Reader
Open on Literotica

Granny and Her Upskirt Stalker

The following is about a very sexy, dominant older woman sexually controlling a reluctant, submissive19-year-old man. It has scenes of forced cunnilingus, analingus, enforced cum eating and panty worship.

*****

Nicole noticed him right away, of course. Observation was at the core of what she did for many years.

Nicole Barrows was retired from running a security company, had been for a few years now, enjoying the life of a divorced, 69-year-old woman blessed with the money to do so. Which meant hiring the best personal trainers to work her amazingly well-preserved body into the shape that seemed to be hypnotizing the young man.

She'd come to her local grocery store, an upscale place where young yoga moms would shop and the price was beyond reasonable, charging too much for high-end goods. But Nicole loved shopping there, it suited her high-end life.

Her notice of him came quickly, as she strolled down one aisle and then the next, a basket hanging from her arm. It was a warm day, and she was fresh from tennis, still sporting her tennis whites of short skirt that revealed her firm, muscular and very shapely legs, tanned from the sun, long, sweeping thighs with only the slightest of sagging flesh, calves diamond-shaped and rippling above her short white socks and sneakers.

Her legs were, she knew, her best asset. And the young man following her, a goofy-looking sort of she would guess to be no more than 19, perhaps 18. He was tall and lanky and wearing glasses - and had a spy camera attached to one toe of his dorky sandals.

She knew spy cams, they were part and parcel of her former trade. And now, she smiled to herself knowing what great lengths this young man was going to to get shots of her crotch.

She knew about the world of upskirt photography; it had made the news in her little town recently when one older, perverted man with a record, had been caught doing what this young man was doing now. Police were called, he was arrested, the case made very public and leading to a new town law that forbade such things, punishable by fine and possible imprisonment, not to mention humiliation.

She stood by the pasta shelves, pretending to reach high up for a particularly brand, stretching to her full 5-8 height. Her long silvery hair was tucked into a youthful ponytail under her white cap. She noticed him sidling up to her, pretending to look awkwardly extending the foot with the camera on it to get shots up the length of her muscular legs, into her crotch covered by a tiny white cotton thong panty.

Smiling to herself, she moved over to the chicken cooler, bending to look inside, feeling her little skirt ride up the backs of her taut hamstrings, giving the young man a show and unfettered access to take photos or videos, whatever he was doing. She sensed him behind her now, looking over her back, or pretending to. She looked down between her slightly spread feet and saw his, the one with the camera.

She continued the ruse of pretention, walking slowly to various areas of the store, allowing the goofy lad to follow, film, continue his surreptitious taping. She couldn't help thinking this sort of person would have never made a good employee, he was far too obvious.

She could have confronted him any time, of course, busted him, alerted store officials to call the police, or just chided him, making him erase the evidence in his camera, and send him on his way, chastened.

But she had a far tastier lesson in mind, smiling to herself thinking about it as she made her way to the check-out line with, of course, the young man coming behind her, that foot extended as she stood to wait her turn.

The faintest of moans escaped his lips as she purposely stood on spread feet, then boldly reaching behind her to scratch the back of one thigh, lifting the short white skirt to do it. The entirety of her left thigh came into view and she flexed it, feeling the muscular hamstring tighten and flex and a moan come from behind her.

"Sorry, what?" she said, turning around to smile at the nervous young man in the ill-fitting glasses that her pushed up his nose. "Did you say something to me?"

"Uh, no, no, just clearing..my throat," he said, faking a cough that he covered with his hand.

She looked down sidelong at his feet as she pushed her few purchases onto the conveyor belt.

"Those are rather interesting looking sandals," she smiled. "Is that what you young people are wearing these days? My grandchildren, they're about your age, which is..."

She waited for the answer. He stammered, "Uh, 19...well, in a couple of months."

"Yes, 19, about their age," she laughed. "Young people and their clothing, I just don't know. Me, I just prefer sneakers on hot days like this, like these beat-up tennis shoes. They're nasty, you know, old and sweaty and not very pleasant smelling, I really need to get a new pair."

He smiled weakly, now tucking the camera-carrying foot behind the other, not wanting to arouse suspicion. He'd carefully masked it to blend into the leather of the sandal, of course; this wasn't the first time he'd done it, taking great pains to ensure his secrecy and in the past year or so, had scored an amazing amount of footage to later pleasure himself to in the bedroom of his parents' home.

