Night with the Nanny

The light streams through a crack in the blinds and I roll over and check the clock. I have only a few moments to lie quietly in bed before the alarm will go off and I will have to get the kids going and off to school. I wonder if he's discovered yet the story I wrote for him last night. I wonder if he played with himself while reading it. I close my eyes to visualize what I hope happened and see him lying on the bed in his hotel room, his laptop open in front of him, the glow of the screen illuminating the rise and fall of the sheets as he touches himself.

BEEP BEEP! My alarm clock pulls me back to reality just as I start to feel my wetness build. I guess that thought will have to wait. I quickly shower and dress, then do the rest of my morning duties, ending with seeing the kids onto the bus to school.

I decide that I'm not going to check his story folder yet. I have some errands to run for myself before I get all worked up again. I hop into my car and head toward downtown as I try to remember where I had seen an adult book/toy store while driving through a few months ago. It takes a few wrong turns, but finally I pull into the parking lot of a nicer, upscale looking adult store.

I get out of my car, and realize how nervous I am as I start to walk toward the door. The few times I've been to places like this, I was never really comfortable. It always seemed weird to me that the other people in the store know what I'm going to be doing later when I buy a toy. I'm thankful that today, there are only a few cars in the parking lot.

I push open the door and find a middle-aged woman behind the counter who smiles at me politely as I walk past. I navigate my way through the store and find a few toys that intrigue me. One is a purple vibrator with a rotating head and the beads that swirl around the shaft. One of my best friends swore by this type of toy. I have always just stuck with external stimulation, but decided that I may as well go for broke and I snatch it from the shelf.

I wander past all sorts of toys, imagining how Mr. Wright and I would use them. There are a lot of bondage toys and my mind returns to my story where I tied him up and blindfolded him. I wonder if he has ever actually done that before.

I then find myself at a section full of anal toys. My ex and I used to dabble in ass play, and I enjoyed the occasional plug up my butt, but I've never used one since him; and never by myself. "Go for broke, right?" I think to myself. I grab one of the smaller ones and a small bottle of lube. Satisfied with my selection, I head toward the register.

I notice the assortment of clothes and outfits of to the side of the register. One in particular catches my eye. It's a pink pleated mini-skirt with matching garter belt, just like the one in my story. It looks exactly how I envisioned it while I was writing. I run my fingers over the pleats on the skirt and wonder if I would be bold enough to actually wear something like that ... for him.

"Wanna try it on, hun?" I turn and see the woman looking at me for an answer. "You'd look amazing in it."

"Yes." My voice cracks as I try to speak the word. "Yes, I would. Thank you." She shows me to the fitting room and I slip inside and close the door. I excitedly take off my pants and slip the skirt up over my legs. The panties I put on this morning are relatively boring and don't match the sexiness of the skirt. I slide them off and throw them aside as I turn to look at myself in the mirror. I check the back out and can see the bottom on my ass cheeks peeking out below the bottom of the short skirt. It's exactly as I pictured it and I feel myself getting aroused as I imagine wearing it for him.

I decide to allow myself a quick moment of pleasure and slide my fingers down to caress my pussy lips. I'm incredibly turned on and feel bolts of lightning shoot through my skin. Not being able to stop myself, I bring my fingers to my mouth and taste my sweet juice. Returning my fingers to their spot underneath my skirt, I rub more quickly and find myself about to explode. I close my eyes as I continue to masturbate, turned on more because I'm doing it in such a public place.

I imagine my boss, my fantasy, standing over me. He pulls out his cock and I quickly take it in my mouth. He runs his fingers through my hair as I start to suck hard. My fingers are working their magic quickly as I picture him start to thrust into my mouth. My pussy is absolutely dripping onto my fingers as I massage and pinch my clit. I imagine his cock pulsing in my mouth as he starts to cum. My own orgasm catches me off guard and I have to brace myself against the wall of the fitting room as I struggle not to collapse. The feeling of ecstasy washes through me, shutting down my thought processes as I shudder and try not to moan too loudly.

