Diamond Jackson has a problem student in her sexuality class. He thinks he knows it all when it comes to pleasing women, but Diamond has a few tips fo...Watch Video
Diamond Jackson is a little concerned about her daughter’s husband. She wants to make sure that he’s fucking her daughter right, so Diamond gives ...Watch Video
[IHaveAWife] Diamond Jackson – 22201...
Tony and Diamond rent a hotel room to take a night off from parenting. Little do they know, jealous Jade has showed up – and it’s Tony’s job to ...Watch Video
[DigitalPlayground] Diamond Jackson & Indigo Vanity – My White Stepdad (Part 4)...
On Diamond’s wedding day, Diamond can’t wait to fuck Tony. She needs to have him right now – right on top of her own wedding cake! Hopefully, th...Watch Video
[DigitalPlayground] Diamond Jackson – My White Stepdad (Part 2)...
When an unsuspecting MILF accidentally backs her mini-van over a grungy skateboarder, she knows EXACTLY what to do to nurture the young lad back to he...Watch Video
[DigitalPlayground] Diamond Jackson – Drive By MILF...
Diamond Jackson caught her stepson beating his meat but before letting her presence be known, she slid her fingers down her panties and inside of her ...Watch Video
[RKPrime] Diamond Jackson – Busting On Diamond...
Tony and Diamond Jackson’s son are hitting the clubs tonight, but Tony is in need of a decent shirt. Diamond allows him to borrow one of her husband...Watch Video
[MyFriendsHotMom] Diamond Jackson – 21819...
Diamond has her son’s friend dropping something off at her house, and little does he know he’s in for a treat of a lifetime....Watch Video
[MyFriendsHotMom] Diamond Jackson – 21657...
Diamond Jackson and Nikki Benz are enjoying a friendly tennis game when suddenly they’re approached by a ball boy, Jordi El Nino Polla. Jordi tries ...Watch Video
[BigTitsInSports] Nikki Benz & Diamond Jackson – Game, Set, Match Pussy...
Preston Parker and his wife are starting to question their marriage. His wife asks her friend, Diamond Jackson, to spice things up for them before the...Watch Video
[MyWifesHotFriend] Diamond Jackson – 21535...
Diamond always rides her staff hard, and today is no exception. A perverted employee is spying on her and she’s ready to put him through the ringer....Watch Video
[BigTitsAtWork] Diamond Jackson – Diamond Is Your Boss...
Shy Crystal Rae has invited over Jessy Jones to her house to play some board games. Only, her horny stepmother, Diamond Jackson, can’t help but spy ...Watch Video