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Most Relevant Video Results: "painful first time anal"

Generation Gape - Part 3: Pig Pose Generation Gape - Part 3: Pig Pose Levi Rhodes, Max Lorde by: NextDoorTaboo Oct 01, 2021 67%
Generation Gape - Part 4: His Cousin's Keeper Generation Gape - Part 4: His Cousin's Keeper Dakota Payne, Max Lorde by: NextDoorTaboo Oct 05, 2021 100%
Generation Gape - Part 5: Fitting Into His Stepson Generation Gape - Part 5: Fitting Into His Stepson Jax Thirio, Mason Dean, Levi Rhodes by: NextDoorTaboo Oct 05, 2021 100%
Gennaro & Jet (Bareback) Gennaro & Jet (Bareback) Jet Davis, Gennaro (CM) by: Chaos Men Oct 10, 2019 77%
Gentle Nights Gentle Nights Tony Rivers, Guy English by: Bear Films Apr 30, 2020 100%
Gentlemen 16: Professionally Pounded (Tomas Brand & Massimo Piano) (Scene 1) Gentlemen 16: Professionally Pounded (Tomas Brand & Massimo Piano) (Scene 1) Tomas Brand, Massimo Piano by: Lucas Entertainment Oct 09, 2019 87%
Gentlemen 17: Oral Office (Sean Xavier Fucks Alexander Volkov) (Scene 3) Gentlemen 17: Oral Office (Sean Xavier Fucks Alexander Volkov) (Scene 3) Sean Xavier, Alexander Volkov by: Lucas Entertainment Oct 09, 2019 86%
Gentlemen 19: Hard At Work (Devin Franco And Lee Santino Flip-Fuck) (Scene 2) Gentlemen 19: Hard At Work (Devin Franco And Lee Santino Flip-Fuck) (Scene 2) Devin Franco, Lee Santino by: Lucas Entertainment Oct 08, 2019 53%
Gentlemen 19: Hard At Work (Drae Axtell's Corporate Threesome w/ Dylan James and Stas Landon) (Scene 1) Gentlemen 19: Hard At Work (Drae Axtell's Corporate Threesome w/ Dylan James and Stas Landon) (Scene 1) Dylan James, Drae Axtell, Stas Landon by: Lucas Entertainment Oct 08, 2019 64%
Gentlemen 21: Top Management: Internship Gone Raw (Shawn Reeve Fucks Dakota Payne) (Scene 2) Gentlemen 21: Top Management: Internship Gone Raw (Shawn Reeve Fucks Dakota Payne) (Scene 2) Shawn Reeve, Dakota Payne by: Lucas Entertainment Oct 08, 2019 61%
Gentlemen 22: Jizz Is The Bizz (Kaden Alexander Pounds Ricky Verez) (Scene 3) Gentlemen 22: Jizz Is The Bizz (Kaden Alexander Pounds Ricky Verez) (Scene 3) Kaden Alexander, Ricky Verez by: Lucas Entertainment Oct 08, 2019 61%
Gentlemen 23: White Collar Breeders, Scene 1 (Dylan James Fucks Jessie Colter) Gentlemen 23: White Collar Breeders, Scene 1 (Dylan James Fucks Jessie Colter) Jessie Colter, Dylan James by: Lucas Entertainment Oct 07, 2019 71%
Gentlemen 24: Man-On-Man Merger, Scene 4 Gentlemen 24: Man-On-Man Merger, Scene 4 FX Rios, Jason Cox by: Lucas Entertainment Nov 19, 2018 100%
Gentlemen 26: Long, Hard Hours, Scene 3 Gentlemen 26: Long, Hard Hours, Scene 3 Arad WinWin, Andre Donovan by: Lucas Entertainment Oct 07, 2019 60%
Gentlemen 27: Corporate Exploitation, Scene One Gentlemen 27: Corporate Exploitation, Scene One Rafael Alencar, Ben Batemen by: Lucas Entertainment Nov 09, 2019 54%
Gentlemen 28: Executive Authority, Scene 3 Gentlemen 28: Executive Authority, Scene 3 Andrey Vic, Drake Rogers by: Lucas Entertainment Jul 03, 2020 100%
