Timmy #09: Car Fun

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.”