Bangin’ the Babysiter

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by Cristiano Caffieri

Blair Somerby never really liked his first name. He thought it sounded too girlie. Coincidentally, Harley Bensen like her given name about as much being cavity searched at the airport (never, ever try to be funny with customs officers). She perceived it as far too masculine. However, one day these two much unloved monikers would lead to some pretty major whoopee!

Blair had just turned eighteen and was just a few short, boring weeks away from finishing high school. At that same time, his widowed father, Stephen, was being called away to South Africa on business. He would never reveal the exact nature of his business but he was reputed to have a very large diamond-carrying anus.

When Blair heard the news of his father’s imminent departure, he smelled “huge blowout party!”

When Blair’s pater told him the news, he feared, “huge blowout party!” Poor dad remembered what he was like at that age. Stephen was the hit of all the school dances due to his ability to smuggle in an entire keg of Budweiser up his colon.

The trip was going to last for five or six weeks. Something had to be done if he was going to still have a house left standing when he arrived back home.

Obviously, you can’t ask an agency to provide a babysitter for an eighteen-year-old so his father decided to engage a temporary live-in companion.


Gladys did not like her job. She was having trouble with her boyfriend. Her hangover did not seem to be responding to the aspirin and Alka-Seltzer. The phone rang.

“Hello,” she Rosanned into the receiver.

“Hi, this is Stephen Somerby and I’m looking to hire a temporary live-in companion.”

“Who for, sweet heart?”

“Blair Somerby. It will be for 4-5 weeks, starting immediately.”

“Immediately, huh. Well, we have Harley Bensen available. 25, very responsible.”

”Sounds great. Listen, I have to go, I’m at the airport.”

“Wow, that sounds great. Listen buddy, I don’t know you but, sight unseen, I would blow you to take me with you.”
”What? They’re calling my flight.”

“Never mind. Just catch your fucking plane and leave me to my misery.”

Stephen had to hang up to go empty his water bottle, take off his shoes, remove his computer from his bag, put his phone and change and keys in a separate container, remove his coat and belt, show strangers what he looked like under his clothes in an x-ray, have a some-guy-only-hired-yesterday-off-the-street pat his inseam and have a young attractive lady inspect his packed underwear and embarrassing ointments.

When the taxi turned up at the front of the Somerby estate, Blair sighed despondently. He was incensed that, at the ripe old age of eighteen, he was not allowed to look after his own affairs and possibly have the odd mind blowing mini-rave. However, when Harley Bensen stepped out of the cab he took an enormous deep breath, filling her chest with the air of a thousand springtimes, all was forgiven. To put it mildly, Harley had breasts most Greek statues would envy!

Blair fell over himself to open the door and greet his “babysitter.”

“Welcome to our humble home,” he blurted out, smiling like an inebriated game-show host.

Harley looked confused and suggested that she might have the wrong house but Blair assured her that he was indeed Blair Somerby and grabbed her suitcase so she couldn’t get away. Before Harley had time to check in with the office or change her mind, her surprise live-in companion was halfway up the stairs with her heavy luggage.

After some wrangling, and every molecule of charm in Blair’s body, the thoroughly beguiled boy convinced his skeptical ward to agree to stay on for at least 24 hours. She would then decide then whether to call the company for a replacement or continue on in his father’s employ.

Haley had to admit that Blair was a pleasant and polite sort of fellow. He was mildly amusing and just possibly had a nice tight ass hanging around in those jeans of his. “He’s only 18,” she told herself. “better be a good girl and keep it in your skirt.”

Meanwhile, Blair was on his best behavior. Actually, way, way beyond his best behavior. He’d never been this considerate and selfless in his life! As he prepared her some gourmet coffee and picked out the very best shaped biscotti, Mr. Gallant couldn’t help but go over in his head how great she looked in that thin cotton dress and the legs she had popping out of the bottom of it. He also spent some time estimating how great her boobs would feel through that flimsy but fetching material. Then Blair was compelled to devote the next five full minutes of brain activity to state capitals and brands of shoe polish in order to shrink his boner to the point where he could go in the next room and serve refreshments.

