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Sissy Punishment Videos, Page 1

Sissy Clamped 5 min

Sissy Clamped
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Punishment part 2 ballbusting my sissy crossdresser 5 min

Punishment part 2 ballbusting my sissy crossdresser
  • 20.5k
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Sissy Roommate Punishment- Dirty Facesitting on Girl 3 min

Sissy Roommate Punishment- Dirty Facesitting on Girl
  • 1.1M
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Nylon Slave Punishment by Redhead Domina 3 min

Nylon Slave Punishment by Redhead Domina
  • 50.5k
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300 with the Hair Brush 76 sec

300 with the Hair Brush
  • 52.3k
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Pegging Compilation Long Movie 76 sec

Pegging Compilation Long Movie
  • 56.9k
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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
  • 284.8k
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Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass 6 min

Dominatrix Mistress April - Cane Training Day 2 - how to get to a 1000 strokes on my slaves ass
  • 57.1k
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Stella's Boot Bitch 10 min

Stella's Boot Bitch
  • 284.3k
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An impactful spelling lesson: sissy learns to spell with paddling 10 min

An impactful spelling lesson: sissy learns to spell with paddling
  • 74.2k
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Goddess Vivian's r.: Strap-on Slut 89 min

Goddess Vivian's r.: Strap-on Slut
  • 84.5k
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Hot anal punishment with dildo 89 min

Hot anal punishment with dildo
  • 1.1M
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Dominatrix Aprils Birthday BDSM movie gallery party with slaves 22 min

Dominatrix Aprils Birthday BDSM movie gallery party with slaves
  • 240.8k
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Humiliating Handjob and Spanking from Penny Barber 22 min

Humiliating Handjob and Spanking from Penny Barber
  • 19.1k
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Teen Loves Anal 16 min

Teen Loves Anal
  • 283.6k
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I will chain you up and tease you hard 16 min

I will chain you up and tease you hard
  • 592.7k
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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
  • 32.6k
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Horny Wife fuck her sissy husband - 15 min

Horny Wife fuck her sissy husband -
  • 352.6k
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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
  • 169.3k
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Rosafuxxxia and her submissive dog massaging her feet. Sissy training 14 min

Rosafuxxxia and her submissive dog massaging her feet. Sissy training
  • 17M
  • new

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