The Babysitter (Part One)

March 13

I come home from my date and walk in the door to find my son, Jason, playing a card game with his babysitter on the floor of the living room. Her name is Danielle, and she’s a lovely young woman with dark brown locks, beautiful light hazel eyes, and a light tan she got over the summer months.

“Little past bedtime isn’t it?” I ask.

“But I was just about to win dad!”

“Oh, yeah, he’s gotten so good at this game.” Danielle turns and gives me a quick wink, telling me she’s throwing the game.

I sigh, “Okay, finish up and then it’s bed time.” A few moments later I’m in the kitchen eating a piece of cold pizza when she comes in.

“Sorry Mr. Reese, I just lost all track of time. You’re home early, date didn’t go well?” She fixes me with an inquisitive look, her eyes sparkling.

“Well, no, we ended up not having much in common. Are you as curious about all your clients dating lives?”

She blushes a bit as she lets out a laugh. “Sorry, sir, just curious.”
That tiggers something in my mind as I watch her grab a hoodie and make her way to the door.

“Oh, Dani, would you come by tomorrow?”

“Yeah, do you need me to watch Jason again?”

“No, he’s actually going to be at his mothers for a few days, there is something you and I need to talk about.”

Her face seems to be warring between curiosity and concern. “Um, yeah, okay I’ll see you tomorrow?”

“Yes, seven o’clock. Sharp.”

She seems to flinch a moment as I spit out the last word. “Yes sir,” she says as she leaves.

The next night I’m waiting by the door at 6:55. A few moments later I see her shadow on the other side of the curtain. She seemed to be pacing a bit, and just as my watch turned to 7 there is a light wrap at the door. I opened it and look at the young lady standing there. She was wearing a denim skirt that came to about halfway down her thighs, a black long sleeve shirt with a deep neckline, and she’s wearing knee length socks that match her shirt with a pair of Converse. Her hair is falling over her shoulders and a lovely scent wafted off of her.

“Hello, Mr. Reese. You wanted to talk to me?”

“Yes, please come in and have a seat.” She nervously sits on one end of the couch and I sit on the other.

After a few moments of silence she finally looks over at me. “Are you mad that I let Jason stay up late? I am so sorry, and it will never happen again. Please, I like Jason so much, he’s such a great kid and I really like...”. She cuts herself off as she looks into my eyes.

“No, Dani, I’m not upset about that. I want to talk about last week when you were here. After you left I was working on my computer, and I went to look for a website for my job, and do you know what I found in my search history?”

Her face turns crimson as she stares at her feet. My voice becomes stern as I stare at her. “Danielle, I asked you a question, and I want to hear your answer. What websites were you looking at on my computer.” She mumbles something towards the floor, and I take her chin in my hand making her look at me. “What was it?”

“I was looking at porn.” I could see tears begin to form in her eyes.

I’m sitting next to her now and I put a reassuring hand on her back. “What kind?”

She’s fighting back tears, I can’t tell if it’s from embarrassment, because she thinks she’s in trouble or a mixture of both. “It was bondage and slave stuff.”

“BDSM is a perfectly natural thing to be curious about. Jason didn’t see anything, did he?”

My reassuring tone seems to relax her a bit and she finally turns to look at me. “No, no sir. He didn’t see anything. He was already asleep.”

“Okay… okay, and you’re 21, so it’s not illegal for you to see them.” It’s the first time I stop and think that I’m 16 years older than her. I begin to second guess what I’m about to do, but then I looked at her angelic face and made up my mind to proceed.

A smile begins to form on her face. “So you’re not mad?”

“More disappointed you didn’t do a better job covering your tracks on my computer.” She looks embarrassed again, it’s a cute look on her. “You really should have used my personal tablet, I have everything book marked.” She looks up at me in shock and I can’t help but smile.

“You mean you... you’re....”

“Yes, I enjoy it too. It’s actually why things didn’t work out with my ex. ” I place a hand on her knee, she tenses for a moment, then relaxes a bit as she takes in what I say.

“So I can keep working for you, and watch over Jason?”

“Yes, you can. But I think we need to talk about this betrayal of trust. I want you to ask very nicely for your job back.”

She looks confused for a moment, then realization dawned across her face. She slides off the couch and kneels at my feet, folding her hands on my knee. “Please forgive me. I enjoy taking care of your son, and I enjoy being here, around you. You are so kind and generous, much more than other parents I babysit for. Pleas sir, I would do anything to make you happy and keep my job.”

