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Sissy Punishment Videos, Page 1

Punishment part 2 ballbusting my sissy crossdresser 3 min

Punishment part 2 ballbusting my sissy crossdresser
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Sissy Roommate Punishment- Dirty Facesitting on Girl 3 min

Sissy Roommate Punishment- Dirty Facesitting on Girl
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Nylon Slave Punishment by Redhead Domina 76 sec

Nylon Slave Punishment by Redhead Domina
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300 with the Hair Brush 76 sec

300 with the Hair Brush
  • 50.6k
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Pegging Compilation Long Movie 6 min

Pegging Compilation Long Movie
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REAL LIFE MASTER TRAIN HER 24/7 HOUSE SLAVE ASS FOR BICK COCKS 6 min

REAL LIFE MASTER TRAIN HER 24/7 HOUSE SLAVE ASS FOR BICK COCKS
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Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass 10 min

Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass
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Stella's Boot Bitch 10 min

Stella's Boot Bitch
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An impactful spelling lesson: sissy learns to spell with paddling 89 min

An impactful spelling lesson: sissy learns to spell with paddling
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Goddess Vivian's r.: Strap-on Slut 89 min

Goddess Vivian's r.: Strap-on Slut
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Hot anal punishment with dildo 22 min

Hot anal punishment with dildo
  • 1M
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Dominatrix Aprils Birthday BDSM movie gallery party with slaves 22 min

Dominatrix Aprils Birthday BDSM movie gallery party with slaves
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Humiliating Handjob and Spanking from Penny Barber 16 min

Humiliating Handjob and Spanking from Penny Barber
  • 18.6k
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Teen Loves Anal 16 min

Teen Loves Anal
  • 276.9k
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I will chain you up and tease you hard 15 min

I will chain you up and tease you hard
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Busted Sissy Maids - Miss Jessica Wood and Mistress Chloe Lovette Punish Naughty slaves 15 min

Busted Sissy Maids - Miss Jessica Wood and Mistress Chloe Lovette Punish Naughty slaves
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Horny Wife fuck her sissy husband - 14 min

Horny Wife fuck her sissy husband -
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from cheater to sissy: punishment pegging from futa mommy - full video on Veggiebabyy Manyvids 14 min

from cheater to sissy: punishment pegging from futa mommy - full video on Veggiebabyy Manyvids
  • 167.6k
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Rosafuxxxia and her submissive dog massaging her feet. Sissy training 13 min

Rosafuxxxia and her submissive dog massaging her feet. Sissy training
  • 9.8k
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Caught trying on your sisters clothes 13 min

Caught trying on your sisters clothes
  • 50M
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