Sex Story – A Babysitter After Dark

September 25, 2015

It’s the beginning of July and I have 3 months of all the time in the world but no money to actually do stuff. I still need to save up a lot of money for university, it’s stressing me out. Why can’t I be like all of my other friends at the moment? They’re spending their Saturday nights drinking shots, dancing in night clubs, getting some handsome studs to finger their tight little cunts while pushing them against the wall.

I want to be doing that all week, every week. I could be making out with a hot Italian stallion with his fingers pinching my nipples hard and his cock rubbing along the dripping slit of my pussy after a night out of drinking…

…but no. I’m not doing that right now because I’m poor.

Babysitter Required

As I sit on my desk chair in my tight lace panties and my see through vest thats clinging onto my breasts, I scroll through pages on the internet, trying to find a casual job with a decent amount of pay. The heat is starting to make me drip between the crevice of my tits, until one vacancy catches my eye. The advertisement reads:





This sounds perfect to me! I wonder if locking my 11 year old cousin out from my room counts as experience? Hah, it doesn’t matter. At least I do have some experience and that I am a minimum of 18 years old. I begin to type in the ‘reply’ box with my name, age, background, and other contact details, ending the paragraph with the sentence

‘looking forward to hear from you.’

I close my laptop and slide my almost bare body onto my bed, kicking off the sheets to expose my long flawless legs. I look up towards the ceiling and see my A1 poster of Robert Downey Jr. topless with his jeans unbuttoned. That God has it all: the face, the shoulders, the arms, the torso…now all I was to imagine his how big his bulging cock must be.

I slide my hand down to my panties as I let my fingers massage the tip of my throbbing clit; I can already feel my juices flow from my pussy. I start to touch myself, imagining Robert Downey Jr. on top of me, licking the whole region of my breasts and having his fingers toying with my fanny. I dream about his hand gliding over me as he tastes and sucks off my cum, savouring the sweetness that drools from between my thighs…

I think I get turned on massively by older men.

Introductions Made

I receive a message replying back from the guy saying that he wants to meet me for a mini interview, just to get the jist of who I am and how I would be the best babysitter to take care of his 4 year old son. I travel to the location of his home, it looks almost like a mansion. White painting, a wooden porch, a patio made out of limestone, this guy must be one rich motherfucker.

I’m wearing a beige blouse all buttoned up with a loose white skirt that goes down to my knees. I try to look as professional as I can, even though I was to rip away all of this unwanted clothing to reveal my busting tits and and firm ass in this humid heat.

I press the doorbell and wait patiently for someone to open the door. I can see through the patterned glass that someone was coming, when the door opens I can’t help but discreetly stare at him.

The first thing I notice is his eyes, they’re as blue and bright as the seas on Costa Rica. His beard is dark and gorgeous, just the perfect length for me to sit and grind against his face. His upper body looks lean and unfaltering, he can probably lift me up in the air while entering his shaft inside me from behind. He’s obviously business man material, the way that he’s wearing his pure white shirt with grey tailored trouses; a definite sign that he can buy a bigger house if he wants to.

He begins to speak.

“Hey, you must be Rebecca.”

“Yeah that’s me, you’re Matthew right?”

“That’s right.”

He leans his hand out towards me to shake mine, before he unexpectedly tugs me from his terrace to enter into his mansion.

The living room he took me into was large, with a chocolate brown rug taking over most of the region in the area. Behind the sofa where Matthew and I sit down on, I gaze over his beautifully decorated garden. The botany is filled with exotic plant life alongside roses and lilacs, but that doesn’t draw away my attention on Matthews soft lips.

“Thank you again for replying to my email.” I begin the conversation.

“It’s no problem at all Rebecca, actually, you were the only candidate who has applied for the position.”


“That’s right.”

He chuckles as he smiles at me, I can’t help but blush a little.

We continue to sit and chat for nearly half an hour about the job prospects and routine until his little blonde haired boy comes running into the room shouting “Daddy! Daddy!” That’s when I remember my theory that he’s already taken.

“So…how about your wife? Is she at work at the moment.”

“Oh, I’ve been divorced for about 2 years.”

I feel like my heart has lifted up at the same time the pulse running in between my legs has rapidly increased.

“So it’s you and your son living here?”

“Yeah I’ve spend the last few months taking care of Caleb, but I need to go back into full time at work.”

“I see…”

I just disregard the mentioning of his ex-wife and focus on the soft growl that Matthew has in his voice…maybe with his tongue, he can fondle with my wet pussy.

“So, can you start tomorrow?”

“Sure, that is no problem.”

I smile back at him as he looks at me with glee.

“Right! Well, I’ll see you here before I go to work, you’ll get paid £50 in cash every shift you’ve finished. I hope that’s alright with you.”

“Yes! That perfect for me.”

Matthew showed me to the door with a gentle pat on the back.

“Well…I’ll see you bright and early tomorrow.”

“Yeah, see you then.”

I wave goodbye as he shuts the door on me. I turn my head away and exhale out of release when I quickly look up my skirt and see the drool of my juices trickling down from my panties. At this rate, I’ll have to wear two sets of underwear when I’m around Matthew.

Cancelling Plans

A month and a half has gone by and I manage to make myself just over £300 as part of my savings. Caleb is adorable and very friendly to get on with, which you would rarely get when encountering with a 4 year old child.

I sometimes feel like I’m being watched whenever I do some housecleaning. Not in the way that there’s a possibility that the whole house is filled with CCTV surveillance but the when he comes home from work and I just need to finish off some chores, I get the feeling that he likes to stare at me, especially with my back turned and my ass in the air.

