+- Story-Portal (https://time-tales.af/storys)
+-- Forum: LGBTQ & Erotic (https://time-tales.af/storys/forumdisplay.php?fid=19)
+--- Forum: Boys & Girls + Bi (https://time-tales.af/storys/forumdisplay.php?fid=20)
+--- Thread: Dear Grandma (/showthread.php?tid=1028)
Dear Grandma - Simon - 11-25-2025
“We’re finally here,” said my father as we stopped at the end of the long, unpaved driveway to my grandmother’s farm.
Even as an eleven-year-old, I knew from all his quiet comments that he wasn't a big fan of his wife's mother. He never looked forward to trips to her farm. Several times during our all-day drive, he told my mother he wasn't sure about her plans for my summer.
"I'm just not sure if spending two months with your burnt-out hippie mother is really the best thing for Luke – he should be taking summer classes and preparing for his PSAT."
My mother brushed aside his objections with her typical grin.
"First of all, she's not burned out, she's retired. Admittedly, she was a hippie and quite unconventional, but that's exactly the point! A summer with her will do him good and boost his self-confidence!"
She turned to me in the back seat and winked at me.
"Don't worry, baby, you're going to have so much fun – you have no idea."
As we got out of the car, I stretched and took in my new summer house. It was idyllic. A well-kept white farmhouse with a huge covered porch, a lush green garden, and abundant flowerbeds, all enclosed by a white picket fence. Behind the house, I could see a large red barn with a fenced pasture. My mother had told me that Grandma used to keep horses there. The house was rustic, but nothing was dilapidated or broken. It was beautiful. I couldn't have imagined a more perfect place for a summer vacation.
The screen door slammed shut, and my grandmother stepped onto the porch. She was like a ray of sunshine. She had long, gray hair, braided into two pigtails, that fell past her shoulders. She was wearing denim overalls and a bright orange sports bra underneath. Even through the overalls, I could see her curves and her cleavage, which spilled over the top of her bra. I suddenly felt warm and embarrassed.
She waved to me: “Oh my God, Luke! Look how you’ve grown!”
She skipped down the steps and met me in the courtyard. She hugged me tightly, my face pressed against her chest. She felt and smelled wonderful. She bent down and looked straight into my eyes.
"I'm so glad you're here, Luke. I've been feeling a bit lonely and could really use some company."
I felt myself blushing again as I said, "I'm glad to be here too, Grandma!"
She took my hand and led me inside.
“Oh, we’re going to have so much fun, I can already tell,” she said with a broad smile.
Grandma showed us around the house and stayed close to me the whole time. My parents filled the guest room, which would be mine as soon as they left. Grandma had made up the couch for me to sleep on.
"Don't worry," she said. "I don't plan on making you sleep on a couch all summer."
The first night was a whirlwind. Grandma cooked a delicious dinner. She and my mother laughed and chatted throughout the meal. I sat right next to Grandma, and she kept reaching out to squeeze my knee or leg, smiling and winking at me. She whispered jokes in my ear. I was instantly smitten.
I was asleep on the couch and woke up to find my parents already packed and getting ready to leave. Apparently, my father didn't want to spend any more time with Grandma than necessary.
After hugging my parents and watching them drive away, I turned around, walked up the porch, and saw Grandma standing there smiling with a hot cup of coffee. Today she was wearing cutoff denim shorts, a black sports bra, and old hiking boots.
Today's outfit accentuated her figure: strong thighs, a large, round bottom, a slight tummy, and enormous, round breasts that spilled over her bra. I wasn't used to seeing women dressed like that, let alone with a figure like my grandmother's. I just stood there and stared. With a knowing smile, she came down the stairs and waved me around the house.
"Come! I'll show you the house!"
Grandma showed me the stable and introduced me to the horses – a large grey stallion named Shadow and a smaller brown mare named Cherry. They each had their own stall, opposite each other.
"Of course we have to keep them apart, otherwise Shadow will cause trouble," giggled Grandma.
I laughed too, even though I wasn't entirely sure what she meant. I had some basic knowledge about penis-in-vagina sex from a book my parents had given me, but otherwise I didn't understand anything about the whole incident—except that I got an erection every time I thought about a girl I found attractive. Which, of course, meant that I could hardly hide my erection all morning with Grandma.
She took me up to the hayloft and showed me how to climb the hay bales and circle them like a fortress. She led me to the pasture and then back down into the woods on her property. There was a small stream and lots of trees to climb – a paradise for a child like me.
When we emerged from the shady trees, the sun was already high, and we were both sweaty and dirty. Grandma wiped her forehead.
"Okay, child, let's go inside, clean up, and make ourselves some lunch, what do you think?"
We went back, Grandma a little ahead of me. As she walked past the laundry room into her bedroom, she quickly pulled off her jeans and bra and threw them into the laundry basket. I stood there with my mouth open. Her thighs and her large, round bottom jiggled as she walked. Her breasts swung as she turned her head toward me.
"Just throw your dirty clothes in the laundry basket, I'll take care of it."
Then she came into her room, and I heard the shower turn on.
