Night with the Nanny

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"Ding dong," I ring the doorbell at precisely 9:00. Usually, one of the kids is bounding down the hallway to the door to greet me but I know that he has probably already had them go to bed. I usually nanny for him only during the week, but he called me earlier today saying he needed me urgently as he had been called away on business. I would be staying at his house for a whole week, taking care of everything in his absence. After ringing the doorbell a second time and realizing he's not coming, I use my key and let myself in, setting my bags down just inside the door.

"Hello? Mr. Wright, it's me, Jackie." I walk down the hallway and can't help but think how different the house looks at night. I'm usually only here during the day while he's at work. I wander through the unfamiliar seeming house and notice that the light is on in the study and the door is halfway open. I walk up to the doorway and gently knock on the door, pushing it open a little more. I see Mr. Wright sitting behind his desk, typing frantically on his computer. "Hi Mr. Wright. I let myself in, hope that's alright."

"That's the whole reason I gave you a key." He smiles big and I'm reminded of one of the reasons I enjoy working for him so much. His smile is absolutely infectious. Even on my worst day, it can make me feel better. I flashback to the day when my boyfriend came over while I was working. It was a nice surprise, until he told me that he wanted to see other people. The rest of the day I was a wreck, and Mr. Wright could tell as soon as he got home from work. I didn't want to tell him at first, but I feel so comfortable with him that we ended up talking about the whole thing. He ordered Chinese that night and invited me to stay for dinner. After the kids were in bed, we talked a little more and after everything, I look back at that day as a happy one.

"And how many times do I have to ask you to call me John?" His voice snaps me back to reality and I blush, thinking somehow he knows what I was thinking about.

"I'm sorry, John. Old habits, right?"

"I suppose" he says. He looks back to the computer monitor and turns it ever so slightly away from me, possibly wondering if I could see what he was working on. "I'm just finishing up some business before I head to the airport. Go ahead and get yourself set up in the guest room and I'll let you know when I'm taking off."

"Sounds good," I say before I turn and walk back down the hallway to get my bags. I head upstairs to the guest bedroom, where I've slept many a night, but never had to occupy for as long as a week before. It feels weird putting so many clothes into the dresser.

After about 10 minutes, John comes upstairs with his jacket on. He explains that he wrote down the phone number to the hotel he'll be staying at in Portland just in case I can't reach him on his cell phone. He also gives me an envelope with some money for daily expenses and a copy of the kids' schedules – like I don't have that memorized by now.

"Thanks again for doing this on such short notice. I hope it didn't rearrange your life too much."

"What life?" I say, smiling. We hear his cab honking outside and wrap up our goodbyes. After he leaves, the house seems so big and quiet. I'm far from tired, and go downstairs to flip on the TV. After about a half hour of flipping through and finding nothing I really want to watch, I go to the study and turn on the monitor. John has made it a point to tell me to make myself at home and lets me use his computer ever since my laptop died on me.

The screen is still up on whatever he was working on, which appears to be a word document of some kind. I just minimize the screen, not wanting to mess up or close anything he was doing. I quickly get bored of my usually Facebook and email activities. My mind goes back to how he turned the monitor away from me, and I become very curious about whatever he was working on when I showed up. I don't know why, as I've never violated his privacy before, but I bring up the screen I had minimized before. I start to scan a few lines and realize it's a story of some sort, and I wonder if it really could be business related. He works in public relations, so I suppose it might be somehow. I scan the page a little more and stop when one word catches my eye: Nanny. The paragraph I'm looking at seems to be describing someone. As I read a little more, certain lines jump out at me. "At 22, she is a beautiful woman, and her smile is absolutely captivating. Her jet black hair and light skin leave an alluring impression." And most intriguing yet, "She normally dresses very conservatively, but occasionally will wear a low cut shirt, revealing plenty of her ample breasts."

I sit back, wondering what it is that I'm reading. Then it hits me as I read more of the description. He seems to be describing not just a nanny, but his nanny. He's describing me, and doing it quite candidly. My mind races the gamut of emotions from flattery to anger, then finally rests on confusion. I decide I need to read the whole of the story for it to make any sense. I get up and go to the kitchen to grab a beer out of the fridge before settling in for what I hope is a revealing read. I scroll to the top and take note of the title, prominently displayed at the top of the page, before I start to read.

