The Anderson Family Journals
Copyright© 2022 by Mr. Here
Timmy #05: Waking Diana
Incest Sex Story: Timmy #05: Waking Diana - A "Journal-Style" story featuring members of the Anderson Family, mostly told through Timmy's POV. ------ I've posted this story to SOL before, though I can't remember how much. I've made some changes, such as making the siblings triplets and aging everyone up to 18. The sex is still hot, won't change that.
Caution: This Incest Sex Story contains strong sexual content, including mt/ft Ma/ft mt/Fa ft/ft Teenagers Consensual Reluctant Romantic Teen Siren Lesbian BiSexual Heterosexual Fiction Cheating Sharing Incest Mother Son Brother Sister Father Daughter Cousins Uncle Niece DomSub Light Bond Rough Group Sex Interracial White Male White Female Oriental Female Indian Female White Couple Anal Sex Analingus Cream Pie Exhibitionism First Massage Masturbation Oral Sex Tit-Fucking Voyeurism Big Breasts Public Sex Small Breasts
Waking Diana
Monday
When I woke, I found a text message on my phone that read: Practice makes perfect. I kept that in mind as I left my room.
The first step outside of my room was the hardest step I had ever taken in life. Diana told me to enter her room at five-thirty in the morning, and I was standing outside of her doorway by five minutes till, looking to the left and right in case my mother or Abbey should appear in the hallway as they headed downstairs. My mom left to work at a quarter to six every morning, and the thumping of my heart intensified every time I looked down the hall toward my mother’s room.
What if she decided to leave early for work today? What if she wasn’t in her room but downstairs, making coffee, on her way back up for something she left behind? I looked over the railing and into the dark living room, straining my hearing, and I thought I heard sounds from the kitchen. What if ... I didn’t know what if, but what if?
My phone ticked to half-past five, and the world outside of my sister’s room faded to a dull, soundless gray. I turned back to the door, grabbed the knob—fearing she had locked it—and turned it. She had not locked it. I pushed in and stepped inside. The soft glow of my sister’s bedside lamp created a small haven of light that shined over the left edge of her bed where she slept. I closed the door, locked it, and walked to Diana’s bed.
From memory, I knew that Diana usually slept in the middle of her bed. The lamplight was for me so that I could see her. I knew that as surely I knew that she wasn’t asleep. All of the massage videos that I had watched from YouTube and porno sites flashed through my head like one of those one-second movies, as did the sleep assault videos, and the Japanese molester videos, and all kinds of perverted shit sexless people watch. And, I watched a handful of those incest scenes where the sister or mother remained silent while their brother or son openly caressed their bodies, yet they admitted to what was going on.
Slow, I told myself. Take it slow.
I told myself that, but I wanted to run to the bed and rip the blankets from my sister’s body. I wanted to know if she was naked. I wanted to touch her and run my hands over her and rub her in the way she had rubbed me on Friday night. The way she had jerked me off and so much more. But Diana had said, “If I’m asleep, then find a way to wake me up that shows me how much you appreciate me. Understand?”
APPRECIATE ME.
Those words shined in my mind like a hot pink neon sign.
I walked to my sister’s bed on quiet toes, moving to the edge where she lay. She lay on her stomach, her blonde head facing me and sunken into her white, satin-covered pillow with her arms underneath it. How’d she get such a nice bed set? That didn’t matter. Her silk sheets—she doesn’t use a comforter—lay across her bare shoulders; they were naked, and I could find no trace of a bra crossing over them.
“Diana,” I whispered.
No answer.
Find a way...
I released a shaky breath. My heart raced against my chest, and it was only growing more frantic. Would this adrenaline rush that exploded through my body whenever I was near my older sister ever end? A part of me hoped it would, but most of me hoped it wouldn’t. I loved—loved?—this uncontrollable, nearly overwhelming excitement that enveloped me every time my sister was going to let me do something forbidden to her.
I reached out with my right hand, forefinger extended, and touched my sister on the middle of her back, where her skin disappeared beneath the blanket.
I said her name.
She didn’t answer.
She didn’t move.
Her breathing didn’t change—such control.
I could hear my breathing; could she hear it? Did I sound like a pervert on the verge of a heart attack? Did that turn her on? Why were all these questions coming to me?
