Anderson Family Journals 21

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#21 Timmy

What Ifs

Where I left off....

Diana had just finished kissing me in front of Abbey, and it had been no ordinary kiss. Abbey had watched the entire time, and then Diana drove us to school.

Friday

After Abbey had left the car--I'm sure she noticed that Diana and I stayed behind--I released a long sigh and hung my head back against my seat's headrest. What had Abbey been thinking after witnessing the kiss Diana had given me back at home? What in the hell had Diana been thinking when she had kissed me in front of Abbey? What was Diana planning? Diana, Diana, Diana....

Diana.

She still hadn't told me if Abbey knew about us. Yes. No. Maybe? My gut told me that Abbey knew what her older triplets were up to but that she didn't want to know, but maybe she did want to know. Maybe. Fuck, my logic was no better than Diana's. (Was I trying to make myself feel better?) Maybe my older sister was losing control of this fantasy life she had built for us. I had lost control of it a long time ago. I mean, I was going to help the wrestling moms seduce their own sons--any son over eighteen, but still, their sons. How the hell had I gotten myself into that situation?

Everything about this scenario was crazy.

Diana had parked in the back lot, facing the auto shop wall with a tarp-covered chain link fence on my side and Lana's big, black F350 on her side. What a truck! What did a petite, big-breasted girl like Lana need with a truck that big? But its tinted windows gave me ideas about how private a big truck could be, compared to my sister's four-door sedan.

"Hey, little brother," Diana said, "are you going to kiss me, or are you going to stare at my friend's truck?"

I snapped out of my daze, unbuckled my seat belt, leaned over the center console, and pressed my lips against my sister's mouth for the second time that morning. Thoughts of Mom and every sexual position I had done with her flashed through me as Diana slid her tongue into my mouth. My sister and my mom... how the fuck had I become their lover? I put my hands in my sister's long, blonde hair, my muscles tensing and my fingers tightening as a surge of rumbling energy shook my limbs. I placed my hands on the back of her head and pulled. She didn't fight the pressure as I lowered her head to my lap.

My mom and my sister! Every young man's dream! Now, if I could only have them at the same time....

My sister undid my buckle in a hurry, my cock in mid-sprout, pushing my Calvin's upward. She peeled back the elastic waistband and uncovered my rising prick, swallowing the spongy meat down to my balls with a soft, wet gurgle.

"Oh god," I gasped as my sister's spit-heavy mouth engulfed my prick. Her lips formed a seal around my thickening flesh while my knob rested on the back of her palate. My dick plumped up in her mouth, growing to full hardness, the tip throwing itself into her throat and beyond. Diana made a

gulping

sound as her mouth seemed to grow around my prick. I slid my left hand from her hair and slipped it between us and around her throat. I cradled her neck in my palm, feeling the indentation of my cockhead against her trachea.

Diana breathed hard through her nostrils, gulping for air and swallowing my meat as fast as she could. Up and down her beauty went, taking my dick without complaint--brother and sister, doing dirty things and loving it. I didn't let her lift her mouth more than a quarter of the length of my cock. I kept her close to my root so I could fuck her face and rub my glans against the wet softness of her throat. My shaft tingled, and my balls tightened as I listened to my older sister struggle around my swollen dick. As she wetly worked my meat, my thigh trembled while pleasure swirled around the crown of my cock, buzzing the corona and tickling my slit.

"Oh, Diana, god, baby," I moaned.

She responded with a series of wet,

mwah, mwah, mwah

sounds, then she forced her left hand beneath her face and cupped my tingling balls in her hand.

"Oh, fuck!" I cried, coming and pushing her mouth down my shaft with my right hand while holding her throat with my left. The ripples of her throat muscles massaged my palm as she swallowed my jizz.

"Fuck," Diana gasped when I let her up. Her face was a mess, her mascara ruined, her blonde hair out of place. She looked so fucking sexy, my beautiful blonde sister.

"You okay?" I asked, breathing hard.

"I need to fix my makeup," Diana said, rubbing her eyes.

She reached into her glove box and pulled out the wet wipes she had kept since we had started fucking in her car. I grabbed the dry napkins next to them and handed them to her as she wiped her face.

"You should do that more often," Diana said.

"Ruin your makeup?" I asked, laughing.

"Ruin my makeup," Diana said, "and ruin my pussy... without asking." She shivered, exaggerating the movement and the excitement behind it. "Sometimes, a girl just wants to be taken." She smiled at me. "You don't need permission with me anymore." She slid her eyes to the side, her smile turning sly. "But it's nice when you do ask. I want you to figure out when you need to ask me for permission and when you don't."

