Night with the Nanny

I wake early the next day and head to the kitchen to make a pot of coffee. As it brews, I look out the window at the sun starting to peek out above the horizon, decorating just the very tops of the trees with brilliantly colored light. As the light slowly creeps further down the branches, I think about the last few days and how different my life was just a week ago. I have experienced so many new and exciting things and feel proud that I have allowed myself to be open to this new world of sexual experiences.

The beautiful aroma of coffee fills the air and snaps me back to reality. I pour a cup and think about what today will have in store for me. After getting the kids to school, there really is nothing that needs to be done. I haven't checked yet for a response from John after writing him my experiences yesterday, but don't know how quickly I should expect one either. Taking the last sip of my coffee, I head upstairs to take a quick shower before starting my kid-related duties.

The warm water slides down my skin as the steam fills the room. The warmth of the shower seems to encircle me in such a comforting way. I feel completely relaxed as I close my eyes and let my mind go blank. As things drift back into focus, my thoughts center on him. My boss, my friend, my lover. I see his face and his amazing smile. I see his eyes and notice a certain feeling of understanding wash over me. I realize how much I long for him to be home, to be in front of me instead of just in my head.

As soon as I think it, my stomach knots up and questions fill my head. What is our relationship going to be like after this week? Will I be able to continue working for him or will things just be too different for us to handle? These thoughts have invaded my head on and off over the past few days and I decide to do what I've done up to this point: ignore them and acknowledge that nothing can be done about them now. We've clearly crossed a line over which there is no going back; so I may as well enjoy the rest of the week and not worry about further implications.

The kids are awake and already trying to conquer huge bowls of cereal when I get back downstairs after drying off and getting dressed. Within an hour, I pull away from the curb at their school after seeing them off. I contemplate what the rest of my day will look like as I drive back to the house. I figure I'll check the computer to see if John has written back and maybe that will determine the path of my day.

Back at the house I throw my purse on the couch and head into the study. I sit down slowly at his desk and flip on the monitor. I try to control my excitement, not wanting to be too disappointed if he hasn't written anything yet. My concerns turn out to be unfounded, however, as there is a new document in the folder that is titled "Amazing." I take a breath and double-click it.

I'm very happy to hear that you followed my instructions yesterday and it sounds like you thoroughly enjoyed yourself! I thought you might like to know that I came back to my hotel room yesterday after a day full of meetings and was almost shaking with nervousness, wanting to see if you had indeed written me about an amazing trip to the store.

You did not disappoint with your rendition of what happened, and I want you to know that I was aroused before the end of the first paragraph. I could feel my cock straining almost painfully against my pants and so I removed them and threw them on the floor. While my eyes darted quickly over your words, my mind filled with the thought of you walking through the store with the dirtiest of secrets.

I placed my hand on top of my hard cock and let out a sigh as I imagined your panties growing wet while you selected the cucumbers. Reading about you bending over the meat counter drove me so wild with desire that I had no choice but to grab my cock fully and start to slowly stroke it up and down. I just about came thinking about the look on your face when you divulged your secret to a complete stranger, but stopped so as to postpone what I knew would be an amazing orgasm.

I continued to read while I stroked my cock and thought about you secretly masturbating in such a public place. Hearing you depict your impending explosion pushed me over the edge and I stroked my cock harder. I erupted just as I got to the part about you making eye contact with the stranger while your pussy exploded into a glorious orgasm.

My heart is beating so fast that I feel as if it will jump out of my chest reading what he had written. I feel a somewhat odd sense of pride that my actions have elicited such a response from him. I take a brief second to acknowledge that a week ago I never would have been this comfortable with my own sexuality. I think about myself a week ago and realize that there is no going back to being that woman. My eyes return to the screen and the end of his paragraph.

Oh, there's one thing I almost forgot. As soon as I started reading your story, I decided to use the webcam on my laptop to record what it made me do. I just haven't decided if I'm going to show it to you yet. I don't even know if you'd be into seeing something like that, but I suppose if you were, you could probably figure out a way to make me comfortable sharing it. Have a great day, my special, beautiful nanny.

