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Sissy Transformation Videos — Page 4

The most-viewed videos tagged sissy transformation 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 transformation videos with 4K views between them. The average video runs 4:12, and the longest is Mexican Mami rides Dildo at 28:27. The most watched is When I do this to you I’ll leave the cage on you, deal? with 220 views. Tags that often appear alongside: sissy, transgender, shemales, homemade, onlyfans.

Top Sissy Transformation videos

  1. Im spread wide and waiting for you to fill me up 💗 0:12 · 156 views
  2. My cocks slick and aching for your tongue on it 🍆 0:12 · 153 views
  3. Doing embarrassing tasks in the park! 0:45 · 149 views
  4. I Really Feel Very Horny for Men 6:02 · 153 views
  5. Desperate sissy fucks stroker with strapon dildo in chastity cage and cums hands-free without any stimulation ft. Hankey's Toys Rentman 7:05 · 147 views
  6. Big brother... please spank my little clitoris...💗crossdresser masturbation 3:16 · 146 views
  7. There's a huge erect dick in my panties 0:20 · 144 views
  8. A compilation of my previews #1 2:41 · 137 views
  9. You gonna slide that cock right in or keep teasing me? 💦 0:12 · 142 views
  10. Gripping Her Tight While She Takes It Deep In The Ass 8:34 · 189 views
  11. Trans babe strokes her cock slow with legs wide open 😳 0:13 · 127 views
  12. Mexican Mami rides Dildo 28:27 · 128 views
  13. Im spreading wide open just waiting for you to slam 💕 0:09 · 125 views
  14. When I do this to you I’ll leave the cage on you, deal? 5:23 · 220 views
  15. Trans girl strokes her cock while kneeling on the floor 😘 0:12 · 125 views
  16. Small cock cleanup after big ass pussy fuck 5:12 · 126 views
  17. I ONLY SUBMIT TO HER 12:16 · 122 views
  18. Trans girl strokes her cock slow with half-lidded eyes 🥰 0:12 · 118 views
  19. Sissy cums in chastity hands-free from fucking her ass with dildo multiple squirting orgasms 9:01 · 131 views
  20. Trans girl leans forward with her cock in hand 🥰 0:12 · 117 views
  21. japanese crossdresser school uniforms bukkake cosplay 1:13 · 117 views
  22. mujer sexi chupa culo de hombre para luego follarlo #012 pegging and rimming PT2 8:31 · 116 views
  23. BEHIND THE SCENES: FIRST TIME COWGIRL ANAL 4:04 · 111 views
  24. Big Tits Sissy MILKED 0:46 · 111 views
  25. No Nut November Chastity Tasks 0:28 · 110 views
  26. Sissy Feminization Class #1 Leave Your Old Life and Choose a New Sissy Slut Name! (English) 10:02 · 117 views
  27. You gonna watch me play or help me out? 🖤 0:12 · 102 views
  28. SHE IS THE BOSS: PART 1 5:08 · 104 views
  29. Rossie Getting Anal Sex Rammed by Fucking Machine Dildo & BDSM Roleplay Deepthroating Pissing Blowjob to Tyler 5:04 · 103 views
  30. An unshaven cock is being jerked off while standing 0:10 · 103 views