Game Night: A Naughty Nanny Story

*** This is a stand alone story starring Jeannine, the Naughty Nanny. Although it can be read alone, you will understand references better, if you read the previous stories. In this story, Jennine gets to know her bosses’ son better, and discovers that she will now be the main attraction during their incestuous family game nights. I hope you enjoy. ***

Chapter 1: Setting up the game

My mind is still reeling. “How the FUCK did I find myself in the middle of THIS?” I have had this same thought far too many times before, in my short 19 years of life. In fact, it was many of those previous times, that forced me to leave my small town in Belgium and come to America. This job, as a nanny for a rich family in California, seemed like the perfect way to get away from my sexual mistakes of the past, and start over fresh. How had my plan spun so far out of control, in just a couple of months?

At just over 5 foot tall, I am short and very petite. However, as one of God’s little jokes, he cursed me with a very large chest and full round ass. As if over night, my petite gymnast body, became unbalanced by tits that grew to be 34DD, and a full round ass, that would make the Kardashians proud. Having always been shy and timid, I was not prepared to deal with how popular, I suddenly was. I was so flattered, that so many guys wanted to be my friend, and take me out on dates, etc., but I didn’t know how to handle it.

Having always been so shy, I was not comfortable saying no, to any of these guys. I was also afraid of losing my sudden popularity. As a result, I found myself being pushed into many sexual situations, that I was not prepared for. Another thing I discovered about myself at that time, was that fear and excitement seem to short circuit my brain, and I have overpowering sexual reactions, to forceful dominant people. As a result, the guys I was with, discovered that they could get me do more and more adventurous sexual acts. To them, it seemed like there was nothing I would or could say no to.

To make matters worse, the guys apparently shared their experiences among themselves. Maybe they fed off each other, because I discovered that each one pushed me into more and more extreme sexual situations. It all exploded on me, when I found myself, basically being gang raped at a drunken party. I can’t really say it was rape, though. I never actually said no, and it was VERY obvious to all, that I came very hard, over and over, throughout the night. That was the straw that broke the camel’s back. When word of this drunken orgy got around our small town, my mother heard about it and forced me to take the position as a contract nanny in America.

With that in my recent memory, I should have known better than to respond to my boss’ sexual advances. Maybe it was my naturally submissive nature or the fact that he is quite hot, and I had not been fucked since I left Belgium, but when he came onto me with such force and dominance, I couldn’t resist. My wildly sexual response, told him all he needed to know about me. He knew that he owned me completely and I would do anything and everything he wanted. In addition to being the live in nanny, I was now his live in sex slave. Apparently, the Wolf family was very open and adventurous about sex, because he not only shared with his wife, what he discovered about me, but he also shared his sexual control over me, with her.

I didn’t have much time to process my thoughts on being James’ and Marie’s personal sex servant, when they started to basically whore me out to many of their friends. Then, as I was getting used to all of THAT and trying to get control of my out of control thoughts, and almost constant sexual arousal, I met the Wolf’s college age son. I didn’t even know he existed, because he was so much older than the other children, I was hired to care for. Additionally, he was already away at USC, when I start the position. Because he looks so much like his father, I didn’t realize it wasn’t James, and I accidentally tipped my hand to Jake, that I was his father’s sexual plaything.

Jake quickly showed me, that he didn’t fall far from his father’s tree. In fact, he was just finishing his brutal fucking of my throat, when his father walked into the house, just as Jake was cumming all over my face. To my shock and surprise, James joined his son, James fucking my mouth, while his son sampled my pussy, for the first time. I am not sure if I was more ashamed when they “high fived” over me, as they fucked me between them, or when I orgasmed HARD from it. Of course, none that maters, because I was FAR more mortified, when Marie walked in on this, and then joined in.

As my brain often does when I am overwhelmed with sexual stimulus, it shut off completely. I was just a lump of wild, sexual responses. With my sexually desirable body, and my seemingly limitless, willingness to sexually please others, the Wolfs decided I was to become their new favorite activity during “family game nights”. When I heard them say something about family game nights, I was thinking of wholesome family fun, sitting around playing board games. I couldn’t be farther from the truth.

