Anderson Family Journals #05

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Sleep-play, pussy fingering, and licking sister's asshole.
3.3k words
4.79
49.3k
45

Part 5 of the 17 part series

Updated 06/12/2023
Created 09/03/2021
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#05 Timmy

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.

Her pussy lips looked swollen, the outer lips thicker than the inner, while her smaller labia lay spread, revealing a slash of pink pussy meat pushed together by the tightness of her inner cunny walls.

"Fuck me," I whispered.

I wanted to kiss her. I wanted to lick her. I wanted to bury my face against the softness between her legs and rub myself in her comfort. My cock hurt. If only Diana would open her eyes and take me in her hand, but this wasn't about me. If I showed her how much I appreciated her body, then maybe next time she'd let me... let me... who knew what she'd let me do, but she'd let me do it.

I swam my fingers over her left butt cheek and then across, stopping when my middle finger rested against her crack again. I dragged my fingers downward. Fuck, she was so hot between her cheeks. She jumped when I touched the rougher, rubbery skin of her asshole. It was a reflex move; she didn't try to get away from me.

I did this several times: rubbing my finger through the length of the crease between her buns. My sister's face flushed, her breathing deepened, and I pushed harder against her so that my middle finger sunk into her skin, dipping into the crater of her asshole.

"Uhmm-mmm," Diana moaned. "Ooh."

I didn't try to finger her butt. I lowered my head, having to bend at my waist as I breathed in the scent of her ass, her pussy, her lotion, her lust, and every fragrance her sexy body could create. Saliva bubbled from the glands in my mouth, and a light rush of awe caused my equilibrium to shift. I kissed my sister's ass cheek before I had a chance to collapse.

Diana moaned.

I licked the curve of her ass.

She moaned again.

I ran my tongue to the bottom of my sister's cheek and then back up, licking closer to her crack as I tasted her skin. A tingle ran through my cock. On the return trip down, I pushed the tip of my tongue into her dividing line and dragged it through her cheeks.

"Umm," Diana groaned when I brushed her asshole with my tongue. Her right leg opened for me; her left stayed near the edge of the bed.

I had just licked my sister's asshole. Fuck me. I did it again, enjoying the friction of her spokes against my tongue as I left her backdoor slick with my saliva.

"Mmm, oh." The sound escaped my sister's lips, soft and far away to my ears. I threw my phone onto the bed. I didn't need it to see what I was doing. I ran my right hand over my sister's right leg, concentrating on the inside of her thigh, feathering my touch across her skin, getting closer and closer to the heat that radiated from deep within her forbidden gateway.

I placed my left hand on the small of my sister's back. I stood, slightly bent over, looking downward as I cupped the inside of my sister's right leg and slid my hand upward with no intention of stopping. My movement started fast, but slowed, and slowed, and slowed until even I thought I wasn't moving at all. The closer to the apex of her thighs I came, the harder it was for me to move my hand upward. Diana's spread her right leg further open; an invitation and my heart jumped into my throat. Pre-cum dripped from my cock with a non-stop flow, and a fuzzy sensation swam through my core and into my groin, tightening my sack and raising my hairs on end.

And then I touched my sister's pussy for the first time, and then I came in my shorts.

Fuck me, I thought as my face clenched, my legs stiffened, and my hips jerked. I had just ejaculated in my pants. Motherfucker, but underneath my palm, and infusing every taut fiber of my being, was the golden warmth of my sister's wet pussy, and that moment would live in my memory forever.

Diana moaned loudly as I came. She opened her right leg, turning her head to the right as she lifted her knee up and out so that her body lay at an angle on the bed. She had opened her legs for me. She had opened her pussy for me, and I didn't know what to do--at least, not with any confidence. That worry came and went faster than the blink of an eye because I knew that as long as I tried to make my sister feel good, appreciated, and loved, that she'd let me try this again and again and again until making her come became second nature to my fingers.

Practice makes perfect, she had said... texted.

I pushed my middle and forefinger against her pussy lips, curling and slipping them between her little curtains, accidentally brushing her clit, making her jump. And then my fingers sank into the warm, cookie-dough-like softness of her steamy, pink pussy hole.

