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Chastity Pegging Videos

The most-viewed chastity pegging 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 Chastity Pegging videos

  1. Pure Prostate Milking Compilation – She Controls Every Load 14:12 · 67K views
  2. I peg my straight man's ass | He cums 3 times 11:22 · 46K views
  3. Full Sissy Transformation by me wife Then Pegged With a 30cm Toy 11:50 · 3K views
  4. FACESITTING! Cheating wife rides her lover's face while he has a dildo in his mouth! 13:15 · 3K views
  5. Alex climaxed very quickly thanks to the huge cock. Pegging. Anal. Romance. 24:00 · 2K views
  6. I Finally Convinced Him To Let Me Peg Him Hard 10:12 · 3K views
  7. Jessica Bloom Swallows Anal Creampie After Getting Fucked And Sucking Cock! 5:18 · 1K views
  8. Locktober 2026 #3: I Give My Sissy Slut A Fake Cock And Drive Her Crazy 9:29 · 1K views
  9. He Showed Me His Cute Butt… I Ate It & Pegged Him Until He Came 7:06 · 1K views
  10. Goth trans woman begs for release from chastity cage 2:49 · 1K views
  11. Locked In Blue Balls: Mistress Pegges Her Obedient Boy And Controls 3 Bad Peach Toys 14:59 · 1K views
  12. Letting A Dominant Futa Ghost Do Whatever She Wants?! (F4M FUTA AUDIO) 27:39 · 953 views
  13. POV pegging with a gothic goddess. Get ready for deep fucking with a long BBC [Full Video] 29:35 · 720 views
  14. Locktober Unlock - Chastity Femdom POV 6:38 · 1K views
  15. Sexy Blonde Trans Girl Fucks Guy with her Thick Girl Dick 8:06 · 758 views
  16. Swollen balls belong in chastity cages, not positions of power! 0:34 · 509 views
  17. She Makes Him Ride Her Strap – Glamping 0:20 · 507 views
  18. Limp and Locked -- Chastity Brainwash 2:33 · 443 views
  19. Locktober 2026 #2: Dolling Up My Sissy Slut For What Comes Next 8:08 · 451 views
  20. Alpha uses Cuckoldress throat 1:04 · 419 views
  21. Femdom dominating her little femboy 5:18 · 427 views
  22. Your Waifus Feminize You! (Sissification, Anal Play, Chastity, NTR, CBT, CEI) (Patreon Preview) 9:02 · 351 views
  23. No Treats, Just Tricks: Pegging With Kylie Moone 1:01 · 331 views
  24. Dog toy breeds my slut. 7:55 · 332 views
  25. Halloween Pegging 4:56 · 353 views
  26. Put him in the chair and had some fun on my Motorbunny. Sucked on him alot. Turned on the machine and pegged him until he came in my mouth. 29:12 · 294 views
  27. Locktober 2026 Day 30: Last Night Locked 0:25 · 230 views
  28. Femdom Gaping, Fisting and Pegging My Stepson 12:36 · 264 views
  29. One more cock locked, one step closer to a Femdom future! 🔐 0:28 · 244 views
  30. Almost No Nut November 11:48 · 223 views