Ruby is broke and needs money ASAP! She can't afford rent and needs to get some cash to pay before she is evicted. Out of ideas, a friend of hers talks her into selling sexual content online. There's just one problem: Ruby is also a babysitter, and Calvin, her boss, has caught her shooting hot videos in his driveway. Worried that his kids will see her, Calvin summons Ruby for a candid talk and tells her to stop what she's doing before she also loses her babysitting job. Ruby's desperation knows no limits, so, as soon as her boss leaves and she has the place all by herself, she starts taking sexual selfies with random things around the house. The plan backfires and Calvin comes back minutes later only to find her naked at her home. When he threatens to fire her, Ruby changes her attitude and starts following each and every one of Calvin's orders. The kinky boss won't let her go with a warning this time. He wants much more and Ruby will have to play nice with her boss' cock if she wants to keep her job. Showing her true colors, Ruby gives Calvin an intense fuck sesh he won't forget.
Claire is the cutest babysitter and she's got just the kind of experience Mr. Paris was looking for. He interviews her for the job and pretty soon he can tell this girl is something special. She really enjoys babysitting and she's done it so much she's practically a pro at it. She dreams about becoming a pole dancer and he can't wait to have her dancing on his pole. As soon as she learns his wife left him, she realizes they're both in need of each other: she needs money to support her lifestyle and he needs someone to take her of his needs, so they can definitely help each other out! She decides it's time to show him all of her skills and prove how much she wants the job, so she pulls his cock out and starts sucking it on the couch. He fucks her pretty face and lays her down so he can pound the fuck out of her pussy, quickly learning her experience goes beyond just babysitting. She should put that on her resume! After railing her pussy on that couch in every position imaginable, she drops to her knees to receive a warm load on her face and the job offer she's been waiting for!
Elias' parents call The Babysitter Club looking for a girl to take care of his younger siblings while they go on a trip, but now that they're gone, he's ready to live like a king for three days straight! He wasn't counting on them sending Megan though, and although she's initially annoyed that he's essentially treating her like a maid, she can see through his real intentions in no time. She knows what this prick is getting at, it's not her first rodeo… he wants her on her knees, with his cock down her throat. Megan needs this job and it wouldn't be the first time she had to suck some dick to keep one, so she does what she needs to do: she drops to her knees and sucks his cock like the professional slut she is! She spreads her legs and lets him fuck the shit out of her, she rides his cock and lays flat on her stomach so he can pound her pussy from behind until he's ready to blow a huge load all over her tits!
Innocent babysitter Jade learns that her client, Peter, is part of the modeling world. She wants to break into the industry and seeks Peter's help. Peter thinks he can help Jade make her dreams come true, but he will need to see some more commitment from her. Jade is amazed at the size of Peter's cock when he whips it out, but stroking it makes her feel horny, and now getting to join the modeling world is just a bonus to riding his dick.
When Mr. Fitzwell catches babysitter Emma trying on his wife's clothes, she's very apologetic but he assures her that he's not mad, in fact, she should try on a lingerie set next. Emma is thrilled with how cute she looks so Mr. Fitzwell promises to keep providing for her if she keeps him happy… starting with a blowjob!
Babysitter Kate gets the kids down for the night before heading down to the couch to study. Later, Donnie gets back home and finds Kate passed out on the couch among her books, turns out she's been studying like crazy lately stressing herself out. Donnie offers her a massage to help her relax, but when his hands start traveling a bit further down Kate just gives in and lets Donnie help her thoroughly relax with a good orgasm!
When babysitter Kimmy asks Rion for a raise he tells her he'll have to discuss it with his wife first, so she fakes feeling faint, and asks Rion for a glass of water. When he leaves the bedroom she grabs his phone and starts taking dirty pictures. He comes back and catches her in the act, but Kimmy tells him she'll send the pictures to his wife or he can just agree to give her that raise. Rion is pissed, and pulling his cock out, tells her that if she wants a raise she better earn it with that pretty little mouth!
Day Dreamer: A Liz Jordan Mini-Series [Part 2 of 3] - In the last episode of Day Dreamer, Liz and her stepdad, Bobby, have a special heart-to-heart. But Liz still has trouble focusing, and her crazy sexual appetite can't be satisfied. Luckily, she might just get what she needs during her babysitting gig. Her boss, Kyle, notices Liz is a little stressed, so he does everything he can to ensure she feels comfy.
When Jason is in dire need of a babysitter the agency sends Harley to save the day, before Jason leaves for work he thanks Harley for coming over so last minute and tells her to make herself comfortable. Harley takes this a little too literal and finds herself masturbating on Jason's bed! Jason gets back to work and catches her in the act, the only thing left to do now is join in!
Leana is babysitting for Ike, taking care of his son, but she's not that good at taking care of the house. When Ike comes back from work to find the house a mess, he scolds Leana and fires her. Leana comes back to beg Ike for another chance, promising that she'll do much better now, and offering to take care of any other services that he might need… like taking care of his hard cock!
Nicky is impressed by Paulina's babysitting skills, and really feels as though he's found the hottest sitter in town. To show appreciation, Nicky pays Paulina more than she's owed, but still, it's not enough for the struggling college student. So, Paulina decides to show Nicky what other services of hers can benefit him.
