Anderson Family Journals #07

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#07 Timmy

Oral Heaven


As I stood at the foot of Diana’s bed in the early morning hours before school, after Mom had gone to work and while Abbey still slept, Dian’s words from the night before echoed through my head: “If you do a really good job of appreciating me, then maybe I’ll do something special for you.”


Maybe might not be a promise, but the implication of all the unknowns to which maybe could allude to had numbed my brain to all thoughts but one: Make your sister cum until she’s begging you to stop, then maybe I’d lose my virginity to her once she had finished wiping away her tears of joy.

I licked my lips as I looked down at my sister. This morning she had slept face up, in the center of her bed, her body covered by a thin satin sheet aligned perfectly crosswise below her big breasts. Those two round jugs lay balanced on her chest like teardrops yet to burst. If I stomped on the ground, would I see them ripple… like vibrations across the surface of calm water? I didn’t know, but I did know that I was going to show my appreciation of my sister to my sister by sucking her peach-tinted nipples between my lips and into my mouth with a slow, methodical delight that would leave her nipples sensitive and her areoles wet.

Diana looked at peace under the soft fringe of light falling on her from her bedside lamp. I almost didn’t want to disturb her–almost–but the hard-on pushing against my loosest pair of basketball shorts had other ideas. I didn’t say her name as I pinched her bedsheets between my fingers and pulled them down her body. They slid down slowly, baring her sun-gold tan in small fractions of length, exposing her naked breasts and their eraser thick, already hard, nipples. My mouth watered as her tits came into view, heavy and perky, upturned and tasty. Lower, I pulled her sheets as the heat within me rose, exposing the dip of my sister’s navel. I licked my lips as if I could already taste the soft depression in her smooth stomach. Diana stirred when the blankets cleared her narrow waistline and the cut of her iliac crest; the sexiness of her sculpted body forced a tremor through my chest.

“You’re beautiful,” I whispered; the sound of my voice was loud in the room.

Did my sister smile? I couldn’t be sure; it happened so fast. I pulled the sheet lower, baring her smooth mound to my eyes. No panties. No fucking panties. My sister was a gift from Heaven. She slept with a slight part to her legs so that nothing between her thighs lay hidden. Her pussy lips pouted softly from her mound, twin bulges that folded together to protect her inner lips and the pink opening between them. The line of her clitoral hood stood out, as did the pink gem popping up from underneath that small roll of flesh.

I don’t know what came over me, but I pulled off my shirt, letting it fall to the floor, where my shorts and briefs quickly joined it. Would Diana get mad if she saw me naked? I didn’t care. The word maybe and my sister’s naked body had driven my heartbeat into overdrive and my mind into the stratosphere, but I would do as she said as soon as she opened her mouth, that I knew. Doing whatever Diana wanted me to do was the only thought that could penetrate the rush of energy surging through me. The energy that commanded me to slide my cock into her and fuck her right then, whether she wanted me to or not–that’s a thought I would never act on, but it was so easy to think and so easy to believe she wouldn’t get mad if I did it.

My thoughts sent shivers through my spine, the kind I’d rather not have, but it also made me look inward, where I saw Diana holding me in the palm of her hand as I waited for her to speak. I was hers and no one else’s. Was this love?

Another shiver ran through me, compelling me to move onward.

I dropped the blankets at the end of the bed, a cotton undersheet, and a satin oversheet. They pooled at the edge, some of the cloth spilling over in a waterfall of black and white. The mattress gave way when I placed my right knee atop it. Diana moved, her legs opening and her pelvis arching as if moving her pussy closer to me. The mattress springs absorbed my weight as I crawled forward, stopping at my sister’s feet. I leaned over her, placing my right hand against her left thigh and my left against her right, and I tried to spread her legs wider.


I pushed harder, facing more resistance. I looked up. There was no doubt about it; a smile now graced my sister’s lips, one she was trying to straighten out but couldn’t. I pushed harder on her thighs, with some real force, spreading her open for me, and that Beşiktaş Escort smile turned into a sigh as her muscles lost the battle against my need. She lay with her legs out, her knees slightly bent, and her pussy lips had parted as her legs had opened. A thin line of glistening pink said hello to me, coated by a glistened honey that shone wetly beneath the light of the bedside lamp.

