Diary, Anal, Ass to pussy, Blackmail, Boy, Coercion, Consensual Sex, Drug, First Time, Fisting, Humiliation, Job/Place-of-work, Male / Older Female, Reluctance, Virginity, Voyeurism, Written by women, Young
All characters in the story are fictional and over 18. The story itself is a figment of imagination and are based on such. Please try another of my story genres if this one does not interest you.
Her ass cheeks were visible, her skirt was that short! I couldn’t help but watch as she bent over to pick up the car keys that had just fallen from her handbag. A hint of her panties could just be seen, a deep red thong. Naughty girl!
I’d been watching her for a while now. Amy was supposed to be baby sitting me, not that I needed ‘baby’ sitting! I was fully capable of looking after myself but my parents hired her anyway. I guess they’d wanted to keep me out of trouble and hiring a leggy 24 year old with long blonde curls and the most perfect set of tits I’d ever fucking seen, was a good way to do that.....
Apparently though, baby sitting a horny teenage boy wasn’t exactly her idea of a fun Saturday night so once my parents had left, Amy invited her friends round for what she called ‘just a little gathering’.
And that’s how I ended up where I am now. Straddling my babysitter on my parents king size bed with three fingers buried deep in her tight, pink pussy.
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Chapter One.
It started about three weekends ago now. Amy had been having one of her gatherings and for the first time she’d invited me to join her and her friends. I’d been so excited, It took me forever to choose what I’d wear even though I was only going downstairs in my own home! When the time had come for my parents to leave and for her friends to come round my heart was racing and my palms sweaty. I knew this was my only chance to make a good impression on the girl I’d fancied for over a year.
The night had started so great! Amy looked amazing in her tight, low riding jeans and a white crop top so short that it barely contained her wonderful tits.When she’d first arrived that evening I’d had to hide my hard on! Her friends had brought the pills and my parents had enough drink in the house to drown us all.
It wasn’t until the pills had kicked in and all the colours had began to dance that I noticed the looks in their eyes, the snide remarks about my age and not being old enough to remember this or that. That’s when I realised why Amy had really invited me. I was the butt of her joke, the jester, there to be pointed and laughed at.
At first I was angry, raging even. But instead of getting angry get I decided to get even.
That night, I took pictures of them all, laughing away, with the pills strewn around them and bottles of my parents expensive booze spilling onto their even more expensive Persian rug.
I hadn’t actually decided or even really given thought to what I’d do with that picture whilst I was taking it. I just knew that to get even without getting caught I’d need some kind of insurance policy, a way to keep Amy quiet if needs be.
The idea had come to me just yesterday when my parents announced that they’d be going out tonight. My mother was dressed in a short, black leather dress with killer heels and my father in a suit that was at least two sizes two big for him. I can only imagine what was underneath. They think I don’t know that they’ve been swinging since before I was born, but I do. I also happen to know that in the spare bedroom connected to theirs is what they call a boudoir. I usually call it a sex dungeon but tonight I’m calling it my goldmine.
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Chapter Two.
I’d watched her walk up the drive from my parents bedroom window where we’d been talking. I had to sit on the windows legs with my leg up to hide my boner when I’d noticed the slither of red between her pussy lips. I couldn’t wait to slide my tongue between them later and the thought of her spread eagle and at my mercy was not helping stem the blood flow to my cock.
As soon as I heard my parents Audi leave the drive I grabbed my phone and found her in the
kitchen.
“So,” I started, keeping my voice friendly and light. “Your friends seemed nice.”
A hint of shock flickered across her face, gone as quickly as it appeared.
“Well, I’m glad that you enjoyed the night.” Her smile that had looked so sweet and pure before now looked fake and forced. She turned back to the bag she was unpacking leaving me to stare at her back, her ass, and wonder what it would look like naked, opened.
“Yeah, it was good. Did my parents mention the missing drinks to you?” Again I kept it causal.
“No! Did they mention it to you? I hope you told them it was your idea!” She span around so fast I swear her tits had to catch up with her body.
“Not quite. They left me a note on my bed for when I got home this afternoon.”
There was no note. My parents have never noticed what I take from the bar.
“Well? What’d it say?” The look of fear in her eyes was what I was counting on. I knew that she needed the job to pay for her student flat and her student lifestyle. And she wouldn’t want to loose that now would she?
The bullshit note had worked an absolute treat and by the time Amy was in my bedroom the pictures of her little gathering had worked even better. I told her her this would go down.
“So what?” She’d argued. “I’ll just get a job somewhere else!”
“No one will hire you after this! I’ll make sure my parents tell everyone in the village and you know just how quickly that sort of news will spread around her. Just imagine the headline in the local paper. Uni woman, taking drugs and drinking with the mayors teenage son!” That, I have to admit, had been an empty threat because I wouldn’t dream of telling my parents anything that might lead to me being cut off financially.