My cock had grown by now, flooded with lust and raging hot energy and all the dirty thoughts that make a young man dream about his family members in all the wrong ways. Would those guys be wrong not to take the plunge into incest if their sisters offered them a taste of that delightful sin? That’s what my sister was doing, wasn’t it, offering me a taste? I’d be stupid not to take it. I really would.
“Diana,” I said as I ran my finger along the blanket line. Her warm skin sent goosebumps through my arms, and in the soft glow of the bedside lamp, I saw the same little bumps sprout across her deeply tanned body. I thought a shiver ran through her and into me, which danced across my shoulders. I closed my eyes, absorbing the moment of unexpected titillation that reached down into my eager, cum-filled balls.
With my finger back on her spine, I hooked the tip beneath the blanket and pulled the covering down Diana’s body. Slowly, I moved so fucking slowly, exposing her slender and small frame, her tight skin, flawless and smooth, with curving contours about its surface that outlined her taut muscles. What was it about young women that made them appear so small and light and flexible? Young women? I’m only eighteen—but it’s true, younger women did look smaller.
Where the fuck were these thoughts coming from, and why was I thinking them?
The blanket had reached below the middle of my sister’s back. I saw no clothing. I moved lower, to the curve of her spine, before the rise of her butt cheeks. I went lower, baring her slender hips down to the narrow crack of her ass and the upward ascension of her crescent cheeks. My sister said nothing. She didn’t stir. I could see the swells of her big breasts pushing outward from her chest, where they mashed into her mattress.
My right forefinger remained on the base of my sister’s spine, but I reached out with my left hand, finger extended, and lightly, with the weight of a feather, I touched the swell of her left breast and slid my finger across the perkiness of her round flesh.
Diana shivered. Her nostrils flared in recognition of what I had done. I watched her eyelids twitch as if she were fighting the urge to open them. My cock strained in my pants with that blatant fuzzy pleasure that demanded I wrap my fist around the head and squeeze.
My fingers left my sister’s tit, and I sighed on the inside. I played with the blanket along her backside before pulling the sheets up the slope of her firm, apple bottom. She hadn’t said I could get her completely naked, but never did she say I couldn’t, either. Halfway up her butt, at the very peak of her hard, meaty hills, I stopped and breathed a sigh of relief. She wasn’t wearing panties.
I groaned with hunger.
The thrill that tumbled through me shook my legs. Maybe one day, the excitement of seeing a family member naked would go away, but today was not the day.
I bent over at the waist and kissed my sister in the middle of her back, planting my lips against her spine. I touched her; her skin warm beneath my lips, and as I pulled away, I slipped my tongue from my mouth and let the tip press into her flesh, wetting her.
Diana moaned; it was a sleepy sound but still a moan.
I kissed my way down her spine, to the base of her ass, to her crack. She smelled fresh and clean, with a hint of vanilla and flowers, probably from her lotion, and her scent held the same quality as her taste. With a quickening heartbeat, I swept the blanket from her body, tossing it to the right with an unintentional flourish that left my sister naked beneath my eyes.
I moaned, the sound appreciative, long and lasting, and I didn’t imagine the smile that pulled my sister’s lips wide. If she were dreaming, then it was a good dream. But she wasn’t dreaming. I knew that much.
What to do now? I had never touched a girl before. Not like this. All the videos, daydreams and wet dreams, and the countless scenarios that I had played through my head had not prepared me for this moment. Still, when I reached my hand outward, I let those memories guide me.
Diana slept with a narrow part to her legs. The dim glow of the table lamp didn’t allow me to see entirely between them. I took my phone out of my pocket and turned on the flashlight, holding it close to my sister’s thighs. I settled my right hand behind her left knee, the one closest to the edge of the bed, and slid my palm upward.
“Mmm,” Diana moan-sighed. Her eyes remained closed; her breathing had sped up, but not much. God, her skin was hot, as if baked in an oven to the perfect temperature for consumption.
I continued upward, using my fingertips, and I danced along the bottom slope of her butt cheek, where it flowed into her thigh. From between her legs, I felt the heat of her sex. My palms dampened, and beads of sweat sprouted on my forehead. My heart thumped, my erection throbbed, and the bright white light from my phone centered on the wet line of pink flesh between my sister’s inner thighs.
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