Jack Bailey

Jack Bailey

Acting

Born October 29, 1997 · 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…

Known for

Twinkology 101

Twinkology 101

2023

Doctor Tapes 4

Doctor Tapes 4

2023

Split Me Open

Split Me Open

2023

Lucas Men Extravaganza

Lucas Men Extravaganza

2023

Johnny Rapid: For the Fans Vol. 4

Johnny Rapid: For the Fans Vol. 4

2023

My Stepbrother, My Bitch

My Stepbrother, My Bitch

2023

After School

After School

2023

Brother Crush Vol. 21

Brother Crush Vol. 21

2023

Acting(57)

2026Jock Breeders 5: Chapters 25-30

2025Scoutmaster's Discipline: Chapters 1-4Scout Jack

2025Twink Swap Party 9

2025Twink Swap Party 8

2025Be My Bitch

2025Camp Bareback Boys 5

2024Lead by Example

2024Camp Bareback Boys 4

2024Penetrated & Pounded

2024A Brat and a Gentleman

2024That Summer

2024A Cowboy and a Gentleman

2024Lessons in Discretion: Chapters 1-5

2024Brother Crush Vol. 23

2024The RecruitToby

2023Asses Topped Off With Cum

2023Butt Slut Tag Team

2023No More Virgin

2023Bareback Auditions 24: Thrusted & Pumped

2023Therapy Dick

2023Rough Enough?

2023Doctor Tapes 4

2023Ready to Hustle

2023Breeding Season

2023Twinky Twinkle

2023After School

2023Brother Crush Vol. 21

2023My Stepbrother, My Bitch

2023My Step-Brother, My Bitch

2023Washboard Worship

2023Loser Has To Bottom

2023Lucas Men Extravaganza

2023Slam That Twink

2023Twinkology 101

2023Johnny Rapid: For the Fans Vol. 4

2023Like Old Times

2023Trick or Treat Gangbang

2023Split Me Open

2022Back in TownSam Romero

2022Learning His Place

2022Bond with Me Stepdaddy

2022Slam-Fucked Delinquents

2022Break Him In Raw 2

2022Cabin Fever

2022No Step-Son of MineToby

2021Secret Sexcapades

2021A Virgin No MoreToby

2021White Boy Sandwich 6

2021Hot Boy Summer 2

2021Can I Use Your Hole, Bro?

2021Too Depraved to Behave

2021Lake Need: A Trip to Remember

Jack Bailey — Watchpile | Watchpile