9 comments/ 60933 views/ 16 favorites Night with the Nanny By: bedtimewords Please vote and leave feedback as this is my first submission. Thanks, and enjoy! "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 Ch. 02 My mind is running through all the questions that have piled up over the last day. Somehow, I pulled myself away from the computer long enough to accomplish my morning duties and get the kids off to school. Now, with the next few hours free, I find myself once again sitting in front of the computer. I opened the story, expecting to find more words to drive me wild, but instead find that he hasn't updated anything more. I then switch gears to decide whether or not I will write something back. I already did a little research online to find out how his computer linking program works. There is a folder on his desktop labeled "Sync." Inside, there are multiple folders, one of which is labeled "stories." That is where the story was saved. It is the only story there, and I wonder how many he was planning on writing. My plan, if I decide to go through with it, is to write my own story, and save it to this folder so that he will see it the next time he opens it. I haven't been able to figure out what the story would entail, only that it really needs to catch his attention if I hope to get a response. I think of different ways I can write it, knowing it won't be as good of a story as he wrote. As I ponder different scenarios, I find myself getting turned on again. My cell phone vibrates and brings me back to reality. I glance at it, and my heart skips a beat to see that it's him texting me, asking how things went last night and this morning. Now is my chance to tell him I found the story and try to get a feel for his reaction. I type "Uneventful night....until I found an interesting story on your computer. Then it was a GREAT night." I don't click send, I just sit there and stare at the words until I get too nervous and replace them with "Good...fell asleep early. Kids are good." I hit send and immediately regret not being more assertive. He sends another text thanking me again and saying he'll call tonight to touch base. I know now that I must send him the best story I can possibly write. Quickly, my fingers fly over the keys and the words materialize on the screen before me. My heart races as the story comes together. A Gift from the Nanny The night is getting late and I hurry to finish my preparations for my boss before he gets home from work. The kids have long since fallen asleep. I finally finish arranging things in the bedroom and light the candles before changing into the special outfit I bought just for him. As I'm putting my other clothes away, I hear the garage door open and know that he's home. The time has come; the moment I have been waiting for ever since I made the decision to stop being with him only in my fantasies. I have been dreaming of him for years now, imagining how he would take me in his arms and ravish me. Many a night when he's working late, I end up on his bed touching myself. I masturbate almost every night I spend at his house and picture him every time I do it. I hear the front door open and hear him take his shoes off and throw his jacket and briefcase over a chair. I am ready for him, waiting for what seems like hours for him to come upstairs and find me. I hear both doors open down the hall as he checks on the kids. My pulse quickens as I know any minute he'll walk into his room and all my cards will be on the table. I stand in the bathroom, watching through a crack in the door as he walks up and stands in the doorway, shocked. He's still trying to process the odd scene as I walk out of the bathroom and lean against the dresser. His eyes widen and his mouth drops open as he stares at me, taking it all in. I stand before him and feel goose bumps run across my body. His eyes slowly move up my body, starting at my feet. I'm wearing black fishnet stockings that sharply contrast my light complexion. Further up my leg, he sees the bright pink garget belt and then the matching pleated mini skirt. The skirt is a lacey one that I bought after I couldn't find one short enough for this mission. I altered it to make it shorter, so short it allows my panties to be seen from the back -- If I wear them. Tonight however, I chose not to. He doesn't seem to move at all as he continues to take me in with his eyes. My arms are covered in fishnet sleeves that match my stockings. A lacey, pink push-up bra struggles to contain my breasts as they rise and fall with my quickened breathing. Around my neck is the necklace he bought for me last Christmas, the ruby sparkling in the candle light. Finally, he brings his eyes to mine. I have on dark eye-liner and a lipstick that matches the rest of my pink ensemble. My hair is up in a slightly