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Sissy Boy Videos — Page 2

The most-viewed sissy boy 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.

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Top Sissy Boy videos

  1. Locktober Unlock - Chastity Femdom POV 6:38 · 1K views
  2. SHAME4K. My Daddy’s Secretary prefers to have Sex with me 15:26 · 1K views
  3. Goth trans woman begs for release from chastity cage 2:49 · 1K views
  4. Letting A Dominant Futa Ghost Do Whatever She Wants?! (F4M FUTA AUDIO) 27:39 · 1K views
  5. Try Not to Cum Challenge - No Nut November - Jerk Off Instructions - JOI - Kayla Summers - Full Video 7:41 · 1K views
  6. Horny Gamer Girl Riding Femboy with Cumshot and Anal Creampie! 7:48 · 1K views
  7. Karwachauth sex with hotel boy- Indian wife Cheated on her husband, She fucked hard after seduced. 13:36 · 1K views
  8. This guy loves sharing his pussy with strangers — a group sex session at a picnic 10:58 · 980 views
  9. Cute femboy SakunoNya and Natsuyue take a bath and have anal sex in a roadside cabin 4:42 · 930 views
  10. No Nut November. Time to lock in. 1:50 · 852 views
  11. A Creepy House and a New Trans Sissy Diaper Mommy 16:15 · 724 views
  12. I Spread My Legs Wide, Rub My Clit, and Fuck Him Harder in the Woods 4:00 · 662 views
  13. Sesnaul Massage Girlfirend ASMR GFE Wet Sounds 10:24 · 642 views
  14. I'm going to call another M-boy now and make him hold back his ejaculation 🌟No, you can't cum, did you almost cum again? 👅You're so quick to cum~♪ 5:37 · 1K views
  15. Locktober 2026 #2: Dolling Up My Sissy Slut For What Comes Next 8:08 · 466 views
  16. Limp and Locked -- Chastity Brainwash 2:33 · 471 views
  17. Stiletto Worship Reward for My New Subby Servant Boy 7:32 · 460 views
  18. Alpha uses Cuckoldress throat 1:04 · 431 views
  19. You Don’t Have Cash. Your Italian Taxi Driver In Rome Collects The Fare With Her Throat | F4M Audio Roleplay 9:20 · 450 views
  20. Be a good boy and write to me via link in bio 😋 1:01 · 393 views
  21. Threesome Menage Com Amiguinha - Sentamos e Gozamos na Rola Grossa 21:37 · 449 views
  22. Sissy Trans Girl Uses Toy For Deepthroat Cum 7:17 · 389 views
  23. Worship My Cock While I Play With It for You 2:32 · 376 views
  24. Your Waifus Feminize You! (Sissification, Anal Play, Chastity, NTR, CBT, CEI) (Patreon Preview) 9:02 · 389 views
  25. In A Green Forest 🌲 2:39 · 368 views
  26. Cute femboy Pinkmoon crawling on a leash and tied up in a full body black pantyhose 1:28 · 313 views
  27. Paying My First Debt in Jail - Prison of Sissy 7:27 · 295 views
  28. Are You A Naughty Boy? 0:06 · 266 views
  29. A Suite Surprise for My Birthday Boy 20:48 · 278 views
  30. KILLERGRAM - Sophie Anderson Brings Sultry Star Power To A High Energy Team Showcase 15:30 · 257 views