Great,

I thought as I nodded my head. She laughed, looking at me, then I leaned over the center console and pressed my mouth to hers one more time, tasting my sister's tongue as the first-period bell rang. Before I got out of the car, Diana told me to meet her at our fuck-room in the drama theater during lunch.

Fuck-Room

Diana was wearing a cropped, pink-and-white-striped sweater, a black skirt, matching knee-high socks, and pink and white tennis shoes. We were ten minutes into lunch, and she had my pants undone, and her boy short style panties lay on the room's makeup counter. My sister straddled my waist as I sat in a high-backed chair, my ass near the edge of the seat as my sister half-stood on my cock. She lifted her body up and down, her athletic thighs tensing as she humped her pussy in a forward-to-down motion over my shaft.

"Mmm, little brother," Diana purred into my ear. "Give me that juicy dick."

I had my hands under her skirt, gripping her naked waist as the pink heat between her legs cradled me between its soft, velvety walls. Lana was in the room, dressed in a plaid dress with short sleeves and a white collar. Her iPhone was in her hands, and she was walking around us, recording us, whispering to us.

"So fucking hot," Lana would say. "You're so fucking sexy, Diana, the way you ride that dick."

Diana looked right into the camera. "That's my little brother's big dick tearing me up," she whispered, "getting all the way up inside me. I can feel him in my stomach."

"So bad," Lana said. "So nasty, you incest pervs." She licked her lips, then pouted: "I want some."

I moaned, closed my eyes, and tried not to come.

Diana pressed her lips to my left ear, on the far side of Lana. "Do you think my friend is hot?" my sister asked. "Do you think her little half-Asian twat is fuckable?"

I groaned.

Lana made a soft noise.

My sister bucked her hips harder, forcing her pussy faster over my prick.

Lana panned the camera behind Diana and told me to lift my sister's skirt. "I want to see that beautiful pussy between her legs getting stretched," she said.

I groaned and pulled my sister's skirt up her ass. Lana pushed the camera close to us, placing her left hand on my right thigh. She squeezed me as my sister slid up and down my pole, bouncing her twat over my slick meat until a creamy mess dripped down to my balls. The wet slapping of skin on skin, cock drilling pussy, filled the room.

"Oh, that's the shot," Lana said.

Diana whimpered, then whined, then she bit her lower lip and came. Heat smothered the length of my cock. I dug my fingers into my sister's firm ass as long buzzes of pleasure raced through my dick. My shaft seemed to grow, then the head expanded, and Lana reached between my thighs and cupped my balls.

"Oh, fuck!" I whined, coming hard as my jizz surged through my shaft, making me shake. I arched my hips upward, lifting my ass from the chair and my sister's feet from the floor.

"Woah--oh!" Diana yelped as I drove myself deeper into her soft, buttery box.

Then she came.

Later, my sister kissed me goodbye as I stayed behind to clean up the room. On the way out of the drama theater, a few of my sister's friends eyed me with silly smiles while giggling and laughing with Lana and my sister while they watched

something

on Lana's phone.

Holy fuck, did everyone know?

Did anyone care?

Diana's Words

I had my sister on her bed. Her head and breasts lay on the comforter, and her back sloped upward, ascending to the twin curves of her golden cheeks, which curved down into her thighs. Her knees dug two small divots into the bedspread. Her shins elongated straight back, ending with her little toes pointing toward the end of the bed.

I smacked her ass.

"Ooh," Diana gasped as the slap filled her room.

Earlier, after stripping my sister of her clothes, I had tied a red scarf she had taken from her closet to each of her ankles, fastening them with a single loop that would slide free if my sister wanted to get out of her

restraints.

The scarves extended to her wrists a short distance away, and her arms lay on the bed, reaching backward toward her feet, her palms up.

A light sprinkling of sweat beaded my sister's body. I had ridden her hard, using her mouth and pussy, while spanking her bare bottom and filling the room with the loud slapping of flesh against flesh, hip against butt, balls against clit. It was late, nearing midnight, and Abbey was in her room sleeping (hopefully), while Mom... well, it didn't matter anymore if Mom heard her children enjoying their sinful delights in private.

