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…
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…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 4 rocks the house with Scott Nails & Jasmine Byrne in a Viagra…
Everything was just fine in Adrian’s life. She was happily married with a good career and a fantastic home. She led a safe, secure, predictable, boring, mind-numbing existence. So her…
A masterpiece of cinematic eroticism shot entirely on HD, by leading female director, Celeste. Jesse Jane® explores the dark boundaries of slave and master and at her lovers request, she…
Blending rock-n-roll with hot chicks and money resulted in Band Camp, the new, musically inspired trip by Digital Playground’s acclaimed director, Robby D. Harmony unravels and tempers flare as budding…
When Jackson breaks up with his significantly younger girlfriend Kennedy, she’s furious – what could this older woman possibly have that she doesn’t?! After looking into Laura on social media,…
Posh Kitten plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing,…
Famed monster hunter Gerald of Vulvia can’t stay out of trouble. He’s always on the hunt for his three favorite things: money, combat, and – most important of all –…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 4 rocks the house with Scott Nails & Jasmine Byrne in a Viagra…
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…
Blending rock-n-roll with hot chicks and money resulted in Band Camp, the new, musically inspired trip by Digital Playground’s acclaimed director, Robby D. Harmony unravels and tempers flare as budding…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
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…
When Jackson breaks up with his significantly younger girlfriend Kennedy, she’s furious – what could this older woman possibly have that she doesn’t?! After looking into Laura on social media,…
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…
Shot entirely on HD, “Control” is harder, faster and edgier than anything Robby has directed before. Delivered on 2 Discs, with 8 full scenes and tons of tease, Volume 2…
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…
Posh Kitten plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing,…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
Alex Blake has a thing for balls, the bigger the better. She rubs balloons against her perky tits in the bathroom as she fantasizes about a cock going balls deep…
Jasmine dreams of being the perfect woman, and decides that plastic surgery is the only way to go. She wakes up after the surgery looking every bit as perfect as…
Little Red Rider journeys through the woods to bring her grandmother some goodies. Sadly, however, Little Red Rider arrives to find her grandmother left for dead. With the aid of…
It’s just another dull day at the bank for teller Joseline Kelly, that is until she’s held up by hot burglar Seth Gamble. He takes her hostage, but Joseline’s so…
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…
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…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
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…
Shot entirely on HD, “Control” is harder, faster and edgier than anything Robby has directed before. Delivered on 2 Discs, with 8 full scenes and tons of tease, Volume 2…
Posh Kitten plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing,…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
Everyone loves a great cosplay scene, and Digital Playground is no different! Six girls, four scenes, and all of the colorful costumes and wigs that you could ask for. Indulge…
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…
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…
Shot entirely on HD, “Control” is harder, faster and edgier than anything Robby has directed before. Delivered on 2 Discs, with 8 full scenes and tons of tease, Volume 2…
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…
Famed monster hunter Gerald of Vulvia can’t stay out of trouble. He’s always on the hunt for his three favorite things: money, combat, and – most important of all –…
Posh Kitten plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing,…
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…