Chapter 2: The game is afoot

The Wolfs wasted no time in setting up the first game night. Since the younger children were already planning to spend the weekend at their Grandparents’ house, tonight was the perfect night to jump right in. As James is leading the children out to his Range Rover, Marie tells me, “While James is gone, I want you to go up to your room and get dressed, into the things I laid out on your bed. You can only wear what is on your bed and you MUST wear everything that is on your bed. Is that clear, slut?” “Yes Miss,” I respond and almost run up the stairs.

When I get to my attic room, I don’t know what to expect. I definitely wasn’t expecting what I found. On the bed, is a pair of sheer white stockings with a white lace garter belt, and a pair of white 4 inch heels. None of this surprises me. What shocks me though, is the white leather collar with the word “slut” in raised red letters, and another thing, which looks like a butt plug with a long tail attached to it. I pick the tail thing up and look at it. Yes, it feels like real fur and it definitely is a butt plug. “What the FUCK do they expect me to do with THIS?” I want to scream.

I quickly dress, and look at myself in the mirror, as I clip the collar around my neck. My eyes fixate on the word “slut”. I think about all of the times I have been called that. I think about how many times I have been on my knees with cocks in my mouth or in my pussy and ass, while guys, and even other girls, called me slut. Is this really what I am? Is this really all I will ever be? I came so far away from home, to get away from being that slut. How did I end up being a different slut, here? Or am I just the same slut? And why the FUCK is my pussy so fucking wet, as I think about this.

I see the slut in the mirror, she is tracing the wetness with her finger, along the swollen, glistening groove of her pussy. I have to agree, “She is a slut. Look at how she can’t keep her fingers away from her needy cunt, as she thinks about all the cocks and pussies she has pleasured. Look at the lust in her eyes, as she fantasizes about all of the cocks and pussies she still wants to please.” I watch as the mirror slut pushes one finger into her pussy. Mmmm, see how she gasps and moans. Look at her other hand trace up her stomach, to trace around her full, round, heavy tits. See how her nipple grows and hardens, as she traces her finger over it. See how she GASPS when she suddenly SQUEEZES her big tit. Mmmm, see how she begins to fuck her fingers faster into her cunt, as she pinches and pulls her nipple. I see all of this and I decide, “Yes, she is a slut… She is everything that everyone says about her…”

SLAP, the sting of a hand spanking my bare ass HARD, rips me from my aroused thoughts. “What the FUCK, you shameless whore??? We are waiting for you downstairs, and here you are masturbating, as you look at yourself in the mirror. You are fucking insatiable,” Marie scolds me. I blush bright red, as I realize, that the shameless slut in the mirror, is me. I cum HARD realizing this. Marie sees this and realizes that I actually orgasmed, as she was scolding me. She SLAPS her hand HARD on m swollen, sensitive pussy and tells me, “You are incredible. You have absolutely NO shame. And why the fuck don’t you have your fucking tail on?”

I see that Marie has the butt plug tail in her hand, just as she pushes me forward. I fall forward, catching myself with my arms on the bed. I feel her shove the tail butt plug into my sopping wet pussy. She fucks it in and out a few times, to get it well lubricated. Then she pushes it hard, into my unprepared butt. I HOWL in pain as the thick plug forces me open suddenly. Thank GOD I am so wet and she was able to lube it with my cum. I think I would be bleeding if she did that to me dry. Still, I feel like I was punched in the guts. She pulls on the tail, to make sure it is fully seated in me. It pulls out just enough, so that when she releases it, it POPS back into me, making me GASP. Pleased with her work, she turns and walks out the door telling me, “Hurry up now slut. The games are about to begin.”

On shaky legs, I hobble down the stairs, as quickly as I can. When I enter the family room, I see Marie, James, and Jake, all stripping off their clothes. I am already panting from running down the stairs after being caught masturbating, so when I say it took my breath away, it is actually very accurate. Seeing mother, father, and son, all getting naked together in the family room, feels surreal. I guess Jake is from his father’s first marriage, so Marie and Jake are not really mother and son, but Jake is definitely James’ son. So, why am I the only one here, who feels weird about this?

Seeing James and Jake naked, I am quickly reminded, why I so easily fell under their control. They have similar, muscular bodies and both have large cocks, with Jake being, maybe an inch longer than his father. I have had each of their cocks in my pussy and ass separately, and each has been in my mouth, while the other was in my pussy. However, I have not had one in my pussy, while the other was in my ass, at the same time. I am sure that this is not far off, and I suddenly fear how those two big cocks will tear me in half. Then, I suddenly feel a gush of wetness in my pussy, hoping for it. I want to so badly to touch myself, thinking about that. The only reason I don’t, is because I know Marie is just waiting for the next opportunity to punish me.

