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Babysitter ~ Allyson Mayfair-Richards

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     I have been babysitting on the side for quite a few years now. I had started when I was around seventeen because I just love kids and taking care of them. Not so long ago, I finished my studies at an art school, dreaming of becoming a real artist. But first I wanted to be financially secure; so I was looking for a full-time job as a babysitter if possible. I was just about to give up, when I was at a friend's dinner party. She introduced me to her boss, Senator Allyson Mayfair-Richards, or as she wants to be called: Ally.

     Ally told me that she had heard a lot about me lately. I blushed. "I hope only good things," I said quietly.

     "Of course," Ally chuckled – the sweetest sound I've ever heard.

     "y/n, the greatest artist of her time." She made a grand gesture with her hands, quoting f/n. I punched my friend's arm playfully. "Going around spreading lies, aren't you?" They just shrugged.

     "Oh, I think they aren't wrong, sweetheart," Ally addressed me. "They showed me quite a few of your paintings."

     My already flushed cheeks heat up even more. Most of my paintings were either portraits of women or naked women, and knowing that she had seen them, made me somehow uncomfortable.

     "Anyways, f/n told me that you're looking for a job as a babysitter?" she asked and I nodded.

     That's how I ended up here, talking to Ally in her house, having a job interview of sorts. Ally tells me about her past experience with Winter, and I promise that I would never do anything to hurt Oz or her. She also mentions that most of the time she's working from home, so I only have to watch Oz a few hours a day. However, there will also be days on which she has to be in her office, and I would have to watch Oz until he goes to bed, possibly having to sleep in the guest bedroom if she doesn't make it home at all. I agree and then Ally leaves the living room to get Oz.

     I am a bit nervous. What if he doesn't like me? What if... Before my thoughts can go any further, a little boy with curly blond hair comes running into the living room, his mother not far behind him. He looks at me curiously. Ally sits down on the couch again and encourages Oz to do the same, which he does.

     "This is y/n. She will be your new babysitter," she says.

     He looks at me with is big eyes. "Are you nice?" he asks quietly.

     "I sure hope so," I smile. "But you can decide for yourself. How about a deal? If you don't like me after a week, I'll leave, and you never have to see me again," I suggest.

     He nods. "Deal."

     So it begins. I talk to Oz for a little bit, while Ally goes to her home office to get some work done. I tell him about my hobbies in exchange for getting to know what he likes to do. He says he thinks it's cool that I'm an artist, because he likes drawing too. I smile at him and suggest to draw with him after lunch. He just grins and nods, full of excitement. He's such a great kid.

     "Do you want to help me prepare lunch?" I ask him. He thinks about it and then agrees. We prepare a few sandwiches, and I slice sweet peppers, tomatoes, and carrots. Once finished, Oz wants us to bring all of the stuff to Ally, so he can show her what we've made. I smile and tell him to lead the way, while I take the prepared plates and follow him. He opens the door without knocking, and Ally jumps a little at the unexpected company. I mouth 'sorry', but she shakes her head and smiles.

     "Mommy, look what we made." He points at the plates in my hands. She looks at the plates, and her smile grows even wider. "Oh, my favorite, well done you two." She ruffles through Oz's short curls.

     "Would you like to have lunch with us, or would you like to eat here and continue working?" I ask her. She puts her pen down, shuts the folder she has been working on, and gets up.

     "Let's have lunch," she says.

     We make our way to the dining room, and I set the table while Oz tells Ally about everything that we've done so far. During lunch, we talk a little and after eating, I offer to clean the dishes, and Ally smiles at me. "Thank you, y/n."

     "Don't mention it," I reply smiling as well.

     Ally goes back to work, and Oz and I start drawing. I show him how to draw simple things, and he is quite the little artist, I have to say. After a while, Ally comes back into the living room, finding us both drawing with immense focus. Both of us are drawing a portrait. Oz uses a lot of different colors, while I only use different nuances of grey. She approaches the table and takes a look at our works.

     "Wow," she exhales. I jump a little, because I have been so focused on the paper that I hadn't heard her come in. She places her hand on my shoulder and laughs quietly, while I stiffen a little.

     "I'm sorry, I didn't mean to startle you."

     "It's okay, I'll live," I tell her, laughing myself. Trying not to develop a crush on my boss is harder than I thought it would be.

     Oz shows her what he drew and tells Ally how amazing I am. I blush a little at his praising words. Ally agrees with him, making me blush even harder. When it's time to say goodbye for the day, Oz hugs me and tells me that he doesn't need a week to decide if he likes me because he already does.

     "I like you too, Oz," I tell him, holding him against me. I look at Ally and see her smiling.

     This smile is definitely one of my favorite things in the world.