spikey style; a way he has told me on multiple occasions that he likes. He tears his eyes away from me as he looks and sees the two dozen candles lit around the room and the bottle of champagne next to the chocolate dipped strawberries on the bed. I move to the bed and pour two glasses while I watch him stand frozen in the doorway. "Come over her and sit down, Mr. Wright" I say as seductively as I can manage. I feel like my voice cracked a little in my nervousness, and hope he didn't notice. He moves toward the bed and takes a glass from my hand. "You did all this for me?" he asks. "Of course, Mr. Wright. I wanted to show you how special I think you are." I answer. Usually he complains when I call him Mr. Wright and not John, but tonight I think it's adding to the fantasy. "And I wanted to give myself to you in ways I have envisioned for a long time." I push his glass to his lips and he tips it back to take a drink as I mimic his movements. As he lowers his glass, I take a strawberry and feed it to him. He bites tentatively at first, but then allows himself the sweet fruit. As I feed him the first one, I take a second one and lower it below my skirt. When I raise it to his mouth, I can see a shimmering wetness on it. He hesitates this time, so I lean in and kiss him full on the lips. He doesn't fight it at all. In fact, his tongue enters my mouth before mine has a chance to enter his. I pull away after our passionate kiss and once again offer him the strawberry that was between my sweet lips moments ago. With the first taste of my juices on the strawberry, he transforms into a different man. He devours the fruit and licks his lips as I rub another one up and down the length of my very wet pussy. He slides his hand under my skirt and takes the strawberry from my hand, continuing to rub it up and down, coaxing my lips further apart as the chocolate begins to melt against my heat. Finally, he removes the strawberry and raises it to my lips instead of his. I seductively lick it with just the tip of my tongue; then take a bite. He comes in closer, and takes a bite out of the other side, tasting my sweet pussy juice. Watching each other eat, I can feel the heat rising between us. I remove the rest of the strawberries and the champagne from the bed, too impatient to finish either one. I sit him on the edge of the bed and kneel down in front of him. I unbutton his shirt and pull open the sides as I lay a gentle kiss on his abs, making his body twitch. "What would you like me to start with, sir?" A shocked look crosses his face. "Whatever you want, I suppose." I slowly creep up the bed, rubbing my heaving breasts against his now exposed chest as I go. I kiss up his body, paying special attention to his nipples and his neck. I lick his ear before whispering, "There will be plenty of time for me to do what I want to do. But for now, I want to hear what you want. I want you to tell your nanny what to do." I pull away from his ear just in time to see the look of shock transform into a wide, school-boy grin. He has obviously never seen this side of me, and I can only hope that he's dreamt of it. "In that case Jackie, I want to see your lips wrapped around my cock." I start to loosen his belt and unbutton his pants, never losing eye contact. "Whatever you say, Mr. Wright." I am able to slide his pants out from under his ass, but decide to leave the boxers on. As I toss his pants to the side, I run a hand up his stomach and over his chest, admiring his body. When my hand returns back down his body, my nails leave five fine lines against his skin. I kiss his stomach as my hand reaches inside his boxers and for the first time, touches his cock. I was hoping it would be starting to get hard, but find instead that I must be doing better that I could ever have hoped to do. The cock in my hand is already rock hard. I pull it out through the fly in his boxers and start to inspect it. This is the cock I have fantasized about for years, and it's finally in my hand. It's about as long as I had hoped, probably right around 7 inches, but much thicker than I imagined. Looking up at him and slowly stroking his cock, I say, "Is this all for me, Mr. Wright?" He starts to answer as I pull it down toward my mouth, but falls silent as I lick up the length of it, starting down at his balls. When my tongue reaches the head of his cock, I run my nails up his stomach and chest before engulfing his cock fully. I can feel the tenseness in his muscles melt away as my mouth covers his cock. I realize I have never had a cock this thick in my mouth before, and I slowly slide it deeper and deeper, testing how much of it I can fit. When I've reached my limit, I slowly and sensuously move my head up and down on his cock, applying pressure with my lips and running my tongue around the sensitive