This site is for adults only. By entering, you confirm you are 18 or older and that viewing adult material is legal where you live.

Recommended for you

Loading videos…

Live models

Crossdresser Sissy Videos — Page 2

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

Watch in HD, without ads

Premium unlocks 1080p and members-only videos. Premium Gold also removes every ad.

More live models

Sponsored

This page lists 30 crossdresser sissy videos with 1K views between them. The average video runs 6:21, and the longest is Live, Laugh, Lobotomy (BBC Training)- Leilah Camus at 33:41. The most watched is Slow Deep Anal In Pink Light With White Stockings with 90 views. Tags that often appear alongside: sissy, sissy crossdress, crossdresser, femboy, trans.

Top Crossdresser Sissy videos

  1. Extreme Sissy Gape & Prolapse: Unmasked Silhouette Training with Double Dildos 6:26 · 72 views
  2. the pink sissy bimbofication 0:37 · 57 views
  3. A girl who loves milk💗💞japanese crossdresser masturbation 7:39 · 60 views
  4. Slow Deep Anal In Pink Light With White Stockings 5:27 · 90 views
  5. filling our holes. Extra long dildo 8:38 · 57 views
  6. EVIL MISTRESS FUCKS AND USES PANTY WEARING MAN 7:16 · 53 views
  7. ASMR Femboy in Dress (no talking) 10:20 · 51 views
  8. Live, Laugh, Lobotomy (BBC Training)- Leilah Camus 33:41 · 51 views
  9. Sissy femboy caged in black lingerie gets her sissy pussy stretched by a big black demon dick from bad dragon 2:57 · 48 views
  10. Sissy Boyfriend Play – I Suck His Cock Rim His Hole and Finger Fuck While Stroking Him 5:19 · 53 views
  11. Pissing... Shut up and drink!! 1:27 · 43 views
  12. Sexy devote Sissy Schlampe 7:43 · 37 views
  13. Sissy uncontrollably shaking hands-free orgasm 2:34 · 42 views
  14. Femboy in fishnets cock | Trans solo masturbation showing her curvy thighs | Sissy hot compilation 10:14 · 30 views
  15. Femboy's Fat Ass Dancing in Your Face – Trans Cock Stroking Compilation 10:05 · 28 views
  16. Sissy Panty Stache discovered by Femdom, Caught being a Sissy 10:53 · 31 views
  17. Fat latina sissy gets big ass fucked hard 0:26 · 26 views
  18. Throwing it back in my new BBC dildo 2:45 · 27 views
  19. Zorrita cocinando su coño 1:16 · 23 views
  20. Squatting Deep On My Thick Cock While She Moans 7:10 · 32 views
  21. femboy lina sissy crosses dress for deepthroat fun 0:11 · 18 views
  22. cutefemboy0987 shows off big ass in public cosplay 1:27 · 15 views
  23. POV: Femboy Touches His Small Dick Under His Panties – Sissy in Lingerie Cock cumshot Compilation 10:04 · 13 views
  24. lolatmylilpeepee crossdresser reveals his small sex 1:25 · 14 views
  25. Mi esposa me folla el culo 7:17 · 12 views
  26. Sissy femboy dressed in black lingerie shows off for her mistress 0:39 · 12 views
  27. SissySubRachel Explores Big Ass Sensations Tonight As Sissy 0:28 · 10 views
  28. jazmine Skye Wearing The Chastity Cage For Solo Fun 1:09 · 9 views
  29. TRANS FAGGOT WANKS HER BIG HOT COCK 24:27 · 9 views
  30. Cumshot on the ass after a good fuck. Full video on my channel 0:34 · 22 views