"Mmm," Diana huffed. Her butt shook, and the wet, rubbery walls of her pussy squeezed my fingers with quick and steady pulses.

I knew from watching videos that a woman's G-spot was located somewhere beneath her mound, so I turned my hand so that my palm faced the bed, my sister moaning as my fingers fought the slippery friction of her cunny grip. Carefully, I curled my fingers downward and rubbed the tender underside of my sister's pubis with soft, circular strokes.

Diana whimpered as the muscles in her back, shoulders, arms, and ass tensed.

My excitement told me to finger fuck my sister's twat until my hand became a blur, but common sense and fear of not making her happy forced me to continue my slow movements. Thick honey with a rich, heady scent slipped from my sister's precious opening. Her wetness coated my fingers, my knuckles, and the crux of her thighs. I lowered my head, unable to reach her pussy with my lips, so I pushed them against her cheeks right above her asshole, then I let my tongue fall from my mouth to linger on her rear door.

"Oh fuck," Diana sobbed.

I continued rubbing the inside of her pussy, knowing that I was missing something important, but I didn't know what. More of her body needed touching. I flicked the tip of my tongue against her puckered asshole, the opening tighter than I ever imagined it could be. What was I missing? What wasn't I touching? What was--

My sister's finger brushed mine between her legs. She was playing with herself, with her clit, with that beautiful pink jewel that I wanted to mount on a pedestal and encase in glass. How could've I forgotten her clit?

It didn't matter at that moment. Diana's whimpers turned into sobs and deep, panicky breathes as if she were about to hyperventilate. I fingered her pussy faster, always making sure to rub the soft underside of her pubic mound. She buried her face in her pillow and fed me her asshole with slow, sensual rotations of her hips that had my tongue fighting the balloon knot protecting her insides from me. I played with her pussy faster, firmer, feeling the vibrations of her fingertips against her clitty, which I had neglected--but never would again.

"Fuck, fuck, fucking finger me," Diana moaned into her pillow, her words muffled but strong, on the edge of turning into shouts. "Fuck, fuck, oh--fuck, oh, Timmy! Finger me! Finger my pussy good, bro."

I did, delving into her pink softness with growing speed, my cock still hard, my balls buzzing, my tongue working her asshole with vigor.

A loud cry left my sister's lips, and then she came hard, shaking and clenching my fingers with a wet grip. She came saying my name, and she said it over and over again as she pushed her ass harder against my tongue and her pussy deeper onto my fingers. Holy fucking hell, I had touched my first pussy and eaten my first ass, and they both belonged to my older sister. I wanted to do it again. God, how I wanted to, but as Diana calmed down, I pulled away from her, wondering what was coming next.

"Timmy," Diana panted, "thanks for waking me up. You did a good fucking job."

"You're welcome," I said, not knowing what else to say or do now that she was awake.

"Same time next Monday, okay," she said, dismissing me.

I held back a sigh, but I left her room, locking her door on my way back to my room to jerk my hard-on off, get ready for school, and make her breakfast.

What a great fucking morning.

Tuesday through Sunday

Some things happened during the week, but I forgot to write about them. I was too excited about what happened on Monday to sit down and record my thoughts for the next six days. Why do I even need a journal? Fuck it; it's not like anyone is ever going to read it, but I'm going to want to remember this one day, and maybe Diana will want to read my memories with me. Maybe she'd be flattered. Anyway, I'll write about washing my sister's panties next week on a day that nothing happens. The second time around was even better than the first.

Timmy out.

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Next time on the Anderson Family Journals, "Tasting Pussy."

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3 Comments
roveroneroverone5 months ago

Nothing tells a woman you appreciate her like tossing her salad....

AnonymousAnonymousover 2 years ago

WAUW !

Thanks for sharing ;-)

MrHereWritingMrHereWritingover 2 years agoAuthor

https://twitter.com/MrHereWriting

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https://www.smashwords.com/profile/view/MrHere <---- For all of my old #1 stories

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I got a little ahead of myself last time I was talking about what comes next. In this chapter, Timmy gets to finger pussy and lick ass, but in #06, he gets to eat some pussy. In #07, Timmy gets to gives his older sister her first ever taste of cock.

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