Their afternoon snack was a very pleasant affair. Blair imagined her glistening puffy lips wrapped around his locked-and-loaded custard cannon and Harley wondered why he needed a full-sized plate in his lap to eat one tiny piece of biscotti. 

That evening, they prepared supper together. Blair quite liked the experience. It was his very first time and he wouldn’t attempt such an a-typical feat again until he was 32. Harley stirred the pecatta sauce to the correct thickness while her sous chef selected a very nice pinot noir for her from his father’s “special occasion” wine rack. He even managed to dig out a couple of candles from the emergency supplies to place in the middle of the table. Harley was a little taken aback when she walked into the dining room and saw, what appeared to be (and let’s face it, WAS), preparations for a romantic evening.

After a very convivial meal, they sat on the sofa together. Harley made sure to keep a safe distance and several throw-pillows between them. The deal was, he got to pick the pay channel and she got to pick the show. He chose STARZ and his blushing supervisor tried in vain to select the tamest fair on the menu.

Blair eagerly clicked the “enter” button. There was a college girl’s shower scene under the opening credits. Heaving breasts and full-frontal johnnies were everywhere Harley tried not to look. Blair’s pants became somewhat tight and her thin, thin cotton dress was suddenly stifling. 

“How am I gonna get a little closer to the only woman I’ve ever loved?” puzzled the junior Don Juan as the people on the screen decided to fire up the heat up on the hot tub. An idea popped! Up he got and darted off to the kitchen for something sweet. When he returned he was carrying a hundred dollar box of chocolates that his father had purchased for his aunt’s birthday. And down he plopped on the other side of the great throw-pillow divide. Blair was now agonizingly close. Their thighs touched as she scanned the upper tray of pralines.

“Don’t jump the gettin’-some-gun,” he resolved. “This is going to take tact and patience.”

At that moment, a woman jumped out of a cake, on screen. Blair pretended to be startled by it and grabbed her leg. Interestingly, it didn’t get lifted off. Hmm. A good sign?

He could feel the warmth of her body and smell the scent of her perfume but what he really, really wanted to do was put his fingers inside her trout cage. The big question remained. When to make his move? This was far from an open-ended opportunity. She may not want to watch a second film, so he dropped a chocolate into her lap.

“Oh, I’m sorry,” he apologized while sticking his hand deep between her legs. The feel of her upper thighs was intoxicating. He fumbled as much as possible, like he was chasing a slippery mouse down there and not an inanimate piece of candy. Once he’d retrieved it, he looked down in horror. “Oh no, you have a little melted chocolate on you.”

Harley, pulled her dress up deliciously high and said, “Well then, you’d better get it off me.”

Blair licked the tips of his fingers and rubbed them against her soft, silky skin. Very slowly, so the chocolate wasn’t gone too quickly. When she didn’t hurry him along, Mr. Poontang Janitor began to clean chocolate spots that didn’t exist. Higher and higher he cleaned and climbed, expecting to get slapped across the ear at any second, but he never was.

And then, much like Sir Edmund Hillary, he had reached the summit. The holy land. The shaved and unadorned holy land. As he felt his fingers squish into the moisture of her welcoming vulva he almost came. Hey, he was only 18 years-old. Harley took in a deep breath and then a slow, sultry sigh drifted out into the room from between her full and scarlet lips.

He continued to rummage through her skirt laundry and she continued to look straight ahead with only a widening of her legs to hint at any acknowledgement of what was transpiring. The more he stroked and circled, the wetter she became and the greater the access he was given to the core of her sex.

At some point, she whispered, “Just a little faster.”

Blair had never concentrated on anything this much in his life. Every ounce of his consciousness was laser focused on what was going to happen in the next minute or so. Firm but not too hard. Speed up but don’t go crazy. Watch your fingernails. Don’t say anything to break her mood. It was all about her and only her.

Harley was now getting close. She began to play with her nipples though her dress. Her breathing became rushed and her hips just would not stop squirming. Finally, the damn burst. She grabbed his hand and pushed it hard into her pussy, making her love button go off like a klaxon. Blair’s hand was now soaked and being forced to take erogenic liberties he wouldn’t have dream of doing himself. He watched her moan and tremble as the orgasm raced through her body like a stampeding herd. When the last little cum bomb had exploded, she retrieved his drenched fingers and put them in her mouth, reclaiming her nectar. 