As if reading my mind, I see a look of pure evil on Marie’s face as she drops her dress off her body, and winks at me. I can’t look away. I feel like a mouse, about to be eaten by a snake. I watch anxiously, as she reaches back to unclasp her bra and let it drop to the floor. I notice how hard her nipples are already. I find myself remembering how Marie’s tits felt in my hands and under my lips. They are not nearly as large as mine, but they are full and very perky, especially for a woman as old as she is. I mean, she is like almost 40 or something.

A tugging on the tail, stuck in my ass, snaps me out of my thoughts about Marie’s body. I turn to see Jake experimenting with my tail. He laughs and tells Marie, “Nice touch Marie. I like how it makes her look like a sexy little animal or something. It should also keep her ass open nicely, for when I need it.”

“With that monster between your legs, she is going to need all the help she can get,” Marie responds, as she lets out an evil laugh.

I look over to see Jake swinging his big thick cock around in circles, like a club, as he tells his step mother, “You always love seeing girls struggle to take my big cock, don’t you mommy dearest? Almost as much as you like feeling it inside you… And I gotta say, I love that look of surprise, every time I bottom out in you. I also love that look of fear, like you are sure I will rip you apart, you feel so full.”

“I do love my big cocks… both yours and your father’s,” Marie tells Jake, as she reaches over to take his big cock in her hand, It looks even bigger in her small hand. I can’t take my eyes off it, as she SQUEEZES it and then weighs it in her hand, as she tosses it up and catches it several times. It makes a loud THWACK sound on her her palm each time. I feel James walk up behind me, as I am watching Marie, playing with her step son’s cock. I feel James’ cock growing between my legs, and slowly pressing along the groove between my ass and pussy. I feel him slowly saw his cock, back and forth, sliding against my sensitive groove, as he reaches around to cup my full tits.

I moan loudly, suddenly overcome by the feeling of James hands and cock on me, as I am watching the wicked display, of Marie stroking her step son’s cock. I feel the heat of James’ breath on my neck and cheek. I feel how excited he is getting, watch his wife appreciate his son’s big cock. As I watch Marie slowly sink to her knees, my breath catches in my chest. I realize that Marie is about to take her step son’s cock into her mouth. The room is completely silent, except for our excited breathing, as Marie takes the head of Jake’s cock into her mouth. She closes her lips around it, and sucks, and licks the head. Her eyes close, as if she is relishing this moment of feeling that big cock head in her mouth. The look of bliss on her face, makes me feel immediately jealous. I want that cock in my mouth.

I am so captivated by the site of Marie sucking Jake’s cock, that I almost don’t realize, James is pushing his cock into my wet and VERY ready pussy. I hear him groan, as he lets me know how very satisfied he feels by the tight, hot grip of my pussy on his cock. He starts to push into me and fuck in rhythm to Marie’s bobbing of her head on Jakes cock. I see this and it almost feels like my pussy and Marie’s mouth are one. It is such a sensory experience, I feel like I can’t hold back my impending orgasm. Marie must see this on my face, and tells me, “First rule of family game night is, who ever cums first, has to pay a penalty, decided by the last one to cum.”

I am not sure if it was my already overstimulated condition or Marie’s implied threat, but at that moment, I have an explosive, leg weakening, heart stopping orgasm. I feel James grab me with one hand on my pelvis and the other grabbing my tits, to keep me from collapsing on the floor. A part of my brain is telling me that I lost, but many other parts of my brain are telling me I soooooo won.

I look up from the floor to see Jake start to spasm and twitch. I see Marie sucking her cheeks in and swallowing rapidly, to take in all of Jakes cum. Just then I feel hot spurting liquid, splash on the back of my neck. In response, I look back, just in time, to see and feel James shoot two more spurts of cum, one on my face and one more on my tits.

I hear Marie say, “I guess I won… and since Jeannine is clearly the loser, I get to pick her punishment.” Her statement combined with her evil laugh, sends chills down my spine. Marie has repeatedly showed me, that she REALLY enjoys sexually humiliating and hurting me. So, why the FUCK does the thought of her punishment, excite me so fucking much???