I open my eyes, suddenly aware and embarrassed by what I have just done. I'm amazed I was able to make myself cum so quickly. I hurry to get dressed again and exit the fitting room, hoping I didn't take too much time trying it on. I quickly set my new toys and the skirt on the counter to purchase them. I can't make eye contact with the woman and I'm afraid my face is flushed and will give me away.

"Told you that you'd look amazing in it." I glace up to see the woman smiling and I can't help but smile back. "Anything else today, sweetie?"

"Yes, actually." I'm so nervous talking to her after what I've just done, but I need one more thing to complete the outfit. "I need a pair of um..." I can't believe how nervous I am. "...stockings."

"Any particular kind?" she asks nicely.

"Yes. Black fishnets."

She smiles and walks to a shelf to retrieve a pair of stockings for me. After ringing it all up and putting it in a bag for me, she hands me my receipt. "Thanks for coming in, hun. Hope you had fun!"

I look at her, caught off guard, wondering if she knows what private and intimate act I just performed on myself in her store. "Thanks." I say as I grab my bag and rush out of the store.

On the car ride home, I think about what I just did. I'm both embarrassed and proud of myself for allowing what I consider to be my sexual growth to happen. I'm amazed that discovering this fantasy of his has opened me up to new experiences so much. After deciding that I didn't bring any panties I would want to be seen in, I make one more stop before heading back to the house.

I settle into the chair in front of the computer and my heart races. I open the folder that his story and mine were saved to, hoping to see a new one for me. My heart drops as I see there is nothing new there. I wonder if he hasn't found my story yet, or if he is too shocked or embarrassed to write back. Worse yet, what if he's mad? I decide that worrying about it won't do any good as I'm clearly past the point of no return. I double click on my story to him, realizing that I never actually re-read through it after I finished it.

I start reading and don't make it more than the first few paragraphs before I start to get horny. I remember my new purchases and run to get them, excited to try them out. I take them both out of the packaging and give them a good soapy wash and bring them and the lube into the office. A thought hits me and I go to grab my phone. I set the toys up on the desk and snap a picture with the camera on my phone.

I connect my phone to the computer and download the picture to the folder with the stories in it. I name the picture "purchased today for you." I figure if that doesn't get a response from him, nothing will. I turn back to my story and slide a finger down to feel the familiar heat building between my legs. I slide a finger deep inside as I read the words I wrote for my boss, just last night. I keep my finger buried deep inside myself and move around just the tip of it, exploring my deepest spots.

I'm about to make myself cum for the second time today, when a box opens on the computer screen. One word appears inside the box, "Synching." When the box disappears, I minimize the story and see a new word document labeled "read me" in the folder. I steady myself as I open it. It reads:

You've been a very naughty girl.

How dare you invade my privacy by snooping on my computer?

I don't even know if I could come up with a punishment suitable for this betrayal of trust.

-JW

My heart stops for a few moments as I read it again and again. What is he saying? Is he really not interested in me? How can he actually want this fantasy to stay a fantasy? I decide to continue going for broke and reply in the same word document.

Sir,

I meant no disrespect to you.

I apologize if this is not what you want.

However, if this is what you want, I feel confident that you could devise a suitable punishment. I will do anything. Awaiting your reply,

-JS

The minutes tick by as I sit and wait for the synching message, which finally appears and disappears.

I'll see if I can come up with something that I feel fits the crime.

You will go about your day and await my instructions, which will come at exactly noon, your time. I need to know that you are going to follow my directions precisely.

For now, you are not allowed to touch yourself in anyway.

Not with fingers, and absolutely not with those new toys you bought.

Am I understood?

-JW

Feeling confident that he's playing along now and not actually mad, my heart finally resumes beating. But how can he tell me not to touch myself? That just doesn't seem fair. Especially since I was so close to making myself cum just minutes ago.

Sir,

I understand and will do as you ask.

