The Babysitter (Part Two)

March 14

* Author’s Note - this one is a little more of a slow burn, but it’s a segue to Part Three (cumming soon)

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Danielle was standing outside my doorway, looking nervous but slightly excited. “Hello, sir, I’d like to learn more, if you’ll teach me.” She stood there wearing a blue floral print sun dress and a pair of slip on flats, her brown hair pulled back in a ponytail and she had put on more makeup than she usually wears when she watches my son.

“Come in.” I motion her inside my hand on the small of her back and position her in the middle of the living room. “Danielle, I am going to place my hands on you, explore your body. I know last night that began to make you uncomfortable, and I want you to be able to express that, but I also want you to be more comfortable with my touch. If I get somewhere that makes you feel uncomfortable I want you to just say ‘yellow,’ I will move my hands somewhere else. Do you understand?”

She finally makes eye contact with me and I can see her chest raise and lower as she takes deep breaths. “Yes sir, I... I think so.”

“Good. If it becomes too much and you want me to stop touching I want you to say ‘red.’ But only use this if you truly wish to stop for the evening. Do you agree to this?”

She seems to be mulling it over a bit, she finally takes a deep breath and fixes her gaze on me. “Yes sir, I understand.”

“Good girl.” She smiles when I call her that. “Now I want you to put your hands behind your back, elbows bent and tucked against your body.” She complies, and I start to walk a circle around her. “Now, kick off your shoes and put your feet shoulder length apart.” Once again she does as she’s told and she stands with her head held up without me even telling her to do it.

I walk behind her and wrap my arms around her midsection, she lets out a soft pleased moan as I lean in and inhale the perfume she’s wearing. I then run my hands from her stomach down both her legs, feeling the lean muscles under her soft flesh. Once I get to her knees I traced my hands back up to the hem of her skirt and lifted it up a bit and was greeted with a lovely sight of a blue lace thong. “These are quite lovely,” I tell her as I hook a finger into the waist band.

“Yellow, yellow.” She looks embarrassed for a moment before she says “And thank you, sir.”

I let the skirt fall back as my hands trail up her side, she bites back a little laugh as she squirms a bit. She’s ticklish, that’s good to know. “Arch your back.” She does as she’s told and her chest is more on display. I can look over her shoulder and see her ample cleavage, and my hands come up and cup her pert breasts in my hands. She lets out another soft moan and I feel her fingers wiggle just a bit. I push her tits together and enjoy how malleable they feel. As my hands begin to travel up, I feel her nipples through her bra and thin dress.

Very quickly her head snaps to the side and I feel her about to step forward. “N- yellow. Yellow, sir.” I let out a small breath in frustration, but I move my left hand back to the bottom of her breast, and bring my right up to her shoulder. I feel her tense a bit as I bring it around her neck, her breaths coming faster and louder. I gently hold her neck as I squeeze her tit. I decide to test her limits a bit and begin to hold her throat tighter as my left hand trails back down to her crotch.

I’m barley at her belly button when she finally croaks out, “Yellow. Please, yellow sir.”

I take my hands off and walk around her again. Once I’m back behind her I grab her ponytail and pull on it lightly as my other hand goes to her ass and kneeds one cheek. After listening to her let out a few satisfied moans I finally speak. “You did very good, sweetie, you remembered to use your safe-words, and let me touch many places. But we will need to work on those ‘yellow’ areas. Why can’t I touch you there?”

She’s silent for a moment as she speaks. “I’m sorry sir. I want you to touch there but... it just feels too good.”

I let go of her and turn her to face me. “What do you mean?”

“When you touched me last night it felt so good, and I was worried that I was going to... want to sleep with you.”

Her words drove a spike into my heart for a moment. I’m still only 37, but there’s some gray in my hair and beard. I’m also a bigger guy, the stress of the divorce and bad eating adding to an already sturdy frame. Why in the world would I think this beautiful young woman would want to fuck me.

She must have seen what I was thinking on my face. “No, no! Oh God that came out wrong. I’d be lying if I said I hadn’t, you know, thought about it. I’m just worried with the situation…” she motioned between the two of us and a photo of Jason sitting on a side table.

“It would be awkward.” I finished.

“Yeah.” She looked down again, as we both fell quiet contemplating everything.

That’s when my stomach broke the silence and let out a loud grumble. I know she hears it because she looks up and gives me a slight smile. “Sorry, I haven’t eaten yet,” I explain.

“Oh, I saw some spaghetti in the cabinet the other day. I can make that for you. If you want.”

“Uh, yeah. Yes, that’d be nice.” I watch in surprise as she quickly runs into the kitchen and begins to prepare a meal for me. Soon I have a hot plate of noodles with a meat sauce in front of me, and my beautiful chef sitting across from me, watching me enjoy the meal.

“This is amazing, thank you. You don’t want some?”

She pulls a few pieces of bread apart and chews on them. “No thank you, sir. I ate earlier, but I like watching you enjoy your food.”

My God, does this girl realize what a natural submissive streak she has in her? I continue to eat my meal as she nibbles at bread.

When I finish I wipe my mouth with a napkin and begin to pick up my plate and Dani quickly hops up and takes it. “No, please, I can do that.” She looks at me for a moment and fights back a laugh. “You missed a spot.” She leans in kisses the corner of my mouth and I feel her tongue get a bit of sauce that was still there. She pulls back a bit and looks into my eyes. “Sorry that was inappropr-“

I cut her off by pulling her back to me and kissing her soft lips. She leans into me and I feel her tongue again begin to part my lips. Once again I decided to test her limits and my hand comes up to her breast, my thumb running over her nipple. I wait for her to use her safe-word, but instead she straddles my lap and wraps her arms around my neck. As I continue to tease her nipple she moans into the kiss and I feel her begin to wiggle her hips a bit.

I gently push her back a bit. “Clean up. Then we need to talk.”

She looks shocked and a little ashamed, but she gets up and removes the dishes as she says, “Yes sir.”

I sit and watch as she works, taking deep breaths trying to fight back thoughts of bending her over the counter and taking her there.

Once she is done she comes back to the table and I pull out her chair and point to it. She pouts as she drops into it. “I’m sorry. Tonight was kind of a mess, huh?”

“No, in fact you have made me very happy tonight. I would like nothing more than to keep training you and see what other surprises you could offer, but I think we need to clear a few things up.” She nods, and waits for me to continue.

I start to feel a bit nervous and tap on the table. “I would also be lying if I said I hadn’t thought about you in that way. And I think we could do this and not change much in the current dynamic. Just… building on it. But only if you’re ready for it.”

She gets an excited look on her face. “Yes, sir, yes I am ready.”

I stare at her for a moment. “Than I think it’s time for us to explore some fantasies we’ve had. Are you ready for that?” She seems nervous for a moment, then nods. “If you are truly ready I want you to go upstairs to my room and wait for me there.”

There is an awkward silent moment where I think she’s about to just get up and leave. To my surprise, she rises up and walks up the stairs. I go to the foot of the stairs and gaze up. Am I really going to do this? Am I ready to sleep with this young woman I met, before my wife and I decided to separate?

Part of me is nervous how this will change things between us all, but another part is more excited than I can handle.

A new idea comes to mind. I go out to the garage and grab a few items, than ascend the steps, getting more aroused with every step.