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The Nanny Diaries

When a nanny finally meets her boss, all hell breaks loose.
This is a work of complete fiction. 


At the age of twenty-two I had pictured myself in college or even finishing up my years in secondary education. Never would I have pictured being a nanny. Though, I loved it, I could have just never imagined being here now.

Sean, the young boy I watch is about three years old and one of the most polite children I've ever met. At six months old his mother passed away because of reasons unknown to me. Apparently it really crushed Sean's father. So that's when he hired me. I knew from the start that he probably didn't look to much into me, and all in all we had never met. He was one of those high class business men, and spent most of his time in the office. As we had never met, and he didn't know much about me, I assumed he knew nothing of what I looked like, or my school schedule. That became obvious when my hours started getting jacked up as he stopped coming home as frequently as any father would. So then, I was practically a live-in nanny, and took my classes at night when the young boy was asleep. To be honest, it didn't bother me too much.

That day was Sean's third birthday to be exact and I had set up a very extravagant party for not only his friends but their high-class parents. Being that it was in the middle of summer, the pool was open and ready for use.

"Ana!" Sean called from the top of the stairs and I turned my eyes up to him, smiling as he darted down in his blue swim trunks. "Can you help me with my sunscreen?" He asked, looking up at me with a beaming smile.

"Of course." I replied and did just that, put the sun screen on. As soon as I was done he heard the doorbell ring and was off like a light. The first of his guests had arrived, toting their parents behind them. With a smile on my face I directed them to the back yard and told them where they could place the presents and where the adults could get their glasses of wine, champagne, or even a beer.

Soon after that the flow of people started to become heavier, and the party was in full swing. Myself though, I was dressed in a white sun dress with my light pink bikini underneath. I knew I was going to have to end up in the pool with Sean, because to him I was just another friend with a little more authority.

All was going well until another guest let himself in and I heard Sean scream. My eyes went wide as I heard the single word.

"DADDY!"

Oh damn, great. Now I didn't just have to worry about running a party, but I had to try and avoid my boss at all costs. This was a terrifying prospect.

"Hey buddy!" The tall, dark, and handsome man spoke as he scooped up his still-dry child. I even allowed myself to glance over out of the corner of my eye to size him up. He was probably about 6'5", nicely built, longish dark hair, and piercing green eyes. Well, he was attractive.

"I missed you." Sean cooed as he hugged his father, both small arms around his dad's neck.

"I missed you too, Sean." He said with a smile on his face, looking around. "This place looks really nice." He commented.

"You should tell Ana! She's been working on this for weeks." He said with a bright smile on his face.

"Oh, Ana? That's your nanny right?" He asked. "Why don't you introduce us?"

"Okay!" Sean said as he beamed, running off with a bright smile. He was all for this, and now I was terrified. I knew he was walking my way, and I tried my best to ignore him, but when I felt his hand tug at my dress a little bit I turned with a winning smile. "Daddy this is Ana!"

I could tell how surprised he was to see that I was young. I ran my fingers through my hair and I took in a deep breath with a small smile on my face. "Hi there." I offered.

"Hi." He said with a smile on his face as he shook my hand. "You've done a great job today." He commented, making me smile bigger.

"Thanks." I said and looked down as Sean asked if I would get in the pool with him, to which I nodded. "Sure."

We wandered into the back yard and I slid my dress off and stepped into the pool, watching as Sean's father, Jack, looked at me. The water from the pool slicked my hair back and when I surfaced it ran down my body, over my breasts and down my flat stomach.

I swam with Sean for a while before pulling myself from the pool, allowing all the water to rush down all of my small body.

The party was over eventually and Sean was tucked up into bed, I was wandering around and trying to clean up before I felt a hand on my shoulder.

"You don't need to do that, the maids will get it in the morning." Jack said with a smile on his face as he motioned to the couch for me to sit down.

Admittedly we had both had a little too much to drink after the party was over so I sat quietly, still in just my bikini, which was now dry.

