A Grandmotherly Pegging For Aaron

This is the first of what will be a series of pieces featuring an older woman and her teenage grandson who are involved in a taboo sexual relationship with one another. There will be little or no back story, plot or character development in these pieces. Rather, the focus will be on graphically describing the details of the couple's sexual encounters. I hope that readers will enjoy these pieces and I would appreciate any feedback or comments that you are kind enough to leave.

A Grandmotherly Pegging For Aaron

Lenore sat with her back against the headboard contemplating the naked form of her grandson sprawled out on the rumpled bed beside her. Ten minutes earlier, Aaron had bucked and writhed wildly beneath her as she straddled him and rode his young cock to orgasm. Now he was absolutely still, eyes closed and a look of contentment on his face.

She was careful not to rouse him from his post-coital slumber. The boy deserved his rest after such a bravura performance, she thought, and besides, his nap gave her a chance to admire his youthful body without making the sometimes shy nineteen-year-old self-conscious.

As she looked down at her grandson, Lenore pondered how different they were physically despite their shared bloodline.

A few inches short of six feet, Aaron was slim, lean muscled and long-limbed. His shaggy blonde hair framed a fine-featured face with blue eyes, sharp cheek bones and narrow nose. Lenore had always thought that Aaron's face was more beautiful than handsome, characterized by a dainty, almost feminine quality that his gentle nature enhanced. But there was nothing dainty about the equipment resting between his legs. When aroused, his cock was formidable with far-above-average girth and length and he was capable of using it with masculine authority and energy, as his grandmother well knew.

Lenore was close to Aaron's height but her body type greatly contrasted that of her grandson's. She was curvaceous and corpulent with wide hips, plush, rounded belly and massive breasts that were surprisingly firm for her sixty-two-years. Her short cropped hair, once brown, had faded to gray as had the frizzy bush adorning her plump pubic mound and meaty labia.

Her face was rotund and chubby-cheeked, and there were fine wrinkles at the corners of her brown eyes and full-lipped, sensuous mouth. She looked her age, she knew, and was not the beauty she'd been twenty-five years and thirty pounds ago. But Aaron's earnest compliments on her face and body lessened her concern over her faded looks. As long as she was still attractive in her grandson's eyes, that was all that mattered to Lenore.

A wave of deep fondness swept over her as she observed the sleeping boy. On impulse, she affectionately placed her hand on his thigh, causing him to stir and open his eyes. He smiled sleepily up at Lenore and said, "Sorry, Gran. I guess I dozed off. I think you must have worn me out."

Lenore laughed softly. If that were true, she thought, it would be the first time. Her grandson's sexual stamina seemed indefatigable and she doubted that wearing him out was even remotely possible. It wasn't unusual for Aaron to come three or four times in a single lovemaking session, ejaculating copious amounts of jism with every orgasm. But she went along with her grandson and said with a twinkle in her eye, "I wore you out? Oh dear, that's a shame. Well, let's see if I can revive you."

She ran her hand up his leg to the patch of golden curls at the junction of his thighs. Cupping his loose, furry sack, she fondled his balls until his cock twitched and began to bloom to its full eight and a half inch glory. As it stiffened under her touch, she playfully admonished him. "Hmmm, I don't think you're being honest with your old Gran, young man. This lovely beastie doesn't look worn out to me. Not in the least."

Lenore bent her head, licked her lips and planted wet kisses on the shaft and head of his cock, causing the boy to suck in his breath through gritted teeth. Almost immediately his rod sprang to life, ready for another round of lecherous play with his grandmother.

"What do you want, darling?" she whispered huskily as she fondled his revitalized cock. "How can your naughty old Gran make you happy?"

Aaron hesitated and blushed before stammering, "Well...like, maybe, uh...you know, uh... the strap on thing?"

"You mean you want Gran to fuck your lovely ass with her strap-on, dear?" Lenore asked, adding gently, "Sweetheart, I know you love being pegged and I love doing it to you so there's no reason for you to be shy or embarrassed about asking for it. It's important for us to be open and straight forward with each other in our relationship."

"Okay, Gran, you're right" the boy replied and then restated his request more boldly. "I'd really like you to fuck me in my ass with your strap on."

"See, now that wasn't so hard was it?" Lenore said, patting his cheek.

She gave his cock a final kiss before swinging her legs off of the bed and crossing the room to her bureau. Taking a rectangular box from the bottom drawer, she placed it on top of the bureau and opened it. Inside was a leather harness and four dildo attachments—two pink and two black—ranging in size from small to extra large.

Lenore had paid top dollar for the strap-on five years earlier and had used it vaginally and anally on her female lovers many times since then. But Aaron was the only male it had penetrated and the joy she derived from screwing her grandson's beautifully contoured butt with the device topped all of her other pegging experiences.

She cinched the harness around her waist, drew the inch-wide center strap between her robust thighs and threaded it through the buckle at the back of the harness. After adjusting the center strap so it pressed snugly against her labia and clitoris, she selected the medium-sized pink dil and snapped it onto the flange on the front of the leather rig. The silicone phallus—seven inches long and six inches in circumference—was a perfect replica of an authentic cock right down to the slight curve midway along its veiny length.

