The Babysitter's Itch
Chapter 1

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Mult, Teenagers, Consensual, BiSexual, Heterosexual, Fiction, Cheating, Humiliation, Cream Pie, Masturbation, Oral Sex, Petting, Safe Sex, Sex Toys, Babysitter,

Desc: Erotica Sex Story: Chapter 1 - Jesse's itch was under her leg cast and she couldn't reach it no matter how hard she tried. So she decides to scratch her other itch in the hope it would distract her from the terrible discomfort.

Jesse was bored beyond belief and dreaded the upcoming Christmas holiday with a dull sense of expected glee at opening presents in which she had absolutely no interest whatsoever. To make matters worse, she had re-injured her twisted knee acquired on the soccer field at a moment of uninspired risk-taking.

It was a moment in time that she regretted with all her heart and soul.

None of the other girls had given her an ounce of sympathy in the aftermath and she was the one that had to hobble back and forth to her classes and did her best to scratch the blasted itch that drove her crazy morning, noon and night just far enough inside her cast to be out of reach for the tools at hand.

The cast was halfway up her thigh and scant inches from her panty line protecting her virgin channel long despairing of receiving male attention anytime soon. It was less likely with the ugly hunk of plaster encasing her leg like some alien experiment from another planet. She had a lot of difficulty in the simple acts of nature and hated to ask any of the girls for assistance in going potty or even doing her more complicated duty with one leg stuck up on the windowsill like some insect with external damage. She was careful to keep the door locked in such circumstances because the thought of any other human seeing her in such a disastrous position was so mortifying that it absolutely defied description. At least in her tinkling efforts, all she had to do was to place the plastic container between her legs and press it hard against her pee-hole and hope she had the angle all figured out. In a way, it was becoming a bit stimulating for her to open her legs and start that process because it relieved the pressure on her bladder and the touch of the foreign object right at that delicate spot never failed to give her nice tingle that sent shivers up her spine as if some boy was taking liberties with her private parts.

Jesse had her share of boys doing just that in various situations and she was unable to gather the nerve to let them continue until they reached the Promised Land. That lack of fortitude left her unable to actually shiver and quake with the joyful satisfaction all the other girls described with consummate lack of delicacy just to show how submissive they were to male naughtiness.

She really envied their lack of concern for moral right or wrong knowing that a desperate pussy or a stiff cock had absolutely no conscience. Jesse could think of at least a dozen situations when she should have given the boys more leeway to make her scream with happiness and have little or no regrets at her lack of character. Most of the sullied females in her class acted like they were Miss Goody Two-shoes in front of all adults but the gleam in their eyes told the real tale of their sordid behavior. Jesse wished she was one of them and not the pathetic virgin stretched out on the sofa with one leg in a cast and lifted so high that her soft white cotton panties were visible to anyone entering the room.

Her silly younger sister Nancy wandered into the room with her boyfriend Dick and started to butter her up with compliments about this and that and the other thing while Dick kept his ogling eyes glued on her camel toe staring him in the face with her leg up high on the bureau like a wanton call-girl advertising her wares. She knew she was blushing because his growing erection was inches from her eyes and all she could think about was the time she saw her sister on her knees in the bathroom with Dick standing in front of her with a happy smile on his irritating face.

The itch inside her cast was terrible now and she wanted to rip it off and scratch until she could smile as happily as her sister’s foolish boyfriend.

She listened to Nancy with half an ear trying her best to ignore the fact that Dick was now on the other side of the bed and his hand was resting accidently on her over-heated cheeks like some invader with total disregard for her feminine privacy. She hoped her sister did not see the way her bottom tensed up and she hoped the quilted cover hid the way he was groping her gaped cheeks with fingers that knew no shame. This was the first time he had taken such liberties with her and she loved every minute of it. However the fact that her sister was on the other side of the bed and could almost inhale her sister’s female heat stirred by her boyfriend’s assertive explorations made Jesse extremely nervous about trouble developing too fast to stop like a runaway train on a downhill track.

“Jesse, Dick and I just have to go to this fantastic party out on Mister Lloyds yacht because it is in nothing but swimsuits and I have that new bikini I bought just for the holidays. I hate to ask you, but can you take my place babysitting the Anderson twins tonight. It is only until midnight unless they get home late from some boring dinner out at the country club. Mrs. Anderson is a bit of a drinker and once she gets to telling stories, she can put away a whole bottle of wine. I feel so sorry for her poor husband Mike. He has to almost carry her up to her bed some nights she is that out of it. It makes me so upset that I swear I will never have more than a beer just to show I am one of the crowd.”

Dick’s hands were partially inside her feminine folds now and she did her level best to pretend she was listening to her sister intently. Jesse felt her juices start to bubble up and all she could do to cover her state of delight was to tell her sister,

“Of course, Nancy, I don’t mind. I have to borrow some of your clothes because I don’t want the Andersons to think I am too old for babysitting. Do you think I could pass for a teenager again?”

Jesse was only three and twenty, but in her sister’s eyes she might have well been an old maid with a moustache growing above her upper lip.

