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The Nanny pt: 01 – The First Time

The Nanny

My Therapist says there is something wrong with me, and honestly maybe he is right. He says that people are not supposed to be attracted to the person who helped raise them. No, not my mother, my nanny…

Alyssa has always been there for me, a beacon of perfection and beauty in an otherwise cold and ugly world. Now it might sound a little cliche, a little like every other sob story, but my mom never had much time for me. When she was not drunk in a bar somewhere then she was always busy on one project or another. My dad had run off shortly after pumping my mother full of cum, making him more of a sperm donor than any sort of actual father. But Alyssa… she was there, for every play, every day when I got home from school. She was almost like family… The difference being that I never considered her family for several good reasons. After all for most of my life I  have considered family a four letter word.

No, she was something more than family, she was my everything. A lot of little kids will say they are going to marry a parent of caregiver when they got older, a treasured loved one, a mother or a father, that sort of thing. It is very common and it is cute, fuck it is down right adorable. However, when I said it I knew I was different somehow.  In my heart I knew that what I was saying, that was the truth. I wanted to be with her until the day I died.

Now I want you to understand something, this is very much a story of love, I didn’t lust after Alyssa, I loved her. Though don’t get me wrong, she was gorgeous. A long flowing mane of artificially bleached hair framed a face that was perfection itself. She had a figure that made her irresistible, and it would be more than fair to call her a knock out. Her breasts were always my favorite part of her (Freud would probably say that I have a fixation because my mother breastfed me for a grand total of 3 days before switching me to formula…), large to the point of being enormous they were easily her most notable feature. She was young when I was born, and she came to work for us when she was just hitting the tender age of 18, young and innocent. Though sadly she did not stay that way for long.

In the end, as the years passed by, she had a number of lovers and relationships, but none of them ever seemed to stick. In my wishful thinking I like to believe that it is because the two of us were meant to be together… but who knows for sure.

Our first time together, after years of not so subtle pining away after her, was sloppy, drunk, and altogether perfect…

The First Time


Ironically for as long as I had lusted after her I don’t really remember much about how we finally got together the first time. What I do remember is that I spent much of my adolescence, following my discovery of the female body (which perhaps is a story for another time), trying to catch her in various states of undress. Although I was usually unsuccessful in my never ending quest, the few times that I was successful fueled my desire for her to unparalleled levels.

I remember the first time I saw her in her panties, doing a load of laundry. She must have believed that I was still upstairs, and presumably in an effort to be efficient she tossed her pants into the load. The firm pale flesh of her buttoks, and the flash of pink cotton that peeked from between her legs as she bent over, contouring to the lips of her cunt, filled me with lust. Her effortless beauty and grace left me breathless. So enraptured was I with the sight of her exposed flesh that I was almost caught in my illicit voyeurism as she made her way back to her room to change clothes, narrowly escaping by ducking silently into a darkened corner.

Although we flirted from time to time, ok let’s be honest I flirted like crazy and she humored me from time to time, she was very scrupulous in her refusal to take advantage of the differences in our ages. Despite the fact that I struggled valiantly to win her over, not one thing happened between us while I was underage. A fact which, while unendingly irritating at the time, made me admire her all the more later on. I wonder at times if she didn’t plan her careful refusal of my advances, knowing that it would fan the flames of my desire.

When at last I was able to obtain the object of my hearts desire, much of my carefully honed skills were lost to alcohols tender care, as from what I do remember our first time was that it lacked any sort of subtlety or grace. But what it lacked in skill it made up for in passion.

Although I would like to say that our first time was magical, romantic, like something out of a story, but that would be a lie. My memories of our first time are largely obscured by a haze of alcohol induced amnesia.

Although she had stopped being my nanny years before my 21st birthday, she remained a close family friend and confidant, with many an afternoon spent together talking about our lives in the ways that only two people who have known each other as deeply and completely as we could manage. So while my mother missed my birthday party, and my friends all canceled at the last second, she was there for me like always.

When she showed up at the house, a bottle of tequila and two shot glasses in hand, I was in the middle of a pity party completely unaware that the moment that I would obtain what I had been seeking for so long was about to occur. We spent the afternoon taking shots and watching cheesy old movies.

