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Sissy Crossdress Videos

The most-viewed sissy crossdress 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 Crossdress videos

  1. Full Sissy Transformation by me wife Then Pegged With a 30cm Toy 11:50 · 4K 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 · 2K views
  4. Letting A Dominant Futa Ghost Do Whatever She Wants?! (F4M FUTA AUDIO) 27:39 · 2K views
  5. Goth trans woman begs for release from chastity cage 2:49 · 2K views
  6. Locktober Unlock - Chastity Femdom POV 6:38 · 2K views
  7. Locktober 2026 #3: I Give My Sissy Slut A Fake Cock And Drive Her Crazy 9:29 · 1K views
  8. Horny Gamer Girl Riding Femboy with Cumshot and Anal Creampie! 7:48 · 1K views
  9. 🎃 Femdom Face Sitting with Dildo gag : Cute Asian Amateur Femboy in Sexy Halloween Latex Cosplay 2:19 · 1K views
  10. Cute femboy SakunoNya and Natsuyue take a bath and have anal sex in a roadside cabin 4:42 · 1K views
  11. 🎃 Cute Asian Amateur Femboy in Sexy Halloween Latex Costume gets intense Cosplay Fuck 2:06 · 964 views
  12. Sexy Femboy getting fucked and dicked down balls deep by Big Hard Cock 8:01 · 836 views
  13. A Creepy House and a New Trans Sissy Diaper Mommy 16:15 · 807 views
  14. 🖤 Cute Asian Amateur Femboy Cosplayer enjoying tight EnX Cosmic Lulum The Little Devil fleshlight 3:24 · 831 views
  15. Teased with Armpit Fetish and a Handjob from behind by Cute Asian Amateur Femboy Krul Tepes Cosplayer from Seraph of the End 4:25 · 849 views
  16. Arknights: Endfield-Cute big-dick femboy cosplaying Rossi play with a fucking machine to cum 5:02 · 883 views
  17. I Fuck Eva In Ripped Black Nylon Pantyhose Till She Cums On My Dick 18:35 · 530 views
  18. Limp and Locked -- Chastity Brainwash 2:33 · 516 views
  19. Locktober 2026 #2: Dolling Up My Sissy Slut For What Comes Next 8:08 · 507 views
  20. Alpha uses Cuckoldress throat 1:04 · 456 views
  21. Your Waifus Feminize You! (Sissification, Anal Play, Chastity, NTR, CBT, CEI) (Patreon Preview) 9:02 · 436 views
  22. Sissy Trans Girl Uses Toy For Deepthroat Cum 7:17 · 406 views
  23. Cute femboy Pinkmoon crawling on a leash and tied up in a full body black pantyhose 1:28 · 349 views
  24. 【Arknights: Endfield】Cute big cock femboy Tangtang cosplay masturbating and cumshot 2:51 · 390 views
  25. Paying My First Debt in Jail - Prison of Sissy 7:27 · 306 views
  26. 2 Cosplay TGirls Fuck Outside with Anal Creampie Ria Bentley Eden Espi 7:00 · 446 views
  27. I'm a trans girl, and I'm working out my butt for you 7:00 · 274 views
  28. Submit To My Feet : Halloween Cei Encouragement 8:45 · 261 views
  29. little trans girl Sasha_Q 8:01 · 266 views
  30. Almost No Nut November 11:48 · 249 views