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Sister Knows Best: A Thorough Stretching

Chapter One: The Assignment

I was lying on my stomach on the bed, my face buried in a pillow as I complained to my sister about the knots in my back. "Come on, sis, can't you help me out?" I pleaded, turning my head to give her a pitiful look.

She stood at the foot of the bed, a mischievous grin on her face as she considered my request. "I could," she said, her voice dripping with suggestion. "But you'll have to do exactly as I say."

I hesitated for a moment, but the thought of her massaging my knots was too tempting to resist. "Fine," I said, rolling over onto my back and lifting my ass up off the bed.

She climbed onto the bed, straddling my thighs as she began to gently stroke my ass. I moaned in pleasure, my eyes fluttering closed as she worked out the knots.

"You like that?" she asked, her voice low and husky.

I nodded, unable to speak as she continued to massage my ass.

"How about this?" she said, her hand drifting lower until she was gently stroking my hole.

I gasped, my body tensing as she teased me. "Sis..." I said, my voice barely above a whisper.

"Do you want more?" she asked, her eyes sparkling with amusement.

I nodded again, feeling bold. "Yes," I said, my voice stronger now. "I want you to fuck me with a dildo."

Her eyebrow shot up in surprise. "Oh, do you now?" she said, her voice dripping with sarcasm. "And how long and thick do you want it?"

I blushed, feeling embarrassed at my own request. "Uh, medium-sized?" I said, hoping I hadn't offended her.

She smirked, climbing off me and heading over to her dresser. She rummaged through a drawer, pulling out a medium-sized dildo. "Alright, get into a doggy style position," she said, tossing the dildo onto the bed next to me.

I did as I was told, getting onto all fours and presenting my ass to her. I felt a mix of nerves and excitement as she put on the dildo and started to fuck me.

"Harder," I moaned, loving the feeling of her inside me.

She scoffed, shoving the dildo into me with more force than I was expecting. I yelped in pain, my body tensing as she continued to fuck me harder and harder.

"Stop!" I cried, my voice barely above a whisper.

But she didn't stop, instead she shoved the dildo into me with even more force. "Is this what you wanted?" she asked, her voice dripping with anger.

"Yes," I whimpered, feeling embarrassed and ashamed.

"Beg for it," she said, her voice cold and cruel.

"Please, sis, fuck me harder," I begged, my voice barely above a whisper.

She pulled the dildo out, a satisfied smile on her face. "That's what you get for asking for too much," she said, tossing the dildo onto the floor.

I lay there, feeling embarrassed and humiliated as she climbed off the bed and headed out of the room. I couldn't believe what I had just done, and I wasn't sure if I would ever be able to look my sister in the eye again.

But as I lay there, feeling sorry for myself, I heard her laugh from the other room. "I was just playing around," she said, her voice filled with amusement. "You didn't really think I was mad at you, did you?"

I smiled, feeling relieved. "No," I said, my voice filled with gratitude. "I didn't."

"Good," she said, her voice filled with playful insult. "Now man up and get ready for round two."

I grinned, feeling excited and determined. I was ready for whatever she had in store for me.

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