Night with the Nanny

I come home late from work, feeling drained from my busy day. I slip off my shoes as I notice how quiet the house is. After verifying that the kids are already soundly sleeping, I go upstairs to the guest room and find the nanny asleep as well. Jackie has been my nanny on and off for a few years now and I constantly find myself thankful I found her. She's great with the kids, and I also really enjoy her company the few times we have the house all to ourselves. We've stayed up many a night talking and sharing stories. It wasn't until recently though, that I started feeling more emotions toward her. It was one night I came home and found her distraught about her boyfriend leaving her. I ordered food and she stayed late into the night. I tried to comfort her as much as I could, and found myself thinking, "What kind of an idiot would leave her?" That's when I realized how much I was attracted to her, both mentally and physically. At 22, she is a beautiful woman, and her smile is absolutely captivating. Her jet black hair and light skin leave an alluring impression. She's about 5'6", with a perfectly curvy figure. She normally dressed very conservatively, but occasionally will wear a low cut shirt, revealing plenty of her ample breasts. A few days after that, I had my first dream about her. Now, they happen a few times a week, and I wake up to find that my cock has remembered the dream as well. She quickly became my secret fantasy after that. I know it's wrong of me to fantasize about someone that much younger than me, but convinced myself that we're both consenting adults; although she's not exactly consenting to being in my fantasies.

I realize I've been standing in the doorway looking at her for a few minutes at this point and quietly slip away to my room down the hall. I strip down and turn on the shower, feeling my stress slowly melt away with the warm water. I close my eyes to relax in the warmth, and find my mind going back to the image of Jackie lying on the bed. I know she's still there, not more than 40 feet from me right now. I picture the curve of her body up and over her butt and I feel a well-known urge growing deep within my body. My hands find their own way down my body and I start to rub my cock. I imagine her rolling over in bed and watch in my head as her breast pops out of her shirt. My cock grows even larger in my hand as I imagine sucking and licking on her soft nipple until it hardens. My eyes still closed, I see her lower her hand inside her pants. She starts to grind her hips up and down against her hand as her neck rolls back and forth and she arches her back. I can practically hear her moan as she plays with her clit inside what I imagine to be the sexiest pair of panties I've ever seen. A moan escapes my own lips as my hand furiously runs up and down my now rock-hard cock. I stroke myself harder and faster as I see her hand moving more and more quickly beneath her pants. I can feel my orgasm building as I imagine what she smells like, and even better, what she tastes like. My cock is throbbing now in my hand as I brace myself against the shower wall. I imagine sticking my tongue out to taste her pussy as she plays with herself and my cock can take no more. I moan (maybe a little too loudly) as I start to cum, erupting and shooting my thick, sticky cum against the wall of the shower. I don't stop jerking myself off until every drop of cum has been released. I simultaneously feel senses of complete contentment and guilt. I know that my emotions took over my body, and pray I didn't get too loud as I was cumming. I relish in the feeling just a moment longer before I finish washing myself and step out to dry off.

I put on my sweatpants and a t-shirt and walk down the hallway again to make sure everyone's still asleep. When I turn the corner to look into the guest room, what I see stops me in my tracks. The scene happening on the bed in front of me is so much like the one I unrolled in my head only minutes ago. Jackie is lying on her back now and the sheets are pulled back to reveal she is wearing nothing but panties. One hand is slid down inside her sexy, black panties, and the other one is gently pinching her nipples. I can't believe what I'm seeing and realize that I don't have any idea how to handle this situation. My eyes are attached to her body in a way I've never experienced and again I feel multiple emotions at once. Passion, excitement, fear and guilt all roll through my body. I hear her moan softly and my gaze returns to her face. I'm instantly frozen in fear as I realize her eyes are now open and staring at me while she plays with herself. She smiles a sly little smile as she moans again. "Are you just going to stand there Mr. Wright, or are you going to get over here and help me cum?"

I stop reading the story momentarily and realize that what I've stumbled upon is his true fantasy, not just some story about me. The second realization that I come to is that I'm really enjoying it. My pussy is long past the point of getting wet and is now practically dripping. I decide to not worry about the ramifications of this story just yet. I feel like I should be able to just enjoy it first. I start to wish I had brought one of my toys with me from home, but quickly decide that I'm turned on enough by what is happen where my fingers will do just fine. I notice my full bottle of beer and take a big swig before sliding my hand down inside my pants and returning my attention to the story.

I can't explain why, other than to say my body took over where my mind was too confused to act, but I slowly walk over to the bed. She reaches down with her other hand to pull aside the thin piece of fabric covering her pussy so I have a clear view of her masturbation. Her pussy is shaved almost entirely, except for a small strip of hair in a line above it. I step closer to her and one of my emotions finally steps up and takes over: Passion. I grab her legs and flip her sideways on the bed so her legs are hanging off the edge. I lower my face to hers and kiss her hard, letting my tongue mingle with hers. But this is not the time for passionate kissing, this is the time to do what I've wanted to do for a long time. I drop to my knees in front of the bed and quickly lower my face to her pussy. Her scent overpowers my senses and I lose control of myself. I stick the tip of my tongue out and lick up the length of her wet slit as she moans and continues to touch her clit. I push my face in against her sweetness and realize just how wet she really is. Her wet pussy drips out onto my face as I lick deeply inside her. A thought crosses my mind, and as soon as it has, I'm not sure how my brain will deal with it. "I'm licking the nanny's pussy." As it turns out, the thought only drives me more wild as my tongue swirls around her wetness faster and faster. I can't remember the last time I had such a young, tight, wet pussy in my face, and I savor every moment of it. Her fingers are flying against her clit now and her moans are getting louder and louder. My cock is already rock hard again even though I just masturbated minutes ago.

