Judy: the Babysitter

by Dapper Dan

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Consensual, Oral Sex, Anal Sex, Voyeurism, .

Desc: Sex Story: A late bloomer finds her sexuality and gets hooked but good. Her babysitting pays extra dividends and then some.

This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. With the exception of the Fab 4, all characters, locations, and events in this story are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.

"Hey," I yelled, "what's all the ruckus in there kids?"

I walked into the living room to separate Billie, age two, and Sally, age four. They were squabbling again over something.

"Bed time!" I hollered again, "Time to pick up your toys and put them away."

They did a fair to middling job of that before I ushered them into the bath. It was a job getting them both stripped down, bathed, and into their PJs, but, eventually, the job was accomplished.

I carried Billie and led Sally by the hand up the stairs to their bedroom and tucked them into their double decked bunk beds. I their favorite book to read them their bedtime story and in less than five minutes, two worn out little ruffians had drifted off into never-never land.

Whew now the rest of the night is mine until Hank and Betty come home.

My name, by the way, is Judy, but my friends call me, Hey-Jude. The Beetles would be proud. I'm a senior in the local high school. I had turned eighteen back in February, lost my virginity to my boyfriend (and discovered-S E X and that I LIKED it) in April on prom night. That night is another and separate interesting story. Graduation was only two weeks away.

I've been baby sitting for spending money since I was eight. Wow! Ten years of TLCing the little ones. That's hard to believe. The Smithsons, Hank and Betty, have been one of my several steady clients since I began baby sitting. They have watched me grow up from a dweeby kid to a vivacious high school senior. I was a late bloomer, both physically and emotionally. Puberty came in early eighth grade with a patch of hair under each arm, but only a smattering of pubic hair.

Puberty also brought menstrual periods, but little other outward physical changes. Acne was nearly non existent, thank God. Tiny little mounds appeared to masquerade as boobs. Hormones were flowing and I had a healthy and high sex drive, but it remained a mostly secret one.

Fulfilling that sex drive was done in private with my fingers or a very slender (and very secret) dildo that, like a tampon, didn't destroy my virginity. I was extremely shy, introvertive, and lacking in self confidence.

All this began to change my sophomore year. I joined a number of school organizations, went to contest in several of them, got on the student senate, and of course, continued my baby sitting. The activities greatly boosted my self confidence.

But the big change was physical. My boobs began growing the second half of my sophomore year. By the start of my junior year, I had a real chest to be proud of. The rest of me filled out from scrawny to more womanly proportions also. I did, however, catch a lot of teasing about the somewhat sudden appearance of my new chest. Not everyone believed the boobs were all natural.

My self confidence grew by leaps and bounds, as did my feelings of self worth. In other words, my maturation spiked--a bunch! I started dating a next door neighbor boy during the summer between my junior and senior year. He had begun to notice at the pool that summer how I'd rapidly begun to look different.

We went together for the remainder of high school and it was at our senior prom two weeks ago that I finally gave in to him, and my own lusts and desires, and lost my virginity to his cock. In the process, as I've already indicated, I found my true love--SEX. There'd been some heavy petting up to that time, but no final intimacy before prom night.

Hank and Betty also noticed I was growing up, especially Hank. I've noticed over the last three years that Hank was paying much more attention to me than when I first sat for them. I'd catch him looking at me from time to time, especially at my newly expanding chest. Over the past year, he began making remarks and innuendoes about dating and sex, getting slowly more explicit as the year progressed.

Hank would find excuses to get close and make some kind of touching or brushing contact with me, but only if Betty was no where around. I liked it, but didn't encourage this behavior. But, I guess by not discouraging it either, I was giving tacit encouragement. That was about to change.

Now Hank is a good looking, well, stud, I guess I would have to say. He's in his late thirties, blond, and built like a somewhat aging body builder. He hasn't gone to seed, but he is starting down that road. Hank has just a hint of a paunch, but no love handles yet.

Hank doesn't have jowls either, but his face and neck are well fleshed out. His hair is starting to thin. Apparently, he does have a very large cock, or so I assume from the very large bulge that results in his pants every time he looks as me for very long. This is especially so when I'm in my bikini in the back yard around the in-ground pool with his two children.
I have two bikinis--one that is conservative, sort of, that I wear around other people. Then there's the second one. That one is an extreme, Wild Weasel that I only wear when I'm alone or with very young children such as now when baby-sitting and before any parents return.

The top is just the strings from the bottom and it widens just enough to nearly cover my nipples, but not quite. The bottom is all string too, just wide enough in the crotch to cover about three-fourths of my outer labia. It doesn't take much wetness to cause the front to sink into my pussy slit in a wedgie to expose ninety-nine percent of my pussy.

The back? That's just a narrow string coming up the crack of my ass to split into two strings coming up over my shoulders to my tits. I might just as well be naked. Depending on my posture, the "suit" gaps completely away from my body parts!

The suit makes me feel sooooo sexy! Only my boyfriend, David, and a few baby sitting charges have ever seen me in this one. Yeah, this one, the one I am wearing at the moment. Anyway, back to Hank.

For some time, he has not tried to hide his big boners he gets from playing grab ass and ogling me. Hank has a look of almost pain on his face at those times. I stifle my giggles and concentrate on the kids. But secretly, so far, I've been thinking about seducing him and fucking his brains out since I found SEX so intoxicating.

I'm now looking for new "experiences" (conquests?) anywhere I can find them. Hank was now in my sights for my next "experience". And, I really did want to find out just how well hung he was. Even though I've only seen one so far and have nothing for comparison, I think I love big cocks.

