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u/MasticatrixPenalty

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1,815 posts found • Page 1 of 19 (100 per page)

Your boss is putting you to work as her stress relief… [AI Image] (punishment81 on ImageFap)

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Your boss is putting you to work as her stress relief… [AI Image] (punishment81 on ImageFap)

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Your boss is putting you to work as her stress relief… [AI Image] (punishment81 on ImageFap)

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Your boss is putting you to work as her stress relief… [AI Image] (punishment81 on ImageFap)

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It can't hurt that badly… [AI Image] (punishment81 on ImageFap)

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It can't hurt that badly… [AI Image] (punishment81 on ImageFap)

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It can't hurt that badly… [AI Image] (punishment81 on ImageFap)

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Never thought she'd love beating his nuts while riding his face so much to change her plans… thank God for smart friends [AI Image] (punishment81 on ImageFap)

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Never thought she'd love beating his nuts while riding his face so much to change her plans… thank God for smart friends [AI Image] (punishment81 on ImageFap)

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Never thought she'd love beating his nuts while riding his face so much to change her plans… thank God for smart friends [AI Image] (punishment81 on ImageFap)

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Never thought she'd love beating his nuts while riding his face so much to change her plans… thank God for smart friends [AI Image] (punishment81 on ImageFap)

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Never thought she'd love beating his nuts while riding his face so much to change her plans… thank God for smart friends [AI Image] (punishment81 on ImageFap)

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C'mon babe, admit you've lost our bet and cum on my tits, so I can decide how to crush your pathetic little balls. [AI Image] (punishment81 on ImageFap)

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C'mon babe, admit you've lost our bet and cum on my tits, so I can decide how to crush your pathetic little balls. [AI Image] (punishment81 on ImageFap)

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C'mon babe, admit you've lost our bet and cum on my tits, so I can decide how to crush your pathetic little balls. [AI Image] (punishment81 on ImageFap)

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You came just from hearing what'll happen to your balls? Pathetic. [AI Image] (punishment81 on ImageFap)

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You came just from hearing what'll happen to your balls? Pathetic. [AI Image] (punishment81 on ImageFap)

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You came just from hearing what'll happen to your balls? Pathetic. [AI Image] (punishment81 on ImageFap)

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Your girlfriend called her about your attitude. Hand-spanking your balls isn't enough; this time, they're getting the belt… [AI Image] (punishment81 on ImageFap)

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Your girlfriend called her about your attitude. Hand-spanking your balls isn't enough; this time, they're getting the belt… [AI Image] (punishment81 on ImageFap)

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Your girlfriend called her about your attitude. Hand-spanking your balls isn't enough; this time, they're getting the belt… [AI Image] (punishment81 on ImageFap)

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You keep saying no, but we both know you'll let me do whatever I want… [AI Image] (punishment81 on ImageFap)

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You keep saying no, but we both know you'll let me do whatever I want… [AI Image] (punishment81 on ImageFap)

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You keep saying no, but we both know you'll let me do whatever I want… [AI Image] (punishment81 on ImageFap)

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I've only kicked your balls a few times, and you're already done? You’ll need to take a lot more if you want your clothes back. [AI Image] (punishment81 on ImageFap)

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I've only kicked your balls a few times, and you're already done? You’ll need to take a lot more if you want your clothes back. [AI Image] (punishment81 on ImageFap)

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I've only kicked your balls a few times, and you're already done? You’ll need to take a lot more if you want your clothes back. [AI Image] (punishment81 on ImageFap)

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I've only kicked your balls a few times, and you're already done? You’ll need to take a lot more if you want your clothes back. [AI Image] (punishment81 on ImageFap)

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I've only kicked your balls a few times, and you're already done? You’ll need to take a lot more if you want your clothes back. [AI Image] (punishment81 on ImageFap)

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Be glad she isn’t showing everyone how tiny your dick is; now take your punishment for wasting her time… [AI Image] (punishment81 on ImageFap)

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Be glad she isn’t showing everyone how tiny your dick is; now take your punishment for wasting her time… [AI Image] (punishment81 on ImageFap)

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Be glad she isn’t showing everyone how tiny your dick is; now take your punishment for wasting her time… [AI Image] (punishment81 on ImageFap)