I lowered my head to my sister's crack and licked the valley between her butt cheeks. Diana hummed, moaning and exhaling, her breath wafting the strands of hair that lay wildly across her face. I pushed two fingers into the pinkness between her bulging pussy folds, moaning as the slippery heat within crushed my fingers.

"Mmm," Diana sighed.

I pulled my fingers out of her cunny, their length covered in crystalized strands of sticky wetness. I pushed my digits back into her muffin down to their last knuckles. A shiver ran through my shoulders as her softness coalesced around my fingers.

"Fuck," Diana hissed.

"You have such a pretty pussy, big sister," I whispered. "So pink and clean and hungry for cock."

"Yeah?" Diana asked, laughing with a breathless expulsion of pride. "Is that why my pussy gets so--mmm--wet? Because of cock?"

I curled my fingertips against her G-spot.

"Yeah," Diana moaned. "Right there, little brother."

I reached underneath my sister's body and cupped her left breast, squeezing the firm but yielding mound in my hand.

"And great tits," I whispered. "Tits that I'm gonna fuck tonight."

Diana made a breathy, naughty sound running with an almost daring essence as if some sensual thoughts had passed through her mind, but she was reluctant to share them with me.

"What is it?" I asked.

Diana shook her head.

"What?" I asked, matching my finger's thrusts to the force of my voice.

"My tits weren't always this big--mmm--you're fingering me so deep," she said, sighing. "Remember?"

I nibbled on my sister's left butt cheek. "Yes."

"Would you try to, mmm, fuck them if they weren't so big?"

"Yes," I said and licked the crack of her ass again, stopping at her rear passage.

"Would you still want me--uh, yeah, fucking lick my asshole--if I had small tits?"

I didn't have to think as I said, "It's you I want, not your tits."

Why was she asking me about small tits?

"Would you still fuck me as good as you do if I had small tits?" Diana whispered, gasping as I sped up my finger-fucking motions. "Little-little itty-bitties?"

"As long as they were your tits, I'd want to suck them." I rolled her thick nipple through my fingers and turned the fingers in her pussy upward, pressing my cum-covered thumb against her asshole.

"So?" Diana whimpered as my thumb probed her back door. "You wanna fuck a girl with small tits?"

I eased the tip of my thumb into her back door, slowly pushing her anal ring open in a circular, outward-spreading motion that loosened the muscles of her sphincter.

"Tell me, now," Diana growled.

"Yes," I hissed and slid my thumb into her asshole.

"Oh, Timmy," she whimpered.

Half an hour later, my sister lay on her back with her tits heaving and her legs open, our cum dripping from between the swollen folds of her cunny. Her lean stomach rolled, the faint outline of her abdominals showing, then growing faint again, then showing again as she sucked in a breath.

"Fuck," Diana whispered. "You're a fucking athlete." She laughed. "And I thought I worked out hard."

"Do you want anything to eat?" I asked. "Or something to drink?"

"Shit," Diana said. "What time is it?"

"Half-past midnight," I said. "A little after."

"Go get me some water and take your time. Leave your shirt off."

I pulled on my wrestling shorts and walked down the hall, stopping at the stairs. After a moment, I continued toward my room, which I seldom slept in anymore, and, by default, towards Abbey's room. I looked down the right-turning hallway and saw that my sister's door was closed. I turned around and walked downstairs, thinking of little titties.

Mom was in the breakfast nook, sitting at the table, sipping from a glass of wine and reading a book--a real book--made of words printed on paper and bound in more paper with glue. She set the book down and stood when she noticed me, her black, ankle-length robe coming apart and baring the smooth curves of her naked body.

"I didn't think you were coming," Mom said. "I've been playing with myself."

Diana,

I thought,

always keeping me on my toes.

Maybe I needed to surprise her more often, as I had with the morning blowjob.

Mom turned away from me, facing the nook's table. She placed her palms on its wooden surface and waited. I walked behind her, my cock growing hard with each step. I pushed my shorts down, the cool air of the kitchen caressing my glans and shaft and sending goosebumps across my shoulders. I stopped behind Mom and put my hands on her waist, squeezing her firm body.

Mom sighed.

Slowly, I tugged the length of her robe up her legs, using my fingers to crawl the silky fabric over her body. When I reached her thighs, I dropped into a squat behind her and pushed the rest of her robe over her butt, flipping it onto her back so that her bare ass and fat pussy bulge stared me in the face.

"Mom," I sighed, breathing out her title as I pushed my mouth forward and slid my lips along the moist cleft below her crescent ass.