While Mr. Sterling's wife is away, he hires Ryan to help around the house. To his surprise, Ryan knows how to do just about everything that his wife does, and even has more to offer. When Ryan starts pursuing Mr. Sterling with a tenacious passion, he's hesitant, but after she threatens to tell his wife, he finds no issue with succumbing to Ryan's wild desires.
Mr. Miles hires Mia Kay as a babysitter and instructs her to take care of his son Jimmy while he's at work. After Mr. Miles leaves, Mia makes sure that Jimmy is still napping and heads over to the main bedroom to send nudes to her boyfriend. Unfortunately, she accidentally sends them to Mr. Miles instead, who rushes back home to scold Mia about it. Mia begs him not to tell her parents about it, and Mr. Miles agrees, but only if she lets him have his way with her!
The stunning Vivian Fox is Brock Cooper's new sitter. As she begins lurking around the house, she finds some curious and kinky stuff that turns out to be BDSM material. Soon enough, she begins experimenting with Brad, discovering how much she enjoys it. After their passionate sexual encounter, Vivian seems to be the partner Brock has been looking for, so when she comes back, she receives the complete naughty treatment, which ultimately turns her into the new sex toy for this hot stud.
Kay Lovely is a fantastic babysitter, and her brother-in-law, Danny Steele, couldn't imagine finding another person for the job. But Kay starts to come on to Danny and leads him into a precarious sexual encounter. Unable to get his wife's younger sister off his mind, Danny pursues Kay in secret, promising to keep their relationship hidden.
When April Olsen is bored on the job, she decides to snoop around the house and open Christmas presents. April finds a curious little satchel and is astonished to find a hot pink vibrator wrapped inside. Unable to resist, April tries the vibrator for herself. But she is interrupted by Mike Avery when he comes home early unexpectedly. After he catches April with the vibrator, she promises to do whatever he wants to keep their little encounter a secret.
Tyler Steel hires Alex Jane as a babysitter and establishes strict rules of privacy, so when he catches Alex taking a video of him while on a private and rather compromising phone call he gets pissed. Alex demands 5000 dollars in order for her to delete the video, so Tyler sets up a secret camera to incriminate Alex. The tables turn when Tyler threatens to call the cops on Alex so she gets her pussy pounded instead as a punishment.
Aubree Valentine doesn't see much when looking at her boss, Donnie Rock. Sure, he's handsome, but he is arrogant and has liked to sleep around ever since his wife left. But when Aubree finds a vibrator in Donnie's bedroom, she tries to think about him from a different perspective. Then, Donnie comes home earlier than expected to find Aubree passed out in his bed. He uses his charm and wits to show Aubree there is more to him than meets the eye.
When Peter Green is in dire need of a babysitter, he calls the company and they send a new girl xxLayna Marie. Peter leaves xxLayna in charge of his son while he's out, but as soon as she gets left alone, she lays down on the couch and takes a nap! When Peter returns, he finds the babysitter napping, and his son is nowhere to be found. As xxLayna panics, Peter gets a text from his ex-wife saying that his son walked all the way over to her house. Peter will now personally punish the bad babysitter… by fucking her hard on the couch!
Natalia Nix is thinking of ways she could make some extra money to buy herself a car, but she's coming up short. Bobby Beefcakes, the father of the kid she babysits, offers to pay her double if she can help him with some extra work on the weekends. Natalia gladly accepts, not knowing that the extra work will be much more enjoyable than she had expected.
Donnie Rock comes home, expecting to find babysitter Laney Grey putting the baby to sleep, but instead he walks in on her filming a video while dancing naked. Laney apologizes and explains this is something she has to do to earn some extra money, so Donnie makes her a bold offer and suggests he can pay her more if she's willing to do whatever he wants.
Dedicated step dad Peter Green has let his babysitter Ada Vera stay with him and his daughter during the lockdown due to quarantine. There's always been sexual tension between the two, but they've been able to keep it professional so far. But after being cooped up together for so many days, they can't keep their hands off each other for much longer.
Johnny The Kid welcomes babysitter Kylie Quinn into his home where she's meant to take care of Johnny's little brother, but Johnny immediately recognizes her from school and remembers how she was rumored to be a kleptomaniac. Before Johnny leaves he sets up a nanny cam and catches Kylie stealing some money as he had expected. When he comes back to confront her, he makes a deal with her, if she satisfies him sexually he'll keep quiet about the theft!
Johnny The Kid is not too happy about his parents getting a babysitter for him, and when Adriana Jade shows up with a list of chores for him, he reluctantly gets to work. Later, he overhears Adriana making some pretty sexual noises so he takes out his phone and starts spying on her. Turns out this babysitter is making some money on the side by selling sexual content online! Johnny threatens to show the footage to all the moms in the neighborhood so Adriana offers to do anything to prevent that from happening.
Cute Carmen Rae has been babysitting for Preston Parker for a while now, and he notices that her home life is kind of rough since she's always walking back home by herself. Carmen confesses that her dad doesn't pay any attention to her, so Preston offers her a place to stay. Later that night, Carmen notices that Preston has been eyeing her, so she takes the opportunity to properly thank him for taking such good care of her.
