Anderson Family Journals #09 to 11

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#09 Timmy

Fooling Around in the Car

Saturday

I awoke Saturday morning with an energy I had never experienced before. Diana, still in my arms, gave me some orders, and I did everything my sister told me to do: shower, dress, pack an overnight bag with dress clothes, casual clothes, and sleeping clothes--why so many clothes? I have no idea because once we arrived at the hotel room she had booked, I planned on stripping down and staying naked until checkout time.

It may have been the excitement of what today meant, or it could have been the things my sister had promised me last night, or maybe it was how close Diana and I had become, but today I felt like Diana's boyfriend. I was still doing everything she said to do, but I sensed that I had earned more freedom when it came to how I was allowed to behave with her. I wasn't her follower anymore; I was her partner.

It was about eleven in the morning by the time I was ready to go. Mom had left for a tennis date, which I took to mean a bump up in her love life, but it was only with a bunch of women, wrestling moms--go figure. The team moms weren't close friends; that I knew of. Yet, whenever the wrestling season started, and it was just about to begin in November, these women would spend more time together, especially throwing "team meals" or "team-building activities" at their homes. It usually involved a pool and food, and moms who tanned and drank wine while their sons built camaraderie, and if they wanted to treat me to a free meal, who was I to complain about a bunch of mothers getting drunk together?

As I sat on the couch waiting for Diana to finish getting ready, the front door opened, and Abbey bounced into the living room. She wasn't alone. By her side was a tall boy I knew by sight, but not by name. He looked like a skater, and my tomboy sister had dressed in skinny jeans, a blue and white baseball shirt, and a backward hat, which was her skater attire.

"Hey," she said, stopping in the act of removing her drawstring backpack. "Where are you going?"

"Who's your friend?" I asked.

"Bye," she said, turning around and taking her friend out the door with her.

The little shit.

Diana came downstairs not long after, wearing an off-the-shoulder, mid-thigh summer dress. It was red with a white floral print, bell sleeves, and an elastic band that kept her sleeves tight to her upper arms and above her breasts, the tops of which were bare. She was also wearing knee-high, brown leather boots and a black choker. With her flowing blonde hair, she looked like she had stepped out of a magazine ad.

"You look beautiful," I said.

Diana smiled at me and spun in place, the hem of her dress twirling. "Think so?" she asked when her spin came to an end.

I stood.

Our mother wasn't home, and Abbey had run off somewhere with her new friend, so I walked up to my sister, put my hands on her hips, and lowered my lips to hers.

"Mmm," Diana murmured. She put her hands to my face as her tongue entered my mouth. "We've got to go soon. Check-in is at noon."

"Where's your bag?" I asked.

"Upstairs."

Diana went to the car, and I ran upstairs to grab her bag. She had two: a bigger and smaller, and I wanted to look through them, but I had the feeling that she'd know if I did. Damn it; who knows how she might punish me if she had discovered I had looked through her things. Why did I want to look through them? Because visions of skimpy lingerie and lacy panties and garter belts and nipples clamps danced through my head. I don't know why I thought about nipple clamps, but my sister owned a butt plug, so why not some nipple clamps?

I hurried downstairs, stopping to call Abbey--twice before she answered her phone--to let her know that we were leaving and to ask her if she had her house key with her. She did, and so I said goodbye, told her "to be careful," and then I ran outside to where Diana waited for me in her gray Honda Civic, her sunglasses covering her eyes and her engine purring.

I asked Diana about Abbey's new friend on our way to the hotel. Diana told me that she advised Abbey to move on to a new boy if the old one wasn't right for her. There was no sense in waiting around for someone who only saw her as a friend and possibly, a little tomboy brother.

"You're trying to get her to date some random guy?" I asked, frowning.

"You don't want our sister to date?" Diana asked. "And her friend isn't a stranger, but if he was, so what? How do you think people meet people and don't say it's different for guys."

I did the smart thing and kept my mouth shut.

I watched my sister as we drove. The skirt of her dress sat just above the middle of her thighs as she worked the pedals between STOP and GO. At the first red light, I reached over with my left hand, hooked my finger in her skirt, and pulled the hem up to her waist.

Diana laughed, but she didn't adjust her skirt or tell me to put it back. I couldn't see her panties, but I saw enough of her lean legs to make the head of my prick expand. At the next light, I reached over and put my left hand on her thigh. A tingle shot through my palm as a light, electric buzz zigzagged through my shoulders.

