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I Fingered My Sister

When my sister came home from work, she slumped down on the outdoor sofa. She looked exhausted. At eighteen, she had just gotten her first summer job as a waitress, but she had already complained to me and our mom that it was tougher and more stressful than she had expected.

I was twenty and working as a programmer from home, so I knew everything about work-related stress.

I decided to keep her company. She was dressed in a short skirt and a fitted top, her glasses slipping slightly down her nose. Ruby was cute in a natural way. She wasn’t a bombshell who turned heads everywhere we went, but that was fine by me. I actually preferred having a normal, approachable sister over someone who would draw attention everywhere we went.

“How’s it going?” I asked, taking a seat next to her.

“It’s fine… but my sleep’s been suffering. I don’t know what I can do anymore,” she said hopelessly.

I felt bad for her. “Did meditation help? The one Mom suggested?”

Ruby shook her head. “Nope. I can barely focus. I regret taking this job. Now that it’s summer, the place is so crowded.”

Her voice sounded defeated. I slid my arm around her shoulders. “I know the feeling. When I got my first job at a drive-through, I thought I’d never last, but you get used to it if you hang in there.”

“It would be easier if I could at least get some sleep,” she said, rubbing her eyes. “Insomnia is ruining everything.”

I pressed a quick kiss to her cheek. “Try not to dwell on it too much. The more you obsess about not sleeping, the harder it is to actually sleep.”

She tilted her head up at me and smiled, pushing her glasses back up her nose. “Didn’t your girlfriend, Ashley also struggle with insomnia?”

“Yes, she did.”

“And what did you do to help her?”

I hesitated. It didn’t feel fair to keep it from my sister, but I was awkward about saying it out loud. The truth was that what helped Ashley sleep was having an orgasm. I used to finger her while whispering soothing words in her ear, and without fail, it worked. I had picked up the idea from some old Chinese erotic story I stumbled across in the library years ago.

“Uh… it was just something,” I said.

Ruby frowned. “Why can’t you tell me?”

“I’m sorry. It’s a little inappropriate.”

Her lips curved into a grin. “Is it sex?”

“Not quite,” I said quickly. “You should really talk to our mom first.”

“Fine,” she muttered, dropping her eyes.

After Ruby’s complaints earlier, I retreated to my room and focused on work. Hours passed with the steady glow of my monitor until Mom came home. We ate dinner together, and our mother was very concerned for Ruby’s well-being. She bought a journal for her and told her to write in it every evening.

“You’ll get better,” Mom told her with a kiss on the cheek. “I promise you will. We are here for you, both your brother and I.”

“Thank you,” she said, a smile tugging at her lips. “It means a lot to me.”

*****

Sometime in the middle of the night, I felt a tug on my shoulder. I opened my eyes, and Ruby stood beside my bed, her hair messy and her nightgown draped loosely around her body. Her cheeks were wet with tears.

“Ruby?”

“I can’t sleep,” she whispered, snivelling. “It’s driving me insane. The more I try, the more it stresses me out. It’s a vicious cycle.”

I pushed myself upright, heart twisting at the sight of her. “Hey, hey, it’s okay,” I murmured, wiping at her tears with my thumb. “Don’t cry.”

She sniffled and bit her lip. “Please… can you help me? I can’t do this anymore.”

I hesitated, knowing exactly what she was asking without her saying it. I couldn’t say no any longer. I felt obliged as her brother to protect her. “Alright,” I said. “I’ll help you. But you have to stay quiet. And you can’t tell our mom, no matter what.”

She nodded quickly, eyes wide and desperate. “I promise.”

I got out of bed and followed her down the hall to her room. The bedside lamp was on, casting a dim, golden color over her room. She sat on the edge of her bed, clutching her pink nightgown close, but the thin fabric didn’t hide much. I could see the soft swell of her breasts, her nipples faintly outlined without a bra. It was slightly transparent.

My eyes flicked for a moment to her nightstand. A small leather-bound journal sat there. I recognized it instantly, the one her mother had given her to “help with insomnia.” She had tried to fill it with notes and thoughts, but judging by the tears in her eyes, it clearly hadn’t worked.

“See?” she said with a frustrated little laugh, gesturing at it. “That stupid journal didn’t do anything.”

I sat down beside her, close enough to feel her warmth through the thin nightgown. “Then we’ll try something else,” I said, patting her back.

Her breathing slowed, her eyes on me, waiting.

I looked her straight in the eye. “You can’t tell our mom about this. Ever.”