It was like I could see the cogs turning in her brain. A brain i never really believe she had before then.
“Fine.” She’d relented. “What do you want? A house party? Some spending money?”
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Chapter Three.
“You can’t really be serious about this!” Amy’s big blue eyes fought to take in her surroundings. I can’t say I blame her for being shocked. I’d been nigh on petrified when I’d first stumbled in here.
The deep red velvet that covered every wall matched the red leather that covered both the four poster bed frame and the handles of the whips that hung on the rack. On the front wall, facing the bed, a 50inch TV clings to the velvet. Around that TV tiny cameras were strategically positioned. The back wall was lined with mahogany draws, each engraved with its contents ranging from paddles and clamps to vibrators and dildos and everything in between. The main attraction however was the fully room, wall to wall mirror that hung above. The ceiling had been lowered for maximum viewing pleasure. Everywhere you are in here you can watch yourself fuck or be fucked. They’d thought over everything.
“I’m absolutely serious. Why wouldn’t I be? I have nothing to gain from joking. And let me remind you, you have everything to loose by saying no.”
Again her brain began to work, maybe working out how she might negotiate, find a way out of the mess she’d gotten herself into. Of course we all ready know, there was no way out and once she’d come to terms with that, it wasn’t so hard to get her panties down her legs and into her mouth.
“Moan for me.” I knew she could do nothing but with her thong down her throat and her lips taped shut. And if that didn’t keep her quiet, the silk pillowcase covering her face would.
I’d been trying to slip my pinky in with the other three fingers for the past few minutes but her cunt was so tight that no matter how many times she cummed around my hand, the last little one just wouldn’t fit. So I gave up.
Standing up I had a beautiful view of my babysitter. Her creamy white skin, her tight pink nipples, hard from the teeth I’d sank into them just seconds earlier. Even her pubic hairs are beautifully trimmed, so light a blonde that they’re barely visible.
My cock is throbbing now, raging to be freed from my boxers and I’m ready to do just that. The tiny, just audible behind the thong whimper that she lets out as my rock hard dick springs free forces me to get harder still. I forgot that silk wouldn’t keep her blinded. Maybe I should blindfold her?
“Turn over.” I’ve kept my commands short, an attempt to keep my voice disguised on the video.
Her little peachy ass is so out of proportion to her massive tits but that doesn’t matter to me. All that matters to me right now is the blonde bombshell that is lead butt naked and waiting for me to fuck the shit out of her and that’s just what I’m going to do.
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Chapter Four.
“Please,” she begs “anything else!” I can just about make out her muffled words but I cant stop now, my hearts already set on taking her anal virginity. I plunge my thumb deeper into her asshole, using her own cum to lube it.
“You want me to stop?” I ask whilst rotating my thumb slowly, working her back passage and getting it ready enough to take my dick.
“Please, yeees!” I can feel her ass tightening, struggling against the invasion. I pull my thumb out just a little to relieve the pressure.
“So you want my parents to see your party pics? Want them to know about your little private gatherings?” I waited, still carefully circling with my thumb. Her blonde curls writhe with every ragged breath that she takes.
“Anything else...just....please!” The muted begging is just making me want to fuck her harder but I want to draw this out just a little longer, give my dick time to calm down. I don’t wanna blow my first load in five seconds flat!
“Here’s the thing Ames,” forcing my thumb all the way back in, I hold still so that I can take in the high pitched squeal she gives out against her make shift gag and also, so she can hear me. “I don’t want anything else.”
Her ass is so tight against the end of my dick that I’m sure she’s trying to keep me out. That’ll only keep her here longer, give me more to edit.
I spend a few more seconds trying to force my cock past my thumb and into her and then I loose my patience.
“Open up.” The growled order comes from so deep that even I don’t recognise my voice. She doesn’t listen and I can’t wait for her to come around.
Putting my free hand against her back, I pinned her to the bed and pull my thumb out. The moan she lets out sounds like relief but I haven’t even started with her. I slide more of her wetness up between her ass cheeks whilst ramming my cock deep into her cunt. With my dick coated in her slickness, I move my hand from her back and grab both of her ass cheeks, spreading them as far as they can go. Her asshole looks raw and kinda swollen and for a second I feel sort of bad but as her hands grip mine and her nails dig in, trying to pull me away, the only thing I feel is horny as fuck as I start thrusting and forcing the thick, angry head of my cock into that same swollen, raw asshole.
Neither the thong, the tape or the silk could do anything to mute the piercing cry that came from my babysitter when I finally managed to tear my way through her anal virginity. Neither could they quieten the the screams I forced out of her as I thrust all 8 inches of my rock hard cock, balls deep into her newly deflowered, virgin asshole.