"Are you wet?" I asked.

Diana looked at me, but I couldn't see her eyes through her sunglasses. "Do you want to find out?" she asked, smiling and shaking her head as the light turned green.

I slid my hand further up her thigh, having to lean over the center console to do so. My sister spread her legs, pushing her left knee against the door but leaving her right leg where it was so that she could maneuver between the pedals. I stopped my hand on the inside of her thigh, where her meat was softest, my pinky finger touching the cotton leg band of her panties.

"I bet you're wet," I said, my heartbeats growing closer together. "I bet you're wet for me, aren't you?" Heat welled beneath my cheeks. "I bet you're wet for your brother."

Diana nibbled on her lower lip as a pink blush spread across her cheeks. Her breasts rose and fell faster than a moment ago.

"Can I touch you?" I asked, my right leg now shaking, my cock pushing forward and growing in my jeans. Here I was, eighteen years old, asking my sister for permission to touch her between her legs.

"Where?" Diana whispered.

"Beneath your panties," I said. "On your pussy."

Diana licked her lips. We turned onto the freeway, driving toward the taller buildings and the more metropolitan area of our city.

"Through my panties?" Diana asked, or maybe she was telling me, I wasn't sure by her tone, but it was good enough for me.

I slid my hand high between my sister's legs, pushing against the seat with the tip of my pinky finger, and touched the soft cotton and lace covering her warm lips. The rest of my fingers followed, pressing into her soft muffin. Diana moaned. I smiled, pushing her panties into the shallow valley dividing her inner labia. Wetness dampened my fingers, and as I rubbed my sister's pussy in a probing circle, her thick, vibrant scent filled the car.

"Mmm," Diana moaned. "You're making it hard for me to drive, little brother."

"Do you want me to stop?"

"No," Dian whispered, shaking her head. "I like this side of you."

I pushed harder against her little pussy hole.

"Mmm, yeah," my sister sighed.

I slid my fingers up her panties, trapping her clit against my middle finger with my ring and forefinger, squishing the sides of her hood as I palmed her mound. I rubbed, and my sister moaned, clenching her ass and pushing her cunny up against my caress.

"Fuck," Diana moaned, changing lanes. She humped her butt on the leather of her seat, gently rolling her clit against my digits.

"You like that," I asked, my heart-stopping, "baby?"

Diana moaned. She squeezed her left leg against her right, trapping my hand between her thighs. I diddled her little twat faster, moving my fingers up and down her lips but always coming back to her clitty to press and polish that pink pear above the cleft of her pussy.

Diana hit the gas, and we sped off the freeway. The car jerked the next time she hit the brakes, but I didn't let go of my sister's snatch. She turned off the highway and into the first parking lot she could find, a gas station, parking behind the convenience store instead of at the pumps.

"Undo your seatbelt," Diana said, unbuckling hers and putting her sunglasses on the dashboard.

For a moment, I thought we were about to fuck right there in her car, forget about waiting for the hotel. And boy, was I ready, with my cock pressing into my jeans, forcing an uncomfortable pleasure through the length of my prick, starting in my knob and ending at my clenching asshole.

I removed my seatbelt as Diana crawled over the center console. She straddled me, grabbing the back of my head and pulling me against her mouth. Our lips connected, our tongues sliding together; we tasted each other without fear of anyone knowing that we shared the same blood. The thought made me gasp against my sister's lips as my balls tightened, and a healthy dose of pre-cum emptied itself into my boxer-briefs through my shaft.

"Make me come, little brother," Diana whispered against my lips. "You get to fuck this pussy at the hotel, but right now, you're going to make me cum." She pressed her mound against my tented jeans. "I want you to lick my cream off your fingers while I watch."

I growled, snaking my right hand around my sister's hip to cup her butt through her dress, and I pushed my left hand between her thighs. I grabbed a fistful of her dress, yanking the hem over her ass. A moment later, I cupped my sister between her legs from behind, digging my fingers into the gusset of her soaking wet, French cut panties. They had a wide waistband but narrowed as they traveled down the crack of her ass, leaving three-quarters of her golden butt cheeks bare. A narrow band sliding through her crack cupped the meat of her pussy, which I used to fill my fingers with a moment later.