tip. He runs his fingers through my hair, occasionally pushing down, although gently, on my head to take him deeper. I allow him this little bit of control, knowing that later he won't have much. One thought keeps circling through my mind as I feel his thick cock pulse in my mouth, "I'm blowing my boss." The thought seems to drive me wilder and I start to move my mouth more quickly up and down his cock, squeezing and massaging each of his balls. He moans loudly and thrusts his hips up toward me, forcing me to take him even deeper. I feel my gag reflex start to kick in, so I wrap my hand around him and stroke him while focusing my attention on the tip of his cock. Still stroking him up and down, I pull my mouth off his cock. "I love feeling you throb in my mouth, Mr. Wright. mmmmm, you want to fuck my mouth, don't you? You can if you promise to be a good boy and not go so deep." I place his cock against my lips and he pushes it up into my face. I run my hands up and down his chest, occasionally squeezing and pinching his nipples, which makes him moan even louder. I can feel every bump and vein in his rigid cock as it slides in and out of my mouth. For the first time, I notice how wet my pussy is and I slide a hand down my body and under my sexy little skirt. My fingers are instantly wet and I shiver as a bolt of electricity shoots from my pussy throughout my whole body. I massage myself now, pinching and rubbing my clit as he continues to fuck my mouth. "Oh yeah, play with that tight little pussy for me" he says. Wanting to prove to him how well I'm doing, I raise my hand to his face and let him lick my juices. I quickly replace my left hand with my right, not wanting to go too long without feeling the amazing sensation. He licks and sucks on my fingers, savoring every bit of my sweetness on them. He starts to push his hips up toward me more quickly, starting to really fuck my mouth hard. I moan while I play with myself, and I know he can feel the vibrations on his cock. I realize I need to take control back from him before he explodes. I pause from typing and read what I have written so far. I can't believe how turned on I am by this story from my own imagination. I can feel the wetness growing in my panties, but more surprising is the heat I feel emanating from down there. It's as if my pussy were being roasted over an open flame. I suppress the deep desire to touch myself, knowing I will have plenty of time for that later. I need to get this all out now while I'm inspired. I do however start to squeeze my legs together, moving my thighs back and forth; a trick in learned in college that I used to use to stimulate myself during one of my more handsome professor's lectures. I would usually rush back to my dorm room after his class and masturbate thinking about him in the nastiest of ways. One time I was even able to make myself cum right there in my seat while he was talking about the law of supply and demand. This trick has the desired effect on my pussy, sending repeating shockwaves to my most sensitive spots. I return my attention to the task at hand. Pushing him back out of my mouth, I stand up and pull a blindfold out from between the mattress and box spring. He doesn't have time to react before I slip it over his head, blocking out the light. "Now it's my turn to do what I want." I push him back a little farther on the bed and pull out the straps I had hidden that are tied to the bedposts. I quickly slide his arms and legs through each strap and pull them tight, covering each arm and leg with kisses as I go. When he's tied and stretched over the bed, I realize I never took his boxers off. I grab them and stretch open the fly until they rip apart and I throw them on the floor. I smile to myself as I stand back and look down on my boss; naked, blindfolded and tied to the bed. I take a quick moment to admire his body. For a busy businessman, his body looks as though he makes plenty of time for the gym. His abs tighten and loosen as he struggles to catch his breath. His strong arms and legs pull against his restraints, flexing every muscle in them. I gently scratch my nails up and down each arm and leg, teasing him slowly. I stand up on the bed and walk forward, placing my feet right above his shoulders. I reach down and grab the headboard as I lower myself down onto him. I adjust my feet to a more comfortable position and end up holding my pussy in the air, only about a foot from his face. I slowly lower it more and once it's about 6 inches away, he sticks out his tongue, signaling me that he can smell my sweetness. I lower my body now until his stretched out tongue is barely rubbing against my most sensitive of spots. I move my pussy back and forth now against his tongue, allowing him to scoop out drops of juice as he licks. I lower myself further