"I would imagine those sandals aren't very comfortable for walking," she said, looking down at his feet, making him more nervous than ever.

"Uh, they're OK...I don't live far, a couple blocks," he said, his voice gone squeaky, his throat dry as he looked down with her, his eyes gazing at her amazing old legs.

He loved old legs. Most of his stolen footage was of the upskirt variety of women like this, 50s, 60s and sometimes 70s, well-built older women, grannies, with incredible legs. And never had he seen legs like this woman's. This would be the crown jewel in his sordid package of private videos.

She made her purchases, paid the gruff clerk, and walked out, bidding the nervous young man goodbye. And she waited, in her car, watching. Sure enough, he came out moments later with a bag in hand and walked through the lot to the street, toward home, she suspected.

She waited until he'd gotten almost to the street before she pulled up next to him, rolling down the window of her Lexus SUV, black, with tinted windows. He looked surprised and anxious when he saw her.

"Did you get some good shots, young man?" she said pointedly.

"What?" he said, quite nervous now. "Shots...what...shots?"

She laughed a dark laugh, the corners of her mouth and eyes flexing into gentle, sexy wrinkles as she did.

"Son, I wasn't born yesterday," she said with a sigh. "I know what you were doing. Your sandal with the camera? Clumsy at best. I'm amazed you haven't been caught already."

"I..I...I..." he stammered.

"Name," she said, the smile melting into a stern look.

"What?"

"Name, boy, your name," she said with a snarl. "First. And last."

"I..." he stammered again.

She picked up her cell, not looking at it.

"We can do this the easy way," she said, "or the hard way. Which will involve calling the police. Now. Name. First and last."

He blinked, totally frightened now, fidgeting on his feet. She felt her pussy moisten. She so loved being in charge, particularly of nervous young men.

"Matty...Matty Lincoln," he said softly. "Please...please, ma'am, please..."

"Mrs. Barrows," she said.

"Mrs. Barrows, please!" he said, begging. "Please don't, I'm so sorry, I..."

"You do this often, I imagine," she said in scolding tone. "Get in."

He hesitated. She keyed the phone, cocking her head at him. He gulped, walking to the other side of the car, getting in. It was hot. She hadn't turned on the AC. He watched those incredible thighs flex as she pressed the gas pedal, wheeling the SUV to a parking spot in the store lot, away from others. She shut the engine off, and he felt the stifling humid air surround him, touched by the scent of her, sweaty and ripe.

And making his dick rock hard.

"You jerk off to the footage, don't you," she said pointedly, turning to face him, spreading her legs slightly. "You shoot up the skirts or shorts of women and you jerk off to it."

"Yes," he moaned, no need to hide it anymore and in fact relishing her up-front candor in discussing it.

She smiled. She turned more, lifting her right leg up, opening both. Her thong flashed into view, and springing out on the sides her thick profusion of sweaty pussy hair. His eyes bulged, staring, confused by but reveling in what appeared to be her permission to look.

"Do it," she said.

"What?"

"Do it," she continued. "Jerk off. This is what you like, isn't it, looking up the skirts, at the legs and crotches of women? And is it just older women? Answer me boy, is it?"

"YES!" he cried out.

"That's somewhat flattering, I guess," she laughed. "Oh, give me your sandal. Now."

He nervously slipped it off, handing it to her. She looked at it, smiling.

"Turn it on," she said. "Go on, I know what's in your pocket, now turn it on."

He gulped and obeyed. She put the sandal on the dash, angling the camera toward him.

"Jerk off, boy," she said, spreading her legs wider, pulling aside her thong, exposing her soggy bush to him, a beautiful, dewy bouquet of silvery hair, dark lips moistening behind it. "Take your cock out. Now."

He looked at her, transfixed, then her big, wet pussy and obeyed. He unsnapped his dorky shorts, sliding them down his pale, skinny thighs, with his underwear and out sprang a smallish cock, about five inches long, on the thin side. She laughed.

"No wonder you live by upskirt video!" she roared. "That's pathetic. Now pull it. Do it, Matty. Jerk. That. Cock."

He blinked in disbelief as she fingered her pussy, watching him stroke his prick.

"Have you ever seen such a hairy pussy, Matty, hmm, have you?" she smiled, eyes heavy lidded as her fingers flew in her gash, squishing sounds filling the air, along with the musky ripeness of her scent.

"No," he groaned with a throaty growl, feeling himself get closer and wondering where he'd shoot his load.

