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Latest updates featuring Sly Diggler

Mila Monet in '- Interracial Pickups'

Mila Monet - Interracial Pickups

Sly works as a courier delivering packages so when he pulls out his phone to take a photo of the delivered package it's just part of the job. They were also trained to use their phones to document any interactions with residents of the homes they deliver to in order to protect themselves and the company. Well today Sly was able to get a little more than that. While documenting his delivery the resident comes out and asks him why he is recording. He tells the young girl that it's so he has proof of his actions. Why would they want to do that, the young lady asks. So Sly starts telling her a story of a worker who there were allegations that he had exposed himself. Now this excites the young girl who wants to see Sly's dick. Sly of course demurs but she pushes on and goes so far as to expose herself. She is determined to see what package he is packing. Feeling he has been asked to release the Kracken he allows the persistent teen to pull out his chocolate thunder stick and the girl is in amazement. Black poles that big need to be shoved into little white holes. She is immediately sucking his cock but like any trained employee he continues to document his interactions while on the job. Soon he is in the house sliding his dip stick into her dripping pink slit. Maybe this is not what the delivery company intended but it makes for one hell of a good memory. He samples that sweet white girl pie for an extended period of time and leaves her with a steaming hot dripping face of spunk.


Scenes from other sites featuring Sly Diggler

Kona Jade in 'Big Tits By Poolside'

Kona Jade - Big Tits By Poolside

Kona Jade was just relaxing by the poolside when I came by. She wasted no time in sharing her amazing boobs and huge ass. As we talk to her, she begins to undress and show off just how big her booty and boobs are. As soon as they are all out to see, I begin to oil up her tits as she jiggles them, same with her big booty. Once she is covered from head to toe in oil, she begins to play with her pussy and beg for some big dick. We take Kona Jade inside the house where she meets Sly Diggler, who has a huge cock, the perfect size for her. She starts sucking on his huge cock and then takes it from all positions until he cums deep inside her pussy.

Sophia Leone in 'Ass Masterpiece'

Sophia Leone - Ass Masterpiece

When a big round Latin ass in a bikini meets a big black cock, get ready for some booty shaking and some hard pussy pounding. Cuz that's what you'll find in Sophia Leone's Ass Fucking Masterpiece.

Kaden Kole in 'Kaden Kole's GIGANTIC Booty'

Kaden Kole - Kaden Kole's GIGANTIC Booty

We met up with Kaden Kole to have a little fun. She paraded her enormous ass for us. This chicks booty can cause a tsunami by her just twerking. After she showed us her amazing attributes, it was time for her to get some dick. She pulled his cock out and started choking on it for some time before she started begging to get fucked. Kaden takes cock in several different positions before she receives a huge load all over her face.

Kenzie Anne in 'Looking For Trouble'

Kenzie Anne - Looking For Trouble

Kenzie's night was a bust… or is it just beginning? Her boyfriend annoyed her earlier, but his hot friend is sleeping over, and Kenzie suspects a late-night greeting might get their attention.

Allie Nicole in 'Take A Dip'

Allie Nicole - Take A Dip

Two beautiful blondes, two little black dresses, two pairs of luscious lips drawn to each other. Plus a room back at the hotel big enough for four. Tonight is about more than girl-on-girl

Lily Lou in 'Eager'

Lily Lou - Eager

Lily looks innocent, but she's been with all kinds of guys. A sweet hedonist with an open mind, a fun attitude, and curves that look luscious in lingerie, Lily is up for adventure… even if she won't be able to see it coming.

April Snow in 'Bye Boy'

April Snow - Bye Boy

You have to watch out for ladies like April. She'll do anything for her man - dress like sex on legs, model new lingerie - but don't leave her stranded, because when this girl up and goes, she'll land on another man in seconds, and she'll rub it in.

Mona Azar in 'Private Party'

Mona Azar - Private Party

Pretty in pink and dolled up for a sexy night of trouble, Mona met a guy at the club who measures up to her fantasies. She's so excited to live out her dreams tonight that she can't keep her hands off herself.


Cecilia Lion in 'Fans Only'

Cecilia Lion - Fans Only

Sexy influencer Cecilia gets picked up by a smooth talker who likes the way she looks in a tiny pink velvet dress. He's even more impressed that she isn't wearing panties under her backside-grazing hemline. After a wild ride, Cecilia's heart is racing fast enough to make some risqué video, saving the best for Sly's eyes only.