onto his face until I no longer need to support my weight, just to steady it. I move my dripping pussy against his face as he excitedly eats me. He pushes his face up into my dripping cunt as much as his restraints allow him to. I moan loudly as my pussy twitches, consumed by the attack of his tongue. I grind back and forth, sitting on his face with all my weight now, smothering him with my sweetest of treasures. I barely hear him moan and groan as he devours my pussy, but can definitely feel the vibrations against my clit. I lean back so I'm pushing against his face at an angle and reach behind myself to grab his cock. It twitches as soon as he feels my fingers wrap around it. I quickly stroke him up and down while his tongue dances around my throbbing clit. I stand up over him and turn around so I can get better access to his beautiful cock. I place my knees on the bed over his out-stretched arms and again lower my pussy against his face, covering his head with my slutty little skirt. His tongue picks up right where it left off, flicking furiously over my clit and licking deeply into my wetness. I reach forward and stroke his cock, watching in fascination as the skin rolls up over the head. I start to bounce my body on the bed, pushing my soaked cunt harder against him, pinning him against the bed. He starts to run his tongue in a repeating circle around the outside of my clit, and I know I won't last much longer. My first orgasm of the day starts deep inside my body, tensing all my internal muscles until I can take no more. I allow myself to explode, grinding against his tongue as I feel my moisture intensify even more. It seems to last five minutes while I bounce on him until my clit is too sensitive and I have to dismount his face. I lay alongside of him for a moment to catch my breath. "How did it feel to eat your nanny's pussy and make her cum, Mr. Wright?" I grab his cock again, and slowly play with it. "Amazing, how was it for you?" "Amazing doesn't even begin to describe it," I say. My pussy has stopped twitching now and I'm contemplating my next move. "I had no idea you were such a sexual being," he says, still licking the remnants of my juices from his lips. "Oh, I can be more than that. I can be an absolutely dirty slut..." I pause. "...for the right person. Do you want me to be your little slut for the night, Mr. Wright?" Before he can answer, I take his cock again into my mouth, impressed by his thickness once again. "Oh yeah" he softly whispers. I don't know if he's answering my question, or just enjoying the blowjob, but I'm going to assume it's both. His cock hasn't lost any of its rigidity, and may have even grown bigger since it was last in my mouth. I suck him for a moment longer and then pull him out of my mouth to position myself on top of him. I sit on him, my pussy pinning his cock against his own stomach. I rub my pussy against his cock just as I had done against his face a minute ago. His cock feels incredible rubbing up and down the length of my cunt, and it doesn't take long before it's covered in my juices. I lean down and kiss my boss, tasting and smelling my own juices, not yet completely dry, on his face. "I love being able to smell myself on my man." I whisper to him. "It drives me wild." I raise my body only slightly and reach down between us to aim his cock up between my legs. As I sit back down, allowing my pussy to slide over the head of his cock, I realize just how big he's going to feel inside me. His mouth opens wide and he tilts his head back in pleasure as I allow him inside me another inch, and then two. I let go of his cock and brace myself against his chest as I struggle to fit him inside me. My body relaxes and finally, I'm sitting against his body, my pussy more filled than it's ever been. I sit still and delight in the feeling while I run my nails over his chest. I gently pinch his nipples, and when he shows me he likes it by moaning, I pinch harder. I have both of his nipples between my fingers when I start to move my pussy around, gyrating it on his cock. I start out only going in circles, afraid that if I rise at all off his body, I won't be able to fit him inside me again. As I loosen and get used to his size, I slowly push my ass up off of him, and just as slowly drop it back down against him. Confident that I can now take him without too much adjustment, I lay my body against his, feeling the heat from his skin. I kiss his mouth again, still smelling myself on his lips. I reach behind my back, unclasping my bra. I slide it off my arms and allow my breasts to fall against his chest. I move my body against his, moving his cock in and out of my pussy, feeling myself spread open more than ever before. As I write, my pussy is throbbing between my legs. I've already been able to make myself cum once