Gentlemen 28: Executive Authority, Scene 4 Gentlemen 28: Executive Authority, Scene 4 Rafael Carreras, Dylan James by: Lucas Entertainment Jul 03, 2020 100%
Gentlemen 29: Servicing The CEO, Scene 1 Gentlemen 29: Servicing The CEO, Scene 1 Tomas Brand, Gustavo Cruz by: Lucas Entertainment Dec 04, 2020 100%
Gentlemen 29: Servicing The CEO, Scene 1 Gentlemen 29: Servicing The CEO, Scene 1 Tomas Brand, Gustavo Cruz by: Sex In Suits Dec 04, 2020 100%
Gentlemen 29: Servicing The CEO, Scene 4 Gentlemen 29: Servicing The CEO, Scene 4 Kaden Alexander, Alexander Volkov by: Lucas Entertainment Dec 04, 2020 0%
Gentlemen 29: Servicing The CEO, Scene 4 Gentlemen 29: Servicing The CEO, Scene 4 Kaden Alexander, Alexander Volkov by: Sex In Suits Dec 21, 2020 100%
Gentlemen 30: Sweating Some Overtime, Scene 1 Gentlemen 30: Sweating Some Overtime, Scene 1 Ruslan Angelo, Gustavo Cruz by: Lucas Entertainment Mar 08, 2021 100%
Gentlemen 30: Sweating Some Overtime, Scene 1 Gentlemen 30: Sweating Some Overtime, Scene 1 Ruslan Angelo, Gustavo Cruz by: Sex In Suits Mar 12, 2021 100%
Gentlemen 30: Sweating Some Overtime, Scene 3 Gentlemen 30: Sweating Some Overtime, Scene 3 Ruslan Angelo, Sir Peter by: Lucas Entertainment Mar 08, 2021 100%
Gentlemen 30: Sweating Some Overtime, Scene 3 Gentlemen 30: Sweating Some Overtime, Scene 3 Ruslan Angelo, Sir Peter by: Sex In Suits Mar 19, 2021 0%
Gentlemen 31: Executive Submission, Scene 1 Gentlemen 31: Executive Submission, Scene 1 Sergeant Miles, Beaux Banks by: Lucas Entertainment Jan 21, 2022 60%
Gentlemen 31: Executive Submission, Scene 2 Gentlemen 31: Executive Submission, Scene 2 Isaac X, Adam Gray by: Sex In Suits Jan 22, 2022 100%
Gentlemen 31: Executive Submission, Scene 3 Gentlemen 31: Executive Submission, Scene 3 Alpha Wolfe, Alfonso Osnaya by: Sex In Suits Feb 04, 2022 0%
Gentlemen 31: Executive Submission, Scene 4 Gentlemen 31: Executive Submission, Scene 4 Beaux Banks, Isaac X by: Sex In Suits Jan 04, 2022 0%
Gentlemen 32: Hard Negotiations, Scene 2 Gentlemen 32: Hard Negotiations, Scene 2 Michael Lucas, Ridick by: Lucas Entertainment Oct 06, 2023 43%
Gentlemen 32: Hard Negotiations, Scene 3 Gentlemen 32: Hard Negotiations, Scene 3 Adam Killian, Craig Marks by: Lucas Entertainment Oct 06, 2023 100%
Gentlemen 32: Hard Negotiations, Scene 4 Gentlemen 32: Hard Negotiations, Scene 4 Leo Bacchus, Alex Ink by: Lucas Entertainment Oct 06, 2023 57%
Gentlemen 33: White Collar, Blue Collar, Scene 1 Gentlemen 33: White Collar, Blue Collar, Scene 1 Charlie Cherry, Kosta Viking by: Lucas Entertainment May 17, 2024 36%
Gentlemen 33: White Collar, Blue Collar, Scene 2 Gentlemen 33: White Collar, Blue Collar, Scene 2 Giuspel, Dean Menace by: Lucas Entertainment May 17, 2024 24%
Gentlemen 33: White Collar, Blue Collar, Scene 4 Gentlemen 33: White Collar, Blue Collar, Scene 4 Michael Lucas, Gio Pilos by: Lucas Entertainment May 17, 2024 44%
Gentlemen 34: Kings of Industry, Scene 2: Hardcore Business Retreat Gentlemen 34: Kings of Industry, Scene 2: Hardcore Business Retreat Kosta Viking, Leo Bacchus by: Lucas Entertainment Aug 12, 2024 0%
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