Babysitter Revisited Ch. 02

Teen (18+)

A continuation of Babysitter Revisited. You are cordially encouraged to read the inaugural chapter before embarking on this journey. You will be glad you did.


It didn’t take long for Allison and I to devise our plan for the following evening. She asked a few questions about the older executive, and Ally’s intuitions were spot-on.

Despite being physically exhausted, the plan was a splendid one, a deliciously sexy and devious plot. One might even say, experimental and fun, especially when it came to Julie’s anticipated surrender.

As we began to doze off in tandem, my last waking thought on one of the most erotic evenings (and mornings) of my life was just how dominant could enigmatic Allison be to the aggressive alpha female Ms. Meenan? Would Julie really relinquish control to Allison’s charms?

Ally seemed supremely confident. “Just follow my lead, lover, I haven’t failed at this yet.”

It would be the worth the price of admission, that was for sure. Only I was going to be a participant, not just a spectator. That’s what made the plan even more brilliant, from my selfish perspective.

Allison’s pretty head cradled against my chest. She was breathing heavily, snoring gently. It was the cutest snore I ever heard. I soon joined her in blissful slumber.

We slept until almost noon, hardly moving, except for Allison to roll over so that we were in a spooning position, my flaccid cock head comfortably nestled between the cheeks of her sublime buttocks. Somehow, even that was a perfect fit.

I was awake for about fifteen minutes, just watching her, admiring her youthful beauty, afraid to move for fear of rousing her. I was content just basking in the glow of our new-found chemistry, and being grateful for my good fortune that I had chosen Panera Bread on Thursday for lunch. That was working out well for me.

Her eyes gradually flickered open, adjusting to the sunlight coming through the blinds, like a tiny bird’s seeing the world for the first time. She yawned, smiled, stretched, groaned, and kissed me on the forehead tenderly. “Good morning, lover,” she said cheerily. “I’m going to brush my teeth. I want you to kiss me like I’ve always wanted to be kissed.”

I looked at the most perfect rear end on the planet wiggle into the bathroom, my incorrigible cock stirring in wondrous appreciation. My former-sitter-turned-torrid-lover returned, smelling orally pepperminty, or peppermintally oral, and peeked underneath the covers to see the south rising again.

She looked pleased to see her present. She leaned down to kiss just the tip of my dick. “Go brush yours,” Ally ordered sternly. Then she figured she should clarify. “Your teeth, that is. I’ll clean the other parts.”

I came back into the bedroom, my mouth freshly foamy, my morning wood more than ready to be polished by my sexy new girlfriend. I had already categorized Allison that way in my mind. I just had a feeling, and not just a wishful one. The look of affection in her eyes as she lay naked on the covers, almost absent-mindedly rubbing her mound, told me that she, too, harbored thoughts that this was more than a one-or-two-nighter.

“I think I’m already in love with your cock, John. It’s beautiful, a true man’s cock.” Naturally, this had the desired effect on my nether region. It stiffened perceptibly as I climbed into bed and kissed the lovely woman twenty-plus years my junior with a deep passion.

“I KNOW I’m in love with your body, young lady. And your mind. You’re exciting, vibrant, and very fucking naughty.” She kissed me back with more than equal fervor, apparently thanking me for the sincere intellectual compliments, my words evoking an animated reaction within her.

Her huge nipples seemed to harden like a video tape in fast-forward motion. Always tell a woman you love her mind, I thought, it works its magic every time.

Allison and I kissed passionately for several long minutes, like two knowing, familiar lovers, kisses of erotic foreplay. Our tongues danced each other’s, alternating between slow dancing and hot, writhing, wild rumbas. We groaned into each other’s mouths, our encouraging grunts echoing within our respective throats. Our hands roamed up and down, exploring our partner’s torso, the soft touching accentuating the lovemaking that was pending.

Ally climbed on top of me, her long, lithe, nubile body straddling me, sitting directly on my thighs, pushing my legs slightly apart. Slowly, she took my engorged cock in her neatly manicured palms and began to stroke me gently, her smoky brown eyes riveted on ground zero, my twitching crotch. Her left hand held steady on my hard shaft down by the testicles, almost holding me in place, assuring that I wouldn’t and couldn’t escape her grasp. Not that I was going anywhere.