With the harness securely fastened to her groin, Lenore returned to the bed. Aaron lay with his head propped up on a pillow and when his grandmother knelt beside him, the dildo jutting out below her flabby belly bobbed freely inches from his face.

"Wow, like, I still can't get over how real it looks, Gran!" he enthused, examining the faux penis with his long, slim fingers. "Just like the real thing almost."

"And if it were the real thing, what would you do with it, dear?" Lenore teased.

Aaron, who had come out formally as bisexual on his eighteenth birthday, grinned mischievously. He slid his lips over the dildo's head and took half its length in his mouth, all the while looking up into his grandmother's eyes.

Lenore giggled at his antics. "Why, you little devil!" she said. "Well, I'm sure you could teach your old granny some of the finer points of fellatio, but right now, let's get you ready for a good pegging, okay? Get on your hands and knees, sweetheart."

Aaron removed the dildo from his mouth and when he had shifted into the position his grandmother requested, she knelt behind him and ran her hands over his butt cheeks. They were firm and pliant and covered in tiny silken hairs that felt like soft down under her hands. The puckered hole between them was pale pink and the size and shape of an almond. So lovely and sexy, Lenore thought, as she gazed at his rosebud: lovely, sexy and—she knew from previous experience—most likely a little raunchy and ripe from Aaron's lack of attention to personal cleanliness, so typical of teenage boys. But the funky aroma did not repel her. On the contrary, she found it erotic and exciting, heightening the heady thrill of the taboo intimacy that she shared with Aaron. She experienced this feeling now as she licked her lips, brought her face close to his ass crack and breathed in its dark, musky fragrance.

Lenore thought of her grandson's asshole as his "boy pussy", and the oral techniques she used to pleasure it were similar to those she applied to the vulvas of her female lovers. She began slowly with light kisses and tongue caresses up and down the inside curves of his butt crease, taint and dangling balls, but purposefully avoided touching her lips to his hole. After a minute or two of this preliminary teasing, she buried her face in the divide between his globes, planted her mouth directly over his pucker and began lapping at it with her tongue. The taste of his hole was a bittersweet blend of sweat and faint feculence with a hint of copper, a manly flavour she thought, befitting a male cunt. As though polishing it, she swirled the tip of her tongue around his anal ring and made it gleam with her saliva.

"Oh my God, Gran," Aaron sighed. "You are, like, such an excellent rimmer. Totally awesome!"

His frank compliments on her sexual skills always thrilled her and spurred her on. She spread his half-globes wider with her thumbs, pressed her face hard into his crack and passionately lashed and jabbed his asshole with her tongue. Aaron moaned and arched his back, reveling in the sensation of his grandmother's warm mouth and tongue pleasuring his butthole.

Lenore continued to orally attack her grandson's boy pussy until the sphincter relaxed enough to allow her to force an inch of her tongue into it. His hole was, she knew, now ready for the second stage of his pegging preparation.

She gave his asshole a parting kiss and lifted her face from his now very wet crack. Pulling open the drawer of her bedside table, she took out a jar of coconut oil, twisted off the lid and scooped her index and middle fingers into the slippery white substance.

"Spread your cheeks for Gran, my stinky darling," she told the boy who obediently reached back with both hands and pulled his buns apart.

She placed the tip of her oiled index finger against his glistening pink ring. It flexed and winked when she touched it, and offered no resistance as she slowly slid her digit in right up to the middle knuckle. She wriggled her finger inside of him until his sphincter relaxed enough to allow her to push her middle and index fingers together into his butt. The boy squirmed and moaned as she slid her slippery digits in and out of him, prompting his grandmother to ask, "Are you ready for something bigger, dear?".

"Oh, fuck yes, Gran!" he said. "I really want that big dil up my ass."

"As you wish, sweetheart," she said as she pulled her greasy fingers out of him.

His asshole was gaped to the diameter of a golf ball now and clearly ready to accommodate the strap-on. But first she wanted him in a different position.

"Okay, darling," she said, "get on your back and let Gran put the pillows under your butt."

He did as she asked and when she'd slipped the pillows beneath his tail bone, he raised and parted his legs and pulled his knees back towards his chest. This maneuver elevated his butthole almost to the level of the phallus projecting from Lenore's pelvis as she knelt facing him.

To make the dildo's entry into her grandson's boy cunt as smooth and comfortable for him as possible, Lenore scooped more coconut oil from the jar and spread it over the head and shaft of the artificial cock.

"Okay, sweetheart," she said. "Are you ready for Gran's nice, big dick?"

He smiled and nodded his head. "Yes, Gran! Totally ready!"

She moved closer to him, grasped the dildo at its base and placed its head against the loose entrance to his anal cavity. Pushing from her haunches, Lenore eased the dildo's greased head into Aaron's anus, taking care not to press too deeply into him before his ring had expanded enough to accommodate the bulbous business end of the prod.