He turned on the television and I sat, transfixed with the channels changing. He finally settled on some sort of late night comedy show, before I shivered. He took that as a hint to put his arm around me, and without any hesitation I cuddled against him, allowing him to even lay a blanket over the two of us.

We sat for a while, before we became bored and started talking about anything and everything. He was actually hilarious, and found a way to keep me laughing. It very well could have been the alcohol rushing through my system as well.

An uncomfortable silence lifted over both of us and we just took a moment to kind of stare at each other. He took that as an opportunity to lean in and brush his lips against mine, which I responded by kissing him feverishly back.

"I shouldn't do this." I said quietly as we pulled back. "You're my boss."

He smiled charmingly as his lips kissed along her neck. "You are here all the time, and I am out all the time. Neither of us get any action, why not?" He asked. And in truth, he was right. I hadn't had a good lay in over a year, and he probably hadn't had a good once since his wife passed away.

"Okay." I said with a smirk, and a small moan as his soft but talented lips, tongue, and teeth assaulted my neck. With that, he scooped me up and carried me almost bridal-style up the stairs.

Once at the top he ventured into his bed room, one I had never been in, and tossed me playfully onto the bed, crawling in after me, finding himself comfortable looming over my body.

I pulled him down by his shirt for another kiss as my legs hooked around his waist and started the slow, sensual grind against him, which caused a groan to emit from the back of his throat. I just smirked against his lips and gave a little nip to it as he slid a hand behind me and untied my bathing suit top completely, tossing it off to the ground, freeing my breasts. The cold air instantly made my nipples hard.

"Wow." He said as his eyes scanned my body, and I smiled a little bit, reaching down to slip my bottoms off as well, showing him my freshly shaved, wet pussy. He took that as an invitation to gently lower his head to my nipple, causing me to moan out and arch a little bit. His fingers slid down my body and they found themselves on my clit, working it as my hips bucked around, causing me to moan out again.

"God, Jack." I muttered and finally started to breathe normal again, until he slid a finger into me, and started to work it against my g-spot, making me moan loudly, and clasp a hand up over my mouth. I really did not want to wake up Sean.

I let him go for another ten minutes before I forcefully rolled us over and tugged his shirt off, exposing his toned chest, and my eyes scanned it when I started to kiss down his body, gently running my tongue over his flesh before I found his pants. Biting down on the fabric I removed the button, and slowly took the zipper into my mouth, dragging it down before sliding his pants off the rest of the way with my fingers tucked into his waistband. Once they were off I gently kissed the tip of his erection from outside of his tented boxers, making him moan a little bit and roll his hips. Once I got the hint I slid them down and sucked the tip of it into my mouth, running my tongue over it and flicking the underside of the head with a smirk on my face.

He was thrashing around a bit, which caused me to understand that it had been a very long time since he had had a mouth around his cock. He was throbbing in my mouth as I sucked, taking him further and further into my mouth, allowing him finally to hit the back of my throat, and give a small swallow to have it tighten around him. That drove him wild, but I continued on, fondling his balls as he moved.

Once I was sure he was about to cum I slid away from him and up his body, causing his eyes to go wide and stare at me, pleadingly. With a smirk on my face I straddled over him and started to grind my wet pussy against his bare cock. My pussy was throbbing, dripping, and hot. I really needed this man.

After I could take it no longer I slid him inside of me in one quick thrust, causing the both of us to gasp and grip for the sheets. I started working my hips up and down, my pussy throbbing around him to milk out whatever I could get. I needed him to cum, as I was almost there. Just watching him moan and squirm with his hot cock in my mouth had been driving me wild.

"Oh holy shit." I gasped out as I felt him start to throb, and he fixed me so that he was ramming right into my g-spot. My eyes wide, and my mind swirled as I felt my toes start to curl, and my body shake. I was cumming, and doing so hard.

"Yes baby." He urged as he did the same, releasing spurt after spurt of hot cum into my pussy.

Once we were both done I crawled away from him and rested next to him, looking at him for a moment or so before his arm slid around me.

Before I fell asleep, I thought briefly of how bad it would be if Sean caught us in the morning. But it lasted not long, as I fell asleep moments after.

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