"Yeah, baby," my sister moaned against my mouth. "Finger my ass and pussy, make me come on your fingers."

Diana kissed me again, hard, mashing her lips to mine, taking control of my mouth. I grabbed her panties in my right hand and pulled them hard to the side, ripping them, but my sister's breath catching was the only sound she made. I did the same with my left hand, pulling her panties to my right, giving me access to the soft-shelled, slippery clam between her legs.

"Both holes?" I asked.

Diana moaned into my mouth and fucked her pussy hard against my hand.

I ran my right hand down her butt to her cunny, wetting my middle finger with her creamy lube, then I pressed my left fingers to her pussy and ran my digits through her dripping wet lips several times. I removed my left hand from between her legs and circled her right hip, grabbing onto the tight, firm meat of her teen ass, and I pulled her cheek to the side, stretching her asshole open.

"Fuck," Diana moaned.

I pressed both of my middle fingers against my sister's butthole, wetting the spokes of her backdoor. Her little crater was like a suction cup. The tight hole grabbed onto my fingertips, and didn't want to let go. I dipped my hand between her legs again, gathering more of her juices and bringing them back up to grease the tight hole of her rear pucker.

"In the ass, baby?" I whispered against my sister's lips. She threw her head back and moaned. I licked her throat, kissed her, then licked her again. "In the ass, big sister?"

"Fuck yeah, little brother," Diana whimpered, taking my right earlobe between her lips. "All the way up it." Then she bit me gently and pulled, her tongue licking wetly against me after she let go.

My cock pulsed, shooting another wad of pre-cum into my pants. Fuck, I wanted to spray my jizz onto her hairless pussy. I gritted my teeth and closed my eyes, pleasure coursing through my crotch and core, making me want to rip my sister's dress off and fuck her right then.

I pushed the tip of my right middle finger against my sister's asshole; her tight flesh gripped me hard even though I had spread her juices across the spiraled crater of her rear door.

"So fucking tight," I growled as I worked my finger between her taut cheeks and into her small hole.

"Uh," Diana groaned when her asshole opened for me. "Imagine, uh, your cock back there, fuck."

I groaned, pushing my finger to the second knuckle up her butt as I thought about backdooring my big sis. Diana gasped, then whimpered, then she settled her ass on my hand, trying to get more of my finger into her rectum.

"You like it up the butt, don't you, you naughty girl," I said as a wave of heat spread throughout my body, followed by the buzzing of excitement. As I watched my sister's face, I slid the rest of my finger up her backside as far as it would go and wiggled it around the hollow of her anus.

"Ooh, ooh, fuck me," Diana whimpered, riding her butt on my finger like a girl atop a pony. "You nasty fucking boy. Nasty fucking brother. Nasty, nasty, nasty."

I pulled my left hand from her ass cheek and slipped it between us, cupping her dripping wet pussy in my fingers. "So fucking creamy," I said, sliding my digits through her bright pink lips.

Diana moaned, rocking herself on my hands as she dug her fingers into my shoulders for balance.

"I want to taste my juices," Diana whispered. "Let's taste my pussy together."

I let go of her pussy, bringing my fingers up between us, brushing her braless breast through her dress with the side of my hand. We looked at my honey-covered digits, and we looked at each other, and then we lowered our lips to my fingers.

Diana's juices filled my mouth with a sweet, almost candy-like taste, reminding me of strawberries and cream. My mouth watered as her tongue entered my mouth, stealing her nectar from me. I wiggled my finger still in my sister's ass in a wave-like arc, forcing soft whimpers from her mouth as I played with the warm canal beyond her pucker.

"Oh god," Diana sobbed, her cheeks turning red. "Mmm, fuck, I'm getting fingered in the ass by my brother. God, I'm getting my ass fingered in a fucking parking lot!"

I pushed my three middle fingers into her mouth. My sister swallowed them, sucking on them the way girls in pornos do right before a guy decides to gag them with his hand.

I didn't gag my sister, but I thought about it. I dropped my hand to her across-the-shoulders neckline and yanked her dress below her breasts. She wasn't as braless as I had thought. A crimson shelf-bra cupped her tits, holding up the bottoms of her breasts and leaving the round swells of her tits uncovered. Her nipples were free to suck, and so suck them I did, lowering my mouth to those thick nubs and slurping them down as I dropped my left hand back to her golden cunny.

