Backseat Bargain on Oak Street

Let me tell you about this wild night when my friends from the office decided to hit up The Tipsy Crow, a dive bar downtown. It was a Saturday, the one night they let ladies in without a cover charge, so we were all in. There were four of us: Mia (the yoga-obsessed health nut), Sophie (celebrating her recent engagement), Lily (the newbie in our department, barely 20), and me. Mia picked us up in her beat-up hatchback, and we rolled into the bar, ready for some fun. We spent the night sipping cocktails, laughing over office gossip, and occasionally twirling onto the dance floor with guys who caught our eye, giggling like teenagers.

The night was smooth sailing until a couple of guys, probably in their mid-30s, started eyeing us from across the bar. They had that confident, slightly weathered vibe-like they’d been around the block but still knew how to charm. Eventually, they sauntered over and asked us to dance. They zeroed in on Lily and me, probably because Sophie was a bit heavier and Mia was too busy scrolling through her phone, ignoring them entirely.

We danced, laughed, and lost track of time until it was nearly 2 a.m. Mia suddenly announced she had to bounce – she was sneaking off to meet her side guy, a bartender she’d been flirting with at her favorite gym’s juice bar. Since she was our ride, we all agreed to head out. We waved goodbye to the guys and piled into Mia’s car. We were cruising down Oak Street toward the freeway when her car sputtered and died, leaving us stranded in the middle of the quiet road. We sat there, frustrated, trying to figure out what to do, when headlights lit up behind us. Lo and behold, it was the two guys from the bar, pulling up like knights in a shiny pickup truck. They offered to check the car, but after poking around under the hood, they admitted they couldn’t fix it and offered to give us a lift.

Mia wasn’t about it – she’d already texted her fiancé, who was on his way, which totally derailed her secret plans. Sophie volunteered to stay with her until he showed up. Lily and I, after some hesitation, figured we’d take the ride. We climbed into their truck, but as we drove, the guys – Jake and Tyler – started suggesting we hit up another spot to “keep the night going.” We shot that down, but they kept pressing, their tone shifting from flirty to pushy, making the air in the truck feel heavy.

Lily started freaking out, her voice shaky as she begged them to just take her home. Her panic hit me hard, so I leaned close to Tyler, the guy I’d danced with, and murmured, “Come on, don’t be like that, just get her home,” my hand brushing his shoulder to keep things soft. He sighed and told Jake, “Alright, man, you’re scaring her. Let’s drop her off.” We got Lily to her apartment, and as we pulled away, Tyler turned to me with a sly grin and said, ” – Ava, guess you’re gonna have to make this worth our while.” His laugh was half-joking, but there was an edge to it that made my stomach twist. I played it cool, replying, “Oh, really? And what’s that supposed to mean?”
Tyler didn’t waste time. He leaned in, his lips crashing against mine, his hands roaming to my chest, tugging at the low neckline of my dress. His fingers were rough, slipping under the fabric to tease my skin, sending a rush of heat through me despite the nerves buzzing in my head. I was caught in this weird mix of arousal and unease, knowing I barely knew these guys. As Jake drove, Tyler’s hands got bolder, sliding up my thigh, pushing my dress higher. I whispered, asking if he had protection, and he nodded, pulling a condom from his pocket.
With Jake still behind the wheel, Tyler fumbled with the condom, his hands shaky with excitement. I shifted, lifting my dress and straddling him in the backseat, the leather creaking under us. The truck’s motion made it intense, my hips rocking against him as I tried to control the pace, wanting it over fast. His hands gripped my waist, pulling me down harder, his breath hot against my neck as he groaned. It didn’t take long before he tensed, letting out a low, “Oh, damn,” as he finished, his body slumping beneath me.
Jake, who’d been stealing glances in the rearview mirror, pulled the truck into a dark parking lot and said, “Alright, my turn.” He climbed into the back, already worked up, his eyes locked on me as he tore open a condom wrapper. I was still catching my breath, my mind racing with a mix of fear and lingering heat. Jake was rougher, flipping me around so I was bent over the seat, my hands bracing against the door. He pressed himself against me, his hands spreading my thighs as he pushed in, slow at first, then harder, his rhythm relentless. “God, you’re so tight,” he muttered, his voice thick with lust, his fingers digging into my hips. I moaned, the intensity overwhelming, my body responding even as my mind screamed caution.
Then, without warning, Jake pulled out, his breath ragged. I felt him spit, warm and slick, before he nudged against my backside, pushing in with deliberate slowness. The stretch was sharp, almost too much, but he paused, letting me adjust, before moving again, each thrust deep and forceful. I gasped, my moans mixing with the creak of the truck and the faint hum of the engine. I don’t know why guys are so fixated on that move, but the rawness of it had me trembling.
Somewhere in the haze, Tyler opened the other door. While I was still bent over, taking Jake’s rough thrusts, Tyler slid in front of me, his pants already undone. He guided my head down, and I let him, too caught up to resist, my lips wrapping around him as he groaned, his hands tangling in my hair. The two of them moved in sync, Jake pounding from behind, Tyler in my mouth, the truck rocking with their rhythm. It was chaotic, overwhelming, my body humming with a strange mix of pleasure and fear until they both hit their peak, Jake grunting as he finished, Tyler pulling away to catch his breath. Jake tossed the condom, then leaned back, asking me to “clean him up.” I hesitated but complied, tasting the latex and sweat, my mind numb.
When it was over, I straightened my dress, my legs shaky, and told them to take me home. They kept asking for my number, saying we should “hang out again,” but I gave them a fake one, just wanting to get out. They dropped me off a block from my place, and I walked the rest of the way, my head spinning. At work, Lily asked if I was okay, her eyes wide with worry. I just smiled and said, “Yeah, all good,” not wanting to tell her what I’d gone through to make sure she got home safe. I made it back in one piece, but that night’s still burned into my memory.

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