-JW

He...recorded...himself!? I guess there really is no limit to the lines we'll cross now. I try to sort out my thoughts and realize that he's trying to bait me into making a video for him! I check the monitor on his PC and find the tell-tale circle on the top that signifies a webcam. I sit frozen for what seems like eternity. I can't cross that line, I just can't. I've never done that for anyone, let myself be recorded.

I stand up and walk out of the room, shocked at what he's asked me to do. Of course, he hasn't really asked me to do anything, has he? Maybe he's just as nervous as I am about it and is looking for confirmation that I actually wanted to see his video. I realize that I've been pacing back and forth in the hallway for quite some time and decide to get out and grab some good coffee while I contemplate my life's big questions.

I walk outside the house and feel refreshed by the cool wind on my face. Within 15 minutes, I'm sitting at a table at an outdoor café and sipping on an overpriced light roast. For the millionth time in the last few days, my mind races as I try to put together my next move to John. I mentally recount everything that's happened; from the first time I sat down in front of his computer all the way up to his most recent words to me. Suddenly a warm, calming sensation sets over me as I realize something. Of all the words he's typed, the words that have affected me the most; in fact the only words that I can completely recall, were the last four he typed. Without realizing it, I say them out loud: "My special, beautiful nanny." Instantly, I realize there is more to my feelings than raw desire. I feel my face flush as I wonder if there is more to his feelings too, or if he just sees me as a means to his sexual end. There must be more! He's far too caring and compassionate of a man for there to not be more. I wonder how long he's thought of me this way and how hard it must have been for him to be around me, to hug me, to console me. I leave my cup of coffee half full on the table as I stand and rush to my car, eager to get back to the house.

I fly into the house and hurry to my room. I quickly rifle through my clothes and find some things that are acceptably sexy. I quickly change into them and head back downstairs. I wake the computer and take a deep breath as I search for the way to activate the webcam. When the window pops open with my image on it, I actually let out a little shriek of surprise. I move my chair to center myself in the screen and try to familiarize myself with the controls on the screen. It seems simple enough. There is a button for recording and also a button for taking snapshots. I decide to start with just a few pictures and I test it out by taking a handful of quick picture in different positions and facial expressions. I find the location that the pictures are being saved to and flip through them to find a good one. I choose a simple one, a close up that shows a really good smile and cuts off right above my eyes.

I take a few more pictures, this time of my body. Some are showing my stomach, my cleavage, my legs and one from the back with my shorts sitting so low on my hips that you can see the top half of my black thong. I sort through them and pick 8 that I'm very happy with. I rename them 1-8 and before saving them to the sync folder, type a quick note to John.

Sir,

In an attempt to make you feel more comfortable sharing the video that you recorded yesterday (which I do desperately want to see) I've taken a few quick pictures for you to flip through. Please view them in the order I have labeled them and let me know what you think. I can't wait to hear from you.

-JS

I save the word file and the 8 pictures to the sync folder and sit back in the chair. I haven't even gotten naked yet for him, and my heart is racing thinking of him opening the photos in his hotel room. I glance over at the clock and realize that it's only 1pm. He's not even going to be back to his hotel room for hours and that at this pace, it'll take forever for either of us to see what we want to see. I decide to speed things up and grab my phone to text him.

Sir, I sent you a few files that I feel need your quick attention. I don't know if there is any way you can get away to review them or not, but it may be in your best interest. I await your reply.

Realizing that I haven't really eaten today, I decide to pop into the kitchen and make a sandwich. I'm slathering mustard on the bread when I hear the text alert on my phone go off from the other room. I dash in and pull up his message.

Thank you for letting me know. I'll see if I can't get away from my last few hours of meetings today, but I have my laptop with me, so I should be able to review them even if I can't respond. I'll be in touch.