She spit a stream of saliva on her right hand and began to masturbate me in a corkscrew motion, accelerating her pace, moving from leisurely to vigorously, feeling my girth grow in response Eskort to her manual enthusiasm.

Her firm release on my shaft lifted and she began to cup my heavy balls, filling with the seed that would soon coat her, somewhere.

She maneuvered her fabulous body so that my cock tip was sliding across the entrance to her pussy, which was blossoming open like a flower waiting to be pollinated by a honey bee, the beauty of natural selection at work.

Her fingers eased their way beneath my balls to the base of my pubic bone, that ultra-sensitive spot that far too few women seem to recognize, at least from my perspective. The fact that this young, sophisticated vixen instinctively knew where to garnish her attention gained her major bonus points. I would have to reciprocate, and I would in time.

But not right now.

Allison gazed down on me, her eyes glazed, half-closed slits of lust, her fingers expertly massaging me into titanium steel. “Order me to suck your big cock,” she said huskily. Hey, for a dom, I could take orders with the best of them. I acquiesced immediately. There was no need to ask (tell?) me twice.

“Take me in your mouth, you beautiful cocksucker.” It seemed appropriate at the time, perhaps it lacked somewhat for tact, but what the hell……..

She snaked her way down my stomach, placing light kisses on my nipples, chest, and along the hairs from my navel leading to the promised land. She purred and licked while staring me in the eyes, lifting my dick flat against my tummy, reaching to the belly button.

“Mmmmm, it will be my great honor, sir, to bring pleasure to this glorious piece of manhood.” Gotta hand it to her, she really knew how to flatter an older guy, this Allison.

Her head began to spin and gyrate wildly, up and down, back and forth, her short hair tossing like a boat’s sail in a stiff breeze, pumping my thickening dick with urgency. I placed my hands on the back of her skull and she sucked me down deep, her nose now tickling against my curly pubic hairs. Deep throat, were there no ends to this incredible woman’s wonders?

Just when I thought I could take no more, she tucked her head back and released me from the back of her throat with a gasp. The gasp was matched by my own. Her eyes were swelling with tears, she struggled to catch her breath.

She looked up at me and asked, almost bashfully, “Like that, Mister McCall? Is that how you wanted your babysitter to suck your big dick?” She took me again to my very length, licking my shaft with her tongue at the same time, how does she do that?

My hands gripped her temples tighter, more to balance myself than anything. My legs swung over her shoulders as she continued her ambitious frontal assault on my cock. I was more than ready to explode inside of her talented mouth. And then……….

She pulled my legs from her back and leaned up with one hand, searching for one of the pillows scrunched against the headboard. She found one she apparently liked, and with the other hand, she cupped my ass from underneath and guided my hips up into the air. Allison propped the pillow beneath my butt, which was now raised slightly enough to give her unfettered access to my balls. And beyond.

Without taking her eyes from me nor her hands from my shaft, she took my right ball sac fully between her lips and started to suck on it eagerly, humming while doing so. I watched intently as she played a solo game of ‘hide the testicle’. I liked this game a lot. Enough to groan with delight when she switched and repeated the action on my left ball.

Equal opportunity nut sucking, what a concept, talented with either ball. As the basketball player once said, “I’d give my right arm to be ambidextrous.”

I applauded her impressive display by grabbing my own dick and gently whapping it on her forehead. It made the sound of polite golf claps. She showed her appreciation by rubbing her palm over that same super-sensitive place, the man’s g-spot, the area between balls and anus. The elusive perineum.

Her mouth joined her palm and together the pair made sweet music with my organs. She was a maestro, determined to bring me to a thunderous, roaring climax. I literally trembled from pleasure, she made oral love to me as if weaned in a textbook. “Cocksucking for Smarties.”

I wanked my own dick, trying to hold back the volcanic ash of hot cum threatening to spurt, when I felt her hot, wet tongue begin to rim my asshole. I whimpered as my ass rose off the pillow in an involuntary reflexive response.

Allison’s tongue next darted into my secret tunnel. She began to tongue-fuck my ass hole. My head spun. She rubbed my pubic bone, causing my dick to wave like a flagpole in a breeze. Her other hand somehow found its way up to my shaft once again, taking its temperature, rubbing its length, calculating when I was going to blow. Which was, as I announced to her….

“…Unngh, now, Ally, now….”

