tagMatureBabysitter Revisited

Babysitter Revisited

byjohnnieblue44©

Having just recently celebrated my forty-eighth birthday, I wasn't used to having a comely young woman about half my age appear to be checking me out as I stood at the counter of Panera Bread, waiting for my lunch order.

Granted, it may have been my imagination or wishful thinking on my part. However, as I shifted my body around to face her, it seemed she was not only checking me out, but perhaps also checking out my, um, package, which was involuntarily rising as the impure thoughts rattled through my head.

I had been doing alright in my rejuvenated sex life since the divorce a few years ago, but half my age? I hadn't crossed that plateau yet.

Still, there was something vaguely familiar about the tall, lean young woman with the short chestnut hair and deep brown bedroom eyes that were indeed running up and down in a visual scan of my torso. As I grabbed my tray, my stiffening prick twitched in gratitude of the attention. She had to notice it. Didn't she?

"Mister McCall, is that you?"

The twenty-something woman stood, revealing a hard, athletic body and long, looong legs that came up and made quite an ass out of her. Figuratively speaking, of course. I unconsciously walked towards her as if in a trance, lunch suddenly forgotten. C'mere, boy.

She threw her arms open wide, and squealed a schoolgirl squeal. Restrained, yet animated enough to get me harder. I plopped the tray down on her table.

"I KNEW that was you!" She leaned into me, pressing her chest into mine, causing an accelerated missile launch sequence within my suit pants. She smelled like orchids and strawberries and she gave me a big hug.

I glanced around nervously for the hidden cameras, sure that I was being 'punked'. That didn't stop me from sniffing her neck and hair, though, while I leaned my pelvis into hers. If this was only gonna last a minute, I was gonna enjoy that minute to the hilt.

She leaned back, her pretty face aglow. All other people in the store, not to mention the planet, had instantly disappeared. She put her hands on her hips, clad in tight denim jeans met at the waist by an olive-colored turtleneck ribbed sweater. Was that a nipple or two poking through the cotton? Yep, me thinks so. Wow!

But..who the fu.......?

"Allison," she said. No help. She scrunched her nose in dismay, but only for a nanosecond.

"Allison Mattern? Your old babysitter? For Lindsay and Thomas, your kids. God, what has it been, ten years? You look great!"

I look great? Me? I thought to myself, Allison, have you looked at yourself in the mirror lately? Now, you my dear, you look mah-velous. This was all in my head, and it dawned upon me that I still hadn't said anything except perhaps a grunt or two. I figured I better snap to it lest she leave my domain as quickly as she had entered it.

"Allison! Oh my gosh. What a surprise. Boy, have YOU grown up." She smiled a winning smile, flashing big, bright, perfect front teeth, Sheryl Crow-type teeth. Chipmunky in a sexy way, a slight overbite, good for gently scraping over a dick. Oh, the way my mind works.

She leaned in and hugged me again, this time holding it for a few seconds longer than necessary, especially in a public place. Not that I was complaining. It's not every day you get a hottie scrunching privates with you at the local lunch joint.

I did the math quickly. Allison baby-sat my two kids when they were about nine and ten. Ally, as we called her, was about sixteen or seventeen then, a junior in high school. She was a long, tall piece of water, not yet filled out, a gangly, awkward teenager.

Cute back then, sure, no doubt. But not the stunner she was now. I surmised she was about twenty-seven now, give or take a year. Amazing the way kids grow these days.

We sat and talked over the next half hour, catching up, making small talk. All the while I was trying to swivel and squirm and discourage my hard-on from distracting me beneath the table. Unsuccessfully.

Because of the threat of raising the table in a penile levitation magic trick of sorts, I did most of the questioning. Allison had graduated from Temple, her basketball career ended by an ACL injury. She then fully focused her attention on her academics, received a masters degree in civil engineering from Lehigh, one of the best engineering schools in the country, and was currently working for an architectural firm.

This was one smart cookie, bright and beautiful.

And something else, as I was about to learn, when she turned the questions on me.

"So, um, if you don't mind me asking, I'm guessing you're no longer with Mrs. McCall?"

I blinked, and for the first time my erection took a brief sabbatical. "Why, yes, that's true. We finalized our divorce a few years ago, once the kids were about to leave for college." I was curious that her intuition was correct. "Um, how did you know that?"