Ruby nodded. “I won’t. I promise.”

I exhaled slowly, my chest tight. “What I did for Ashley… It was simple. I fingered her until she climaxed, and I whispered to her the whole time. It relaxed her. She fell asleep right after, every time.”

Her cheeks pinked. She blinked at me, nervous but curious.

“If you’re not comfortable, we don’t have to do this,” I added. “I won’t be mad. But you need to be honest with me.”

Her lips trembled into a desperate smile. “I don’t mind. I’m desperate, and I… I’m not against you fingering me. I mean, it doesn’t count as incest, does it?”

“I’m pretty sure it does,” I said.

She shrugged. “Well, I don’t care. If it helps, that’s all it matters.”

I swallowed hard, my cock already straining in my shorts. “Alright. But you have to stay quiet. No moaning too loud.”

“I’ll try,” she whispered.

I patted the mattress, and she lay back on the bed, pulling her pillow under her head, the lamplight washing over her pale skin. I slid closer, my hands shaking a little as I gripped the hem of her nightgown. She nodded, giving me permission, and I gently pushed the garment up her thighs.

The sheets rustled as I rolled them aside. My eyes widened when I saw her.

Her pussy was smooth, symmetric and perfectly shaved with not a stubble in sight. Her lips were creamy pink like an erotic dream. A delicate, sweet scent drifted up, feminine and pleasant, unlike anything I had smelled before. The sight of her lying bare, waiting for me, felt forbidden in a way that made my cock throb.

I tried not to ogle too much. I was doing this for her and not my own sexual fantasies. I reached out, brushing my fingers lightly over her folds. Ruby shivered in pleasure, closing her eyes as she bit her lip.

“You’re so warm,” I whispered, sliding my hand more firmly against her vagina.

She let out a gasp and then covered her mouth with her hand. Her body shifted under my touch, her thighs spreading a little wider to invite me in.

The heat of her arousal clung to my fingers as I slipped one inside, slowly, testing her pink hole. She arched her back, her eyes closing tighter, but her hand pressed against mine as if to beg me not to stop.

“Good girl,” I whispered in her ear, my lips close enough to brush her skin. “Just relax for me. Let it feel good.”

Ruby whimpered softly, her chest rising and falling faster as my fingers began to move inside her, stroking her in slow, steady motions, along the walls, over her lips and briefly over her clit.

Her body trembled as I slid my fingers in deeper, curling them just right in a come-hither gesture. She pressed her face into the pillow to stifle her sounds of pleasure, but I leaned down, close to her ear.

“You’re so beautiful,” I whispered. “You don’t even realize it. You’re important to me, Ruby. You always have been.”

Her lips parted, and she let out a shaky breath. Tears welled in her eyes, but they weren’t from stress this time. She smiled through them, small tears of joy spilling down her cheeks as my fingers kept exploring her intimate, sensitive flesh.

While keeping my pointer and index finger inside her, I brushed my thumb against her clit, circling gently, and she moaned louder against her hand. Her thighs tensed, her hips rolling up to meet every stroke.

“That’s it … You are the most beautiful sister in the world. The sweetest girl I’ve ever known. You mean the world to me, Ruby,” I murmured, my lips brushing the shell of her ear. “You can let go. I’ve got you. You’re safe with me, and you always will be.”

The scent of her musk and honey grew stronger, and I felt her wetness cover my fingers as I kept going, whispering loving words in her ear while fingering her beautiful pussy. Her nipples had stiffened to daggers as she was experiencing a pleasure she probably had never experienced before, and the warmth radiated from her pussy like a blast furnace.

Her moans grew quicker, her body shaking as the tension inside her coiled tight. Then, with a sharp gasp, she climaxed hard. I slowly withdrew my fingers from her slit, but warm liquid squirted across my hand as her hips jerked and her body writhed.

“Geeze…” I breathed, stunned by the release and squirt.

She sighed long and deep, the tension in her face finally gone. She opened her eyes for a moment, dazed. I grabbed a towel from her nightstand, wiped her honey from my hand, and then I cleaned her up carefully, making sure she was comfortable, my chest swelling at how peaceful and pretty she looked.

“Thank you,” she whispered, her voice muffled by the pillow.

I opened my mouth to say, “You’re welcome,” but before the words left my lips, she was already out cold, her breathing slow and steady.

I smiled, leaned down, and pressed a kiss to her forehead. “Sleep well,” I murmured, happy that she had finally found some peace.

The end.

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