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Gay Sissy Videos

The most-viewed videos tagged gay sissy this week. Everyone shown must be an adult, and the material must be consensual and lawfully published.

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This page lists 30 gay sissy videos with 45K views between them. The average video runs 8:17, and the longest is My Sissy Boy Loves Fuck Busty Babe And My Cum In His Ass at 26:12. The most watched is Femboy big cock explodes with cum from a big dildo with 3K views. Tags that often appear alongside: sissy, transgender, femboy, trans, femdom.

Top Gay Sissy videos

  1. Femboy big cock explodes with cum from a big dildo 12:25 · 3K views
  2. Little sissy gets hard cock ass massage and fuck 0:59 · 3K views
  3. When I do this to you I’ll leave the cage on you, deal? 5:23 · 3K views
  4. Virgin Transgirl Chasity Cage Kink Compilation 7:09 · 2K views
  5. Your Loser Girl Failure Roommate Can’t Stop Stroking Her Cock… (F4M FUTA AUDIO) 20:19 · 2K views
  6. JOI - Jerk Off Instructions 8:21 · 2K views
  7. I Spread My Ass and End Up With My Hole Full of Cum 9:17 · 2K views
  8. LalaThePala Riding me until I cum inside her! 11:02 · 2K views
  9. Edge with me - Pussy Pocket Edition (NNN CEI) ✶·⊰₊‿︵‧˚₊⊹ 12:34 · 2K views
  10. Femboy taking big dildo 1:52 · 2K views
  11. She doesn't remember a time when she got to cum like a boy. 2:53 · 2K views
  12. TGirl milked by automatic masturbator 5:02 · 2K views
  13. 【Honkai: Star Rail】Cute big dick femboy Silver Wolf cosplay using a fucking machine cumshot 5:00 · 2K views
  14. Tgirl cum in cage 11:41 · 1K views
  15. Jessica Bloom Chastity Sissy Roulette Tasks And Cum Swallow 8:08 · 1K views
  16. TS Junna – Cute Asian Trans Girl's First Bondage Anal Experience! A Humiliating 3P Encounter with Two Older Men 3:09 · 1K views
  17. Gripping Her Tight While She Takes It Deep In The Ass 8:34 · 1K views
  18. I Fuck My Chastity-Locked Slut With a Strap-On 12:29 · 1K views
  19. Dominant Girlfriend Fist Trains Her Femboy 5:31 · 1K views
  20. Pounding Her Hard In Leggings On The Edge Of The Bed 6:18 · 1K views
  21. Cocksucking Selfie 2:23 · 1K views
  22. My Sissy Boy Loves Fuck Busty Babe And My Cum In His Ass 26:12 · 1K views
  23. Femdom SPH Bi Sissy Conditioning for my Slave in Bondage 1:42 · 987 views
  24. Pegging My Live In Slave BF - Femdom POV 3:25 · 1K views
  25. Surrendering *Completely* To The Futa Orc Queen..... (F4M FUTA AUDIO + BLOWJOB INSTRUCTIONS + ANAL) 18:23 · 940 views
  26. アナルオナニーしてるところを正面と下から撮影されて興奮する男の娘 10:29 · 883 views
  27. Slow Deep Anal In Pink Light With White Stockings 5:27 · 834 views
  28. Stepbrother femboy with a big dick masturbates to orgasm 13:08 · 759 views
  29. Little, Horny Femboy Hungry for Cum 8:31 · 731 views
  30. Cute trans babe getting heavy deepthroat cum 0:29 · 735 views