My fingers and panties are soaking wet now as I read the words on the screen. A thought occurs to me. Did he want me to find this story? Had he finally had enough fantasizing about me without me knowing it and decided to finally do something about it? Is this how he's letting me know his feelings? He left the story up, but he could have simply forgotten to save and exit in his rush to get to the airport. I decide to worry about it later as I drink the rest of my beer, smelling my own juices on my fingers as they get close to my face. That turns me on so much that I return my fingers to their rightful place and read on.

"Go around to the other side of the bed," she says. I quickly follow her orders as she slides back further so her head is laying upside-down just slightly off the bed. I approach her and she grabs my ass and pulls me toward her. I feel her take one of my balls into her waiting mouth as her hand returns to its spot between her legs. Her mouth expertly sucks on both of my balls, alternating back and forth, pulling gently on them while her free hand starts to slowly stroke up and down the length of my rigid cock. She pulls my cock down toward her now and I feel the heat of her mouth as she wraps her lips around me. I lean forward to give her a better angle and find myself once again only inches from her sweet-smelling cunt. I am watching close-up as her fingers move quickly, rubbing and pinching her delicate little clit, as her tongue rolls circles around the head of my cock. Her free hand now grabs my ass and pulls me deeper into her mouth as she opens wider to take me in. I'm quickly grateful for the orgasm I just had, or I know I would have exploded in her mouth at this point. I lower my mouth to her pussy and once again lick up and down, now fighting her hand for position on this vital piece of property. After only a moment, we find a position that allows her fingers access to her swollen clit and my tongue access to her warm depths. She stops moving her mouth along my cock and instead grabs my ass and pulls me in and out of her mouth, effectively making me fuck her face. After a while, I take over and slowly start to pump my cock in and out of her mouth. Her moans are getting louder and louder now and I can feel the vibrations deep in her throat against my cock as she works her tongue against my head.

I continue to lick her sweet cunt faster and faster until I can tell she has reached the point of no return and I feverishly start to lick her clit as her fingers rub against it. As her orgasm starts, she arches her back off the bed, pushing her pussy harder against my face. I can feel her sucking and licking hard on my cock now as I feel my own orgasm building. She gasps against my cock as her pussy explodes against my mouth. She removes her fingers from her clit and pumps her crotch against my face hard. I can actually feel her clit throbbing on my tongue as I let her grind against me. My cock is pulsing in her mouth now as I feel it start to release its sweet prize to her. My cum erupts from my cock and I can feel her struggle to keep it all in her mouth. I pump a few more times into her willing mouth as she moans and groans against it. When I'm done, I stand to see a single drop of my cum fall off of her lips onto the floor before she swallows the rest. I bend down and kiss her hard, tasting the remains of myself on her lips.

The story ends there abruptly and I'm pinching my clit hard as I start to cum. I'm only able to re-read a few of the last lines to push me over the edge right before my pussy explodes against my hand in an orgasm that my body seems incapable of surviving. I lay against the back of the chair as the throbbing in my pussy finally starts to subside. I assess myself and realize that I have completely soaked everything around me. Not just my hand, panties and jeans, but also his very nice, executive leather chair. After I'm done basking in my post-orgasmic glow, I get up and head to the kitchen to get something to wipe off the chair, then change my mind and decide that I'll leave that trace of myself for him to find.

Quickly, the feelings and thoughts converge upon my brain all at once. I feel so dirty, so wrong for invading his privacy. What does this mean for my job? Can I keep working for him? Does he really want more of a relationship? Luckily, my escapades have worn me out to the point of exhaustion, so I head upstairs to go to bed. I don't even bother taking off my wet clothes before falling into bed and burying my face in my pillow.

I get up early the next morning, feeling refreshed in a way I haven't in a long time. I shower, dress and, realizing the kids won't get up for another hour, return to the scene of last night's crime. I flip on the monitor and reopen the story for seemingly no reason at all. I don't read it so much as I just look at it, remembering highlights as I go. When I get to the end, what I see makes my heart jump in my chest. The story is the same right up until where it ended, but now there is an additional paragraph! It's a sappy part about falling asleep in each other's arm and waking up the next day. I search my memory for the possibility that it was there all along, but I know that it wasn't. My mind races as I run through the possibilities. Did he come home and not tell me? Was someone else here? I truly have no idea how this could have happened, and I feel a knot form in my stomach. Then I remember something he told me once about his computer. His work laptop is linked to his home PC so he can access any information from either one no matter where he is. He wrote the last paragraph from his hotel room, 2000 miles away! Then, just as suddenly, a second realization hits me. I could write back.....