"Oh," Mom moaned. "Oh, baby, yes." She pounded her palm on the table once, the slap echoing through the kitchen.

I licked my tongue through her pouty furrow, loving the feel of her plump pussy lips and the tender flesh squished between her thighs. Mom tasted sweet, her juices coating my tongue in a creamy layer of thick, taboo honey. I stood, my hard cock dangling between us, the head brushing my mother's thighs, then her cunt, then prodding her pussy lips apart as I grabbed onto her hips and pushed her legs open with my right foot.

"What do you want, Mom?" I whispered.

"Your cock."

"Who's cock,

Mom?"

"My son's cock," she pouted. "It's so big and hard."

I nudged my dick forward. Mom's pussy flesh sunk inward beneath my rigid fuck-stick. Heat enveloped me, and her liquid warmth spread over my crown like butter melting in the sun. I entered my mother's cunny, groaning as her pussy lips stretched around my thickness.

"So fucking tight," I moaned. "Like a fucking teenager."

"Ooh," Mom moaned. "Fuck me, baby. Fuck Mommy."

I pumped my cock in and out of my mother's snatch, humping into her like a pumpjack, my movements soft and slow, rotating up and down and all around her sticky insides. I ground my hips against her butt every time I pushed into her depths. My balls slapped her clit, forcing gentle whimpers from her throat. I sped up, and Mom fucked her pussy back against me, creating a steady rhythm of flesh slapping flesh as her pussy quivered around my prick.

"Ah, ah, ah," Mom moaned. "Fuck, ah, mmm, uh, fuck, mmm, uh."

My mother's slutty fuck sounds made me light-headed. I sped up, watching her pink lips spread around my cock, her hole looking too small for my piece of thick, teenage meat. I slid my hands up her back, around her ribs, then up to her breasts. I cupped her tits as I lay my forehead on the back of her neck and slowly kissed her skin.

I sped up again, feeding my mother's slippery twat firm strokes that rocked her into the table, creating a wooden ringing that was too loud in our quiet house.

"Uh, uh, uh," Mom gasped with each inward stroke.

With her moans spurring me on, I thrust to the bottom of my mother's pussy and swelled my cock, then flexed my ass as I tried to get deeper into her maternal hole.

"Uh, fuck," Mom grunted. "God, Timmy, you're a beast."

Heat bloomed between my mother's thighs. Her pussy trembled across my length. Mom dropped to her elbows, panting, her butt absorbing my harder strokes as my heartbeat sped up and sweat formed across my skin. Mom squeezed my cock with her walls and stroked my shaft with her inner muscles. Her skin warmed, as did mine, and her moans filled the kitchen. I raised my left hand to her mouth to quiet her, and she sucked them into her oral cavity and came on my cock at the same time.

Mom cried out, and her cum flooded our groins as though someone had dumped a bucket of warm water between us. I lasted a moment longer, coming when Mom bit down on my fingers, reminding me of Diana's off and on again brutality.

"Mo, you bitch," I groaned, clenching my teeth to keep from shouting. Several long strands of cum shot from my cock, sliding up my shaft so thick I could feel the tingling sensation leaving my body as I emptied my spunk into my mother's warm snatch.

"Yeah, baby, give me that seed," Mom whispered. "Make a mess in there."

Before I went upstairs, Mom reminded me that I was supposed to help Prisha and Justin move some things around her house tomorrow. "Remember, baby," she had said, "the Team Moms are counting on you."

When I returned to my older sister's room, her bedroom door and her closet door were open a crack. I couldn't remember if her closet door had been open or not while we had been fucking, and I don't know why I noticed it now, but I knew that I had left her bedroom door closed. I sighed and looked through my sister's wall toward Abbey's room.

Back in bed, with Diana laying over my left side, I whispered, "I have promises to keep to Prisha and Mrs. Nguyen this weekend."

"Hmm," Diana hummed, using her throat to utter the noise. "Nervous?"

"No."

"Liar."

I smiled in the dark.

"Whatever you help them with," Diana said, and I could hear the sly smile in her voice, "remember that they have to pay you for your time."

Since Diana was lying on my left side, I slid my left hand down her back, took one of her muscular, round cheeks in my hand, and squeezed it.

Diana made a soft, happy sound, then, in a half-asleep voice, she whispered, "I want to talk to you about Lana and her cousin, Vicki." She yawned. "You know, Abbey's friend, but that can wait until later."

My first thought was,

Lana didn't have small tits.

My second was,

Does Vicki?