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first time chastity pictures and galleries

A Sir decided it was time to lock me up. It's my first night caged and I can't wait for many more.


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First time in chastity - 24 hours in.


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My First Time in Chastity


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Trying chastity cage for first time


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Need some first time help


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Taking Chance for the First Time


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Familiar with chastity, new to sissification. First time poster. Am I doing this right?


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Got sissied up for the first time with my cage on and took some pics!


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Crazy to think my first time with dick inside my hurt and I thought I’d never want it. Now I crave it and I’m making this face. I’d like to thank my cage for that. :)


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Gave a blowjob for the first time yesterday and I loved every second


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Today I put a wild pig in chastity for the first time. He needed to be restrained for my safety.


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I fucked myself for the first time while caged earlier!


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First time!!!!


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First time showing my face while being caged and fucked


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First Time!


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Bondage Chastity Brandynette - First time i tie myself a cage. SissyGasm is awesome and the balls cool down fast!


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Enjoying a bath after her first time in a chastity belt


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First metal cage: is it ok for the tip to poke through like that all time?


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First time upload & sissygasm after being locked in chastity for 3days, teased with hypno, please call me a sissy and emasculate to keep me motivated!


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First Time Posting (pt. 1)


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Taking [M]y M/F Elliott past his massive coronial ridge for the first time. I have never had another toy make me quiver before just by inserting it.


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