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  • Chapter 4 - Grandma Get Rolled By Her Grandson

    Chapter by ninhjimmy007 · 15 Jun 2025
  • Granny Gretchen is now Liam's 4th girlfriend and his very own grandmother, this is kinda great as he can't believe he have a GILF girlfriend. Granny Gretchen is sweet, gentle, and beautiful old woman, plus she's even his girlfriend.
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  • Three days had passed since Granny Gretchen had become Liam’s fourth girlfriend. It was the end of the month, and Liam still couldn’t believe his luck. He had gone from dating a fiery redhead to a sophisticated British MILF, then a sassy ebony goddess, and now a sweet, gentle GILF who also happened to be his grandmother. Life was certainly interesting, and Liam was enjoying every moment of it.

    Granny Gretchen was unlike any of his previous girlfriends. She was sweet, nurturing, and had a warmth that made Liam feel cherished in a way he hadn’t experienced before. She was beautiful in her own way, with her soft silver hair, her cat-eye glasses, and her pearl necklace that always seemed to catch the light just right. And those breasts—saggy and massive, a testament to a life well-lived.

    One morning, Liam woke up to the smell of freshly baked cookies and muffins wafting through the house. He stretched and made his way downstairs, where he found Granny Gretchen in the kitchen, humming to herself as she pulled a tray of cookies out of the oven.

    She was dressed in a classic granny dress, the kind that exposed just a hint of cleavage, enough to drive Liam wild. Her hair was piled up in a big bun, and her glasses perched on the tip of her nose as she smiled at him.

    “Good morning, dear,” she said, her voice warm and inviting. “I made your favorites.”

    Liam grinned, his heart swelling with affection as he looked at her. “Good morning, Granny Gretchen,” he replied, his voice filled with admiration.

    He sat down at the table, watching as she placed a plate of cookies and muffins in front of him. He took a bite, the sweet flavors exploding in his mouth as he savored the treat. Granny Gretchen sat beside him, her eyes sparkling with happiness as she watched him enjoy her baking.

    “You’re amazing, Granny Gretchen,” he said, his voice filled with sincerity.

    She giggled, her hand reaching out to pat his cheek. “You’re too kind, dear,” she replied, her voice gentle.

    They spent the day together, their bond growing stronger with each passing moment. That night, they cuddled on the couch, watching an old show on TV. Granny Gretchen’s eyes grew heavy, and before long, she was fast asleep, her head resting on Liam’s shoulder.

    Liam couldn’t blame her. She was an older woman, after all, and the day had been long. He carefully lifted her into his arms, carrying her to his room and tucking her into bed. He leaned down, pressing a gentle kiss to her forehead.

    “Goodnight, Granny Gretchen,” he whispered, his voice filled with affection.

    She stirred slightly, a soft smile playing on her lips as she murmured his name in her sleep.

    The next few days were filled with similar moments of warmth and tenderness. Liam and Granny Gretchen spent time with her senior friends, playing games and chatting like old pals. It was a different dynamic than what he had experienced with Chloe, Beatrice, or Jasmine, but it was comforting in its own way.

    A week later, they found themselves at the park, sitting on a bench as they enjoyed the sunshine. Granny Gretchen’s hand rested in Liam’s, her eyes soft as she looked at him.

    “You know, dear, I never thought I’d find myself in a situation like this,” she said, her voice filled with sincerity. “But I’m glad I did.”

    Liam smiled, his heart swelling with emotion as he looked at her. “I’m glad too, Granny Gretchen,” he replied, his voice steady and sure.

    He leaned in, capturing her lips in a gentle kiss. She sighed into his mouth, her body melting against his as their passion ignited. It was different from the fiery encounters he had shared with his previous girlfriends, but it was no less intense.

    Another week passed, and the next month was about to begin. One evening, Granny Gretchen entered Liam’s room wearing a sheer nightgown that left little to the imagination. She giggled as she approached him, her eyes sparkling with mischief.

    “You’re still up, dear?” she asked, her voice a gentle purr.

    Liam grinned, his eyes roaming over her body as he nodded. “I am now,” he replied, his voice filled with admiration.

    She leaned down, capturing his lips in a passionate kiss. Liam groaned, his hands reaching up to cup her saggy breasts as he deepened the kiss. Granny Gretchen moaned into his mouth, her body melting against his as their passion ignited.

    They undressed each other slowly, their hands exploring each other’s bodies with a sense of wonder and excitement. Liam marveled at the softness of her skin, the fullness of her curves, and the way her body responded to his touch.

    He positioned himself between her legs, his cock hard and ready as he teased her entrance. With a gentle thrust, he filled her completely, their bodies moving together in a slow, sensual dance.

    Granny Gretchen’s moans filled the room, her body trembling as she neared her climax. Liam could feel his own pleasure building, his cock throbbing as he drove into her with deep, powerful thrusts.

    “Yes, Liam! Fuck me, dear!” she cried out, her nails digging into his back.

    Liam groaned, his hips pistoning as he drove into her with relentless force. He could feel her walls clenching around him, her body trembling as she teetered on the edge. With a final, powerful thrust, he sent them both over the edge. They cried out together, their bodies shuddering as they rode out their orgasms.

