Tag "Jack Bailey"

Disruptive Films: Dale Savage fucks Jack Bailey and Scott Finn in "A Virgin No More"

Disruptive Films: Dale Savage fucks Jack Bailey and Scott Finn in “A Virgin No More”

  PUBLISHED: May 6, 2022 COMMENT

Jack Bailey and his best friend Scott Finn are getting fucked by his dad’s best friend in “A Virgin No More: The Offering“. The young boys bottom for daddy Dale Savage in this Disruptive Films video , which has been directed by Walden Woods. After Toby (played by Jack Bailey ) loses his virginity

Greg McKeon fucks Jack Bailey

Disruptive Films: Jack Bailey bottoms for his former teacher Greg McKeon in “Be”

  PUBLISHED: February 11, 2022 COMMENT

Director Walden Woods has paired up Jack Bailey and Greg McKeon. These horny guys suck and fuck in this Disruptive Films release, called “Be“. Years after graduating, Sam Romero gets in touch with his former English teacher, Mr. Howard Dennison. After reconnecting on social media, they decide to meet up. Sam

Carter DelRey, Trevor Harris, Jack Bailey & Dakota Payne fuck in "Twinkology 101"

Carter DelRey, Trevor Harris, Jack Bailey & Dakota Payne fuck in “Twinkology 101”

  PUBLISHED: February 4, 2022 COMMENT

This Next Door Studios update is a bareback foursome starring Carter DelRey, Trevor Harris, Jack Bailey, and Dakota Payne. The script of “Twinkology 101” has been written by Dakota. Young students Carter DelRey , Trevor Harris , and Jack Bailey are horny as fuck. They decide to seduce their sexy Professor, Dakota Payne . Lucky for them, the hot

Next Door Studios: Jack Valor, Jack Bailey & Jax Thirio fuck in "We Met At The Prep Clinic" (part 2)

Next Door Studios: Jack Valor, Jack Bailey & Jax Thirio in “We Met At The Prep Clinic” (part 2)

  PUBLISHED: January 11, 2022 COMMENT

This homemade threesome is the second part of the Next Door Studios series “We Met At The PrEP Clinic“. This scene, starring Jack Valor, Jack Bailey, and Jax Thirio, is partly in POV-style. The guys make out on the bed before they get naked. It doesn’t take long before Jax

Damien White fucks Jack Bailey and Trevor Harris in "Washboard Worship"

Next Door Studios: Damien White fucks Jack Bailey & Trevor Harris in “Washboard Worship”

  PUBLISHED: December 25, 2021 COMMENT

This Next Door threesome – starring Damien White, Jack Bailey, and Next Door Studios exclusive Trevor Harris – is called “Washboard Worship“. Damien gives both twinks a deep, raw pounding. Jack Bailey and Trevor Harris are thirsty and the only thing that can quench their thirst is getting a piece of their hot roommate, Damien White .

Hot House: Jack Bailey gets his ass fucked by Chris Damned in "Inseam" (scene 1)

Hot House: Jack Bailey gets his ass fucked by Chris Damned in “Inseam” (scene 1)

  PUBLISHED: November 3, 2021 COMMENT

This scene – starring Jack Bailey and Chris Damned – is the opening scene from the new Hot House movie “Inseam“. The movie has been written and directed by Trenton Ducati and contains some very hot scenes. The remaining updates from this movie will be added to the Hot House members

Next Door Taboo: Jack Bailey gets fucked by Justin Matthews in "My Stepbro's Dildo"

Next Door Taboo: Jack Bailey gets fucked by Justin Matthews in “My Stepbro’s Dildo”

  PUBLISHED: August 28, 2021 COMMENT

Director Conrad Parker has paired up Jack Bailey and Justin Matthews and they’ve delivered a hot scene. This family roleplay video from Next Door Studios is called “My Stepbro’s Dildo“. Jack Bailey is a naughty little stepbrother. When he finds his big stepbrother Justin Matthews ‘ dildo, he decides to give it a whirl. Justin

Next Door Studios: Jack Bailey bottoms for his stepdad David Skylar in "Am I Qualified?"

Next Door Studios: Jack Bailey bottoms for his stepdad David Skylar in “Am I Qualified?”

