Waking The Babysitter | Reena Sky, Tiffany Watson & Tommy Pistol | 2018
Frustrated Father Takes Advantage of Babysitter During Sleepover
SCENE opens late one night as David, a middle-aged husband and father, and his wife, Maureen, are driving home in the backseat of a taxi. David was just made a partner at his company and the CEO threw a party in his honor — but the night has been a disaster. His wife, a bored stay-at-home mom, got totally wasted and embarrassed him in front of all his co-workers. You can see the tension in his face as he tries to give the driver directions while she giggles, slurs her words, and pokes fun at him for being such a party pooper … especially after the big bonus he just got. She even makes a clumsy pass at him … suggesting they fuck around when they get home. Irritated, David tells her no … not only is she inebriated but he keeps trying to call the babysitter’s cell to no reply and he’s worried about their son. Maureen reminds him that she already told the girl, an 18-year-old named Cindy, to spend the night in their guest room since they were going to be out so late. She’s probably already in bed. David hangs up the phone and the display picture on the phone catches his eye – the picture he set for her contact info. His hand moves subtly from his lap to his groin, before he’s interrupted as his wife slumps over in his lap laughing and he continues to stare at the picture on the phone with a stone-cold expression on his face.
David helps Maureen into their darkened house and up the stairs to their bedroom. He lays her down on the bed, barely conscious, before leaving to fetch her a glass of water from the bathroom. When he comes back, his wife is passed out … still half-dressed. He stands over her, looking angry, before sighing and drinking the water himself.
David decides to check on his son before going to bed so he walks down the hall to the boy’s room. He opens his door, leans in to hear the soft sound of breathing, and then slowly closes it. As he makes his way back to the master, he passes the guest room. The babysitter has left the door open, presumably so she could hear if his son woke up. He stares at it for a moment before slowly walking over and leaning in. He sees Cindy on their guest bed. The teen girl has left the blinds open and the moonlight is streaming in. She’s kicked her blankets off and is lying on her stomach, her ass up, and her head buried in a pillow. Her loose-fitting nightie has slipped up and is bunched around her neck, exposing the 18-year-old’s perfect backside. David stares at her, almost transfixed. He finds himself slowly stepping into her room and closing the door.
Alone in the room, David silently creeps over to the guest bed where Cindy is resting. He kneels and studies the girl … taking in every detail. Her tiny white cotton panties are wedged up into her crack and her tits are pressed against the sheets. He cannot believe how sexy she looks. She has been his family’s babysitter for years and he always thought she was cute but had never considered crossing a line. He debates about leaving before deciding to take a few photos for himself first. After all, she’ll never findout. Nervously, he pulls out his phone and starts to snap photos. At a certain point, Cindy rolls over on her side and he panics, dropping under the bed. But the girl is still out … so David slowly stands back up. He knows he should leave but he is extremely excited, so he decides to quickly masturbate. He pulls out his dick and starts stroking, while taking pictures and moving around her to get different angles. The girl shifts again, this time rolling into a position where her hair covers her face. David decides to quietly brush her hair back, so he can have a better view. He lightly moves her hair from her face, tensing up at the thought of almost making contact. Then he continues to masturbate. Cindy rolls into a ball, her legs bunched under her and her ass up in the air. David stares at the panties wedged inside her. If only he could taste that pussy. It would be enough to finish him off. He puts the phone down and decides to try and slide them off. Without touching her, he slides her panties down to her knees and then cautiously all the way off. He stuffs his face into the wet cotton and licks them feverishly, while trying to jack off. Suddenly, the innocent babysitter wakes up!