My Boyfriend’s Brother Took My First Night / Chapter 5: Ferris Wheel Fears
My Boyfriend’s Brother Took My First Night

My Boyfriend’s Brother Took My First Night

Author: Brett Donaldson


Chapter 5: Ferris Wheel Fears

The next week blurred by in laughter and adventure. Derek took me everywhere—downtown, to the riverside park, for burgers and milkshakes at the old diner. Every day was a new date, every night I fell asleep smiling.

A year of missing him faded behind us. With him by my side, love felt easy again. The ache of long distance melted away with every shared moment.

When the new semester started September first, I moved into the dorms. Derek upped his boyfriend game: every morning, he showed up outside my dorm with coffee for me and donuts for my roommates, like he was trying to win everyone over.

We’d meet for lunch, and every few days he’d surprise me with little gifts—T-shirts, bracelets, movie tickets. I overheard my roommates whispering, "Natalie’s so lucky—her boyfriend’s tall, cute, and totally spoils her."

It felt good. I let myself enjoy it.

But then, out of nowhere, Derek got busy. Like, barely-has-time-to-text busy. In over two weeks, I could count on one hand the number of times I saw him.

He said the university basketball team had made it to a city-wide tournament. Derek was a starter, and practice was nonstop—morning, noon, and night. Our Labor Day plan—a Ferris wheel ride, just the two of us—was canceled.

My family lived hours away, and flights were expensive, so I stayed in the empty dorms. Netflix and takeout became my weekend routine, but the disappointment lingered.

Halfway through a rerun, my phone buzzed. Caleb’s name lit up the screen. I answered, surprised. "Natalie, are you alone at school?"

"Mm-hmm," I muttered, curled up in bed, hugging a pillow.

"Come out later. I’ll pick you up and take you out."

I blinked. "Huh?"

"Derek asked me to look after you."

It made sense, sort of. Still, I tried to let him off the hook. "Caleb, you really don’t have to. I know you’re busy. I’m fine with Netflix."

"It’s no trouble," he said, and hung up before I could argue.

An hour later, his sleek black Tesla waited at the west gate. I spotted him—sharp suit, focused eyes—and hurried over, nerves buzzing in my stomach. Being looked after by Derek’s older brother felt almost unreal.

First stop: dinner at an upscale steakhouse at the top of a glass tower, white tablecloths and a view of the city. We sat outside, wind in my hair, the soft sound of a piano nearby.

Halfway through, fireworks exploded over the skyline—reds, blues, golds lighting up the night. I stared, awestruck, my steak forgotten. It felt like magic.

Afterward, Caleb turned to me. "Anywhere else you want to go?"

"I want to ride the Ferris wheel next to us," I blurted. My face flushed, but he just nodded.

The Ferris wheel glowed, each car lit up like a lantern. My knees bounced. The cabin creaked, and every time it swayed, my stomach dropped like I’d missed a step. I’d never told anyone, but heights made me anxious.

Caleb noticed. "If you’re scared, you can hold my hand," he offered, voice low and gentle.

I grabbed his hand without thinking. His palm was warm and steady. It grounded me, made the world shrink to just us.

Inside the cabin, the air was tinged with his clean cologne—a scent that was becoming too familiar. My skin prickled. I tried to focus on the city lights, but my mind kept circling back to the man next to me.

By the time the Ferris wheel descended, I let go, pulling my hand into my lap. "Caleb, I… I’m fine now. Not scared anymore." I kept my eyes down.

He didn’t say anything, just watched the city below. I glanced at the next cabin—a couple sat close, the guy in a gray hoodie, the girl tucked into his side. For a moment, I could’ve sworn the guy looked like Derek.

I squinted, trying to see, but Caleb shifted, blocking my view. "Natalie—" His voice was close. He leaned in, taller than I remembered. I saw the faint shadow of stubble on his jaw.

He reached out, gently brushing something from the corner of my eye. "You had something here."

I exhaled, flustered. "Th-thank you—" My heart hammered, my face burning. I’d thought he was going to kiss me, and I froze.

When the ride ended and we walked back to his car, my face was still on fire.

"Caleb, thank you for today. I’ll head back now. Drive safe," I said, trying to sound normal.

"Mm. Rest early," he replied, waving as the Tesla disappeared into the night.

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