She smirked, and touched my ring finger. "You used to wear your ring and almost flaunt it, at least in my opinion. I was so jealous."

Her mere touch resurrected the arousal. "Jealous? Why?"

Allison leaned forward, her body language betraying her. I'm usually unlike most males, I have to be totally convinced by a woman's less-than-subtle cues that she is interested. She licked her lips, tossed her hair from her forehead, and moved closer to me. The seductress trifecta. She was interested, despite my disbelief. What she said next only augmented my desire for this young woman, no longer awkward, no longer a geek.

"I used to have the biggest crush on you, Mr. McCall. In fact, you gave me my first orgasm."

A thin slice of turkey sandwich caught in my throat as I absorbed this tidbit.

She took inventory of my reaction and giggled in a low guttural tone. "Well, you didn't know it, of course. But I used to leave after my sitter duties, go home, and masturbate, thinking of you."

I reached for my iced tea, to unclog the bread, to save me from choking.

She continued, her voice low, deep. "In fact, one time, just to be naughty, I went up to your bed once the kids were asleep, and I took your wife's hair brush, and I had the most amazing orgasm, right on your bed, frigging myself into ecstasy. I got so turned on knowing that you would come home with your wife and be completely unaware that my teenage virgin cum was all over your sheets."

Now even an ice cube lodged in my esophagus. Allison, a teenage virgin no longer, went on. "That same week, I gave my boyfriend at the time my first blow job. I had absolutely no idea what I was doing, but I was so enthusiastic." Our eyes met. She rubbed her neck softly.

"Because I was fantasizing it was you. In my mind, I wanted it to be you that I was sucking off, Mr. McCall."

I was stroking the straw of my drink now, not realizing it, not fully consuming what I was hearing. The best I could come back with was a schoolboy-like inquiry.

"Um, how about now, Allison? You must have a boyfriend...." I let the words trail off, leaving it as an assumption rather than an inquisition.

She twirled a finger around her tight locks, one strand falling down on the right side of her face, partially covering her smoky brown eye. She raised that same eyebrow, and shook her head. "No, I don't want to be tied down." She laughed at her own double-entendre, intentional or not. "Not in that way, at least." She stopped again, knowing full well the effect that she was having upon my middle-aged libido.

"I like to be free to, well.......experiment. I'm still learning, still exploring." Pre-cum squirted from my slit. My cock tightened with each syllable. " And sometimes with other women. I like to have explore. Have fun. How about you, Mr. McCall, do you like to explore...and have fun?"

I glanced at my watch as a defense mechanism. Shit! One forty-five. I had a conference call at two. I had to move fast, I was not going to miss this golden, once-in-a-lifetime quirk of fate. Filled with the confidence that Allison's brazenness had provided me, I dropped my own gauntlet.

"First of all, Miss Mattern, my name is John, not Mr. McCall any more, got it?" She demurely nodded her head, happy to let me, the supposedly mature older man, take back a semblance of control. She appeared anxious to see where I would take her obvious offer to proceed further.

"Good," I said, acknowledging her understanding. "Second, yes, I like to have fun, a lot of fun." Her eyes blazed into mine, her lips curling almost into a sneer, a young lioness trying to impress the alpha male. "You'd be surprised the fun things I can teach you, young lady."

She licked her lips. She was all in.

"Third, I have to get back to my office soon. But you are going to be my date for our company Christmas party tomorrow night, so that I will leave a lasting impression on my envious colleagues and their spouses, with you on my arm. Eye candy."

She leaned back from the table, listening intently. Her heel began to rub up my ankle and onto my calf. The nipples of her smallish tits poked through the fabric of her sweater visibly.

"You will tell me where you live, I'll pick you up at eight, and you'll be dressed in something that no babysitter would EVER wear." She shuddered quietly, the tables officially turned. I went on. "And by the end of the evening, you'll no longer have a need to harbor any jealously and we'll discover how much experimental fun we can have together."

I stood to leave, and recoiled when she tried to get up herself. I didn't know if she wanted to hug me, kiss me, or suck my dick right then and there. But I knew if I stayed another minute that I was going to miss my call. Besides, I sensed she wanted to fuck, now, a quickie, fulfilling a fantasy of her own. But I wanted something more, and quite honestly, I wanted to make her wait.