     I've been working for Ally for four months, and I have definitely developed a crush on her. At first, I tried to deny it, but it didn't work. I only fell harder for her. It also didn't help that Ally was working from home most of the time, because she would often appear out of nowhere and witness the most embarrassing things. One time, I danced a little with Oz, fooling around, and as the song ended, I saw Ally standing in the doorway, smiling. Or another time, I sang along to a song, which was playing on the radio, while Oz was reading a comic book on the couch and I was cooking in the kitchen. Once again, I found her standing in the doorway, smiling at me.

     I stayed a few times overnight already while Ally had to stay in her office, finishing up some work. Today is one of those days. I cooked dinner, Oz and I watched TV, and then I tucked him in. Now I’m desperate for a shower, so I walk into the bathroom, close the door, undress, and get into the bathtub. After cleaning myself, I dry my hair with a towel and wrap another one around my body. I open the door, intending to go to the guest bedroom, which is only two doors away, when suddenly Ally is standing in front of me, still dressed in her work clothes – a red pantsuit and black high heels. I'm so shocked, I almost drop the towel, but I somehow manage to avoid doing that. Ally just stares at me. I'm basically naked in front of her with my hair damp, single drops of water running down my body. I blush a dark shade of red. The way Ally is staring at me is turning me on, and I feel even more embarrassment stirring up inside me. I mumble a soft 'sorry' as I make my way to my room. Once there, I put on underwear and a shirt before I sit on the bed.

     It's already midnight, so I guess I'll stay here, even though Ally is here now. Half an hour later and Ally didn't come to talk to me, so I guess she is just as embarrassed as I am. Now that I think about her again, I can't seem to ignore the tension in my lower belly. Not hearing anything, I assume Ally must have gone to bed already. So I lie down on top of the sheets, one hand starts kneading my left breast, while the other one makes its way into my underwear, lightly rubbing my clit. Closing my eyes, I imagine Ally on top of me doing these things to me. I whimper softly as I enter myself with one finger, thinking about one of Ally's slim fingers making its way inside me. As I grow more frustrated, I pull my finger out and start rubbing my clit while stroking my nipple and squeezing my breast a little harder. I'm so close so I speed up, moaning Ally's name quietly.

     The next thing I know is that the bed is moving slightly, and as I open my eyes, I see Ally on the bed beside me, biting her lip, her eyes roaming my figure. I stop promptly, my cheeks turning red as I stay frozen in my current position. The lack of movement doesn't go unnoticed by Ally and she speaks hoarsely.

     "Oh, don't stop on my account. I was enjoying the show."

     "I-I…" I try to speak, but I don't know what to say. Ally crawls on top of me, and finally, I unfreeze and drop my left hand that's holding my breast, while pulling the right one out of my underwear. But before I can do anything else, Ally is grabbing my right hand, looking deep into my eyes as she takes the one digit, which was previously inside me, and puts it into her mouth, licking it clean. She moans, and that sound is something I will never forget. After sucking on my finger for a bit, she slips it out of her mouth with a soft pop. Then, she looks straight into my eyes and asks if she may kiss me. I don't reply; instead I pull her down and crash my lips against hers, both of us moaning quietly. The kiss grows more and more intense, and Ally starts to grind down against my center, as my hands slide down her back and grab onto her ass to support her movement. I start groaning softly into her mouth, trying to be as quiet as possible in order to not wake up Oz.

     She starts to trail kisses down my neck, stopping when she reaches my shirt. Not wanting to waste any more time, Ally pulls the shirt over my head, leaving me bare underneath. Her pupils dilate even more as they settle on my naked chest. She starts kissing and sucking on my neck again, moving quickly towards my left breast while massaging the other one with her hand. After worshipping both of my breasts, she settles between my legs, pulling my underwear down. Ally locks her eyes with mine and dives in. Her tongue circles around my clit as I bury my hands in her hair, bucking my hips a little. As she enters me with her tongue, I moan her name. Her right thumb starts circling my clit, while her tongue restlessly pushes its way in and out of me. Within a few minutes I come undone, turning my head and moaning into the pillow. After I calm down, Ally crawls back up my body and pecks my lips, biting her lip as she looks into my eyes again.

     "Do you want to go on a date tomorrow?" she asks me, and I start laughing.

     "Of course, I'd love that," I kiss her softly, switching our positions. "But first let me return the favor."

     She's about to protest, but her words die in her mouth as I slip my hand into her pajama bottoms. Upon finding no underwear, I groan quietly into her ear.

     "You're driving me insane, Ally," I whisper, while sliding my middle finger through her slit, gathering the arousal that has already built there. She moans as I slide two fingers into her. I start at a teasingly slow pace, wanting to enjoy this moment as long as possible.

     "Please, y/n," Ally whines.

     I don't need her to tell me twice. I lean down, kissing and sucking on her neck, while speeding up my movements and rubbing her clit with my thumb. It doesn't take long until I can feel Ally's walls tightening around my fingers. I let her ride out her orgasm as I keep on kissing her neck. Once her movements stop, I pull my fingers out of her and lick them clean, moaning at the taste, while Ally is watching me with her beautiful big brown eyes.

     "So about that date…" I begin to say, smiling down at her.

-the end-