A moan escaped my lips. Hot, hungry, and horny, those three elements infused the sound I had made. My head lowered on its own, though I would have done it myself if I was capable of thinking. I acted on instinct and the desire to taste my sister’s cunny upon my tongue. And a moment later, I had my mouth pressed against her pussy.

Diana’s hot wetness opened for me, as soft as warm pudding, and I sank right into her pink cove as deeply as my tongue could manage. Diana moaned as I pressed my face into her muff, her right hand grabbing my head, her fingers curling around the strands of my hair.

I licked, and Diana uttered a soft, “Mmm,” tightening her fingers, hurting me in a way that made my cock and balls tingle.

I licked my tongue through my sister’s pussy crease again, and she moaned “Timmy” until my name faded from her lips like a whisper in the wind.

I brought my right hand between her legs, palm skyward with my middle finger extended, the tip brushing her wet asshole. Pussy juice drenched Diana’s rosebud, probably there from before I had come to her room to appreciate her. The pressure of my finger against her ass made my sister moan. She wiggled her butt against the bed, but there was nowhere for her to escape. I placed my left hand across her mound with my thumb down, pressing down on her magic button.

Diana jumped as her clit squished beneath my touch. I pushed the tip of my middle finger through the rigid tightness of her anal ring–the short journey slow and agonizing as her muscles struggled and stretched, fighting the tip of my probing digit in a losing battle to protect her ass.

“Uhhhhh,” Diana groaned as her asshole opened for me. She lifted her feet from the bed and raised her knees, pulling them back so that her feet were in the air. Her fingertips dug into my skull, but her short, manicured nails helped to keep the pain of her clawing to a minimum.

Strangely, the pain made my rock-hard rod even harder.

With my thumb pressing down on my sister’s clitty, and my middle finger in her ass, my sister’s pussy creamed. Honey dripped from her snatch in a thick river of white liquid, lubing my finger and her asshole even more. I circled her pink jewel with my thumb and pushed my finger deeper into her butthole. She clenched her cheeks tightly against my digit, the strength of her rubbery asshole raising goosebumps along my arms and shoulders.

“Oh, you fucker,” Diana moaned as my second knuckle slid past her anal ring. “You fucking bastard. Did a finger in your ass feel this naughty for you too?” My sister groaned again. “This fucking sexy?”

I moaned into my sister’s pussy, licking her gushing wet meat. To answer her, I eased the last of my middle finger into her butt, bring a long sigh from her lips. My hands were bigger than hers, my fingers longer, thicker, rougher, the grind against her sphincter nowhere near as soft as her silky fingers against mine–but her fingers probing my asshole had made me come harder than any solo jerk off session in my life ever had.

“This is already, mmm, better than I had expected it to be,” Diana murmured, the sound of sleep fading from her voice. “Timmy, make me come. Make me come hard. Understand?”

Fuck yes, I did.

I wiggled my finger in her butt, touching dark places that held so much heat I thought my finger would melt. And if her asshole could melt me, I couldn’t imagine what her pussy could do to me. My sister’s body had never burned this hot before. I darted my tongue into her, concentrating on tongue-fucking the pink circle of flesh leading deeper into her cunny tunnel.

“Mmm, fuck, yeah,” Diana moaned, holding my head against her muff and grinding my face into her twat as she lifted her ass off the bed. She spun her pussy around my mouth, wetting my upper lip, my cheeks, my chin–my fucking face–doing her best to fuck herself against me while I ate her pink pie with as much skill as I could manage.

The rubbery jewel above her pussy throbbed against my thumb. I pressed down hard, squishing it against her pubic bone, but not too hard, swishing the nub of flesh side to side while curling my fingertips over her smooth mound. The finger in Diana’s ass–my fucking finger up my own sister’s butt!–started moving back and forth without needing my mind’s consent. Diana moaned, long and low, her cries picking up speed when I rubbed her clit up and down while lapping at the sides of her wet pussyhole with my tongue.

“Umm, mmm, uh, uh-nuh-uh,” Diana whimpered, nearly sobbing. Her Beylikdüzü Escort legs trembled, and her fingers knotted themselves in my hair. She humped her pussy up at my face, rolling her twat against my fingers and tongue like a little whore gone wild.

I loved it.