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Be glad she isn’t showing everyone how tiny your dick is; now take your punishment for wasting her time… [AI Image] (punishment81 on ImageFap)

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Be glad she isn’t showing everyone how tiny your dick is; now take your punishment for wasting her time… [AI Image] (punishment81 on ImageFap)

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Good news: she's removing your chastity cage. Bad news: she's outsourced your punishment to a surprising pair of specialists: your own mom and sister [AI Image] (punishment81 on ImageFap)

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Good news: she’s removing your chastity cage. Bad news: she’s outsourced your punishment to a surprising pair of specialists… [AI Image] (punishment81 on ImageFap)

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Good news: she's removing your chastity cage. Bad news: she's outsourced your punishment to a surprising pair of specialists… [AI Image] (punishment81 on ImageFap)

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Good news: she’s removing your chastity cage. Bad news: she’s outsourced your punishment to a surprising pair of specialists… [AI Image] (punishment81 on ImageFap)

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Your ballsack looks way cuter now… [AI Image] (punishment81 on ImageFap)

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No cap, does it still hurt down there? Interviewing guys leaving the Male Correctional Center on livestream [AI Image] (punishment81 on ImageFap)

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No cap, does it still hurt down there? Interviewing guys leaving the Male Correctional Center on livestream [AI Image] (punishment81 on ImageFap)

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Your ballsack looks way cuter now… [AI Image] (punishment81 on ImageFap)

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Your ballsack looks way cuter now… [AI Image] (punishment81 on ImageFap)

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You thought you could ask me out with karma that low? Real Redditors only. A loser like you needs punished… [AI Image] (punishment81 on ImageFap)

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You thought you could ask me out with karma that low? Real Redditors only. A loser like you needs punished… [AI Image] (punishment81 on ImageFap)

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You thought you could ask me out with karma that low? Real Redditors only. A loser like you needs punished… [AI Image] (punishment81 on ImageFap)

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Her new hobby: hurting your junk every day, however she wants. Don’t worry, she won’t torture your dick forever… [AI Image] (punishment81 on ImageFap)

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Her new hobby: hurting your junk every day, however she wants. Don’t worry, she won’t torture your dick forever… [AI Image] (punishment81 on ImageFap)

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Her new hobby: hurting your junk every day, however she wants. Don’t worry, she won’t torture your dick forever… [AI Image] (punishment81 on ImageFap)

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Locking your cock has made you a better employee, but your boss thinks you need more… [AI Image] (punishment81 on ImageFap)

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Locking your cock has made you a better employee, but your boss thinks you need more… [AI Image] (punishment81 on ImageFap)

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Locking your cock has made you a better employee, but your boss thinks you need more… [AI Image] (punishment81 on ImageFap)

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Locking your cock has made you a better employee, but your boss thinks you need more… [AI Image] (punishment81 on ImageFap)

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She’s done with your sick fantasies; your jerking off to her ends now… [AI Image] (punishment81 on ImageFap)

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She’s done with your sick fantasies; your jerking off to her ends now… [AI Image] (punishment81 on ImageFap)

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Begging for mercy under her boots already? [AI Image] (punishment81 on ImageFap)

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Begging for mercy under her boots already? [AI Image] (punishment81 on ImageFap)

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Begging for mercy under her boots already? [AI Image] (punishment81 on ImageFap)

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New medical tech let the masticatrix take her sweet time; she set a new personal record [AI Image][Extreme] (punishment81 on ImageFap)

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New medical tech let the masticatrix take her sweet time; she set a new personal record [AI Image][Extreme] (punishment81 on ImageFap)

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New medical tech let the masticatrix take her sweet time; she set a new personal record [AI Image][Extreme] (punishment81 on ImageFap)

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She unlocked your dick after six months in a cage, but never said you could cum. Hold it all in, little bro, or big sis'll beat your balls [AI Image] (punishment81 on ImageFap)

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She unlocked your dick after six months in a cage, but never said you could cum. Hold it all in or she'll beat your balls [AI Image] (punishment81 on ImageFap)

