Jack Bailey

Biography

Known For

Split Me Open

25 January, 2023

Lucas Men Extravaganza

24 February, 2023

Johnny Rapid: For the Fans Vol. 4

1 February, 2023

My Stepbrother, My Bitch

2 May, 2023

After School

12 May, 2023

Brother Crush Vol. 21

9 May, 2023

Loser Has to Bottom

14 March, 2023

Like Old Times

1 February, 2023

Ready to Hustle

30 June, 2023

My Step-Brother, My Bitch

2 May, 2023

Breeding Season

14 June, 2023

Washboard Worship

18 April, 2023

Secret Sexcapades

31 December, 2021

The Code

4 August, 2023

Dirty Move

22 June, 2023

Twinky Twinkle

18 May, 2023

Twinkology 101

7 February, 2023

Doctor Tapes 4

23 August, 2023

Rough Enough?

14 September, 2023

Open Up

22 September, 2023

Therapy Dick

22 September, 2023

Break Him In Raw 2

20 May, 2022

Cabin Fever

2 May, 2022

No More Virgin

10 October, 2023

No Step-Son of Mine

25 January, 2022

Bond With Me Stepdaddy

24 July, 2022

Hot Boy Summer 2

1 July, 2021

The Recruit

30 January, 2024

Brother Crush Vol. 23

13 February, 2024

Inseam

3 November, 2021

Asses Topped Off With Cum

12 December, 2023

A Cowboy and a Gentleman

12 March, 2024

Back in Town

27 December, 2022

A Virgin No More

17 September, 2021

Too Depraved to Behave

3 March, 2021

Penetrated & Pounded

10 May, 2024

Bareback Auditions 24: Thrusted and Pumped

29 September, 2023

Trick or Treat Gangbang

1 February, 2023

Camp Bareback Boys 4

1 July, 2024

Dig Deeper

22 June, 2024

A Brat and a Gentleman

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Learning His Place

19 September, 2022

Lake Need: A Trip to Remember

1 January, 2021

Butt Slut Tag Team

23 October, 2023

Slam That Twink

22 February, 2023

Slam-Fucked Delinquents

17 June, 2022

Lead by Example

19 November, 2024

Accidental Gangbang: Chock-Full Of Jocks

26 August, 2022

White Boy Sandwich 6

20 July, 2021

Camp Bareback Boys 5

27 May, 2025