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Sissy Chastity Videos

The most-viewed sissy chastity videos this week, hand-picked from across the web and refreshed daily. Everyone shown must be an adult, and the material must be consensual and lawfully published.

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Top Sissy Chastity videos

  1. Full Sissy Transformation by me wife Then Pegged With a 30cm Toy 11:50 · 3K views
  2. lucyylux takes her big cock deep inside 8:13 · 3K views
  3. Jessica Bloom Swallows Anal Creampie After Getting Fucked And Sucking Cock! 5:18 · 1K views
  4. Locktober 2026 #3: I Give My Sissy Slut A Fake Cock And Drive Her Crazy 9:29 · 1K views
  5. Cute femboy SakunoNya and Natsuyue take a bath and have anal sex in a roadside cabin 4:42 · 825 views
  6. Horny Gamer Girl Riding Femboy with Cumshot and Anal Creampie! 7:48 · 877 views
  7. Goth trans woman begs for release from chastity cage 2:49 · 833 views
  8. Locked In Blue Balls: Mistress Pegges Her Obedient Boy And Controls 3 Bad Peach Toys 14:59 · 882 views
  9. Letting A Dominant Futa Ghost Do Whatever She Wants?! (F4M FUTA AUDIO) 27:39 · 773 views
  10. Locktober Unlock - Chastity Femdom POV 6:38 · 807 views
  11. Swollen balls belong in chastity cages, not positions of power! 0:34 · 502 views
  12. A Creepy House and a New Trans Sissy Diaper Mommy 16:15 · 544 views
  13. Limp and Locked -- Chastity Brainwash 2:33 · 426 views
  14. Locktober 2026 #2: Dolling Up My Sissy Slut For What Comes Next 8:08 · 424 views
  15. Alpha uses Cuckoldress throat 1:04 · 410 views
  16. Sissy Trans Girl Uses Toy For Deepthroat Cum 7:17 · 332 views
  17. Your Waifus Feminize You! (Sissification, Anal Play, Chastity, NTR, CBT, CEI) (Patreon Preview) 9:02 · 317 views
  18. Paying My First Debt in Jail - Prison of Sissy 7:27 · 261 views
  19. Cute femboy Pinkmoon crawling on a leash and tied up in a full body black pantyhose 1:28 · 263 views
  20. Locktober 2026 Day 30: Last Night Locked 0:25 · 223 views
  21. little trans girl Sasha_Q 8:01 · 215 views
  22. One more cock locked, one step closer to a Femdom future! 🔐 0:28 · 224 views
  23. Almost No Nut November 11:48 · 213 views
  24. Caged Lance Aches As Tony Pounds Abbie Sykes Wet Pussy 7:30 · 250 views
  25. This was hard to get out! 0:10 · 199 views
  26. No Nut November. Time to lock in. 1:50 · 363 views
  27. Submit To My Feet : Halloween Cei Encouragement 8:45 · 192 views
  28. Mon soumis pathétique baise sa poupée avec sa petite bite 2:10 · 172 views
  29. Femboy Rating 0:28 · 164 views
  30. I'm a trans girl, and I'm working out my butt for you 7:00 · 171 views