Marie announces, “Well, since James did not get to participate in our whole family fucking of Jeannine yesterday, I think he should be rewarded with that pleasure today. Since you just got done with the whore’s sloppy cunt, why don’t you take her ass this times, James. Jake, you are bigger than your father, so maybe you can still feel something in her sloppy cunt. I will smother the cunts face with my pussy. When I say “switch” James, you will move to her mouth. Jake will move to her ass. And I will slip into my little friend, and fuck her cunt with my strap on. At the next “switch” We all move in the same rotation. If the slut is still conscious, maybe we will complete this cycle again…”

I am stunned into silence, as Jake lays back on a large ottoman, and pulls me onto his huge cock. Even though I am very wet, and have already been fucked by his father, his cock feels like a battering ram, pushing up into my guts. He grabs me around the neck and pulls me down, so that my chest is squashed on his chest. I suddenly feel someone POP the tail butt plug out of my ass. I feel hollow. Then I feel someone spreading my ass cheeks, and pushing several wet fingers into my sensitive ass hole. The fingers are quickly replaced with a thick cock. James wastes no time pushing his large cock into me. I immediately feel the difference, because I am already so full and tight with Jake’s large cock inside me. My whole body shivers with the electric jolts that shoot through me. I feel like I am being torn apart. I start to scream out, but my scream is muffled by Marie’s pussy suddenly smothering my mouth and nose.

As my scream turns into a sudden need to breath, I am terrified that I can’t get any air. Marie is literally smothering me with her pussy. I reach up to try to push her off, but unseen hands grab my arms and pin them down. At the same time, I feel Jake and James start to fuck in and out of me with increased speed and urgency. The sudden thrusting into me, makes me gasp, and I feel more desperate for air. My fear spikes, as I start to think that I will suffocate, if Marie doesn’t let me breath soon. My mind races. I am overwhelmed with this thought, that I am actually going to be fucked to death. As if understanding my fear and wanting to increase it, Jake and James fuck even harder and more brutally into me. I feel them slamming into me at the same time, crushing me between them, brutally beating up my guts.

Just as I am feeling like I will pass out, I hear Marie shout, “SWITCH.” I feel James pull out of my ass. His cock makes a slurping, POP sound, as he pulls out. Then, Jake almost tosses my body off of him, as he pulls his cock from my pussy. Most importantly, Marie pulls her pussy off my mouth and nose. I suck air desperately. I look like a fish out of water. I am not sure how long I laid there over the ottoman, catching my breath, but it must have been long enough for Marie to slide on her strap-on dildo. As Jake easily lifts me off the ottoman, Marie lays on it. Jake lowers me onto his step mother’s very large strap-on cock. Then, as he holds me down on it, he spreads my ass cheeks, and pushes his large cock into my already gaping ass. His cock is very large, but I have had it in my ass already. However, this is offset by the fact that Marie’s strap-on is already filling me so full.

The pain is immediate and STRONG. Again I SCREAM, but just as I open my mouth to scream, James shoves his cock deep into it, and it pushes into my throat. As I gag and try to breathe, I hear James say, “My GOD, I love how her screams around my cock feel. It is like the best vibrator, combined with the tightest, wettest pussy. And the way her throat squeezes around my cock, as she struggles to breathe, WOW, it is like a shiatsu massage for my cock.”

I hear the words, but my oxygen starved brain can’t understand them. All I can think is “air, PLEASE…” and my whole body seems to spasm and clench. Feeling this, Jake says, “WOW, you should feel THIS… She is SQUEEZING around my cock so tight. I have never felt anything so tight and hot on my cock.” Marie laments, “I am sorry that this strap-on cock isn’t real. I would love to feel our whore CLENCHING around my cock.”

Apparently, all of my clenching and spasming pushes James and Jake over the edge. Almost simultaneously, I feel James’ cum surge into my throat, while at the same time, I feel Jake’s cock grow even bigger in my tight ass, and then I feel the hot surge of his cum, shooting deep inside me. All of this overwhelms my short circuiting body, and I cum so hard, I feel like my heart actually stops. I collapse on top of Marie, stabbing her fake cock DEEPER inside me. This sets off additional explosions of pleasure, and I feel completely overpowered by the strength of my orgasm.