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Sissy Training Videos — Page 3

The most-viewed sissy training 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 Training videos

  1. fucking the neighbor in an abandoned house 9:04 · 942 views
  2. He Trained Her Ass 11:01 · 834 views
  3. Have A Quick Fuck with Your Stepmom Mindi Mink 5:07 · 944 views
  4. Caught Watching Cheerleader – Creampie Punishment 10:22 · 793 views
  5. Did my stepsister catch me messaging on a dating site? 11:52 · 746 views
  6. A Creepy House and a New Trans Sissy Diaper Mommy 16:15 · 683 views
  7. Beat the Pussy - Pussy Licking Slave Femdom Game Real Orgasms 0:54 · 599 views
  8. Tattooed Blonde Catches Him Stroking, Then He Eats Her Pussy Standing 2:13 · 613 views
  9. With anal training anything is possible, that's why my asshole is so gape and loose 11:29 · 558 views
  10. Winter Rae's Busty Bimbo Sex Training 7:29 · 557 views
  11. Girlfriend makes me train her friends tight ass and I fall in love ❤️ 13:10 · 470 views
  12. Anal slut gets fucked hard and deep!! 16:17 · 484 views
  13. Limp and Locked -- Chastity Brainwash 2:33 · 456 views
  14. Locktober 2026 #2: Dolling Up My Sissy Slut For What Comes Next 8:08 · 459 views
  15. Venezolana esclava lo deja usar su cuerpo para jugar 7:14 · 1K views
  16. Alpha uses Cuckoldress throat 1:04 · 424 views
  17. Stiletto Worship Reward for My New Subby Servant Boy 7:32 · 431 views
  18. Sissy Trans Girl Uses Toy For Deepthroat Cum 7:17 · 373 views
  19. Your Waifus Feminize You! (Sissification, Anal Play, Chastity, NTR, CBT, CEI) (Patreon Preview) 9:02 · 369 views
  20. I Filmed Myself Squirting Multiple Times With the Dildo 10:51 · 341 views
  21. Cute femboy Pinkmoon crawling on a leash and tied up in a full body black pantyhose 1:28 · 299 views
  22. Paying My First Debt in Jail - Prison of Sissy 7:27 · 277 views
  23. Slutty German girl almost caught fingering herself in Thailand ( JOI - POV) 6:07 · 304 views
  24. Shy Stepsis Had The Best Sex Orgasms From His Step Bro _Pure Taboo FULL VIDEO 7:42 · 298 views
  25. I masturbate with my toys, come watch me. Part 3. Spanish porn. 13:24 · 235 views
  26. little trans girl Sasha_Q 8:01 · 226 views
  27. Almost No Nut November 11:48 · 226 views
  28. double vaginal in acuckold threesome with my ass being fucked too 9:36 · 231 views
  29. ! Suite Ultimate - Window Masters ! Miles got caught right while fucking by the window. 0:48 · 227 views
  30. This was hard to get out! 0:10 · 204 views