Your Mundane Life

ST. JACK CONFIDENTIAL Time and time again you see those around you progressing in life you wish you were one ...
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Chastity Slave

ST. JACK CONFIDENTIAL Have you ever actually served a mistress before as a chastity slave? I bet you think it ...
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How to get My Attention

ST. JACK CONFIDENTIAL Time and time again you see those around you progressing in life you wish you were one ...
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Did You Know I Am a Pro Domme

ST. JACK CONFIDENTIAL Did you know I am a Pro Domme? Do you even know what that means? Well, just ...
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Stair Pervert

ST. JACK CONFIDENTIAL Are you one of those perverts who walk too close to me when I am going up ...
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Big Ego, Small Cock

ST. JACK CONFIDENTIAL Your ego is big but your cock is small and pathetic. Your cock has never served you, ...
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Cuck Humiliation

ST. JACK CONFIDENTIAL You are worthless to my pleasure. When I wanted more sex and kink, you were already finished ...
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Devotional Wallet Drain

ST. JACK CONFIDENTIAL I want you to show me just how devoted you are, you must drain your wallet in ...
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Fat Fetish

ST. JACK CONFIDENTIAL I know you are a sick fuck and have a fat fetish. You think about women getting ...
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Hiding Your Secret Obsession

ST. JACK CONFIDENTIAL Are you having trouble hiding your secret obsession with me? I bet you spend more money on ...
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Vanilla Life Is Boring As Fuck

ST. JACK CONFIDENTIAL Your vanilla life is boring as fuck, there is no love, sex or excitement in your life ...
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Toothpaste Jerk Off Challenge

ST. JACK CONFIDENTIAL Do you want a challenge? I know you enjoy slave tasks. pushing your body and pleasing your ...
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Small Penis Humiliation

ST. JACK CONFIDENTIAL Your little dicklette is a pathetic excuse and a waste of skin. You are useless to a ...
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Slave Steak Off

ST. JACK CONFIDENTIAL How far would you go to please and amuse your Mistress? Would you be a good boy ...
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Playing Hooky

ST. JACK CONFIDENTIAL Have you been naughty? I know you played hooky from work to jerk off. You're horny! Your ...
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Latex Slave

ST. JACK CONFIDENTIAL I know you have been creeping around on my social media accounts looking for pictures of me ...
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Tribute Slave

ST. JACK CONFIDENTIAL Do you think you have what it takes to serve me? Look at me and tell me ...
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Losers Spend Money On Me

ST. JACK CONFIDENTIAL Are you now just realizing that losers always spend their money on me? You are no better ...
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