Serena Santos in 'Wild Night'

Serena Santos - Wild Night

Sexy Serena is hanging out and having fun but nothing would improve her night like a hookup. Check out this curvaceous vixen in velvet fulfils her appetite for adventure.

Ariana Marie in 'The Hot Wife Getaway'

Ariana Marie - The Hot Wife Getaway

Ariana loves to share, but more than that… she loves to be passed around like an expensive toy. Fortunately, Ariana's husband loves to show off what he has: a gorgeous brunette wife with a billion dollar body. So who will he loan his favourite plaything to this time?

Avi Love in 'One Night'

Avi Love - One Night

Best friends Avi and Kira spot Sly on their way back to their hotel room and Kira pulls pickup duty. The girls are showing a mile of leg and then some and Sly would be a fool to resist. Sometimes all it takes to land a threesome is being in the right place at the right time... with the right dick.

Alicia Williams in 'And Chill'

Alicia Williams - And Chill

In this connected new world we live in, fans have ever-greater access to their favourite celebrities… and vice-versa. Why would girls go after regular guys when they can reach out to rappers? When hot young blonde Alicia's favourite rapper responds to her DMs and sets up a get-together, she's expecting a quick fuck and some signed merch. When Sly doesn't rush her, Alicia is more attracted to him than ever, and decides to take the initiative.

Lauren Phillips in 'Hotwife Goals'

Lauren Phillips - Hotwife Goals

Busty Lauren is one kinky girl. When her husband is away on business and a new guy tries to hook up with her, Lauren has a pass to play… provided she takes video. Lauren squeezes into a sexy vinyl miniskirt and puts on a show any husband would have a hard time forgetting.

Avery Cristy in 'No Turning Back'

Avery Cristy - No Turning Back

Who in their right mind would cheat on a gorgeous blonde like Avery? Someone who doesn't know what he has. But Avery knows her man has been going behind her back, and she also knows how to take revenge: an eye for an eye, a screw for a screw.

Avi Love in 'New Kid'

Avi Love - New Kid

Sly needs a bigger challenge, so we called in the big guns, and now Avi and Adriana are making their way to his bed. With these two sexbombs about to explode all over him, we almost feel sorry for him. Almost…


Blake Blossom in 'Coping'

Blake Blossom - Coping

If you're looking for someone to share a living situation, you could do worse than rooming with Blake. This cute coed is super respectful and keeps to herself… unless her roommate's boyfriend swings by when Blake is alone in the house. Then again if you're dating Blake's roommate, it's an ever better deal!

Natalia Queen in 'Stay awhile'

Natalia Queen - Stay awhile

There are reasons they write songs about California girls. You hear a lot about Southern hospitality but you'd be surprised by just how warm and accommodating two sweet young blondes from the OC can be to their houseguests. When Sly and Prince Yoshua drop in on Emma and Natalia, these girls roll out the red carpet, Hollywood-style.

Lilly Bell in 'Rise and Grind'

Lilly Bell - Rise and Grind

Rise and Grind

Jill Kassidy in 'Surprise For You'

Jill Kassidy - Surprise For You

Surprise! Sexy Alexis knows how to keep a man satisfied: when he least expects it, she invites Jill - the friend he has always wanted to fuck - over for a threesome, and films the whole thing so he'll have proof that he was lucky enough to experience anything so incredible.

Chloe Cherry in 'Too Strong'

Chloe Cherry - Too Strong

Cherry is addicted to sex and is seeing a therapist to help her curb her problem. Unfortunately, even as she waits in the waiting room she can't hold back her urges.

Vanna Bardot in 'The Big Payback'

Vanna Bardot - The Big Payback

After discovering her man is cheating on her, Vanna devises the perfect plan to ensure that he gets the ultimate payback, and at the same time, making sure she enjoys every second.

Jazmin Luv in 'New Plan'

Jazmin Luv - New Plan

Jazmin calls her man to tell a little white lie, telling him her girlfriend is feeling unwell and she will be staying with her. The fact is, she has a much more exciting evening planned...

Laney Grey in 'Yes Please'

Laney Grey - Yes Please

Laney exudes class and poise and can turn heads by simply being in the vicinity. Her biggest fantasy is being with a black guy, and Sly is certainly the man who can make that fantasy come true.


Maitland Ward in 'Muse Episode 3'

Maitland Ward - Muse Episode 3

Adriana's relationship hits a breaking point, sending her running to the only doorstep she can think of in the city. Maitland answers. The two men just behind her wait patiently. Gabbie finishes her work in a rush of inspiration.