"Yeah, oh yeah," Diana sighed. "Suck on my titties, little brother. Bite them. Pull them. Hurt them."

My teeth snagged my sister's right nipple, pulling the peachy nub away from her tit. Diana gasped and groaned as I nibbled her nipples and finger-fucked her ass with deep thrusts. Then, on instinct, I pushed my ring finger against her asshole alongside my middle just as my left thumb found her clit, and my middle and forefinger thrust into her pussy.

"Oh, fuck--umm!" Diana groaned, the sound guttural, coming from deep within her breasts.

I watched Diana's face as I filled her tight holes and played with the pink pleasure pearl topping her pussy. As my fingers slowly opened her asshole wider, beads of sweat appeared on her forehead. She stared at me, her expression one of shock, her mouth hanging open in an 'O' shape and her eyes wide. She shook her head at me, but she didn't say no, and as my fingers slid through her wet and rubbery tightness, her cheeks turned a deep pink in color.

"You're the best big sister ever," I whispered as I pushed my thumb hard against her clit.

"Oh, oh, oh, fuck!" Diana cried, trembling and releasing a howl of pleasure from her throat. Her hips ignited, shifting into over gear as she rode my fingers as fast as a jockey on a thoroughbred. Her movements shook the car, rocked my body, and caused the passenger seat to squeak, but I held onto her, letting her gallop her way to the beautiful orgasm I wanted to give her.

"I'm coming, coming, coming!" Diana whimpered and sobbed, her pussy walls clinging to me, her asshole cutting off the blood flow through my fingers. "I'm fucking coming on my little brother!"

Wetness drenched my left hand. Hot, liquid-cum spilled from her small pussy hole, ruining my pants, staining her thighs, coating my fingers. My sister had never come so much before. Her body shook, her tits bounced, and her ass rode my butt-fucking digits hard, sucking them deep within her hot guts. She grabbed onto my shoulders and humped her pussy against me several more times, the way a man would fuck his cock into his girl when he wanted to get the last of his cum out of his balls and her womb.

"Fuck me," Diana moaned, collapsing against me. "Fuck me, you little bastard. You little sister-touching fucker."

I didn't want to take my fingers out of her, but I had to, and so I did. I straightened my sister's dress as best as I could and her panties, apologizing for ripping them. She didn't mind. After getting off me, Diana sat in the driver's seat, a mellow expression crossing her face. I thought she was going to pass out.

"You okay?" I asked.

Diana's eyes focused on my tented pants. "Are you okay?"

I shook my head.

"Do you want me, Timmy?" she teased. "Do you want to fuck your older sister right now?"

"Yes."

"Look at us," She said. "A pair of incest-loving freaks." She leaned over, pressing her lips to mine. "I wouldn't have it any other way." She paused and looked down. "If you stay hard, in public, all the way up to the hotel room, I'll suck your cock for you."

"Only suck?"

Diana smiled. "We have plenty of time for sex tonight, but I want to spend the day with you, like a real couple."

She started her car, and off we drove. I watched my sister drive, still tasting her cunny on my tongue. I licked my fingers, even the one that went into her ass--it was clean, she had seen to that before we left the house--and while she didn't look at me, her mouth did pull into a smile.

Fuck this, I thought as we pulled into the hotel parking lot, my cock still hard. I'm not waiting until tonight, even if she says no.

I don't know why that turned me on, but it did. And I knew it would turn my sister on as well. How did I know? Because I'm her brother, and I wouldn't do anything to hurt her.

Timmy out.

#10 Timmy

The First Time

Saturday, in the Hotel

The hotel loomed above us, a pretty building of white and peach stone with a circular parking lot and a several-storied parking garage behind it. Diana parked in the garage. She led the way to the hotel's entrance as I walked behind her, both of her bags held in my left hand, and my bag was in my right, held in front of my tented jeans. Each uncomfortable step I took made me grit my teeth behind the flat line of my lips. My eyes searched everywhere for anyone who might notice my crotch's predicament.

We walked into the lobby, and Diana headed straight to the front desk. I stood near her in line, and she smiled as I held my bag in front of me. She shook her head. I shook mine. She shook her head again, tugged at her lower lip with her teeth, and jerked her head to the side several times.