I am not sure when it turned sexual. One moment we were talking and laughing as we reminisced about some obscure event from my childhood, and the next I had drunkenly pulled her into my lap.

She resisted at first, protesting halfheartedly, but in time her body melted against mine as her flimsy pretense of resistance caved to the desire that ran through to her core. At last our lips met, and although the stench of tequila colored both of our breaths neither of us cared. For all that she had protested at first, her mouth was hungry, and her hands grasped at my body with silent desperation. Our kisses turned more passionate, and our hands started to explore each other’s bodies. She moaned into the hollow of my neck as my hands found the swell of her breasts, clasping at her flesh through the flimsy material of her bra.

We pawed at each other, urgently striving to strip away the layers of clothing that separated us.

I remember struggling with the buttons of her blouse, valiantly attempting to undo the confounding contraption while she giggled at my struggle until at last I grew frustrated and ripped the garment asunder in a fit of passionate anger.

The image of her breasts, obscured only by the sheer lacy fabric of her bra, penetrated the drunken stupor and etched itself into my mind. The full rounds of her breasts filled my gaze, heaving with breathless desire as she waited on bated breath for my touch to come again.

The next pieces of my memory of missing, tequila having robbed me of the moments that followed. One moment I am standing over her, gazing down at an expanse of exposed flesh, the next we lay entangled in each other’s arms.

She dropped down on her hands and knees in front of me, her ass and pussy exposed. She presented her body like a bitch in heat, begging to be fucked.

What can I say? No one with a pulse could have resisted her in that moment.

The warm, wet sensation that enveloped my cock as it slipped into her silken pussy was heaven. By the throaty moan she made in response I gathered that she felt the same way. I grabbed her hips, thrusting into her wet hole with animal like abandon, all raw passion and force. The sounds of our passionate joining filled the house, her cries mixing with mine in an orgasmic symphony of pleasure and desire. Her breasts swayed with each thrust, a shudder running through her body as my cock slammed into her pussy.

It could have been moments or hours, for all that our drunken minds could tell, when her first orgasm rocked through her body. Her cries reached a fever pitch, her face flushing red as she shook and thrashed on my cock.

I seized the moment as she was caught still within the entanglement of her orgasm, limbs still responding sluggishly under the influence of her pleasure, and pushed her onto her back. Now at last all of her body was exposed to my gaze. The smooth, hairless lips of her pussy parted to accept my cock again into her. Her breasts swayed as I thrust again within her in renewed vigor. She lay back, parting her legs as wide as she was able. Her hips rocked and writhed in time with my thrusts, meeting and matching my movements with her own. Our bodies were red and flushed, a result of the mixture of our passion and the tequila, and our breath came out in ragged pants. I lost myself in the give and take of our passion, the world contracted around us until all I could focus on was slipping my cock into her.

She moaned and begged, and though the vast majority of her words were lost to ears deafened by passion, her incessant plea to be fucked harder, to be used like a whore, penetrated my alcohol addled brain, and I was more than happy to oblige her. What little restraint I had been able to muster previously fell away and I thrust into her in reckless abandon.

In the end it was this loosening of my control that doomed us, as before I had be striving to please her and I strove to stretch the moment of our act for as long as possible. But when I surrendered fully to the act I was lost. My orgasm came upon me suddenly and without warning, my cock sputtering and throbbing as it pumped my virile cum into her unprotected cunt. She moaned, a cry of pleasure and sorrow mixed all together. She came again, thrashing beneath me as my cum filled her, and we knew in that moment that we were joined now, bound together.

In the weeks that followed our tryst she tried to assure me, firmly at first but with less and less resolve over time, that what had happened had been a one time thing, a mistake of the moment. But the more that she protested, the more that her eyes and her body betrayed her. While before she had worn conservative, almost matronly clothing, hiding her curves beneath layers of clothing, now she flaunted her body. Layers of obscuring cloth gave way to low cut shirts and tight pants, until at last she could deny her desire no longer.

From that point on she was mine, as I was hers. We were joined together in the bonds of our illicit affair, and I could not be any happier…

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