I needed a third hand to fuck Diana’s cunny with. A spark ignited in my head, and I switched the places of my thumb and tongue. Without warning, I fucked two fingers into my sister’s steamy snatch and thrust my middle finger all the way up her little butt hole, burying my fingers deep inside of her warm guts.

“Ohhh–oh fuck!” Diana whined. She lifted her head and shoulders, straining to look at me as her toes curled. She let go of my hair, pushed her arms between her open legs, and pulled her elbows back behind her knees, pinning her legs to the bed. Her pussy and ass tilted upwards, opening her pubis for a final three-fingered fucking between her two holes.

Talk about flexible, I thought for some reason. I rose to my knees, looking down at my sister as she spread herself wide before me, looking lewd and slutty and dripping with wetness. All this for me, I thought as I pushed my two fingers into her pussy, mesmerized by her soft folds melting around my digits while I finger-fucked her butt with deep pokes. It was all heat and warmth and thick cream between my sister’s legs, and I couldn’t get enough of her.

My sister dropped her head. The strained look on her face as she struggled to come made my balls throb. Her pussy walls trembled around my fingers, and my sister tightened her inner cunny muscles around my probing digits–and boy was I probing her deep, getting as far into her hidden pinkness as I could.

“Fuck, oh fuck!” Diana shouted, her eyes snapping open. She stared at me, intense, not caring that I was naked in her bed with my dick as hard as iron above her pussy. Her gaze drilled a hole of sexual anger right through me. “Fuck–fuck Timmy, ooh! I’m going to come, little brother. That’s it–oh, god, yeah–do it, make your sister come!” She nodded her head at me, speaking so loud anyone outside her door could have heard us. A sob left her lips. Her glare turned helpless as a pink flush filled her cheeks, and Diana turned her head to the side, biting her lower lip. Her breasts heaved, her cheeks turned rosy. She swung her eyes back at me, they shimmered, and as I sunk my fingers as far into her ass and pussy as I could, Diana came.

Loud doesn’t describe how hard she cried–and she did cry. Tears fell from her eyes as her body trembled beneath me. She let go of her legs. They shot forward, landing sole-first on the bed, her toes digging into the mattress. Her hands clawed at her bottom sheet, rumpling and creasing the fabric. Diana stared at me, her glare a mixture of awe and defiance and so fucking sexy in a hot, “I’m going to fuck the hell out of you for doing this to me,” kind of way.

My cock jumped, spitting a small wad of pre-cum between my sister’s legs where her spasming holes gripped my fingers as if they’d never let go.

Diana took a long time to calm down after her orgasms rolled through her. Small tremors shook her body as her pussy, and asshole slowly loosened their grip on me. She dropped her head to the mattress, stretched her limbs outward, breathing in shaky lungfuls of air that made her breasts rise and fall on her chest.

Her tits! I had forgotten all about my sister’s tits the moment I had seen her pussy lips part when I had pushed her legs open. How could I have forgotten her tits? I fell forward over her body, my cock leading the way as my wet but clean fingers slid from her openings. I circled her breasts with my fingers, coning them. My mouth followed with open lips. I closed them around her right nipple and sucked. Diana groaned. Her hands dug into my shoulders, pushing against me, but she didn’t say ‘No,’ and I didn’t let her push me off her either. And I wouldn’t, not until she told me to leave her alone. Until then, I was going to do to her whatever the hell I wanted, and she was going to have to accept that.

“God, Timmy,” Diana groaned when I nibbled on her left nipple, not hard but firm. “Mmm, umm, fuck, bro.” She strained against me, really pushing against my shoulders. “God, fuck, oh god, oh god.”

I hunched my hips upward. My pre-cum dripping knob touched the wet mess of cum between my sister’s legs.

“No!” Diana cried out, her voice hoarse. “No, no, no!”

I stopped, but before I could pull back, she had her hands around my cock, squeezing me hard. I gasped as pleasure shot down into my balls. We shuffled around the bed, locked in a strenuous wrestling match that ended with me on my back and Diana on top of me, her pussy in my face and her mouth over my dick.

Diana’s mouth! It took one second for my mind to realize what this meant, what it could mean, what that maybe had meant, and then my sister’s lips closed Beyoğlu Escort around my knob, and every ounce of air left my lungs. I sighed long enough to decompress my body of all things tangible.