“Anything?” She nods enthusiastically as she looks up at me. “Than I think you will need to be punished for being such a naughty girl.”

She smiles slightly at me waiting for my directions, my heart melts and my crotch begins to bulge in my jeans. “I want you to lay across my lap, on your stomach.” I sit on the edge of the couch and hold my arms out.

She slowly stands and looks a bit nervous as she finally asks, “What kind of punishment?”

I fix a stern gaze and answer, “You will have to be spanked. I think twenty swats will suffice.”

“O-okay.” She slowly lays across my lap and her legs dangle to the floor. I can feel her begin to breath harder.

“I’m going to lift your skirt up, do you agree to this?”

“Y-yes, okay.”

“Yes, SIR,” I correct her.

“Yes, sir, I agree.”

“Good girl,” I hear her let out a happy sigh as I say that. I grab the hem of her skirt and slowly pull it up until I can see the black and white striped panties she wore. I never noticed what a nice ass she had, but now it was all I could look at. It was pert and perfectly round and just invited attention.

I place my hand on it and begin to gently massage it. She lets out a soft moan, and I grab her panties and pull them a bit so her cheeks are more exposed and it rides up her crack a bit. My hand rests on her rear as I look back at her. “One more thing. After each swat I want you to say ‘I’m sorry sir.’ Do you understand?”

“Yes sir, I understand.” I bring my hand up and then back down on her rear. It makes a delightful slapping sound as her cheek jiggles in response. But the real prize was the sharp gasp of *** and surprise she lets out, and just as I’m about to think she forgot her instruction she suddenly blurts, “I’m sorry, sir!”

“Good girl.” I continue to rain down slaps, each time she lets out a small ***ed noise and tells me she is sorry. I vary the s***d I use, sometimes hitting twice or three times in a row. Sometimes I would bring my hand back and wait for her tense up in anticipation then swat her again.

After about a dozen blows her noises of *** and surprise begin to morph into soft moans of arousal, and her whole ass beings to turn a pretty shade of pink.

My last swat comes down across both cheeks. “Ooh, I’m so sorry sir!” I can see a thin sheet of sweat on her brow and her breaths come heavy and steady. My hand stayed planted on her ass and I began to rub it again, listening to her moan a bit.

“I forgive you. You did so good, and I’m proud of you.”

She seemed unsure what to say next. “Thank you, sir.” She began to rise up, but my free arm rested against her back pinning her in place a bit. My hand begins to travel between her legs and I suddenly feel the dampness that’s has started there.

But as soon as my fingers touch that sweet little spot she suddenly bursts out of my hold and she takes several steps back. “No! No, no, please.” She pulls her skirt back down, and her face, flushed red, stares at the floor refusing to look at me. “I-I’m sorry sir, but...”

I stand up, but keep some distance from her. “No, I’m sorry Danielle. I took it a bit to far.”

“No, it’s okay I’m just.... I’m just not ready for that yet. Are you mad?”

I smile at her, “No, I’m not. You did as you were told, and took your punishment. I pushed a bit further than you were ready to go. If you still wish to, I need you to watch Jason next week after school while I work a few late days.”

She finally smiles. “Yes, yes I can do that.”

“Okay, good. He will be back from his mother’s on Sunday, if this is something you would like to keep exploring you can come over anytime this week, at this same time.”

She makes her way to the door, her walk a little different. Probably a mix of her growing excitement and her sore backside. “I will remember that. Thank you. Sir”

She quickly runs out the door and I watch her hop into her car. She sits behind the wheel for a moment taking some deep breaths before she drives off.

That night I think about the feel of her plump ass against my hand, and the sweet noises she was making towards the end. I begin to stroke myself when I remember her reaction to my wandering hands and I stop as I scold myself for pushing her a bit too far.

The next day I can barely concentrate at work in the wood shop. My thoughts going between beating myself up for trying that with someone so quickly and hoping she comes back sometime this week. I was lucky I didn’t lose a finger.

That night, I’m making a dinner for one when I hear a soft rap at the door. I look at my watch and see it’s 7o’clock on the dot. I walk briskly to the door and swing it open.

Danielle looks at me, cheeks slightly red. “Hello, sir, I’d like to learn more if you will teach me.”