Curvy redhead Summer Hart is Jimmy Michael’s personalized AI assistant. When Jimmy’s date stands him up, Summer comes to life in order to help the poor guy satisfy his needs….
Kendra and Keiran aren’t sure Adriana is good enough to date their son. They’ve just met her and she seems like a nice girl, but Kendra senses she might just…
Van’s date kept him waiting while she applied her makeup, and gave him just enough time to get an eyeful of her hot mom. Ashton Blake’s deep cleavage, raunchy tattoos,…
Macey Jade is on an extremely boring first date. This random asshole is doing his best to flirt, seduce, and talk, but it’s just nothing but unwanted opinions, obnoxious advances,…
Scott Nails has just spent the night out two best friends – blonde Charlotte Sins and brunette Sofi Ryan – and after a long night he’s finally crashing at home…
Melissa Moore and Riley Reid are the sexiest sluts on the block who always crave a new cock. Melissa and Riley have been best friends ever since they started putting…
Nina Elle has just come home from a disappointing date. Luckily for her, her babysitter Sean Lawless is there to hear all about it. The considerate young lad even offers…
Mick is new to the whole online dating scene, so when his latest hookup shows up with her best friend he’s a little confused. Mandy explains that she’s just there…
Jordi’s girlfriend finally gets him alone for a date night while Rebecca can’t help but be a bit jealous. The two are just about to relax when his girlfriend’s sister…
Hot milf Makayla knows she shouldn’t be dating a married man, but she can’t help herself. After a steamy date she’s so excited to get fucked, especially when her boyfriend…
It’s day one for the Summer Interns at Brazzers, Johnson, and Dick. When Angel notices a budding attraction between two of the interns, she finds it endearing and tries to…
Crystal is always planning special dates for herself and her boyfriend Keiran – the least he can do is show up on time! Today she’s booked a couples massage, and…
Justin has always had the hots for his best friend Zoe. He’s been trying to get out of the friend zone forever. The trouble is, Zoe’s about to leave for…
Keiran’s girlfriend wants to spice things up, so for date night she suggests they try going to a strip club together! But once they get there she’s disgusted and demands…
Looking for love, Anissa agrees to go on a blind date with Danny. She didn’t set her expectations too high, but the date isn’t going as well as she imagined….
Busty blonde MILF Nina Elle’s stepson Oliver is heading out on his first date, but she doesn’t thing someone his age should be doing anything physical just yet. Storming through…
Busty nude model Lily Love is a big fan of erotic photoshoots, especially when the photographer’s got a big black dick she can fuck! Ricky Johnson knows how horny these…
Marilyn Mansion prides herself on being a perfect student and with college admissions just around the corner, she’ll do whatever it takes to get an A+! Professor Charles Dera is…
Xander Corvus has been bugging his girlfriend Keira Croft for anal sex for years, but the girl won’t budge; she’s not ready. When she leaves for work, Xander decides to…
Some guys just have all the luck. Raul is on a hot date with the stunning Liya Silver, which would be enough excitement for most men. While Liya is freshening…
Maggie Green make look like a sweet stepmom, but looks can be deceptive! Maggie’s stepdaughter has her date, Johnny The Kid, over at the house, but Maggie keeps butting in…
Casca Akashova is a beautiful blonde big titty MILF just trying to help her son apartment hunt. It’s not her fault that the happened to knock on Ricky Johnson’s door,…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Akarra has had her eye on her sexy boss for a long time, but he’s always dated only the hottest models who audition for his agency. When she learns that…
MILF-tastic Cherie Deville is on a romantic date with her boyfriend, until she sees the waiter. Just one look at him and her panties are soaking wet. He offers to…
Mystical Lady Kaguya leaves her castle in the spirit realm once again to try to heal humanity’s anguish, but her fortune-telling service isn’t getting many customers until shy nerd Satoshi…
After erogame artist, Kisara, fucks consultant Tomoya, then tells him their sex was strictly business, he decides he’s free to help scriptwriter, Momoka, make her scenarios more erotic when she…
