The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 10 is over 2 hours and features Stoya in a brand-new, amazingly ass-a-liscious…
Big-tittied MILF Joslyn James is preparing dinner for her husband JMac but he’s grumpy when he comes back home from work. The neighbor is being a dick again and parked…
Mature mavens Syren De Mer and Madeline have been swapping spouses for years! So imagine their surprise when the boys start servicing each other’s peckers during their most recent party….
Magnificent red haired Destiny Mira teases us by the poolside before getting in a steamying hot sex scene with Damion Dayski. Uploaded: 2024.02.10 2024.02.09 Show more…
Little Asian girls love extra stimulation, so getting taped up with red duct tape and having electric shockers placed all over her body is very arousing to this horny little…
Lena Paul is a smoking hot actress from Kentucky that has been in the industry for almost 4 years! This babe has the most luscious natural titties and she loves…
Missy Maze, Kayla West, Savannah Snow and Andrea Sky invited their best and hottest friends over for an all female orgy. Every once in a while women just need to…
Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…
Nina Pink is stunning in a tight yellow dress that flaunts her petite yet curvaceous figure. It’s hard not to notice how good she looks, especially for her mover Keiran…
A group of seven close-knit friends plan what might be their last big blowout weekend getaway together. The only single member of the bunch, Sarah (Paige Owens), has a plan…
Jayden Lee’s boyfriend loves her tight booty and big tits, but trying to tear her away from her video games long enough to fuck him is getting harder and harder…
Study Break Dickdown Bespectacled babe Cece has a secret crush on her mom’s hot new boyfriend, Oliver Flynn. When Oliver returns home from a sweaty workout and takes off his…
All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s new POV Playground, YOU will…
Megan can’t wait to fuck her boyfriend Jordi, and today they have the whole house to themselves – or so they think. Jordi’s stepmom Ava comes home and sees the…
A seedy motel provides the backdrop for a crumbling affair whose end triggers a night-long series of events that span espionage, and the ruining of two public figures. Pro-environment politician…
Madison Wilde is ready to try her hand at a casting interview. She’s been paired up with spunky sweetheart Katerina Deville for a Q&A session followed by some BG action….
Lacey Duvalle was hanging out at our place today and she started complaining about being hungry and wanting to go grab something to eat. We started thinking of places to…
Sexy nerd Charlotte Stokely has her college bully, Violet Starr, all to herself when she has her over for a private study group session. Violet has no idea what’s in…
During a moment of quiet repose in her boudoir, blonde bombshell Jennifer feels a wave of desire wash over her. But with her boyfriend an ocean away, what’s a lonely…
You never know when inspiration will strike! When sweet redhead Maddy has to strip off her shorts after spilling nail polish on them, it gives her BFF Karlee an idea!…
Investigative journalist, Charles Dera, goes undercover to expose the seedy practices of a Banana Shop. This business is known to offer sucking and fucking if you make the right order….
Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera….