I was baby-sitting at the Smithsons again and it was a very warm Friday night in May. And I, speaking of bikinis, was still in mine, mostly. As I said, this is the very skimpy and revealing one. The kids and I'd been swimming earlier and I'd not yet gotten around to changing back into my street clothes.

I was thinking of doing so when I heard a car drive into the garage.

Oh Oh, shit! I am nearly naked and here comes Hank and Betty, damn.

It was a few minutes after midnight. And then, in walks Hank all alone. He stopped dead in his tracks and just stared openly in total amazement, mouth hanging open, eyes bulging. I'd a nipple slip that became a full boob slip (you know, a wardrobe malfunction) as I jerked to a stop at his entrance.

We stood there, face-to-face, about ten feet apart, just staring at each other. I think he actually began to drool, just a bit. He got an instant and monstrous bulge in his pants which he made no effort to conceal. His pants tented out so far, his cock must have been really hurting.

He stammered, "I-I-I had to dr, dro, drop Betty at her p-p parent's house, her m, m, mo, mother came down very ill. I came on home to be-be-be with the kids for tonight"

"Oh," I said, rather lamely, "I was just going to change into some clothes now that the kids are asleep."

I hadn't made any attempt to cover my exposed boob, or I should say boobs, because the string strap had slipped free of my other boob as well, There wasn't much to cover it with anyway.

I recovered first. I slowly turned and started for the bedroom where my clothes were. I could feel his eyes on my swaying and exposed butt as I walked across the kitchen. The bikini, as I have already said, left me ninety-nine percent naked.

And believe me, Hank damn well noticed. He jolted out of his trance an I heard him run after me. He caught me in the kitchen doorway into the central hall. He put his arms around me from behind and locked his hands on my naked tits.

"Whoa there, where are you going so fast?"

Of course, I was jerked to an instant stop. It took less than a second for me to decide how I was going to handle this. By accident, my seduction plan for Hank was underway. I relaxed and leaned back against him.

"Nowhere, Hank, nowhere," I said, giving in to my own lust as well as his.

My butt backed into his bulge and Hank jerkily moved that cloth covered missile up and down my butt crack. In a flash his hands went into motion to play over my luscious tits and nipples. My nipples exploded erect as Hank caressed and tweaked them.

Hank moaned, very loudly and said, "Oh God, Judy, I have wanted you for a very long time."

As I said earlier, by my senior year, my self confidence and my desire to express my sex drive, had grown tremendously. And, I also realized I was no longer interested in expressing that drive solo. I was already so hot my juices were flowing freely at that moment, already dripping down onto my inner thighs.

Hank backed off slightly, just long enough to pull open the knot of my Wild Weasel and drop it to the floor. I heard his zipper crash down and knew he had that bulge out in the open now.

The big stud again crushed his now naked dick into my equally naked butt. This time he guided it downward so that it slipped between my legs along my gash as I spread my legs a bit to accommodate him.

God, is he ever huge!

His arms went back around me, but this time his right hand went to my tits and his left hand went to my then fully naked and dripping pussy. With his cock sliding up and down along my butt crack and gash, with my tits getting full attention, and with fingers on and in my pussy, I was getting worked into a sexual frenzy of pure, unadulterated lust.

Except that damned zipper of his was rubbing my butt raw!

"Hank, lose the clothes, FAST!"

I think he nearly had them off by the time I turned around to face him. Not quite, but close. Jesus, what a one eyed monster that was, staring straight at me and dripping. When he was naked, I put my arms on his shoulders and jumped up with my legs around his waist.

Recovering instantly from his surprise, Hank guided his huge erect missile into my cunt hole and I sank down to his balls on that stiff piece of man meat with a loud, long sigh of pleasure and contentment.

Since we had both been leaking so much sex juices and my cherry had already been popped, the slide down was smooth and effortless. We both just stood motionless to savor the moment and the feelings. God, waves of desire and electric shocks were flooding upward from my pussy through the rest of my body. We were both moaning continuously by now.

Suddenly, Hank swung me around with my back up against the kitchen wall and started violently and rapidly to thrust in and out of my sopping pussy. I dug my fingers into his back, drawing blood. Our coupling motions increased even more in tempo. Hank's very rapid pistoning in and out of my cunt had me pinned to the wall. He was going at it so hard, the wall was vibrating from our thumps against it.

A nearby knickknack on a small display shelf fell to the floor and shattered. The telephone hand set on the wall next to us fell from its seat on the phone and cracked hard onto the counter below. My cervix was taking a pounding as Hank was getting all the way up there. What a beautiful damned cock he had. And, oh, did he knew how to use it. I was going to be mighty damned sore the next day, no doubt about it.

Hank got in more thrusts than I figured he would, he was so psyched up and horny, before we both exploded into a mutual and very messy orgasm. He must have dumped a ton of cock cream into my pussy and that, mingled with my pussy juice, was overflowing past his cock and smearing us both as the excess dripped onto our legs and the floor.

He collapsed into me against the wall and groaned, "Oh, sweet Jesus, I haven't had it that good since my honeymoon, eighteen years ago."

To boost his ego, I replied, truthfully, "Well, it is the best I've had in my short sexual life, by far. And by the way, you don't have to worry about coming in me, I've been on the pill for eight months now. I hate those damned rubbers with a passion."

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Story tagged with:
Ma/Fa / Fa/Fa / Consensual / Oral Sex / Anal Sex / Voyeurism /