Awaiting your instructions,

-JS

I sit back from the computer and glance at the time. It's only 10:30am, and so much has happened this morning. I try to process how I feel about this turn of events, but the hunger growing between my legs won't allow me to think badly of any of it. I decide that I need to take my second shower of the day, this one much colder than the first.

In the shower, I wonder what he's doing right now in his hotel room. He could be typing my punishment, reading my story, or even just doing some work. That is, in fact, why he went on his trip. The thought that he may so easily be able to turn off his desires and do work makes me jealous. Finally, the cold shower overcomes my burning desire to touch myself and finish what I started, and I step out to towel off. I wrap myself in the towel and collapse on the bed, wanting so badly to be able to rest my brain.

I slowly open my eyes, not realizing at first that I dozed off. What time is it? I hope I didn't miss my punishment. Shit, I hope I didn't miss picking up the kids from school! The clock slowly comes into focus, 12:11. Thank god, I still have hours before the kids are done with school. I quickly make my way over to the computer and am excited to find the new file labeled "Instructions." I click on it and start to read as my heart races.

I'm glad you have accepted the terms and agree to do exactly as I ask. These instructions are written in multiple parts, and each will end with telling you when to read the next one. You are not to read ahead. You will need to email these instructions to your phone as you will be leaving the house to complete them.

-JW

Leaving the house? What the hell does he have in store for me? I'm nervous now, but something inside me is telling me to relax and go with the flow.

#1. Change into a skirt. If you did not bring a skirt, you will have to buy one. Pack your purse with both of your new toys and some lube. If you do not have any lube, there is some in my nightstand you can bring with you. Once you are dressed and packed, I need you to go to the grocery store for me. Once there, proceed to the bathroom. Only then, read your next step.

Wow. He's really going all out on this. He's obviously put a lot of time into this, and although I'm tempted, I decide not to read step #2 yet. I did bring one skirt with me to his house, a casual brown and white striped one, so I put it on after putting on some of the new panties I bought just this morning. A plain white bra and light pink top completes my outfit. I slip on my shoes and pack for my trip. I barely remember to email myself the file with my boss' instructions before leaving the house.

As I drive, I wonder what exactly he has in store for me. I'm nervous, but I never remember being so aroused in my life. I can already feel my panties getting wet just imagining what lies ahead. I park and walk into the grocery store. I've shopped here many times and a lot of people here know me. That makes me even more nervous. I walk straight to the bathroom, entering the first stall I come to. I grab my phone out of my purse and open up my email. I watch the icon showing me it's downloading the file, and the anticipation is killing me. Finally, it opens and I scroll down to #2.

#2. Pull your panties down and sit down on the toilet. Take the lube and butt plug out of your purse. Apply a generous amount of lube to your toy, and push it against your asshole. Rub it up and down slightly, feeling your ass tense every time the toy touches the center of your button. You are not yet allowed to touch your pussy. When you are ready, slowly press the plug into your ass until it settles inside you. Take a moment to adjust to the feeling before putting your panties back on and leaving the bathroom. Read on to #3 when you are in the produce section.

Holy shit, he's twisted! I haven't even touched the toy yet and I'm getting so turned on just reading about what I'm going to do. I don't think I'll be able to bear not being able to touch myself much longer. With my panties around my ankles, I retrieve what he's asked me to. I leave my skirt on as I squeeze the lube onto my butt plug. It's been a long time since my ass has been a part of my sex life, and I wonder how easily it will accept my new toy.

I reach down and pull the front of my skirt up as my other hand guides the toy down below my ass. When I lift up my skirt, I get a whiff of my sweet-smelling pussy. I'm almost dripping already and it hasn't even been touched. The tip of the plug is now pressed against my sensitive asshole, and I do just as described; moving it slightly up and down, teasing myself while making sure to stay away from my aching pussy.

Finally convinced I've teased enough, I press gently with the toy, testing my ass to see how it will respond. My tight asshole spreads ever so slightly, then more and more as I push my plug further into it. I catch a moan before it's able to escape my lips as the full length of the plug slides inside me, now held only by the thick base on the bottom. I stand up and move my hips around, trying to determine whether or not it will stay inside me while I move throughout the store. Convinced that I should be ok, I pull my panties back up and collect myself before exiting the stall. I wash my hands, dry them off and walk into the store.