I hadn't really explored masturbation at that point, and I'd never experienced an orgasm. I'd played with myself like all boys do, but I'd never reached that climax of release. So, standing in the shower with my 10 cm penis harder than ever, I was practically beside myself. I couldn't help but stroke it, but that only intensified my desire. When I finished showering and was drying myself off, I was still standing there, tenting my towel. I was hoping and praying I'd make it down the hall to my room before Grandma came out to see me like that.
Unfortunately, I was in such a hurry that I bumped right into her and dropped my towel. Fresh out of the shower, she was wearing a thin tank top that clung perfectly to her breasts. Her wide, round nipples were clearly visible. She was wearing boyshorts that had been washed hundreds of times and were so tight they covered her thighs, creating a deep cameltoe. None of it helped me, and my grandma got a full view of my hard little cock.
She suppressed a laugh as I tried to cover myself and helped me up.
"Oh, it's nothing, darling! Nothing I haven't seen before. But why didn't you take care of yourself in the shower? I did."
Her face was so kind and unprejudiced. I had my towel in my hand again to cover myself, but now I paused.
"Wait, what do you think, Grandma?"
Finally, she laughed out loud.
"Well, to bring yourself to orgasm, of course! You look like you desperately need it."
“I… I just don’t know how,” I said.
She put her hands on her hips and looked at me, her eyes full of compassion.
and warmth.
“Oh, my poor boy,” she said, shaking her head. “What’s wrong with my daughter?”
"Just done?"
She knelt down, kissed me on the forehead, and hugged me tightly.
"How long have you been suffering like this? Without any relief?"
She leaned back and looked into my eyes.
"Darling, you don't have to say yes, but would you like Grandma to help you? I can teach you, and honestly, I think we can have a little fun too."
Her concern transformed into a mischievous smile. Never before had I felt so safe and comfortable. Never before had I felt such warmth in my chest.
“Yes, please, Grandma,” I said.
She kissed me again, this time on the lips. She stood up, took my hand, and led me into her bedroom.
She had a king-size bed covered with a large, very soft quilt.
"Jump into bed, baby, leave your towel on the floor."
She saw me hesitate – although I felt so safe and cared for, I was still embarrassed by my situation.
"Here," she said. "Perhaps you'll feel less ashamed if I join you."
She took off her top and then her shorts. She stood proudly naked before me. She was so beautiful. Her skin was covered in freckles. Her breasts were large and hung low on her chest, but they didn't sag. Her nipples were large and light pink. She had a tummy, and her thighs touched. Between her legs was a thick strand of gray pubic hair. I noticed she also had hair under her arms. She smiled at me and stared.
"Well, sweetie, are you feeling better now?"
I nodded, dropped my towel, and climbed onto the bed.
She climbed up as well and knelt in front of me. My penis was tense and hard, so sensitive that it almost hurt.
"You see, baby, there are ways to touch ourselves and each other that feel good."
She stroked my chest with her fingers.
"And there are places that feel really good."
She lightly stroked the shaft with her fingers and swirled them around the glans. My hips lifted, and I moaned softly.
"Hehe," she laughed. "You know what I mean? But baby, if you play with yourself and don't give yourself an orgasm—what most of us call coming—what feels good at first will end up feeling unpleasant."
She leaned back and spread her legs. Even through her wild bush, I could see she was soaking wet—her thighs were covered in a sticky substance. She sensually rubbed a finger along her cleft and gasped softly with pleasure. When I lifted them, they were covered, and as I pulled them apart, I could see her semen clinging to them in threads. She absentmindedly sucked her fingers clean.
"I'll show you how I come, and then I'll help you do it too, okay?"
I nodded and was unable to speak.
She began rubbing herself up and down her cleft. I could hear the smacking sound as she became increasingly wet. With one hand, she pulled back her pubic hair, revealing her full lips and throbbing clitoris. Her hand moved skillfully around her clitoris, rubbing faster and faster. A moan escaped her lips, and then another, and another. She closed her eyes and threw her head back.
"My God, sweet boy, you've excited me so much that I'm about to come."
Suddenly she tensed up and began to tremble all over. A sticky fluid spurted out between her legs and landed on the bed, my chest, and my small penis.
I scooped some up and licked it off, just like she had done before. It was thick, sticky, sweet, and musky. It was one of the best things I'd ever tasted. She watched me, pleased that I was following her lead. After a moment to catch her breath, she got down on all fours. "Okay, my beautiful boy, now it's your turn." She bent down and took my cock in her mouth. Instantly, I lost myself in the most intense pleasure of my life. I writhed and moaned as Granny held my hips. She circled my head with her tongue, dodging my entire cock. "Oh, oh, oh!" was all I could manage. I don't even know how long it lasted, but finally, my very first orgasm washed over me. I shuddered and lost myself in spasms until it was over. I fell back, not knowing what to think. Finally, I opened my eyes and stared at the ceiling. Grandma climbed over me, her breasts resting on my chest, her smiling face replacing the ceiling in my field of vision.
"Are you feeling any better, my dear?"
I nodded weakly, but happily.
“Okay,” she said. “Let’s make lunch. And once we’ve rested, we’ll see…”
"Do you feel like playing a little longer?"