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She unlocked your dick after six months in a cage, but never said you could cum. Hold it all in or she'll beat your balls [AI Image] (punishment81 on ImageFap)

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She unlocked your dick after six months in a cage, but never said you could cum. Hold it all in or she'll beat your balls [AI Image] (punishment81 on ImageFap)

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This villainess finds your attempt to get in her way pretty ballsy… [Superhero comics][AI Image] (punishment81 on ImageFap)

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This villainess finds your attempt to get in her way pretty ballsy… [AI Image] (punishment81 on ImageFap)

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This villainess finds your attempt to get in her way pretty ballsy… [AI Image] (punishment81 on ImageFap)

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This villainess finds your attempt to get in her way pretty ballsy… [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation… with a twist [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation, after you first use your tongue to "thank" the woman performing it… [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation… by your own mother [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation… with a twist [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation… with a twist [AI Image] (punishment81 on ImageFap)

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After your third strike for misogyny, the judge sentences you to painful public emasculation… with a twist [AI Image] (punishment81 on ImageFap)

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Your girlfriend was right to send you to therapy for not licking her enough, because I have a plan to treat that… [AI Image] (punishment81 on ImageFap)

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Your girlfriend was right to send you to therapy for not licking her enough, because I have a plan to treat that… [AI Image] (punishment81 on ImageFap)

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Your girlfriend was right to send you to therapy for not licking her enough, because I have a plan to treat that… [AI Image] (punishment81 on ImageFap)

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She didn’t plan on this career, but here we are, with punishing your balls next up on her busy schedule [AI Image] (punishment81 on ImageFap)

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She didn’t plan on this career, but here we are, with punishing your balls next up on her busy schedule [AI Image] (punishment81 on ImageFap)

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She didn’t plan on this career, but here we are, with punishing your balls next up on her busy schedule [AI Image] (punishment81 on ImageFap)

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[ Removed by moderator ]

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Are your big sister's kicks hurting your balls too much? Easy fix: cage your dicklet and give her the key. [AI Image] (punishment81 on ImageFap)

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Are her kicks hurting your balls too much? Easy fix: cage your dicklet and give her the key. [AI Image] (punishment81 on ImageFap)

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Are her kicks hurting your balls too much? Easy fix: cage your dicklet and give her the key. [AI Image] (punishment81 on ImageFap)

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Are her kicks hurting your balls too much? Easy fix: cage your dicklet and give her the key. [AI Image] (punishment81 on ImageFap)

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Are her kicks hurting your balls too much? Easy fix: cage your dicklet and give her the key. [AI Image] (punishment81 on ImageFap)

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Cry all you want, you're the only one here with balls… for now. [AI Image] (punishment81 on ImageFap)

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Cry all you want, you're the only one here with balls… for now. [AI Image] (punishment81 on ImageFap)

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Cry all you want, you're the only one here with balls… for now. [AI Image] (punishment81 on ImageFap)

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Cry all you want, you're the only one here with balls… for now. [AI Image] (punishment81 on ImageFap)

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She doesn't usually talk to a guy when bringing him to medical after his punishment, but today she's got to ask: was that your mama in the front row? [AI Image] (punishment81 on ImageFap)

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She doesn't usually talk to a guy when bringing him to medical after his punishment, but today she's got a question she just has to ask you… [AI Image] (punishment81 on ImageFap)

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She doesn't usually talk to a guy when bringing him to medical after his punishment, but today she's got a question she just has to ask you… [AI Image] (punishment81 on ImageFap)

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She doesn't usually talk to a guy when bringing him to medical after his punishment, but today she's got a question she just has to ask you… [AI Image] (punishment81 on ImageFap)

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Report the details of your pain while I liquefy your balls in acid… for science. [AI Image] (punishment81 on ImageFap)

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Report the details of your pain while I liquefy your balls in acid… for science. [AI Image] (punishment81 on ImageFap)

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Report the details of your pain while I liquefy your balls in acid… for science. [AI Image] (punishment81 on ImageFap)

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What her friend Lisa did has given her ideas… [AI Image] (punishment81 on ImageFap)

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What her friend Lisa did to her own son has given your mother ideas… [AI Image] (punishment81 on ImageFap)

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