"Have you ever...even seen ANY pussy, Matty?" she snarled, fingers flying harder and deeper, three gouging her wet cunt, glistening and thick with her fluids.

"No...God, no..." he moaned, feeling his balls throb.

Suddenly, his world erupted in a blistering sensation of smell, sight and taste. She'd torn her soaking fingers from her cunt and rammed them into his face, holding his hair with her other hand as she wiped her gel on his mouth, up his nose, and then in his lips.

"Taste me, bitch," she barked, licking his cheeks clean of her fluid. "Smell me..."

He groaned, jerking harder, inhaling her scent, a ripe, sweaty aroma, tasting her juices, sucking her fingers madly as she fucked his mouth with them.

"Oh...GOD!!" he yelled around her plunging fingers.

She yanked them out and now strapped them around the base of his tiny cock, squeezing brutally hard. He looked down at the tanned, freckled hand, the strong fingers crushing his orgasm to nothing. A tiny white blob of cum welled in his desperate dick head as he thrust off the seat, anxious for release. She would give him none.

"I didn't tell you to cum, did I?" she growled, kissing him deeply and wetly, savoring her own scent and flavor, her clenched thighs quivering against her clit. "You don't cum until I do, and even then, maybe I won't let you..."

She looked down at his cock going purple in her strangle hold, the veins in her neck bulging from the effort of squeezing it, the tanned, sinewy forearm flexing. He let out a low growl, fearful and longing. She finally let go, dipping her head to his cock and slowly, very slowly, lapping the single gob of cum from it. She lifted up, extending her tongue where the gob lay in a pearly round.

He didn't resist, couldn't resist as she thrust it into his mouth to be sucked clean. He blanched but swallowed. She sat back, laughing, spreading her meaty thighs wide, putting the right foot up on his seat and then at the back of his head, pulling him over the console awkwardly until his face was inches from that very hairy, very sweaty, and wonderfully smelly cunt.

"Eat me," she said simply. "You never have, I know, but just stick out your tongue. I'll do the rest."

The taste was metallic, salty, his tongue lancing the furry folds of her lips, thrusting into her silky, slimy hole. She let out a long, sibilant hiss as she felt it enter him, and now cupped the back of his head in her hands, grinding her clit against his nose. His eyes darted side to side as he watched those tanned, rugged thighs slowly fold around him, capturing him around the neck and ears, squeezing. The power was amazing as he felt her socked feet lock behind him and the thick tension of her muscular inner thighs crush his skull.

He moaned in pain, and pleasure, as she used his face, punishing him in her thighs, squeezing harder and harder, grinding her hairy pussy to his lips, her clit to his nose, pressing so hard he thought she'd break it. His eyes watered from the pain, and overpowering, cheesy ripe sweaty scent of her cunt, as it completely covered his face, sealing his mouth at the drippy hole.

She grunted, pumping and thrusting, powering her quim against his trapped face. The fluid shot from her cunt, thick and creamy, filling his mouth as her powerful thighs quivered around his head from the squeezing effort of her orgasm. He looked up as best he could, unable to move any part of his scissored head other than his eyes, and he saw her face, biting her upper lip as she came, eyes closed. She had her head tucked toward her chest, her neck meat pressed down, beautiful folds of silky, tanned flesh, an exquisite ripple of wrinkles that he thought looked incredible beautiful.

"UNGH! UNGH! UNGH!" she screamed, punctuating her orgasm with her shouts and matching jolts of her locked legs, bending her feet up and slamming them out straight, pulsating ripples of power crashing through her muscular old thighs and into his skull.

He felt himself go dizzy as she finished off on her face, now locking her legs out fully, squeezing, thighs trembling, his face soaked with her in a thick bubbling blanket of woman cream. His hands pulled at the thighs for release and he fought for air. Just before passing out, she released him, legs springing open. Matty flopped back in his seat, gasping for air, his face completely soaked with her.

She relaxed against the door, a pensive, dreamy smile on her pretty face. She looked at him, his cock stabbing into the air, unsatisfied. Looking down between her spread thighs, she looked back at him. She lifted her legs up, holding them under the knees. His eyes focused on the dark cleft of her ass, a furry ring around her rectum, thickly plugged with her orgasm.

"You've made a mess," she snarled. "Lick it up. Lick my cum out of my asshole. Now."