Vicki Chase in 'Ready For You'

Vicki Chase - Ready For You

They say three is a crowd, but where Vicki and LaSirena69 are concerned, it just makes things better and better. They are all dressed in their little black dresses and ready for some sharing and caring.

Eliza Ibarra in 'Sweetening The Deal'

Eliza Ibarra - Sweetening The Deal

Eliza is a personal trainer who wants to do more than workout with the married client, Sly. Sly resists temptation, so Emily steps in to help Eliza seal the deal.

Skylar Vox in 'Handful'

Skylar Vox - Handful

Skylar and Sommer look unbelievable, all dressed up in outfits showing each of their voluptuous curves. the lucky man of the moment is Sly - who is about to enjoy both of these beauties to the max.

Gabbie Carter in 'Come Get Me'

Gabbie Carter - Come Get Me

Gabbie looks adorable in her pink dress as she video calls her favorite man to pass some time. when he arrives at her hotel, she is more than ready to start the evening's fun.

Kymberlie Rose in 'Get it'

Kymberlie Rose - Get it

Kymberlie's man loves nothing more than watching her satisfied. When she tells him what she has planned for the evening, he is almost as excited as she is. She promises she will catch every second on camera just for him, and then leaves for her night's entertainment.

Naomi Swann in 'Symbiotic Relationship'

Naomi Swann - Symbiotic Relationship

Naomi has a strange relationship with her neighbor. He's a voyeur and she's an exhibitionist. At random times, he'll send a guy over to go fuck her while he watches from his window. It's a win-win for both parties.

Maitland Ward in 'Fertile'

Maitland Ward - Fertile

There's nothing that kills a relationship than it becoming stagnant - and this is where Maitland finds herself - wanting so much more than she gets, and the thing she wants most is a baby. Maitland will get what she wants - no matter of the price.


Nia Nacci in 'After Hours'

Nia Nacci - After Hours

Beautiful Nia enjoys a soak in the tub before receiving a phone call from her BFF - unfortunately she isn't up for a night on the town, but she does have an idea. Even though Nia has a boyfriend, her plans for unwinding for the evening are about to take an unexpected turn.

Valentina Nappi in 'Hungry'

Valentina Nappi - Hungry

Beautiful Valentina is in Hollywood and looking so good. After a mediocre pizza experience, she is in search of something much more tasty to enjoy. Luckily she finds it in the shape of Sly, who is more than happy to satisfy her appetite.

Riley Steele in 'Step It Up'

Riley Steele - Step It Up

Slender Riley is hot as hell in her red dress and heels - and after her last intense experience with BLACKED RAW, she can hardly wait for the next one. This time she is going bigger and better and is on her way to see if he lives up to her expectations.

Tiffany Watson in 'Wet And Wild'

Tiffany Watson - Wet And Wild

Tiffany can't believe her luck when she catches a glimpse of her driver. It leads to a night of passion that she can hardly believe possible. Get ready to see her satisfied in more ways than you can imagine.

Lexi Belle in 'Night Out'

Lexi Belle - Night Out

Undeniably beautiful, Lexi is a vision walking the city streets. After telling her man she's out on a girls night, she makes her way to her real rendezvous - with someone that is certainly give her more fun than any sleepover ever could.

Lulu Chu in 'So Deep'

Lulu Chu - So Deep

Lulu is an aspiring actress in town for some auditions. She rented a pool house at a rich guy's house to motivate her to see what success in la looks like. When she's woken up early the next morning, shes met with a pleasant surprise.

Alix Lynx in 'Bringing Him Back'

Alix Lynx - Bringing Him Back

Alex has just got back from a girls night after meeting a super hot black guy. Now she's off to meet him alone. Her voice brimming with excitement, she makes her way to the food truck where her night's entertainment is about to start.

Alexis Fawx in 'Straight To The Point'

Alexis Fawx - Straight To The Point

After admiring herself in the mirror, Alexis is happy with what she sees, and now she is more than ready to take on her challenge for the evening - and she can't wait.


Cory Chase in 'The Chase Is On'

Cory Chase - The Chase Is On

Mature blonde Cory can compete with girls half her age when it comes to raw sexuality. All dressed in a gorgeous red number for tonight's entertainment, she retires to the hotel where she can get her hands on exactly what she wants.