The thought of it makes my nipples perky when he turns his head slightly, possibly imagining how his cock would look if it’s rubbing the inside of my asshole. I try to hold in my giggles whenever I catch him and he looks away.

It’s late afternoon on a hot steamy Saturday and I’m in the mood for vodka and table top dancing.

I text my friends to let them know that I’m available to come out tonight to go out on a club crawl. They all message me back with phrases like ‘It’s about fucking time.’ or ‘ready to get your gash pumped up?’ crude fuckers they are – I love it.

As I’m about to sort out which skimpy dress I want to wear that will struggle to control the size of my bust, my phone begins to buzz and as I reach my hand over to pick it up, the caller ID shows that Matthew is calling me. I look at my phone with a curious look on my face before I press the button to accept the call.


“Hi Rebecca. I’m really sorry to call you quite late in the day but, can you watch over Caleb this evening?”

“Er-r…Are you going somewhere this evening?”

“Yeah, I’m having a dinner date with a female co-worker.”

My heart sicks to the pit of my stomach.

“Oh…ok, erm…”

“Please Rebecca, I’ll even pay you double!”

The proposition of raising my wages for the evening makes me turn a corner.

“Ok, I’ll be over at your place in half an hour.”

“Thank you so much! You’re such a darling.”

I release a sigh from my lips as I put the phone down. Rubbing my hand on my forehead I text back to my friends saying that I have to annul our plans. One of them replies back saying ‘Pfft, loser.’

Gee, thanks.

After the kid goes to sleep

It’s 10 in the evening and I’m just waiting for Matthew to come back home and give me the £100 that he owes me for tonight. Caleb is already asleep and I’m just leaning against the counter tops in the kitchen, looking through all the Facebook pictures of my friends having the time of their life…most of them would be back at some handsome strangers place, sucking the cum of off their lips after going deep throat on their pulsating cocks.

I hear the door opening as I jerk my head up towards the hallway. Matthew’s shirt was unbuttoned revealing his impeccable chest, as he comes closer I can get the small scent of whiskey from his breath.

“Hey, how are you doing?”

“I’m good thanks.”

He notices that I’m not my spunky self this evening.

“I’m sorry if you already made plans this evening.”

“Well…yes I did, but I knew in the end that I needed the money.”

Matthew tosses his blazer onto the sofa and walks closer to me.

“Maybe I can make it up to you.”


He comes around the counter and makes me walk back into a corner. His hands cage me as he leans his chest in towards me. Ever so slowly, he drifts his lips onto the skin on my neck and begins to kiss along the nape. I try to catch my breath quickly, thinking about what to do.

I don’t know whether he’s doing this intentionally or if he’s under the influence of alcohol. Then I think about all the other horny action my friends are having, and lift Matthew’s chin up as I dive my lips into his.

We breathe into each other’s mouths as the intensity grew between each other. He wraps his hands around my waist and slowly drags them down to get a feel of my ass. I moan into the air while my nails trail along his back. Within that little moment, things start to get rough.

He forces my back onto the counter top and rips through my shirt revealing my tender breasts, before yanking away my skirt and panties to expose my cute shaven pussy. Matthew’s cock is just begging to be released from the entrapment of his trousers. I spread my legs out further, stroking my slit and feeling the damp sensation of my clit.

He bends down to place my legs over his shoulders before he plots a course on my pussy with his tongue, licking the sides and all around as well pushing his tongue inside my tiny wet hole. I try to hold back my moans to avoid waking Caleb up, so I end up holding my hand over my mouth but this just makes Matthew nuzzle his face into my cunt harder and faster.

If he carries on, he’s gonna make me squirt all over his face and shirt. He notices that my breathing is quickening and my diaphragm is moving up and down, so he stops.

He twists me over onto my front and spreads my ass cheeks apart. He licks my asshole as I still try to hold my breath before he undresses himself to show off his majestic manhood. Teasing my asshole with his tip, he takes me by surprise by driving it right inside my ass, making me scream out a little.

This man does not waste time fucking.

I clutch hold onto the rim of the work top while he rams into my asshole over and over again. Matthew then lifts one of my legs up to get more access in between my thighs, feeling my juice sprinkle a little onto the kitchen floor.

“Does this make you feel good? Better than fucking some teenage prick in a nightclub.”

He groans into my ear.

“How do you feel when you’re getting fucked by an older man? Who knows where to touch? Where to lick and where to suck?”

He traces his hands along my slit and begins to rub, before entering his fingers inside my other whole. I feel like I’m going crazy. I feel like I’m going to burst.

“You know I’ve been thinking about you a lot. While I was out, I couldn’t help but think about eating you out rather than eating my dinner.”

My moaning increases in volume as I just couldn’t control myself any longer. The climax is near, and he knows that I am going to cum soon has his thrusting gets harder and faster.

“I’m gonna cum…I’m gonna cum…I’m gonna cum…I’m gonna cum!”

All of a sudden, I squirt all over his kitchen floor as I can feel Matthew’s load emptying his cock and filling my asshole. He continues to rub my clit while I quiver from the sensation of climaxing, until he tries to catch his breath and leans his chest against my back.

“How was that for you?”

He pants into my ear.

“That was fucking amazing.”

I whisper back.

Matthew helps me dress myself back up, still trying to feel my tits and ass before I walk to the door.

“When are you heading off for uni?”

“In September.”

“Well then…I know how to keep you occupied until then.”

I smirk back at him cheekily before he kisses my lips.

“I’ll see you on Monday.”

“See ya.”

As I make my way back home, the whole sex scenario plays back in my mind like a film screening. The only problem I have now is just trying to walk back without looking so awkward, since I begin to feel his cum dripping out of my asshole.

I’ll definitely have to wear two pairs of underwear whenever I see him now.

Zoe Jaspers
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