"Is this alright, darling?" she asked the boy as the dildo disappeared inch by inch into his butt.

He nodded and she continued to press into him, watching his face grimace with pleasure as the dildo stretched and filled his anal canal. When she had sunk the phallus up to the hilt in his sphincter, she carefully pulled back until only its head remained inside him After a pause, Lenore again slewed the prosthetic penis forward into the depths of his rectum. As she repeated this back and forth motion, his asshole slackened further, allowing the phallus to glide in and out of him more freely. The pressure of the dildo against her pubic mound as she pushed into him and the sensation of the lower strap tightening against her thick pussy lips and swollen, throbbing clit when she withdrew was deliciously sensual. But as usual she was more concerned with the boy's pleasure than she was with her own.

"Is this what you want, Aaron?" she whispered. "Do you like the way your old Gran is fucking your asshole?"

"Oh Gran, it's awesome!" he replied. "I love it! But can you fuck me harder? Please Gran!"

Taking him at his word, she ramped up the tempo of her rhythmic pumping, thrusting the phallus harder, faster and deeper into his hole. The prod churned the coconut oil in his butt canal into a white froth that seeped out of his anus and spread over his ass cheeks as she reamed him furiously. Lenore's exertions made her pendulous tits jounce and sway above him, and Aaron could not resist reaching up to fill his hands with their soft weight, kneading and squeezing his grandmother's big-nippled breasts as she pounded him.

Every time the phallus rammed into his asshole, the jolt made Aaron's enormous cock bounce on his flat belly. As Lenore's anal pummeling became more frantic and rapid, the boy's tool flopped about on his abdomen like a just-landed trout. It caught Lenore's eye and without slowing her rhythm, she grasped his dick in her oily hand and began stroking it.

"Oh fuck, Gran!" the boy cried out. "That feels sooo fucking good!"

Lenore was panting hard now and the sensation of the center strap chaffing her engorged clit was pushing her towards the brink of orgasm. The rivulet of precum leaking from Aaron's cock onto her fingers told her that the moaning boy was fast approaching the same point.

"Come on, baby!" Lenore urged. "Come to Grandma!"

Lenore shoved the dildo hard into Aaron's asshole and held it deep in his bowels while she furiously frigged his cock. Guttural sounds of animal pleasure escaped from Aaron's mouth as his turgid organ spasmed in Lenore's fist and spurted spunk into the air with such force that globs of his man cream splattered his grandmother's face, udders and belly. Lenore barely felt her grandson's semen dapple her skin, overwhelmed as she was by a powerful orgasm that surged up like a tsunami of molten lava from her crotch and spread its heat throughout her belly and beyond. A stray bead of jism sluiced down her cheek as she arched her back, threw back her head and let out an urgent, primal cry.

As if paralyzed by the exquisite pleasure of their shared climax, the pair froze, connected by the dildo pressed deep inside Aaron's anal tunnel. They remained as motionless as two statues as the last vestiges of their orgasms ebbed and their straining bodies relaxed. Opening her eyes, Lenore looked down at her grandson and saw that a thin stream of cum still oozed from his cock. As if determined to wring every last drop of jism out of her beloved grandson, she gently milked his softening tool with fingers already sticky with his warm gooey semen.

"Oh my God, Gran," Aaron said passionately. "You're incredible. That was, like, unbelievable! Even better than getting fucked by a real cock!"

Lenore smiled, happily basking in his enthusiastic praise as the blush of afterglow washed over her body.

"You're the incredible one, darling," she said as she leaned down to kiss his his mouth with lips that only moments earlier had intimately explored the pungent cleft of his buttocks. The couple exchanged more kisses and sweet words before Lenore straightened up and slowly eased the dildo from the clutch of his anal canal. She unbuckled and removed the harness from her waist, leaned over the edge of the bed and dropped the rig on the floor. Later, when Aaron had left, she would disassemble the device, wipe the phallus and center strap free of the lubricious substances that coated them and return the strap-on to its box. But now she wanted only to stretch out beside her grandson and snuggle her bulk against his sweaty body.

When she lay next to him with her head on his shoulder, he turned to look at her. "You're so beautiful, Gran," he said tenderly. "So beautiful and hot as fuck."

"Oh, what a lovely thing to say, darling," she replied, a radiant smile lighting up her face. "You're hot and beautiful too and I love you to pieces. Now, let's hush and rest awhile. Your poor old Gran needs to get her strength back. And when I do, I'm going to give you a very special treat."

She took his hand and placed it on the pudgy bun of furred flesh between her thighs. Aaron sighed happily, massaging his grandmother's damp, beefy vulva as she drifted into sleep.

He knew that the treat Lenore had in mind would be quite unlike the goodies that traditional grandmothers typically feed to the grandchildren who they adore and spoil. But it would taste and smell at least as rich and delicious as those more conventional treats and she would serve it to him with a generous helping of tender, grandmotherly love.

THE END