  PUBLISHED: August 18, 2021 COMMENT

This is a super hot member fantasy video from Next Door Studios. Member JTennis6 wanted to see hunky David Skylar and twink boy Jack Bailey together. Director Big Mike made it happen. Jack gets fucked by his hot stepdad David in “Am I Qualified?“. It’s Jack Bailey ‘s first day at the new job.

Next Door Taboo: Jack Bailey bottoms for Johnny Ford in "Secret Sexcapades" (part 3)

Next Door Taboo: Jack Bailey bottoms for Johnny Ford in “Secret Sexcapades” (part 3)

  PUBLISHED: April 26, 2021 COMMENT

This is the third part of the “Secret Sexcapades” series from Next Door Taboo. Twink boy Jack Bailey needs a good fuck and goes to see muscle hunk Johnny Ford, who’s always happy to help a boy out. Since Jack Bailey is pissed at his ‘stepfather with benefits’ Roman Todd , he’s off to see

Next Door Taboo: Stepdad Roman Todd fucks Jack Bailey in "Secret Sexcapades" (part 1)

Next Door Taboo: Stepdad Roman Todd fucks Jack Bailey in “Secret Sexcapades” (part 1)

  PUBLISHED: March 22, 2021 COMMENT

Next Door Taboo has released the first scene from a brand new series, called “Secret Sexcapades“. Jack Bailey has it bad for Roman Todd, which is…pretty bad considering Roman is Jack’s stepfather. Jack wants more than a ‘Stepdad With Benefits,’ which is all Roman is willing to give. After a passionate fuck,

Alex Meyer fucks Jack Bailey and feeds him cum in "Bored Stepbros"

Brother Crush: Alex Meyer fucks Jack Bailey and feeds him cum in “Bored Stepbros”

  PUBLISHED: March 3, 2021 COMMENT

The latest Brother Crush release is called “Bored Stepbros” and brings together Alex Meyer and Jack Bailey. Now and then, cute Alex Meyer and his young stepbrother Jack Bailey get too bored for their own good. To liven things up, they please each other’s tender cocks, sucking and fucking until they’re drenched in each

Next Door Studios: Jack Bailey gets fucked by Jax Thirio in a homemade video

Next Door Studios: Jack Bailey gets fucked by Jax Thirio in a homemade video

  PUBLISHED: February 20, 2021 COMMENT

Jax Thirio has filmed another homemade video for Next Door Studios. He has invited Jack Bailey over and makes sure that the boy won’t forget their little get-together. Jax Thirio gives it to Jack Bailey good and hard and Jack loves it. The horny twink deep-throats Jax’s meaty cock. Jax prepares the boy’s tight hole

Next Door Studios: Jesse Bolton fucks Jack Bailey's tight boy hole in a homemade video

Next Door Studios: Jesse Bolton fucks Jack Bailey’s tight boy hole in a homemade video

  PUBLISHED: January 2, 2021 COMMENT

Jesse Bolton is back for his second Next Door Studios scene! This is a homemade video in which he fucks twink boy Jack Bailey, who makes his first appearance on Next Door Studios. Jack Bailey and Jesse Bolton don’t waste any time and barely introduce themselves before getting down with the action. In a passionate

Sketchy Sex (Suffocating Semen): Leo Silva, Danny, Andrew Powers, Aiden Asher, Jay Tee & Jack Bailey

Sketchy Sex (Suffocating Semen): Leo Silva, Danny, Andrew Powers, Jay Tee & more

  PUBLISHED: September 3, 2020 COMMENT

The latest release from Sketchy Sex is called “Suffocating Semen” and stars Leo Silva, Danny, Andrew Powers, Jay Tee, Aiden Asher, Jack Bailey and Danny (aka Martinez). It’s a hot and raunchy update! Typical roomie time, waiting for the first round of tops to suffocate our holes. We

Load Count: Andrew Powers, Leo Silva, Aiden Asher, Jack Bailey, Danny & Jay Tee

Sketchy Sex (Load Count): Andrew Powers, Leo Silva, Aiden Asher, Jack Bailey, Danny & Jay Tee

  PUBLISHED: August 7, 2020 COMMENT

This week’s release from Sketchy Sex is called “Load Count” and stars Andrew Powers, Leo Silva, Aiden Asher, Jack Bailey, Danny (aka Martinez from Military Classified ) and Jay Tee. Every now and again we all play a game to see how many loads we can fit in one hole.