The last thing I saw before the bright lights flashed inside of my eyelids was Allison’s model-pretty face rising to catch the first hot shot of seed. It splashed against her cheek like a bursting cum-filled water balloon, splattering all over, followed by one load after the other after the other.

The most powerful orgasm of my forty-eight years rifled through my being. She smiled up at me, face coated in a mask of milky semen, dribbling off of her chin. One lonely stream dangled perilously off of one impossibly erect nipple. She looked down to see what I found so mesmerizing, saw the cum on her nub, and wiped it off with her pinky finger and brought it to her mouth.

I collapsed on the bed and groaned in thoroughly sated ecstasy, my chest heaving, my legs quivering like jelly. I gazed up in awe at my smiling young Aphrodite, goddess of oral. “Fuck, amazing, Ally. Christ, you can’t kill me yet, we have a hot night tonight, remember?”

“Oh, yes, I almost forgot. Well, then, you’ll just have to do me now, I suppose,” she smirked, rolling over on her belly.

Her pale ass cheeks stared back at me. Between them, her winking asshole peeked out at me like a camera lens. Ass Cam. If I hadn’t known better, I could have mistaken her buttocks for two taut bongo drums, waiting to be playfully smacked.

I resisted the urge to go Hawaii-Five-O on her ass, and instead began to massage her toes, deciding I’d start from the tippy toes and work my way up to the really good stuff. After all, we had plenty of time, and I wanted to play my with new instrument.

“Mmmmm, that feels good. I love to have my toes massaged. And I love your touch. A great daily double,” she purred contentedly. While making her way up to her sinewy calves, I decided to ask her a question. Inquring minds wanted to know.

“So, young lady, have you ever had a foursome before?” I sort of winced while asking it, not sure if I truly wanted to know, anticipating a litany of carnal experiences. Instead, she barely moved, just moving her head enough from being buried in the pillow to respond.

“Nope, believe or not, I haven’t. Mainly because I was afraid I would scare off whoever I was with at the time, thinking they might view me as an insatiable freak or something. But with you, I feel very comfortable, very safe, like I won’t be judged.”

She glanced over her shoulder to see my reaction. I smiled down at her, trying not to look too paternal. I touched the back of her knees, making her shiver slightly. Goose bumps rose up on her athletic thighs.

Her words led me to conclude that we were indeed leading towards something more intimate, a relationship where we could truly be ourselves. At least, I hoped so. God, how I hoped so.

Allison had already become my fountain of youth.

Age is just a number, right, I reasoned. After all, when she’s forty, I’ll only be…..gulp.

I went back to a safer subject, enjoying being the provider of the sensuous massage as much as she was reveling in being the recipient.

“How about a threesome then?” I asked. “Have you dabbled?”

I listened as she recited the memory, never once opening her eyes.

“Ah, yes, a MMF.” My cock now joined me in listening intently. It damned near cupped its own head to my ear to make sure it didn’t miss a word.

“As I recall, a casual lover, his friend, and I were sitting around enjoying cocktails in grad school when the conversation turned to sexual experiences. We all discussed and agreed that we had never had a threesome, MMW, so we moved our conversation to the boudoir and began to explore each others bodies, sharing kisses and caresses, building in urgency as both men undressed me, revealing slowly and softly, with some hesitation, my breasts.”

My dick and I said nothing, which was penis-talk for, “Please go on.” She did, her voice barely audible.

“I recall a mouth for each mound. My own hands reached down to firmly grasp one free swinging cock in my right, and another very hard cock restrained within jeans, begging to be free, stroking one cock, skin against skin, and running my fingernails tantalizingly teasing the cock restrained. Releasing my grasp on both and running my hands up my body to find two hungry mouths still licking and sucking my tits. I inserted two fingers in my sopping cunt and withdrew to cradle two chins in my hands, easing my finger into their mouths to let them taste me.”

I noticed her hand had disappeared beneath her body now, and she began to squirm. Playing with herself. Lost in the memory. I pushed her legs apart slightly with my knees, my hands working her thighs now. Allison went on, her voice husky, an octave deeper than I had ever heard it.

“At my request, both men lay back on the bed as I enjoyed rubbing my body along theirs. Straddling one lover without allowing penetration, I made a fucking motion as my hands worked feverishly to relieve my other lover of his jeans. As is my pleasure, my mouth found his cock as my pussy grew ever wetter and juices flowed freely on the cock which now had full attention from my snatch.”

