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Jack Bailey & Killian Knox Chapter 2 Jack Bailey & Killian Knox Chapter 2 Killian KnoxJack Bailey BY: JockPack's Jock Breeders Mar 08, 2023 2.3k 43%
Jack Bailey, Killian Knox Bottoms: Encounter 2 Jack Bailey, Killian Knox Bottoms: Encounter 2 Killian KnoxJack Bailey BY: Twink Loads Dec 16, 2022 3.3k 50%
Jack Bailey, Romeo Davis Bottoms: Encounter 2 Jack Bailey, Romeo Davis Bottoms: Encounter 2 Romeo DavisJack Bailey BY: Twink Loads Jan 12, 2022 3k 33%
Jack Bailey and Romeo Davis Chapter 1 Jack Bailey and Romeo Davis Chapter 1 Romeo DavisJack Bailey BY: RawFuckBoys Dec 22, 2021 2.5k 100%
Jack Bailey, Killian Knox Bottoms: Encounter 1 Jack Bailey, Killian Knox Bottoms: Encounter 1 Killian KnoxJack Bailey BY: Twink Loads Dec 17, 2021 3.3k 0%
Jack Bailey, Chapter 2: Getting Pumped Jack Bailey, Chapter 2: Getting Pumped Dolf DietrichJack Bailey BY: Twink Top Dec 14, 2021 3.7k 0%
Jack Bailey's Steamy Debut with Stud Kane Fox Jack Bailey's Steamy Debut with Stud Kane Fox Kane FoxJack Bailey BY: Cocky Boys Dec 07, 2021 5.5k 100%
Jack Bailey, Romeo Davis Bottoms: Encounter 1 Jack Bailey, Romeo Davis Bottoms: Encounter 1 Romeo DavisJack Bailey BY: Twink Loads Nov 03, 2021 3.3k 100%
Jack Bailey, Chapter 1: Top Training Jack Bailey, Chapter 1: Top Training Jack BaileyLance Charger BY: Twink Top Oct 17, 2021 6.9k 75%
Jack Bailey, Jax Thirio Bottoms: Encounter 1 Jack Bailey, Jax Thirio Bottoms: Encounter 1 Jax ThirioJack Bailey BY: Twink Loads Oct 06, 2021 3.7k 100%
Jack Bailey, Deepdicc & Ray Diesel Jack Bailey, Deepdicc & Ray Diesel Deep DicRay DieselJack Bailey BY: Blacks On Boys Apr 04, 2021 5.7k 75%
Chapter 2: Luke Hudson & Jack Bailey Chapter 2: Luke Hudson & Jack Bailey Luke HudsonJack Bailey BY: Jock Pussy Jul 17, 2026 1.5k 67%
Luke Hudson and Jack Bailey Chapter 6 Luke Hudson and Jack Bailey Chapter 6 Luke HudsonJack Bailey BY: Jock Pussy Feb 18, 2024 6.1k 40%
Head in the Clouds with Jack Bailey Head in the Clouds with Jack Bailey Mickey KnoxJack Bailey BY: Colby Knox Jun 28, 2023 2.8k 40%
Luke Hudson & Jack Bailey Chapter 4 Luke Hudson & Jack Bailey Chapter 4 Luke HudsonJack Bailey BY: Jock Pussy Jun 08, 2023 2.5k 36%
At The Park With Jack Bailey At The Park With Jack Bailey Darron BluuJack Bailey BY: GayRoom Feb 04, 2023 8.4k 75%
STORY, Jack Bailey: Romeo Davis Bottoms: Encounter 3 STORY, Jack Bailey: Romeo Davis Bottoms: Encounter 3 Romeo DavisJack Bailey BY: Twink Loads Jun 08, 2022 4k 60%
Breeding Jack Bailey Breeding Jack Bailey Masyn ThorneJack Bailey BY: Raunchy Bastards May 19, 2022 6.6k 71%
Tom Bentley & Jack Bailey Chapter 2 Tom Bentley & Jack Bailey Chapter 2 Tom BentleyJack Bailey BY: Jason Sparks Live Apr 15, 2022 3.3k 50%
Sub Boy Jack Bailey Sub Boy Jack Bailey Jack BaileyOwen HawkDavid Eck BY: TopFanVids Mar 17, 2022 4.3k 0%
Scout Jack Bailey, CHAPTER 2: Lessons in Discretion Scout Jack Bailey, CHAPTER 2: Lessons in Discretion Jack BaileyPatriarch Smith BY: Carnal+ ScoutBoys Dec 08, 2021 9.2k 100%
Boy Jack Bailey, CHAPTER 1: The Grooming Boy Jack Bailey, CHAPTER 1: The Grooming Jack BaileyLance Charger BY: Carnal+ Boy For Sale Nov 25, 2021 3.6k 50%
Tom Bentley & Jack Bailey BAREBACK Tom Bentley & Jack Bailey BAREBACK Tom BentleyJack Bailey BY: Jason Sparks Live Sep 08, 2021 2.7k 100%
Meet Jack Bailey Meet Jack Bailey Mickey KnoxJack Bailey BY: Colby Knox Jan 11, 2021 3.8k 100%
Johnny Rapid's Pretty Little Twink Threesome Johnny Rapid's Pretty Little Twink Threesome Johnny RapidAlex MeyerJack Bailey BY: TopFanVids Mar 03, 2022 3.4k 56%
Dale Savage Compilation Dale Savage Compilation Brandon AndersonCalvin BanksAdam AwbrideDale SavageEric CharmingChris DamnedJack Bailey BY: Disruptive Films Nov 04, 2025 8.5k 50%
Detention Wedgie Detention Wedgie Reese RideoutJack Bailey BY: GayRoom May 09, 2025 3.8k 100%
First Time Sharing a Bed First Time Sharing a Bed Jack BaileyDamian Rose BY: Brother Crush Jul 03, 2024 5.8k 60%
Penetrated & Pounded, Scene 2 Penetrated & Pounded, Scene 2 Jack BaileyGustavo Cruz BY: Lucas Entertainment Feb 26, 2024 6.2k 55%
Lake Need, Scene 1 Lake Need, Scene 1 Johnny RapidJack Bailey BY: JohnnyRapid.com Jan 05, 2024 3.7k 40%
A Brat and A Gentleman A Brat and A Gentleman Jack BaileyColt Spence BY: Disruptive Films Dec 24, 2023 5.4k 50%
11-Inch Stuffing 11-Inch Stuffing Jack Bailey11inchking BY: Raw Fuck Club Nov 24, 2023 10.5k 83%
Trick or Treat Gangbang: Part 2 Trick or Treat Gangbang: Part 2 Jack BaileyOwen HawkCockSwingFarmerRick Gonzales BY: Raw Fuck Club Nov 06, 2023 5.3k 62%
Trick or Treat Gangbang Trick or Treat Gangbang Jack BaileyOwen HawkCockSwingFarmerRick Gonzales11inchking BY: Raw Fuck Club Oct 29, 2023 8k 59%
Making Daddy Proud Making Daddy Proud Nate GrimesNico NovaBama RomelloJack BaileyChase Steele BY: HIMEROS.tv Sep 18, 2023 6.6k 44%
Relaxin' With Jax Relaxin' With Jax Jax ThirioJack Bailey BY: Dad Creep Aug 04, 2023 5.7k 38%