Holy shit, I didn't even think about him having his laptop with him for his meetings. I was picturing him opening the pictures in the solitude of his hotel room, not around other people! I'd almost rather he waited instead of running the risk of someone else seeing them. I shouldn't have sent them until I knew he would be at the hotel. Mental note for the future taken, I head back into the kitchen to finish my sandwich and wonder when I will hear from him again.

I spend the next hour or so lounging on the couch reminding myself how much I hate daytime television. Somewhere in the middle of a talk show I can't even identify, I hear my text alert again and I grab my phone. Reading his message, I can feel my face blush.

I was able to sneak out of the conference room and review your files in the hallway. I must say, I'm very impressed with the obvious amount of time and energy you put into them.

My pulse has quickened and I can feel my hands start to shake as I hold the phone. Another text comes through.

After review, I immediately started thinking about an appropriate response.

Three dots pop up signifying that he's typing. After a few seconds, his message comes through, but I'm surprised to see that it's not a message in the form of words.

The picture that I'm staring at on my phone is something that catches me off guard. It's clearly John, and he's standing in what appears to be a bathroom stall. His button-up shirt is open and his T-shirt is lifted to show the sexiest set of abs I've ever seen on a man. Before I've completely processed the picture, three more dots pop up on the screen. In a few more seconds, a new picture arrives, with almost the same scene except now his belt is undone and his pants are hanging slightly below his waist. I can see his boxers and what I think is a large bulge in them. As I stare at the picture, I realize that my hand has found its own way down into my shorts and I've starting touching myself. I focus on the bulge in the picture and am quickly bringing myself toward orgasm.

As if my unspoken prayer has been answered, another three dots appear, followed quickly by another picture. This time, the head of his cock is sticking out above the top of his boxers. It's so beautiful and I imagine being able to touch it and kiss it as I pinch and rub my clit furiously. I quickly feel myself start to climax. Staring intently at my boss' cock, I scream loudly as my pussy explodes in wave after wave of irrepressible pleasure. My chest heaves up and down as I can feel my clit throb against my fingers. Before I can catch my breath and pull my hand out of my panties, another message appears.

I hope you've enjoyed the preview of tonight's festivities. I need to return to my meeting, but know that I'll be thinking about you. I'll be in touch later tonight; my special, beautiful nanny.

I can still feel my clit throbbing against my fingers and I don't want this feeling to end. I alternate between scanning up at the pictures and down at the last line of his text; "my special, beautiful nanny." It's like he already knows that these four words affect me the way that they do. As I finally pull my hand out of my panties, I realize that my cheeks hurt slightly and then I realize that it's from smiling so hard. As I head to the shower to clean up, I wonder how many days straight I've been smiling.

The rest of the day goes by pretty uneventfully as I manage all of my official nanny duties. I amaze myself by being able to take my mind off of the unofficial nanny duties I've recently taken up and focus on my job. Once everyone has been tucked away safely in bed, my mind wanders to John in his hotel room. He must be back from his meetings by now. Is he trying to decide whether or not to send the video, is he taking a steamy shower, or is he very anti-climactically taking a nap? I change into my pajama pants and a tank top (forgoing any underwear) as I sit down in front of the computer.

He hasn't uploaded anything yet and I wonder if he's waiting for a reply from me before he sends anything else. He was the last one to send anything, so maybe he thinks it's my turn. I decide to test my teasing skills and send him something new. I turn on the webcam again and try a few different poses before coming to the conclusion that I need to step up my game. I adjust my chair backwards so that the camera captures from right underneath my chin down to my lap. I slide one hand down inside my pants and start to touch myself.

I find that watching myself on a screen is a very unnerving experience and I grab my phone and open his last texts to take my eyes off of what's happening on the monitor. I glance one last time at his final words to me before scrolling up to view the pictures again. I start to feel my wetness build as I stare intently at his body. First I look at his abs, then his bulge, and finally on the head of his beautiful cock. Before I can talk myself out of it, I reach up and hit record on the webcam. My clit feels somewhat raw from all of the attention it's gotten in the past few days, but it aches in such a delicious way and demands more attention. I rub myself in circles and can feel my pulse quicken and my wetness spread.