“Oh god,” I moaned, crooning the words as I stared up at the wet seam of my sister’s freshly-fingered pussy. I wish that I had lifted my head to lick her crease and taste the bulging meat between her legs, but Diana’s lips sinking down the length of my shaft froze me solid.

Diana gagged, not even halfway down my pole. I closed my eyes, knowing that my dick was the first dick ever to enter my sister’s mouth. I don’t know why that was important to me, but it was.

She did her best. Whether it was a good blowjob or bad, I didn’t know because I had never had one before, but I knew one thing for certain: No matter how Diana’s cock-sucking skills evolved from that moment onward, no future blow job could top how much this first blowjob meant to me.

And then I came so fucking fast I wanted to cry.

Fuck! I came so god damn fast, thinking my stupid thoughts, that the blowjob had ended before it had begun. The tingling sensation that pulsated through my shift hit me hard, so hard that I barely felt the light and anxious wetness of my sister’s tongue skirting across the tip of my knob. My balls swelled, my sack tightened, and before I knew it, my hips bucked upwards, releasing a whoosh of cum that flooded through me and into my sister’s mouth.

Diana gagged at first, then she swallowed, tightening her lips around my glans and bobbing her head a few times before stopping and just swallowing as she jerked my thick cock off. God, it felt so fucking good. So fucking good. My heart hammered within my body. My chest heaved. I lost the chance to lick my sister’s snatch for a second time that morning, but I’d make it up to her as soon as I could.

I lay staring upward for an unknown length of time. Diana turned around and fell across my chest, her breasts crushing against my body. She kissed me several times along my jaw before sealing her lips to mine. Her tongue entered my mouth, moving across my tongue with slow licks that built a tender heat between us. I didn’t want this kiss to end–I could taste our mixed juices on her tongue–and I wrapped my arms around her back as she cradled my head in her hands.

“I’m sorry,” Diana whispered when she pulled her lips from mine. “I want to fuck you, Timmy, so fucking bad. I do. I mean it, but not here. Not yet. But soon, I promise.” She kissed me several times, her words coming fast and lost, almost as if she were talking to herself. “We’ll get a hotel room where we can be alone, and then I’ll give you every piece of me there is to give for as long as you can take it, I swear. I promise, but not here. I’m sorry.”

Why was my sister apologizing to me? This was great! This was better than when I had first discovered Christmas presents.

“I just want it to be special,” Diana whispered. “Soon, little brother, so fucking soon.”

That worked for me.

When I left her room, I caught Abbey in the hallway. Had she been sneaking away from Diana’s door? She jumped and turned around when she knew that I had caught her. “I just need to use the bathroom,” she said.

I told her to get ready for school then I went back to my room.

At school, before getting out of her car, Diana kissed me on the lips right in the fucking parking lot where anyone passing by could see. She had parked between two trucks and had faced a brick wall, but still, the danger was real. After the kiss, she told me that I looked good naked, and even though undressing myself had surprised her–even scared her a little–she had been too excited by what I was doing to say anything.

What a great fucking morning.


Something had changed. I still did everything Diana wanted me to do–without question, I was happy to do it–but Diana wasn’t as forceful with me as she had been. My older sister smiled a lot around me. She stared at me a lot. She found reasons to share the couch with me–she didn’t need reasons, but sometimes Abbey or Mom or both were in the living room with us, and then she needed a reason to lay on the couch with me or cuddle with me. Diana spent Thursday night cradled in my arms, showing me naked pictures she had taken of herself on her iPhone while our family watched TV around us. I loved it.

Mom noticed our closeness, but I didn’t know what to make of that.

Abbey spent a lot of time watching us. A lot of time. More than once, I found her already awake when I went to get her out of bed. Once, I found her standing outside Diana’s door before I got there in the morning. Abbey had jumped when she saw me, but she also looked disappointed at finding me walking toward her. I’m not stupid; I knew that she had heard us on Monday, and I knew that she was trying to listen again. At least, I think that’s what was going on. I’d have to tell Diana about this.

Roy asked about Diana at wrestling practice. He and I had never talked much, less now that he isn’t dating my sister, but he seemed relieved when I said she didn’t talk about him. I’ve never had a girl break up with me, so I can’t guess what’s going on inside of his head. Diana was his loss, but my gain and I wouldn’t have it any other way.

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