just by grinding my thighs together, but I know my pussy demands much more direct attention. Just as I slide a hand down inside my panties, my phone rings on the desk and I'm so startled, I almost fall out of the chair. I look at the phone display and see that it's him. I try to slow my heart rate before answering, but it doesn't seem to work very well. I answer "Hi, Mr. Wright, how's your trip?" "Not bad, how are things around there?" His voice now really turns me on for some reason. I have already decided to allow myself this experience completely, so I slide my hand back down to my dripping pussy. Night with the Nanny Ch. 02 "You know I can handle anything that pops up." I'm trying hard now not to moan or breath hard, but don't know how well it's working. "Well, my conference was cancelled today; the keynote speaker couldn't make it. And it's really raining hard so I'm just hanging around my hotel room, getting some work done." My fingers are flying over my clit now and covered in my sweet juices, listening to the sound of his voice and wondering if he's really doing work, or possibly typing another story about me. "Well, hope you don't get too bored. If you do, you could always take up writing. Didn't you tell me once that you used to write in college?" It's not until after I say it that I realize how brazen it was, and I stop quiet to see how he responds. There's a long pause before he answers "I did? I mean, I did write a little, but don't remember telling you that." "Well, you must have, I didn't just guess it. But I don't want to take up too much of your time, I'll let you get back to whatever you were doing." "Alright, I'll call again tonight just to check on you guys." We say our goodbyes and I hang up the phone. I wonder if I should have done anything differently, bet decide I'm happy with how the conversation turned out. My pussy on the verge of exploding, I return to my story. This time however, I type with only one hand. I sit up slightly and put a hand behind the back of his head. I pull his head up toward me and guide my breast to his mouth. His tongue flicks and licks my nipple just as expertly as it did on my pussy. He nibbles gently as I bounce up and down on him. "Harder" I say as I pinch his nipples again. He takes the cue and bites harder on my nipple, making me moan loudly. He sucks hard, pulling my nipple out and stretching it. I mirror his movements on his own nipples, pinching and pulling on them. I'm bouncing my ass on his lap hard now, forcing his cock deep inside me. His mouth pulls off of my reddened nipple with a popping sound. "I can't handle this anymore" he says. "Let me loose." I don't answer at first, but continue to grind my pussy against his cock. "But if I let you loose, how do I know you'll behave, Mr. Wright?" "You'll just have to take my word for it." Always intending to free him, I decide now's as good a time as any. I reach over and undo the harness on his left hand, and then his right. When his hands are free, he quickly reaches back to grab my ass and squeezes it hard while he pumps his cock up into me. His hands spread my ass cheeks apart as his cock continues to thrust, faster and faster. "Now it's my turn again" he says. He sits up, making me sit up with him. His hands reach down as he frees his legs from the bonds. In one fluid motion he lifts me up off the bed and all of a sudden we're standing, my legs wrapped around his waist, his cock still deep inside me. He raises me up off of his cock and throws me down on the bed. I look up to see a fire in his eyes I have never encountered before. "If you like tasting yourself so much, then taste it off my cock. There's plenty of you on there." Smiling, I scoot forward on the bed until my mouth is level with his cock. This time, there is no slow, sensual sucking, no passionate kissing on the tip of it. I take his cock in my mouth and suck it for everything I'm worth. My hand flies up and down the length of his shaft as I suck hard. The smell of my pussy on his cock as I blow him turns me on even more and I grab his ass and push his cock further into my mouth. I am able to push past my gag reflex, and soon his cock is in my throat and his balls are resting on my chin. I take his cock out and back in deep a few times before he pulls my face off of it. He stands me up and turns me away from him. He pushes me over the bed, making me present my ass to him. I feel his hands reach between my legs and spread them slightly before I feel his cock positioned at the entrance to my pussy. His cock quickly slides into me and I allow myself to be impressed that I have grown to be able to take him so easily. As he starts to thrust into me, I really feel his thickness spreading me apart. After a few minute of his body slamming against mine, his hands spread my ass cheeks