Chastity Sissy Megan – Page 2 – My sissy adventures in bondage and chastity

Sissy Choice

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Sissy's Choice

Sissy Diary (Week of 2024-07-21)

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Sissy Megan

July 26, 2024July 26, 2024 1 min

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Sissy's Choice

Chastity Diary Week Two 1/30/2022 to 2/5/2022

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Sissy Megan

February 8, 2022February 15, 2022 1 min

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Sissy's Choice

Chastity Diary Week One 1/23/2022 to 1/29/2022

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Sissy Megan

January 29, 2022February 15, 2022 2 mins

Chastity Sissy's Choice Weekly Chastity Diary

Chastity Diary Week One 1/23/2022 to 1/29/2022

<img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

Sissy Megan

January 29, 2022February 15, 2022 2 mins

I have started another very long Chastity Lockup. My two key holders have told me that it will be several months before I my clit is free of its little cage again. God I am so horny thinking about that as I write this. I figure I tell you how the keys are secure. The […]

Chastity Megan's Chastity Bondage Slut

Sluts new ring.

<img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

slut

January 22, 2022 1 min

Alpha got us up early Sunday 1/16/22 and took us to breakfast. We then walked around some stores. Alpha took me to a piercer and we told the piercer why we wanted my PA and what happened last time. Then I was pierced again. This time a full year with this ring, and they will […]

Bondage Bondage Play Sissy's Choice

Alpha and Slut Play 1/14/22

<img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

slut

January 22, 2022January 22, 2022 1 min

Once all nice and secure in Alphas hotel room, thought it best to jump Alpha while I had the chance. Pushing Alpha to the bed, I quickly removed his shirt. Then placed the mittens on his hands. nice and locked, added a hood to end the remaining fight in him. With the hood done, I […]

Bondage Bondage Play Sissy's Choice

1/15/22 Attack before Dawn

<img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

slut

January 22, 2022January 22, 2022 1 min

I awoke with morning wood, and looked over. Sir was comfortably sleeping. So I jumped him. Securing him quickly. Tucking him back in, he was very hard and his wood was ripe for the picking… To bad it would not be allowed this time. With that taken care of, it was time for me to […]

Bondage Bondage Gear Bondage Play Chastity Sissy's Choice

Night Play 1/15/2022

<img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/79290615846948ebaa548af430b4c91e?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

slut

January 22, 2022January 22, 2022 2 mins

After a long day of fun out and about in the city, Sir treated me to a very nice dinner at Hard Rock Cafe. We then went back to the room. Offering him a chance to be uncaged as I held the keys, he volunteered and I was able to restrain Sir for some much […]

Bondage Bondage Play Friends Megan's Chastity Bondage Slut

Sissy Megan Self Chair Bondage 2021/12/04

<img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' data-src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' data-srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo lazyload' height='32' width='32' decoding='async' src='data:image/gif;base64,R0lGODlhAQABAAAAACH5BAEKAAEALAAAAAABAAEAAAICTAEAOw==' style='--smush-placeholder-width: 32px; --smush-placeholder-aspect-ratio: 32/32;' /><noscript><img alt='' src='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=32&d=mm&r=x' srcset='https://secure.gravatar.com/avatar/2e82f0e7121df98ad9f8dd2b0422ef9b?s=64&d=mm&r=x 2x' class='avatar avatar-32 photo' height='32' width='32' decoding='async'/>

Sissy Megan

December 5, 2021December 16, 2021 1 min

I did a self bondage session in my chair last night. It lasted just over 2 Hours before one of my cuffs failed and I was able to release myself. I had gagged, blindfolded my self, and added an isolation hood. I couldn’t see what was going on or know how much time I had […]

Friends Sissy Sissy Lifestyle Sissy Slut Jessica

Sissy Megan & Jessica’s Matching Sissy Uniform 2021/11/29

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Sissy Megan

November 29, 2021November 29, 2021 1 min

My sissy sister and I match uniforms today, Hope you all like them and please comment below