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Sissy Content Videos — Page 3

The most-viewed videos tagged sissy content 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 sissy content videos with 5K views between them. The average video runs 6:41, and the longest is Mexican Mami rides Dildo at 28:27. The most watched is Jessica Bloom Chastity Sissy Roulette Tasks And Cum Swallow with 287 views. Tags that often appear alongside: sissy, sissy training, sissygasm, femboy, sissy femboy.

Top Sissy Content videos

  1. [M4M] " I Love Being Your Femboy Maid, But It's So Embarrassing..." 💕🍆💦 {Lewd ASMR} 24:30 · 219 views
  2. There's a huge erect dick in my panties 0:20 · 169 views
  3. Im teasing myself slow just to watch you squirm 👅 0:12 · 166 views
  4. Desperate sissy fucks stroker with strapon dildo in chastity cage and cums hands-free without any stimulation ft. Hankey's Toys Rentman 7:05 · 179 views
  5. Doing embarrassing tasks in the park! 0:45 · 170 views
  6. Sissy cums in chastity hands-free from fucking her ass with dildo multiple squirting orgasms 9:01 · 166 views
  7. Mexican Mami rides Dildo 28:27 · 154 views
  8. Jessica Bloom Chastity Sissy Roulette Tasks And Cum Swallow 8:08 · 287 views
  9. Plowing Your Cute Femboy Friend Is Not Gay, It's Just Bro Love!~ ♂️💕🍆💦 {Mini Lewd ASMR} 1:15 · 162 views
  10. Barebacking a Slutty Trans - 50% Off Onlyfans Veronica Sanders 7:14 · 195 views
  11. Sissy Feminization Class #1 Leave Your Old Life and Choose a New Sissy Slut Name! (English) 10:02 · 159 views
  12. russian slut nicole murkovski fuck her wet greedy hole in a split imagining your throbbing dick 0:25 · 162 views
  13. Small cock cleanup after big ass pussy fuck 5:12 · 149 views
  14. Ebony Big Ass Doggystyle 7:44 · 152 views
  15. متحول جنسياً ذو قضيب كبير يجعل امرأة ناضجة تبلغ من العمر 60 عاماً تمص القضيب🏳️‍⚧️ 🥵 8:08 · 151 views
  16. I ONLY SUBMIT TO HER 12:16 · 150 views
  17. Trans babe strokes her cock slow with legs wide open 😳 0:13 · 140 views
  18. Which hole do you like the most? - Maiskiii 11:48 · 179 views
  19. Trans Girl Locks Her Tiny Cock in a Cage and Has Multiple Sissygasms from a Huge Dildo in Her Ass 11:25 · 150 views
  20. Destroying My Hole With Huge Spiked Plug in Fullbody Fishnet +Fisting 5:06 · 138 views
  21. Trans girl leans forward with her cock in hand 🥰 0:12 · 125 views
  22. Big Tits Sissy MILKED 0:46 · 125 views
  23. Full video on OnlyFans: Blowjobs, sex and doggy-style, homemade content 6:49 · 189 views
  24. No Nut November Chastity Tasks 0:28 · 120 views
  25. BEHIND THE SCENES: FIRST TIME COWGIRL ANAL 4:04 · 119 views
  26. SHE IS THE BOSS: PART 1 5:08 · 126 views
  27. Trans babe bent over showing her cock and round ass 0:12 · 120 views
  28. Rossie Getting Anal Sex Rammed by Fucking Machine Dildo & BDSM Roleplay Deepthroating Pissing Blowjob to Tyler 5:04 · 117 views
  29. My pussy wants your dick - Maiskiii 10:45 · 123 views
  30. BIG TITS FEMDOM SLAPPING HANDJOB 7:39 · 113 views