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Prison Roleplay Videos — Page 2

The most-viewed videos tagged prison roleplay 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 prison roleplay videos with 42K views between them. The average video runs 11:13, and the longest is [F4M] Long Distance Girlfriend Surprises You With A Toy She Controls [POV Audio Roleplay] at 26:41. The most watched is POV! Fucking my new girlfriend in the ass—the condom got stuck in her anus. with 3K views. Performers who appear most often here: Seth Gamble, Abella Danger. Tags that often appear alongside: roleplay, blowjob, blonde, big tits, pov roleplay.

Top Prison Roleplay videos

  1. Abella Danger Joins Group Fuck With Cum Swapping Finish Behind Bars 16:17 · 2K views
  2. Police Girls Prison Strap-on Lesbian Sex - AI Made. 3:10 · 2K views
  3. I Play Truth or Dare With my Stepsister! What a Tight Ass She Has. 18:30 · 2K views
  4. Me atraparon robando y terminamos follando 14:31 · 2K views
  5. Mi esclavo enmascarado me come y me cumple en el telo 10:16 · 2K views
  6. Robot Breast and Ass Expansion - Fansly Preview - VRChat ERP 4:43 · 2K views
  7. Christmas Elves Kimmy Kimm, Bianca Bangs & Sawyer Cassidy Put their Free Use Pussies to Work Riding Stepbro's Candy Cane 15:20 · 2K views
  8. I didn't have any money... but I have another way to pay. 9:59 · 2K views
  9. Accidentally Fucked My Girlfriend’s Step-Mom Thinking She Was My Wife 14:35 · 2K views
  10. CHIFRANDO o corno 7:20 · 1K views
  11. 237 FULL Video Blowjob Facial Maid Roleplay BBC Cowgirl Lingerie High Heels Dripping Messy Amateur Homemade OnlyFans 5:04 · 1K views
  12. Abella Danger Deepthroats Cock in Sloppy Behind-Bars Threesome 4:13 · 1K views
  13. Let the Naughty Dice Decide Our Position 12:29 · 2K views
  14. سكس مغربي اصلي صوت واضح حوا ترمة مغربية طبون كبير تاتحوا من لور moroccan sex with big booty arabic sharmota 7:09 · 1K views
  15. A Handmaid's Tale - Cuckquean Wife Holds Handmaid While Husband Breeds Her 11:53 · 1K views
  16. Hot sinister furries use you... 6:38 · 1K views
  17. POV! Fucking my new girlfriend in the ass—the condom got stuck in her anus. 8:50 · 3K views
  18. OUT OF THE FAMILY - Lexi Smith Pulls Out Her Tits And Makes Cheating Easy Hardcore 15:40 · 1K views
  19. Maid Monika Fox Masturbates And Plays With Toys In Excitement At Sight Of Two Gentlemen 7:46 · 1K views
  20. Angry Ghost Fucks You After Failing To Scare You || ASMR Audio Roleplay For Women [M4F] 20:28 · 949 views
  21. Horny Free Use Roommate Craves Your Cock During No Nut November 3:28 · 947 views
  22. Goth girlfriend catches me cheating on her she hate fucks til i cum inside her 7:00 · 1K views
  23. Stepmom masturbates and milks her breasts roleplay 7:31 · 921 views
  24. Redhead Cleaning Lady Used Her Own Squirt to Wipe the Floor 14:12 · 961 views
  25. THE EXOTIC - Mi Hermanastra Tiene El Culo Mas Apetecible De Todos 12:04 · 998 views
  26. My Idol Is Too Good at Pleasing Me 🩷 3:36 · 843 views
  27. [F4M] Long Distance Girlfriend Surprises You With A Toy She Controls [POV Audio Roleplay] 26:41 · 785 views
  28. Dads Friend Fails NNN {M4F] [MDOM] [NO NUT] 20:13 · 1K views
  29. My Step-Son’s Bully Seduced Me Into an Affair 11:44 · 845 views
  30. This useless servant-stepdaughter must fully taste the dirt from the floor like the piggy she is - hardcore BDSM domination, lesbian hand over mouth 15:18 · 729 views