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Sissy Updates

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chained sissy maid

Featuring: Misty May
  • 205 Photos, 26:03
  • Jul 4, 2025
  • 4.5

never too late to be a sissy princess

Featuring: Cheryl Summers
  • 183 Photos, 27:35
  • May 30, 2025
  • 4.5

fantasy football loser

Featuring: Jossilyn Swallows
  • 180 Photos, 26:53
  • Jun 14, 2024
  • 4.6

trained and turned into a sexy sissy

Featuring: Jeni Justice
  • 191 Photos, 26:49
  • Sep 1, 2023
  • 4.6

she now only exists to please him

Featuring: Sissy Poptart
  • 187 Photos, 25:03
  • May 19, 2023
  • 4.6

always there for his pleasure

Featuring: Sammi Swallowz
  • 182 Photos, 25:48
  • Nov 3, 2021
  • 4.6

cocksucking femboi is back and looking FANTASTIC

Featuring: JJ Del Rey
  • 64 Photos, 12:44
  • Nov 9, 2019
  • 4.6

sissy princess earns her crown

Featuring: Jeni Justice
  • 161 Photos, 21:54
  • Nov 10, 2023
  • 4.6

her training is almost complete

Featuring: Vicky Fatale
  • 138 Photos, 22:45
  • May 12, 2023
  • 4.5

completely giving up on ever being a man again

Featuring: Lauren Promise
  • 176 Photos, 26:37
  • May 26, 2023
  • 4.5

mature sissy knows her place

Featuring: Slave Anna
  • 234 Photos, 27:07
  • Mar 6, 2022
  • 4.4

always ready to please her master

Featuring: Sissy Jade
  • 154 Photos, 27:25
  • Mar 31, 2023
  • 4.5

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