Adults only · 18+. By continuing, you confirm you are an adult and that viewing adult material is legal where you live.

Latest videos

Loading videos…

Live models

Sissy Chastity Videos — Page 2

The most-viewed sissy chastity 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.

Watch without ads

DISCOVYX Premium is coming soon.

No adsHD playbackFull-length videos

More live models

Sponsored

Top Sissy Chastity videos

  1. Locktober 2026 Day 26: Why I Locked You Up 0:30 · 172 views
  2. Locktober 2026 Day 28: Fucked, Not Freed 0:25 · 169 views
  3. Caged Cuckold Aches As Abbie Sykes Rides Tonys Cock 7:30 · 150 views
  4. Sissy Destroyed ass after hardcore anal machine fuck really fast and hard with big dildo in ass and gape 5:08 · 124 views
  5. sex machine fucks a femboy 0:41 · 123 views
  6. Locktober 2026 Day 27: This Is What You Wanted 0:25 · 118 views
  7. AMATEUR INTERRACIAL FUCK WITH SMALL COCK 6:02 · 115 views
  8. imlooona surrenders to rough anal play 6:22 · 105 views
  9. amateur desi fuck session in her pussy 6:07 · 128 views
  10. Skipping Work to Have Some Femboy Fun | ASMR 5:39 · 103 views
  11. Dark Angel Takes All Your Pleasure This Halloween 0:48 · 101 views
  12. Sexy sissy goth Miss Jess in a slutty little black latex dress invites you over to tease you by watching her play with herself!💋🖤 15:23 · 84 views
  13. Trans girl kneels low, cock in hand, eyes half shut 🤤 0:12 · 88 views
  14. Boss's Personal Feet Worshipper! POV Foot Fetish Chastity JOI Roleplay Femdom 0:20 · 96 views
  15. Locktober 2026 Day 31: Judgement Day 0:25 · 122 views
  16. Trans girl tease 7:11 · 76 views
  17. Sissy Training #1 - Suck and Swallow | Beta humiliation 7:36 · 80 views
  18. Sissy has handsfree orgasm from walking in high heels 0:09 · 65 views
  19. Big booty tgirl rides bbc dildo 0:30 · 88 views
  20. Im grinding down on this toy just picturing you behind me 🫦 0:12 · 61 views
  21. Sissy girl fucks her ass and cums handsfree sissygasm 0:12 · 63 views
  22. Trans girl teases her toy slow with red lips parted 💗 0:12 · 62 views
  23. Trans babe spreads wide, cock pointing up as she leans back 🍆 0:12 · 59 views
  24. Jakey crossdressing 4:02 · 58 views
  25. Big cocks only 0:10 · 52 views
  26. Trans Girl Next Door Invites You Over for a Movie 14:44 · 74 views
  27. sexy bubble ass huge dildo riding 6:06 · 45 views
  28. Red Light District Definite Edition Crossdresser Trans Solo Compilation - Sissy Cum Crossdress Cuckold Tits Stretched Balls Cumshot Crossdressing 2:05 · 45 views
  29. Trans girl strokes herself slow just for you to see 0:12 · 48 views
  30. Im bent over just for you, cock dripping and ready 🔥 0:12 · 42 views