-dress thing, and just ended past Holt's thighs. But Aram enjoyed looking at Holt as did other men (and some women)in the...

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...

Life and Time of Lady Vargos Ch. 10

by rik581 on Mar 25, 2019
Transgender & Crossdressers

Chapter Ten "The Vow and Portrait Ceremony" It would be a night to remember for the guest that were arriving at the manor and a night Martin would never forget. Martin sat in a comfortable chair with his hands on the arms, his legs crossed as he listened to Phoebe's questions. The only other person in the room was the photographer, who had already snappe...

Accidental Cuckold Ch. 06

by Brass_ankle on Aug 31, 2020
Interracial Love

2009 Seattle, WA "Thomas! You're my lawyer!" Cassy said sternly to the very uncomfortable man across from her. "I need options, not problems!" "Ah... yes... ok..." Stammered the bald man as he adjusted his collar, Cassy had a way of getting him flustered. The petite black haired woman with a streak of red towards the front huffed as she paced his office...

Chastised, Feminized, Sodomized

by Stefani on Sep 25, 2017
BDSM

My name is Kim Lee. I am half Korean and half Chinese. My first name got me teased quite a bit when I was in school. Nor did it help that I am a bit small and slender. Consequently I grew up rather shy and reserved. I never really had many girlfriends, as most women that I ever met seemed to prefer bigger, more macho guys. So I was not prepared at all when I...

Innocence Lost Ch. 36

by bradley_stoke on Sep 16, 2017
Novels and Novellas

In Which the virtues of Innocence are spread throughout the world and are prominent in Congress; Innocence and Virtue are conjoined, old friends are reunited and Chastity is resolved to the service of Innocence. * * * * * Innocence found that her fame brought with it not only the material rewards which meant she was able to exchange her Congress flat for...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...