He dove to his task, moaning, fitting his mouth to her pucker, spearing it with his tongue, ignoring the salty, rank taste and scent, sucking her cum from it, drawing it into his mouth to savor it and swallow it down. He heard her laughter building from a chuckle to a throaty roar as he feasted on her orgasmic slime covering her hairy asshole.

"Oh, God, you young ones, you will do ANYTHING, won't you!" she laughed, shaking his face away and pushing him back into his seat. "ANYTHING! You're so cute in a really pathetic way, all of you. Especially you."

She looked at the sandal on the dash as she said it. He blushed deeply, head bowed. Looking at his dripping cock, small, hard, ready.

"So pathetic," she sighed, slipping out of her thong and showing it to him, the crotch panel wet and slightly yellow. "Pathetic."

She grabbed his head with one hand, ramming the filthy fabric to his face with the other, grinding it into his nose and mouth, transferring the foul scent to him. Then with a dark smile, she dropped that hand to his cock, bunching up the panty around it and rapidly stroking.

"This what you want, boy, you wanna cum, you wanna cum in what you were just taking videos of, my disgusting, piss-scented panty, is that it, that what you want?" she said through clenched teeth, his mouth next to his ear as he looked down at that muscular forearm and pumping hand.

"Yes, yes, YES!!" he screamed.

He came in the panty she bunched around his cock, his balls pumping out the biggest load of his young life, a seemingly endless stream of cum that completely soaked the foul-smelling fabric. She continued to pump him, milking him dry. He twitched and fidgeted under her hand job, the good feeling long gone, that super-sensitiveness now taking over as she continued to stroke his spent dick.

"That doesn't feel so good, does it, Matty?" she teased, dropping the soaking wet panty on his legs and using her bare hand to stroke him up and down, cupping her strong fingers around the head, pulsating them on him, making his entire body tremble and low groans of agony escape his lips. "No, it never does, it never does when I milk them after I make them cum. Take it, bitch!"

She grabbed the base of his cock in her hand, squeezing it to keep it semi-hard, and now used the other to work the tip, her old fingers dancing up and down it, making him bellow in pain. Laughing, she now cruised the soaking wet palm of that hand around the head in fast circles, the flesh tickling the sensitive underside brutally hard, his body consumed by the tickling sensation.

"More baby, I want more, I want more of your hot, disgusting cum, I wanna milk your balls DRY!!" she screamed, biting his ear.

Impossibly, he stayed hard under her hand that she now strapped to his cock, using his cum for lubrication, masturbating him furiously, his moans and the squishy sounds of her hand job filling the confined space. She glared at him, eyes wide open, a maniacal smile on her face as she worked his young cock.

"Gimme that cum, boy, gimme that cum," she barked.

Amazingly, just five minutes after giving up the load of his life, he gave up another, and she quickly grabbed the cum-soaked panty on his legs and jerked him off into it, her strokes slowing as he filled it again, her mouth open in a wide smile as she worked his nuts dry.

And once again, she continued to stroke him, using that palm again to cruelly circle his ticklish cock head to an excruciating degree, making him push back into his seat to escape her punishing hand.

"One more...one more...one more..." she laughed, keeping him hard, stroking him.

He was in another world now, head back on the seat, lolling side to side as her cum-soaked hand worked his cock up and down, holding it stiff with the other. His balls ached horribly, empty and useless, but she wouldn't stop, laughing as she jerked him, her fingers and hand completely coated with cum, a thick blanket of white.

"It's there, boy, it's there, you young ones are so predictable, dumb and full of cum," she hissed, jerking faster and harder, his dick red under her mad stroking.

It took awhile longer and was a much smaller load, an oozing, really, as his balls trembled and gave up whatever they had left. It dribbled out over her pumping hand and she cooed as she watched it mix with the old cum already there, her whole hand now covered with his spunk. She stopped, mercifully, and grabbed the soaking wet panty to wipe it all up.

"I never want you to forget this, Matty," she said with a smile, lifting the panty to his mouth and stuffing it inside, the boy too weak to stop her, feeling his three loads coat his cheeks and slither down his throat, the smell a mix of her piss, pussy scent and his seed. "This will help. Leave it in your mouth until you get home. I WILL be following you to watch."

She straightened herself out as he did, slipping up his shorts over his raw cock, wincing at the sensation of his underwear on the sensitive flesh. He turned to look at her; she was completely composed now, the picture of elegance once again, her smile warm and inviting. She pointed to the door but not before grabbing his sandal and tearing off the camera and dropping it into her purse.
Log in or Sign up to continue reading!