Right at that moment, the adroit Dick touched her trigger point and she sighed with blissful confirmation of a shuddering orgasm. She pretended to cough in order to hide her satisfaction and Dick hastily withdrew his hand not certain if he had hit pay-dirt or not. Nancy was so enthused by her sister’s agreement to fill in for her that she leaned down and kissed her cheek with heartfelt joy because the bikini party was going to be the highlight of the holiday and she was certain to be seen by oodles of eligible men all yearning for delectable teenaged flesh. That alone was enough to make her slightly wet down below but she was not going to tell her silly boyfriend Dick because he would just tell her to “bend over” for you know what.


The Anderson house was well-lit with Christmas decoration both inside and out and the huge Christmas tree was perfectly visible from the curb like a beacon of seasonal celebration. Mrs. Anderson was all bubbly with good will and never even noticed that it was Nancy’s sister and not Nancy herself. Mister Anderson did notice mainly because of her ugly cast and her short skirt borrowed from her sister to make her look a few years younger. When she bent over to shed her boots, her holiday panties were on full display with little Christmas trees decorated with candy canes and candles with bright lights at the very tip. She could tell Mister Anderson was equating her panties with a Christmas present he wanted to open without his wife’s knowledge at the earliest opportunity. That depraved thought ran through Jesse’s mind like wildfire and the message sent a signal to her private female parts that this evening might develop into actual action of the most sensuous nature.

After the Andersons departed for the booze-fest of a dinner, Jesse sat watching a silly sit-com on the television and then decided to hobble into the master bedroom after checking that the twins were still sound asleep in the nursery. The huge king-sized bed had a mirror in the ceiling that convinced her that the Andersons were a lot more fun than the average suburban families with conventional humping only on Saturday nights. She carefully fiddled inside their bedside bureau and extracted a twelve inch dildo with attached straps. It looked from the length of the straps that it was Mrs. Anderson that would wear the strap-on and apparently she was using it on her husband or perhaps some lucky female companion with anal interests. The thing was spotlessly clean but she detected the musky scent of recent use and reached out her tongue to taste the tip. That was enough to set her itch off again under her cast and she rubbed her slit instead because she knew she wouldn’t be able to reach the site of the itch until the cast was taken off. The long thick pole slid effortlessly between her legs aided by her shameful excess of lubrication betraying her desperate need for a good hard cock in her secret garden.

She moved the thing back further and allowed it to probe her crack with dreadful precision. Jesse moved back against the thing and felt it push her sphincter muscle aside like defense without any hope of success. Now she felt fully stuffed and the feeling was making her innards churn with anticipation of deeper penetration.

The sound of a car in the driveway made her jump up off the bed and she hoped she didn’t leave any evidence of her guilty depravity. Jesse wiped the dildo off with tissues from Mrs. Anderson’s bureau and shoved the thing back into the bottom drawer with a jumble of skimpy thongs.

She limped back out to the sofa knowing her heated pussy and scent of female passion was too strong to be overlooked so she sprayed her hair with some of her sister’s scent that she “borrowed” just in case it was needed. It seemed overpowering to her but it was better than the alternative of being discovered as a degenerate sinner.

Mister Anderson came in the front door carrying Mrs. Anderson just like her sister had described to her. It looked almost like they were newlyweds on their honeymoon except for the fact the wife was snoring to beat the band and looked like she would be in slumber-land for the rest of the night.

Shortly after that, Mister Anderson came back down the stairs and told her,

“I am afraid my Mabel will be out for the duration. Would you mind staying overnight to look out for the girls just in case they might wake up?”

Jesse nodded her head in agreement and replied,

“I can sleep in my undies right next to the nursery if that is all right. Unless your wife has a nightie I can borrow because we seem to be the exact same size.”

She followed him to the spare room and when he handed her the silk nightie, she asked him to help her get it on because of her silly cast and her inability to stand and dress at the same time. He looked at her a little strangely and helped her out of her vest and her mini-skirt leaving her standing there in her Christmas tree panties and push-up bra. She rested her hands on Mister Anderson’s sturdy shoulders and he pulled her nightie down over her hips patting her bottom with hands that sent a message of pent-up desire to stretch her womanhood to the limit with his married cock. He was already semi-erect and when he mauled her ass cheeks with his hands, she saw that the huge thing stood up at a sharp angle pointing almost up to the ceiling at attention and ready for immediate action.

He spun her around and told her,

“Grab hold of the bed rails and don’t move unless I tell you.”

She spread her legs and hoped her leg with the cast would not get in his way.

A moment later she felt his shaft enter her from the rear and her fears were washed away with the juices from her greedy slit. Jesse knew she was groaning and moaning in a very unladylike fashion, but she couldn’t help it and just let Mister Anderson pump her full of married man cream until it ran back out in guilty evidence of her naughty submission.

In fact, she gave Mister Anderson several repeat performances using all of her openings like a dedicated babysitter devoted to serving her employer.

His parting words the next morning filled her heart with special speculation.

“We would like to have you again next weekend. Plan on staying overnight because it will be a night filled with lots of hard work.”

She smiled all the way home and suddenly her itch didn’t bother her at all any longer.

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