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Sissy In Chastity

Sissy In Chastity

Off And On

Off And On

How I Bent The Bars On May Cage To Make It More Comfortable

How I Bent The Bars On May Cage To Make It More Comfortable

Spiked Cage And A Wevibe. Very Effective Tease At A Distance

Spiked Cage And A Wevibe. Very Effective Tease At A Distance

Just Started For A Week But I Want To Take It Off So Bad.

Just Started For A Week But I Want To Take It Off So Bad.

Miss Says To Post And Then I May Pleasure Her

Miss Says To Post And Then I May Pleasure Her

Need Some First Time Help

Need Some First Time Help

Too Much Skin- Need Advice

Too Much Skin- Need Advice

Our Device

Our Device

Sissy Needs A New Keyholder Please Inquire Inside

Sissy Needs A New Keyholder Please Inquire Inside

Watchful Mistress From Mature Metal

Watchful Mistress From Mature Metal

Before And After.

Before And After.

My Wife Originally Felt Some Guilt In Locking Me Up. Not So Much Anymore.

My Wife Originally Felt Some Guilt In Locking Me Up. Not So Much Anymore.

My New Cage Fits Me Perfectly! What Do You Guys Think?

My New Cage Fits Me Perfectly! What Do You Guys Think?

Balls Cupped In

Balls Cupped In

Pro Tip: You Can Tuck Your Cage Into The Little Pouch In A Pair Of Panties To Hold Your Cage In Place.

Pro Tip: You Can Tuck Your Cage Into The Little Pouch In A Pair Of Panties To Hold ...

Couldn't Find A Proper Chastity App To Track My Time Locked, So I Created A Quick One. I Hope To Stay Above The 50% Mark At The End Of The Year

Couldn't Find A Proper Chastity App To Track My Time Locked, So I Created A Quick ...

Day 1 - Any Advice?

Day 1 - Any Advice?

This Is By Far The Most Comfortable Device I Have Ever Worn. Cheap Metal Knock Off From Amazon

This Is By Far The Most Comfortable Device I Have Ever Worn. Cheap Metal Knock Off ...

Switching To A Smaller Ring, Hopefully Should Help Keep It Secure.

Switching To A Smaller Ring, Hopefully Should Help Keep It Secure.

Struggling To Stay Soft

Struggling To Stay Soft

New Cage, How Does The Fit Look?

New Cage, How Does The Fit Look?

Spikey Business

Spikey Business

Is It Meant To Go Down So Low?

Is It Meant To Go Down So Low?

Does Anyone Know What Brand/Model This Device Is?

Does Anyone Know What Brand/Model This Device Is?

Smaller Cage Ideas??

Smaller Cage Ideas??

What Was Your Training Schedule? Longest For Me Is 2 Weeks With Ht But Can't Get Past 3 Days With The Cherry Keeper.

What Was Your Training Schedule? Longest For Me Is 2 Weeks With Ht But Can't Get ...

Are You Also Hooked?

Are You Also Hooked?

Starting To Play Around With Chastity. As A Grower It’s Usually Fine And I Can Feel The Direction Getting Trapped And Stopped By It. But This Happens With Morning Wood. I’m Assuming That’s Not Supposed To Do That. What Am I Doing Wrong?

Starting To Play Around With Chastity. As A Grower It’s Usually Fine And I Can ...

Can I Get A Size Check?

Can I Get A Size Check?

Semi Hard, But Just For A Few Seconds

Semi Hard, But Just For A Few Seconds

How Do You Stop The Base Sliding Down When You Get An Erection? Is It Just A Smaller Ring?

How Do You Stop The Base Sliding Down When You Get An Erection? Is It Just A Smaller ...

My First Device 1Day

My First Device 1Day

Could This Be A Better Fit?

Could This Be A Better Fit?

How To Stop Skin Bunching Up

How To Stop Skin Bunching Up

Does My Cherry Keeper Look Properly Sized?

Does My Cherry Keeper Look Properly Sized?

First Day Locked, How Do I Stop Getting Half Erect?

First Day Locked, How Do I Stop Getting Half Erect?

Hope You Like It

Hope You Like It

Think It's Time To Get A Smaller Cage

Think It's Time To Get A Smaller Cage

First Metal Cage: Is It Ok For The Tip To Poke Through Like That All Time?

First Metal Cage: Is It Ok For The Tip To Poke Through Like That All Time?

Is Ring Too Tight?? Please Check My Device

Is Ring Too Tight?? Please Check My Device

Learning To Stay In Her Control No Matter How Hot She Looks!

Learning To Stay In Her Control No Matter How Hot She Looks!

Shy First Timer Here With A Small Member. Think Im Ready To Try A Cage. Have Been Doing Alot Of Research But Could Use Some Help.

Shy First Timer Here With A Small Member. Think Im Ready To Try A Cage. Have Been ...

Just Got The Htv3 Short. Wondering If It’s Too Small For Me. I Can Never Seem To Get The Ring To Fit Tight Enough Against My Body - On Any Device.

Just Got The Htv3 Short. Wondering If It’s Too Small For Me. I Can Never Seem To ...

Does Anybody Know This Extreme Micro-Cage?

Does Anybody Know This Extreme Micro-Cage?

Is There A Way I Can Trim These Edges On A Silicone Cage?

Is There A Way I Can Trim These Edges On A Silicone Cage?

Keeping Track Of Being Locked Up. I've Improved A Lot And Now Can't Stop.

Keeping Track Of Being Locked Up. I've Improved A Lot And Now Can't Stop.

Still No Luck Getting Anything More Than A Little Leaking Out Of My Nub, Any Tips For Fucking The Cum Out When Locked Up?

Still No Luck Getting Anything More Than A Little Leaking Out Of My Nub, Any Tips ...

Was This A Sissygasm? It Sure Feels Like It And I Was Stirring Up My Prostate Real Good With My Vibrator. I Know The Fluid Is Clear And Viscous But It Didn't Feel Like Peeing

Was This A Sissygasm? It Sure Feels Like It And I Was Stirring Up My Prostate Real ...