I slid a business card into her palm. "My personal e-mail is on the back. Send me your address, and while you're at it, tell me how you used to masturbate when you were in high school. Because tomorrow, I'm going to watch you act out your narrative."

Allison nearly swooned, and I purposely let my rock-hard cock swipe against her body, still seated, before I departed.

"And then, former babysitter, I'm going to do things to that fabulous young body that will bring a new definition for what you consider 'experimental'.

Always leave 'em wet, I snickered to myself. Always leave 'em wet.

When I arrived home that evening, I opened my personal e-mail, something that I never do at work, since one never knows what the IT police might be watching. In this case, it was a good thing I waited.

The e-mail that I was looking for was from an address that I didn't recognize, but I had a pretty good idea when I saw the caption, "A Picture is Worth a Thousand Words", with an attachment.

I opened the attachment, with the resurgent bulge in my pants indicating that my southern equator was as eager as my northern to examine the contents.

The image formed, tantalizingly slowly, frame by frame, on my laptop. I hit 'full screen' just before it blipped into life.

The photo was time stamped at five-oh-nine that afternoon, or about three hours since my impromptu meeting with Allison. The camera was positioned on the floor, apparently, as my all-grown-up former babysitter was lying on a sofa, the same olive turtleneck pulled up to her neck, showing her pert breasts, with distended nipples that looked like they were the size of my pinkie finger to the first knuckle.

She was naked from the waist down, her impossibly long, tapered legs spread lewdly, one on top of the sofa back, the other on the floor, and she was on her side at a forty-five degree angle from the lens.

One hand held a bullet vibrator which was imbedded several inches into her anus. The other had two fingers pulling apart a bright pink swollen pussy with her middle finger stuffed deep inside her slit. Her luscious thighs were coated with a gleam of milky moisture.

Written below the photo was a succinct electronic salutation: "Here's to experimental fun. And fun experimentation. Love, your no-longer-jealous babysitter."

Her address in Berwyn, a tony suburb about twenty minutes away from my house, was included.

I was right on time knocking on her townhouse door the next night as I tightened the knot on my necktie, my Lexus parked in her driveway, my dick as stiff as the brisk December wind.

The door swung open and for a second, I could only see perhaps a dozen or so candles scattered throughout the living room. Allison was behind the door, so at first, I could only see an impeccably manicured set of fingers gripping the door. But I could already smell her. Orchids and strawberries. Strawberries and orchids. And, maybe....? The slightest hint of womanly arousal on those lovely finger tips as I took one into my mouth before I even saw her.

She emerged as I swirled my tongue across three digits, licking her painted nails one-by-one, sucking on the same middle finger that was buried in her cunt in the photographic tribute she had sent to me twenty-four hours before.

Her short hair was loosely spiked up with gel on her cropped temples, while the locks in the middle cascaded down onto her forehead. Somehow, it looked sophisticatedly slutty, appropriate for the formal cocktail party that we were headed to, but with the hint of provocation of what would ensue post-party.

She stepped out from behind the door as I still orally massaged her fingers. Her eyes were half-shut and she moaned almost inaudibly. I didn't realize it at first, but her other hand had hiked up the gray sequined hemline of her skin-tight dress, and was hidden from view, wiggling under her dress. The masturbation show had already started.

The charcoal dress ended just above her knee. It had a slit up the right side that went almost to mid-thigh, showcasing her lean yet muscular calves, and she wore a light choker necklace and three-inch satin pumps. Again, navigating the always tenuous tightrope between tasteful and promiscuous. It had a midnight blue border on the sleeves, which contrasted the hues splendidly. A perfect outfit for a winter formal, certain to send my male colleagues into a drooling frenzy, and their spouses or significant others into the sad realization that they would not be the hottest woman at the bash. Allison made sure of that.

She reached around me, shutting the door, and essentially pinned me against it. Her strength surprised me. Her sinewy biceps rippled as she used one arm to push me backward, and the other arm was still busy, connected to her fingers, three of which were diddling her cunt. I knew this because my own hand was now beneath her dress. I joined her in finger-fucking teamwork, not surprised in the least that my path was not blocked by any undergarments.

She brought her mouth to mine and her tongue danced into my mouth, slippery, hot, talented. How did she put it while self-describing her first blow job technique yesterday?