I glance up at the computer monitor and am in awe of the figure that I see. I don't immediately recognize the person on the screen as me. I can see my hand moving around inside my pajama pants and am turned on even more by how my body is starting to writhe on the chair. I'm surprised by how much my chest is heaving up and down and by how much bigger my breasts look than they usually do. I move to set my phone down on the desk but realize that this is an opportunity to really show him what he does to me. Instead of setting the phone down, I turn it around to face the webcam. The screen very clearly shows the pictures that he sent me earlier that day. Satisfied that he'll understand what I'm thinking about while my hand is in my pants, I set the phone down.

I reach up with my free hand and trace the outline of my hardening nipple. I squeeze and massage my breast through my shirt as I concentrate on my image on the screen. As the pressure between my legs builds under the soft touch of my fingers, I pull my breasts out of the top of my tank to let them be shown for the glory of my recording. The webcam makes my nipples look darker than they are and I start to pinch them even harder. I start to moan uncontrollably as I watch myself on the screen and imagine John watching this video in his hotel room. I'm so turned on by it myself that I can't image he'll be able to get through the whole thing without cumming quickly.

My hand is moving so fast inside my pajamas as my moans turn louder. I watch on the video as my back arches and I pull hard on my nipple. I watch it stretch as I feel my pussy start to clench, building quickly to the sweet release that I've become more acquainted with this week. My legs straighten as I pull on my other nipple now, still rubbing furiously against my most sensitive spot inside my pajama pants. I watch my breasts heave on the screen as I start to cum.

I can feel my orgasm start in my belly and run outward over the entirety of my body before centering on and homing in on the spot between my legs. I pull hard on my nipple now, feeling a lightning bolt that travels directly between it and my pussy. My breath catches in my throat and I struggle to not fall out of the chair as my pussy continues to erupt. I hold my fingers tight against my clit and feel it throb for what seems like minutes. I watch the image on the screen gently convulse as I finally feel the pleasure slowly leaving my body. I lay there for another minute with my hand still in my pants and my eyes on the screen as I admire my body and my bravery.

After what seems like an hour, I sit up and stop the recording. Before I can give myself a reason to chicken out, I quickly move the recorded file to the sync folder and make sure it saves. I pull my breasts back inside my tank top and head out of the room to shower for the third time today.

I allow myself to relax for a long time in the shower, savoring the feeling of the soft water against my skin. All of my senses feel elevated from my orgasm and I want to make the most of it. The warm water on my flesh, the cold metal tub spout that I brush my leg against, the steam on my face, the soap bubbles gliding over my curves; it all feels so amazing. It's not until I feel the water turn cold and notice the wrinkles on my fingers that I realize just how long I've actually been in there. I turn the water off and step out, grabbing a towel off the hook and draping it over my body. Even the soft fibers in the towel feel great against my skin and I wonder just how long this feeling will last.

I head back down to the office with one towel wrapped around my body and another wrapped around my hair. With great anticipation, I look in the sync folder but see nothing new. I let out a sigh and head back to my room to put on some fresh pajamas. I grab a beer and turn on the TV as I sit down on the couch. I flip through the channels mindlessly as I wonder how long he's going to make me wait.

I slowly open my eyes and it takes me the better part of a minute to realize that I'm still on the couch and that it's almost time for my morning duties. I quickly pop into the kitchen to dump my still-full beer down the drain before heading over to check the computer again. My eyes widen when I realize that there is a new file in the sync folder. Even more exciting than that, it's a video file! I glance at the clock and although I really want to watch it, I decide that I really shouldn't get into it until I can give it my full attention. With a heavy heart, I grab my phone off the desk and head back to the kitchen to get my morning coffee started. I turn on my phone to see that I have a new text from John.