apart and I feel a finger placed on my asshole. I push back against his finger, wanting so badly for him to do whatever he wants. My pussy is positively twitching by the time his finger pushes inside my tight little ass. I moan loudly as it slides deeper and deeper. "Ohhh yes! Fuck me Mr. Wright. I love how your cock feels inside me." This must encourage him even more because he starts to fuck me harder. His free hand reaches around and grabs my tit, squeezing and pinching my nipple, pulling it tight as he fucks me. Each time his cock buries itself inside my dripping wet cunt, he runs it into me so hard I can hear the slap and feel my ass ripple. He pushes his finger deeper in my ass and I can feel it rub against his cock through my thin inner walls. I can feel his cock tighten inside my pussy and know that he's close to climax, so I urge him on. "I want to feel you explode inside me, Mr. Wright. I want to feel your hot, sticky cum fill my pussy, and I want to feel it drip out when you're done." He drops his hand down to my pussy and rubs my clit as he fucks me harder and harder. He's panting and moaning as he pushes his cock into me and massages my clit between his fingers. My orgasm starts first, and when he senses me cumming, he speeds up everything he's doing. The finger in my ass slides in and out quicker, his fingers manipulate my clit at blazing speeds, and most importantly, his cock plunges in and out of me so fast my whole body is shaking. My pussy tightens for the second time today and I try to prevent my orgasm until the last possible second. I bury my face in a pillow and scream as my body shakes violently and my pussy explodes. The orgasm affects every inch of my body, making me feel satisfied in a way I never have. His cock is pulsing and throbbing deep inside me now and I feel him tense up. I feel his cock pulse hard now as he starts to explode. My amazement in the thickness of his cock was nothing compared to the amazement of how hard he cums inside me. I feel every blast of cum shoot deeply into my pussy and it seems to last for minutes. By the time he's done filling my pussy, there is already some dripping out. We lay there for a moment before he pulls out of me. When he does, I stay propped over the bed, allowing the cum to run out of me, loving the feeling of it dripping down my leg. I look back to see that he's staring at me, watching his own cum drip out. "Thank you for fucking me, Mr. Wright. It was just what I needed." By the time I finished my story, I'd made myself cum a total of 3 times. My clit is raw as I pull my hand out of my panties and lick my juices off my fingers. I make a mental note that I have to either make the one hour trip back to my apartment to get my vibrator, or I'll need to buy a new one. I don't think I'll survive this week without one. I decide to save the story without reading it from the beginning, worried I might chicken out and not save it. I save it to his story folder and wonder how long it will be until he sees it. I go upstairs to take a shower and do my afternoon duties while I await his reply.... Night with the Nanny Ch. 03 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: Night with the Nanny Ch. 03 "Hi." I say, calmly and quietly. "Did you like what you saw?" He stares at me, dumbfounded, not sure how to respond. "Look, I'm sorry, I didn't mean..." "Shhh, it's ok." I place my hand on his shoulder. "I wanted someone to watch me. And since it was you, you get rewarded with a little piece of information." My heart feels like it's going to beat right through my chest. For a split-second I forget just how turned on I am, and all I can feel is nervous. I move closer to him, guiding his ear toward my mouth with my hand on his shoulder. I whisper as quietly as possible. "I just want to let you know that right now, as I speak to you..." I can practically feel the sweat running down my forehead " ... there is a big, black, butt plug deep inside my ass. And I love how it makes me feel." Without looking at him, I turn around and stand in front of him in line. Instantly, my nervousness is gone and is replaced with an uncontrollable desire to touch myself. I can barely walk straight, feeling my ass stretched and the heat burning between my legs. As I walk toward the counter to order my meat, I can feel his eyes burning a hole through my ass. After I get my steaks, I make my way to the coffee shop and order a mocha. I finally look back, but don't see the man I just spoke with. I wonder where he went and what he's thinking. I get my drink and head to the far back corner and take a seat, setting my basket on the floor next to me. I adjust my ass in the seat, feeling the plug move deep inside me. The feelings I'm experiencing right now are torturous. I take a sip of my coffee before opening my phone again.