Jack Bailey
Acting
Born 1997-10-29 · Missouri, USA
With his sweet face and slim, sexy body, Jack Bailey is a twink who caused a stir amongst porn fans when he arrived on the scene in 2020. You can enjoy one of his earliest performances in Himeros TV’s “Good Game, Bro,” sucking and riding Andre Donovan. This interracial scene is based on the popular fantasy of two hot jocks embracing their gay desires. Jack soon followed this up with “Meet Jack Bailey” and “Colby Chambers Fucks Jack Bailey” from Colby Knox.
Filmography
Scoutmaster's Discipline: Chapters 1-4
Dec 27, 2025
Twink Swap Party 9
Sep 19, 2025
Twink Swap Party 8
Jun 6, 2025
Be My Bitch
Jun 3, 2025
Camp Bareback Boys 5
May 27, 2025
Lead by Example
Nov 19, 2024
Camp Bareback Boys 4
Jul 1, 2024
Dig Deeper
Jun 22, 2024
Penetrated & Pounded
May 10, 2024
A Brat and a Gentleman
Apr 23, 2024
A Cowboy and a Gentleman
Mar 12, 2024
Lessons in Discretion: Chapters 1-5
Feb 16, 2024
Brother Crush Vol. 23
Feb 13, 2024
The Recruit
Jan 30, 2024
Asses Topped Off With Cum
Dec 12, 2023
Butt Slut Tag Team
Oct 23, 2023
No More Virgin
Oct 10, 2023
Bareback Auditions 24: Thrusted & Pumped
Sep 29, 2023
Open Up
Sep 22, 2023
Therapy Dick
Sep 22, 2023
Rough Enough?
Sep 14, 2023
Doctor Tapes 4
Aug 23, 2023
The Code
Aug 4, 2023
Ready to Hustle
Jun 30, 2023
Dirty Move
Jun 22, 2023
Breeding Season
Jun 14, 2023
Twinky Twinkle
May 18, 2023
After School
May 12, 2023
Brother Crush Vol. 21
May 9, 2023
My Stepbrother, My Bitch
May 2, 2023