I feel like I'm walking funny, aware of the new sensation inside my panties. It takes me a while to get used to it and feel like I'm actually walking normally. I look around the store, glancing at all the people, wondering what they would say if they knew my little secret. I walk quickly to the produce section, eager to read on. I turn on my phone again.

#3. The first thing on my grocery list is 2 cucumbers. I need you to make sure that they are firm. As you look through them, pick them up one by one and stroke them up and down, testing for firmness. As you do this, close your eyes and imaging that it's my cock you're touching. Imagine that you can feel it pulse. Imagine you hear me moaning your name while you squeeze my cock. Feel the tightness in your ass caused by the invasion of your new toy while you pretend to fondle my cock. You are not allowed to move onto the meat department until you have thoroughly soaked your panties. Read #4 at the meat counter.

As I pull my eyes away from my phone, I realize that I probably look unusual staring at my phone so intently like a dog looking at a meal, eyes wide and ready to pounce. I walk to the cucumbers and pick up the first one I see that looks right. Looking around tentatively, I wrap one hand around the tip while I hold the bottom of it with the other hand. Feeling relatively confident that no one is watching, I close my eyes briefly and move my hand down the length of the shaft. I have no problem imagining that John's cock is in my hands and I can feel my pussy coating my panties in wetness.

I open my eyes, not slowing my hands down as I continue to stroke and squeeze, testing for firmness. I put the first on in my basket and pick up a second. I discretely move my ass cheeks back and forth, making sure I can feel the plug that's buried deep inside me while I stroke the next cucumber. Again I close my eyes and imagine him standing over me. My boss, with my hands wrapped around his cock, looks at me with fire in his eyes.

I can actually feel my wetness now starting to spread to my inner thighs as I put the second vegetable in my basket. I can smell my sweet aroma as I make my way to the meat counter, confident that I have fulfilled every aspect of his instructions so far. I'm third in line at the meat counter, so I flip open my phone to see what he has in store for me.

#4. Walk along the glass case, stopping to bend over and look at every piece of meat in it. Make sure you bend at the waist and show off that sexy body of yours. I want you to do this until you draw someone's attention. It will most likely be a man. Once you've caught his eye, bend over as far as you can to look in the case, then look over at him and smile. He will undoubtedly smile back. When he does, walk over to him and make him aware of the toy you have stored deep inside your ass. Do this however you see fit. Then, purchase two T-bone steaks and make your way to the coffee shop in the corner. Order a coffee and sit at a table in the back corner. Then read #5.

I can't believe the affect his words are having on me. My panties are completely drenched, and I'm aching to touch myself; to make myself cum. As I walk toward the glass case, I can feel the thin, wet fabric of my panties brushing against my burning pussy. As I bend over to look into the bottom of the first section, the butt plug shifts slightly in my ass. I had been so distracted by the sensations coming from elsewhere under my panties, I had almost forgotten about the plug.

I shift my weight from one leg to the other while I'm bent over and can feel the plug rubbing inside me. The feeling of being stretched open back there in such a public place is amazing to me. I don't notice anyone yet looking at me, so I move to the next section and repeat my performance. The sensations are repeated too; feeling my panties rubbing against me, feeling the plug shift back and forth, and feeling my wetness grow even more. This time as I bend over, I look back to notice a man walk up a take his place at the end of the line.

He sees me and I go back to looking into the case. I wiggle my ass for him, hoping he hasn't yet taken his eyes off of me. I'm getting nervous now as I realize what I have to say to him. I look back at him to see that he is, indeed, still checking me out, my ass on display for him. I smile as wickedly as I can manage, realizing just how nervous I am. I very slowly stand up, never breaking eye contact with him. He smiles awkwardly as I walk over to him. He looks nervous, like I'm going to be mad at being checked out. I stop in front of him.