Ah, yes, that's it. Enthusiastic. She was most certainly orally enthusiastic. And the early returns indicated that she was also quite orally gifted as well. Our tongues fought with the same zeal with which our respective fingers scrimmaged in her sopping young cunt.

She withdrew my fingers by grabbing my wrist. "Patience," she said simply. She took my hand and led me into the living room, as I stared from behind at the tight ass sashaying beneath her dress. The young ass that I was determined to have later this tonight.

She pushed me down gently into a plush armchair across from the couch. Gazing into my eyes intently, she lowered the straps pf the dress from her shoulder and brought it to her navel. Though small in the chest, her nearly chocolate areolas were disproportionately large, with those same rubbery nipples that I had ogled in the e-mail. They had to be at least an inch long, just begging to be pulled and sucked.

"Take your cock out, Mr. McCall," Allison said huskily, pinching her nubs between a thumb and index finger of each hand. 'I've been waiting to see it for ten years."

I got up and took off my suit jacket slowly, folding it over the arm of the chair. I liked this game that we were about to play. You show me yours and I'll show you mine. I liked it a lot.

Ally stood by the edge of the couch, her blazing eyes locked on my lap as I unbuckled my belt and tugged at the zipper of my pants. I motioned for her to reach her own zipper on the side of her dress. "You first," I dared, teasingly.

With a wiggle or two of her slender hips, her dress fell to the carpet. I held my breath to stifle a gasp as I surveyed the beautiful womanly form in front of me. Her stomach was perfectly flat, like an ironing board, tapering into a "V" at her pelvis, and cascading down into a valley of closely cropped chestnut pubes. The shiny trimmed hairs served as a visual welcome mat. Her vulva was already puffy from the fingering, and her outer labia were pushing outward, exposing bright pink vaginal flesh within.

"Jesus, Allison," I whispered, truly in awe. "What a sensationally beautiful woman you've become."

It wasn't exactly the most eloquent thing to say, I realize. I'm sure that she hadn't become this sensational beauty overnight, but what the hell, I hadn't seen her from seventeen to twenty-seven. What I saw before my eyes now was perhaps the best body I'd ever seen. Men who insist that women have to be big-breasted to be sexy are quite sectarian.

Allison seemed to dismiss the compliment, ignoring the fact that she was naked in front of me. Her mind was one-track at this point. "Your cock, John," she demanded. "I need to see your cock."

I let the pants drop to my ankles and stepped out of my shoes. Her eyes never left my crotch as my manhood popped into view when I removed my boxer briefs. It pointed straight to the ceiling in salute, all seven-plus inches harder than should be anatomically possible for a forty-eight year-old cock.

"Ooooh, fuck," she hissed through her ivory teeth, almost a whistle. "I knew you'd be hung." She spread her legs and began to rub the top of her mound with her palm, one finger dipping into her warm abyss. "C'mere."

I walked towards her, stopping about five feet away. I could clearly smell her nectars even from that semi-safe distance. We looked intently at each other's crotches for a short time while we entertained ourselves as well as our one-person audience. I stepped closer, my cock nearly grazing her cheek now. "Lay down," I said softly.

She complied and lay prone on the couch, two fingers now buried in her quim. I reached down and took her by the shoulders and spun her until her head was over the edge of the couch. I made one stride forward so that my swollen balls dangled directly over her face. Essentially, she was now peering right up my ass hole.

Her tongue snaked out and she lapped at my testicles while her free hand reached up to cup my sac. In reciprocation, I bent at the waist to accommodate her grasp, and this position also allowed me access to her elongated, rubbery nipples. My touch alone initiated the electrical spark in her body. Her flat tummy rippled and her thighs tightened and a low, guttural groan escaped from somewhere deep in her nether region.

The former babysitter's hips bucked and heaved animatedly off of the couch, lost in the throes of a powerful orgasm now, as she furiously fingered her young cunt and I pulled her nipples roughly perhaps three inches off of her skin.

"Unggh.....uhhhhh.....aaoooaahhhhh....fffffuckkkkk........" Her sounds alone would have been enough to induce my own orgasm, but when she wrapped her long fingers around my dick in a vice-like grip, I could withstand no more sensory overload. Whippets of hot semen shot from my slit and lathered her breasts and collarbone and stomach in strings of milky-white cum. The proverbial protein bath, good for the skin.

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