Blair gulped, not quite knowing what to expect next.

She turned to him meaningfully and stared deep into his eyes for what seemed like an eternity. “Take off your clothes, little boy,” she instructed, “teacher wants to suck your cock.”

Blair didn’t even know if he was capable of standing after that declaration but bravely managed to get to his feet. It freaked him out a little, having her watch him like that as he stripped for her. He suddenly felt very young and slightly embarrassed. When the last sock was removed, he stood there and anxiously awaited further instructions.

“Show me how you masturbate.”


“Please don’t talk. Just do as I say and you will remember this night for the rest of your life.

That sounded like a pretty good deal. Awkwardly, at first, he began to stroke his manhood, though it felt more like his boyhood as this older, fully grown woman watched him pleasuring himself. Eventually the nut-nummies rising up from between his legs caused the nervousness to ebb.


He complied and waited once again.

“Step closer to me.”

She opened her thighs to allow him to get in tight. He could feel his knees touching the couch cushion and stopped his forward motion.

“Don’t look down at me.”

Blair felt a small warm hand on each leg as he stared at the pastoral print mounted on the far wall of the living room. Soon, small delicate fingers were teasing and tickling his nards. He may have gulped a second time. Now, he felt long and finely manicured nails softly scraping up and down his scrotum. Blair had no idea sex could be this good and she hadn’t even touched his dick yet. Eventually, his patience and obedience was rewarded. She was literally holding him in the palm on her hand.

“Don’t cum, you fucking moron,” Blair politely advised himself.

Too late. Massive spurts of salty semen shot out the end of his beaver basher hitting Harley in the eye, nose, cheek and lips. Blair’s goolies must have been working overtime because it just kept on coming (pardon the pun) until big splotches of splooge were dripping off her chin and drizzling down into her cleavage.

“Wow. Sorry about that,” he almost died.

“A little more warning next time, perhaps,” she suggested, wiping the cock snot off her face with her fingers and consuming it.

Watching her swallow his man goo caused an unexpected re-inflation of his manhood. Hey, he was only 18 years-old. Harley jumped up and tore off her dress. He’d seen pictures on the internet but sensation of experiencing a naked woman in real life, right in front of you, can’t even be imagined.

“Quick! You’d better hurry up and fuck me before that thing goes off again.”

Back down onto the couch she flopped. Her legs were splayed and all that was sacred on this good Earth and beyond was beckoning him forth like some mythical sirens call. But instead of a screaming, watery grave, all that awaited Blair was a gurgling pudding pit of ultimate ultimateness. He clambered on top of every man’s dream, floating on a sea of flawless, fecund flesh.

The entry into her inner sanctum almost set off his party-popper again but he managed to staunch a second plaster disaster. Harley grabbed onto his buttocks and almost pulled his cock up into her lungs. He tried to match her pelvic thrusts so it seemed like he was actually contributing to the proceedings. Blair had really hit the jism jackpot. Harley was undulating like a runaway Orgasmatron beneath him. She placed her tongue in his mouth with such prurient intent; it almost blew the top of his head off. His man-stick felt like it was jam-packed with Poprocks straining to ignite.  

Harley came first, with a violence that almost threw Blair off her and onto the floor. Only his vice-like grip on her ass cheeks enabled him to complete his quest. And crossing that finish line turned the bulb of his penis into a Gatling gun, relentlessly riddling her womb with cum bullets. The newly deflowered virgin lay there like a just-shot deer on a jeep hood, drained of every vital fluid in his body.

The following five weeks were the most obedient and physically taxing of his young life. She really whipped him into shape. And sometimes she just whipped him.

It was a sad, sad day when Blair waved goodbye to his live-in/stick-your-cock-in companion. Although she was gone, he’d never felt happier or more fulfilled. Now, all he had to do was explain to his father why he gave her the family car and the flat-screen from the living room.  

book number one

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THE END Copyright 2014 – 2016 Cristiano Caffieri

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