    As the waves of pleasure subsided, Liam collapsed beside Granny Gretchen, his chest heaving as he tried to catch his breath. He turned to look at her, a satisfied smile playing on his lips. But what he saw made his eyes widen in shock.

    Granny Gretchen’s body was glowing, a golden light emanating from her skin. She gasped, her back arching as the light intensified. Liam watched in awe as her body began to change, her features shifting and morphing before his eyes.

    Her silver hair darkened, turning into a rich, chestnut brown as it cascaded down her shoulders in loose waves. Her skin took on a warm, olive hue, her features shifting into those of a stunning Latina woman. Her body filled out, her hips widening, her waist narrowing, and her breasts swelling to a massive size.

    Liam’s cock twitched as he watched the transformation, a mix of shock and arousal coursing through him. The woman before him was no longer Granny Gretchen, but a sexy Latina MILF with an air of confidence and sensuality.

    The woman gasped, her eyes fluttering open as the transformation completed. She looked around, confusion etched on her face as she took in her surroundings. Her gaze landed on Liam, and she gasped, her hand flying to her chest.

    “Mijo, what are you doing?” she asked, her voice carrying a sultry Latina accent. “We’re in the middle of… oh my, you must have hit your head.”

    Liam was taken aback, his mind racing as he tried to process what had just happened. “Granny Gretchen? Is that you?” he asked, his voice uncertain.

    The woman frowned, her brow furrowing in confusion. “Granny Gretchen? Who’s Granny Gretchen? My name is Isabella Diaz, mijo,” she said, her voice firm yet gentle. “I’m your stepmom, mijo.”

    Liam’s mind was reeling, but he couldn’t deny the attraction he felt towards this new woman. Isabella was stunning, her exotic beauty a stark contrast to Granny Gretchen’s gentle warmth. And despite her confusion, there was a familiarity in her eyes that drew him in.

    Isabella seemed to sense his turmoil, her expression softening as she reached out to cup his cheek. “You alright, mijo? You look like you’ve seen a ghost,” she said, her voice filled with concern.

    Liam swallowed hard, his eyes flickering down to her massive breasts before meeting her gaze again. “I’m fine, Isabella. It’s just… a lot to take in,” he managed to say.

    Isabella giggled, a playful glint in her eyes. “Well, I must say, it’s not every day I wake up to find my handsome stepson in bed with me,” she teased, her hand trailing down his chest.

    Liam’s cock twitched at her touch, his body responding to her despite the confusion in his mind. He couldn’t explain it, but he felt a connection to her, as if she was still Granny Gretchen in some way.

    “Well, you’re still my girlfriend, right?” he asked, his voice hopeful.

    Isabella’s eyes widened in surprise, but she didn’t deny it. Instead, she leaned in, her lips brushing against his in a soft, tentative kiss. “I suppose so, mijo,” she whispered, her voice a sultry purr. “But let Latina mommy help you, okay? Slow down.”

    Liam groaned, his hands reaching up to cup her breasts as he deepened the kiss. Isabella moaned into his mouth, her body melting against his as their passion reignited. The confusion and questions could wait. For now, all that mattered was the connection between them, a bond that transcended time and transformation.

    As they kissed, Liam’s hands explored Isabella’s new body, marveling at the softness of her skin and the fullness of her curves. She was different, yet familiar, and he couldn’t resist the pull he felt towards her.

    Isabella broke the kiss, her eyes dark with desire as she looked down at him. “I may not remember everything, mijo, but I know I want you,” she whispered, her voice husky with need.

    Liam didn’t need any more encouragement. He flipped her onto her back, his body covering hers as he captured her lips in another searing kiss. His cock was hard and ready, and he wasted no time in positioning himself between her legs.

    Isabella gasped as he thrust into her, her walls tightening around him as he filled her completely. She wrapped her legs around his waist, pulling him closer as she matched his rhythm.

    “Yes, Liam! Fuck me, mijo!” she cried out, her nails digging into his back.

    Liam groaned, his hips pistoning as he drove into her with relentless force. He could feel her walls clenching around him, her body trembling as she neared her climax. He reached between them, his fingers finding her clit as he rubbed it in tight circles.

    Isabella’s moans grew louder, her body tensing as she teetered on the edge. “I’m gonna cum, Liam! Don’t stop!”

    Liam’s own pleasure was building, his cock throbbing as he felt her walls tightening around him. With a final, powerful thrust, he sent them both over the edge. They cried out together, their bodies shuddering as they rode out their orgasms.

    As the waves of pleasure subsided, Liam collapsed beside Isabella, his chest heaving as he tried to catch his breath. He turned to look at her, a satisfied smile playing on his lips. Despite the confusion and the questions that lingered in his mind, he couldn’t deny the connection he felt to her.

    Isabella turned to him, her eyes soft as she reached out to cup his cheek. “I may not remember everything, mijo, but I know I want to be with you,” she whispered, her voice filled with sincerity.

    Liam smiled, his heart swelling with emotion. “I want to be with you too, Isabella,” he replied, his voice steady and sure.

    As they lay together, their bodies entwined, Liam couldn’t help but feel a sense of excitement for the journey ahead. He didn’t know what the future held, but he knew that he wanted to explore it with Isabella by his side. And as they kissed again, their passion reigniting, he knew that their story was far from over.
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anon_add7613c6253 ∙ 29 Jul 2025