It was as if she were telling a fairy tale now, but it was obviously so very vivid, so real.

“Hands everywhere, reaching, grasping, stroking and finding my cunt. One lover pulled my hips upward and in one full swift thrust, aaah, my pussy was as full of cock as it had ever been. I continued my oral libations, reluctant to give leave of the delicious hard cock in my throat. Everyone was moaning as one and sweat provided ample lubrication for skin-on-skin delight. I was spit-roasted now, one cock pounding my cunt, one in my throat.”

I stuffed the pillow under her tummy, raising her sweet ass in the air, making damn sure nothing was clogging my ears.

I hung, if you’ll pardon the expression, on every word. She went on, verbally climaxing, so to speak. Her words ran together in one long run-on sentence, heating the room with each syllable, her breaths now were in small staccato rasps.

“Talking and fucking and sucking I heard the voice behind me describe the sensation of his “about-to-cum” experience, pushing his cock deeper inside me while my vaginal muscles feverishly stroked his rod and my clit pulsed while he pounded me relentlessly and I sucked on the other throbbing member in my mouth, my screams broke the air as cum erupted on my ass and my face simultaneously, driving me quickly to my own intense orgasms as both men then focused their fingers to my wildly swollen cunt, penetrating me digitally, making me cum, and cum and cum again…..”

Not surprisingly, Allison came hard just then. Loudly. A screaming, writhing, deja vu orgasm.

I took the occasion to bury my face between her ass cheeks and pussy, which was streaming like a self-induced waterfall.

I parted her legs and flicked my tongue gentled over her still leaking pussy. She sighed and let the passion of the moment over take her. My tongue first slid up and down her sopping slit, careful not to enter. I then grazed her hard clit, flicking it back and forth, and then placed my entire mouth on top of the tasty pearl.

As Ally’s tiny nub began to swell, I pressed my hand against her buns. Her hips rose up towards my hand and mouth, lifting herself onto all fours, straining for more.

I sucked and licked her clit hungrily now, pulling on it, savoring the sweet taste. Her body wass taut with desire. She reached back and spread her asscheeks apart with one hand, courteously providing me even more access to her wet pussy and beautiful light brown sphincter.

I slipped a finger into her asshole and simply held it there, buried into the first knuckle. I could feel her anal muscles clenching it, gripping it tight, and sucking it in. I moved my finger in … and out … in … and out (slowly) all the while licking and sucking the ever-blossoming slit of her cunt.

Her nub was incredibly swollen and erect, jumping each time my tongue circled it. I next inserted two fingers into her anal cavity now. Pumping in and out.

Her head was thrown back, eyes rolled back, back arched. I became bold, inserting three fingers. She moaned out loud, seemingly not caring that the entire community could probably hear her cries, declarations of one orgasm after the other.

My long tongue continued to lick and suck her clit. The three fingers were fucking her beautiful crinkly asshole faster now. I slid my tongue down her slit and into her rear hole, replacing my fingers.

Ally gasped as my tongue explores her anal channel. Her hips began to rise up and down, bucking like a bronco on my face. My thumb caressed her clit roughly with my tongue now diving deep in her anus, fucking her like a little penis.

I could feel her tight backside gripping and squeezing my tongue. Her muscles contracted with every lick, every tongue fuck. I grabbed her hips with my hands and orally searched … searched for that love spot, the one that would send her into orbit.

Intuitively, her hips moved and with the movement, it served to guide my tongue deeper into her musky-flavored anus. My fingers in her humid cunt finally grazed her g-spot.

She muffled a scream by literally biting the pillow, her teeth biting down on the cotton like a puppy with a chew toy, whipping her head around like a puppet. She was propped up on one hand now, her other hand wass caressing her breast, pinching and pulling her nipple while I fingered her red-hot cunt and ate her asshole.

She tried to hold back from collapsing in a puddle of her cum, the juices running down her muscular thighs, not wanting me to finish yet. Little did she know I was far from done with my afternoon appetizer of cunt and ass, kind of a surf and turf thingy. (Kind of.)

My tongue continued to delve even further into her tight hole. Exploring, driving her closer to going completely over the edge. I grazed her g-spot with my finger once again, this time staying there, flicking back and forth. She pushed her anus further against my face, into my mouth. Her body tensed rigidly.