It was June 2014 and I had just gotten out of a bad relationship at the beginning of the year. Now, some people, especially the exes friends would say that I was an asshole because of the way I ended things. It was a few weeks before her birthday, but I knew that I just wasn’t feeling it anymore, we are grown further and further apart, and we both wanted different things in life. I want to go ahead and move to Chicago so I can learn more about the entertainment industry as well as learning more about finance while my ex wanted to stay home because that’s where she felt comfortable, being around her family and not trying to move to a different state with me. I have met up with my friend Will over at Starbucks one afternoon because me and him had to discuss some business opportunities and network as well. Brandon knew about my goal and how I wanted to head to Chicago to challenge myself to become a better person and also find someone that I can share a life with. I wasn’t looking to get the traditional life such as being married and having a family. No, I want to have someone who I can build an empire with. I wanted to get onto the media and entertainment industry because that’s always been a passion of mine and I want someone who can share that passion without having the burden of being tied down by a family. for some reason, Alex did not understand it and she wanted to stay home and be close to her friends and me personally? We grew up here so why would we want to stay here and be close to our friends when we could just call them? But anyhow, I met up with Will and one of his friends had also just got out of a bad relationship. He knew that I wasn’t looking at anything serious so he wanted to introduce me to his friend, Sierra who from the looks of it wasn’t normally wanted to type of girl so that would go after because she was dressing very conservatively for a 75° day. And to be quite honest, she wasn’t really giving the vibe that she dated men based off how she was looking. I’m talking about she had on a loose long sleeve shirt and some baggy pants and some flip-flops so I was like OK. Maybe this girl could be somebody who I can bring on and we could have a business relationship only and I say that because from what he mentioned to me, she was pretty smart and had just started attending MSU. Now to be honest, I’ve known her since junior year in high school and again she wasn’t someone who I looked at in a romantic way mainly because she came from a super conservative household, and she wasn’t like the rest of the girls at our high school. I’ve known Will since elementary school so me and him were basically like brothers at this point and I say that mainly because we live three blocks away from each other and our parents always had these huge cookouts during the summer holidays. Me and Will order our drinks and I asked Sierra if she wanted anything. She said no thank you because she was on some weird diet or whatever but that’s neither here or there. We sit down at a table closest in the back to discuss some opportunities and Will was looking into getting into some property management company so that way he can own his own real estate company at some point. I knew who to put them in touch with because my aunt worked with the city and had contacts that I can put him in touch with so that way he could buy some of the property that’s been laying around. but he’s also been looking at starting his own landscaping company as well and again because my family was very well-connected for the most part with the city and county when it came to contracts he knew that I was the one who could help him out. an hour and a half later we’re going over everything and his phone rings, I recognize that ringtone from anywhere and I know that was his girlfriend. He excuses himself and steps to take me and Sierra at the table to make small talk. I asked Sierra how life is going and she mentions that she recently took a break from her boyfriend because things was getting too complicated with him. I didn’t really feel like getting into knowing what the problem was because judging her based off her High school years, I knew that it was her own fault when it came to whatever happened between her and her boyfriend. I heard the rumors that who by the way was an outstanding basketball player wanted to go ahead and go to college out of state so that way, he could potentially get drafted. Apparently, Sierra‘s family did not think that was a good career choice for him and that led to some issues when it came to the games and her family not showing up for her because she was a cheerleader. I still can’t believe that she was a cheerleader in high school because of just how conservative she dresses and her family is background. She asked me what’s going on in my life and I told her that I’m getting ready to possibly move to Chicago to learn more about media and potentially start my own business. Now I’ve always been the kind of guy that’s always that’s had a weakness when it comes to a woman’s eyes. And Sierra does this thing with her eyes and I don’t know if it was the lighting or she was wearing her hair. Because we locked eyes for a second and something sparked inside of me. So I tell her that I’m leaving probably towards the end of summer so I’m not really looking into anything serious especially because I just got out of a relationship in the beginning of the year. she understood that actually and had mentioned that she just wants the one who she can hang out with that. She doesn’t look at as a brother and I told her that well we could possibly hang out together or if you like you can join me on this trip and I’m going on in a few weeks. I can tell that she’s thinking about it and I can sense that she thinks that I’m trying to plot on her with her current situation, so I tell her that she doesn’t have to worry about anything, we’re literally just friends going on a trip for a week and if it makes her feel better, we can even get separate rooms. Again, something with her eyes had me mesmerized and the way she said we don’t have to have a separate room kind of had me curious, but I didn’t want to, show my hand just yet. There’s something about her that I can’t place but it’s making me extremely curious because she’s not the type of girl that I would pursue and the way she’s dressing it’s just odd to me. I happen to look up and I see Will coming back inside and I look at Sierra and I give her my number and tell her to text me to let me know if she’s down to join me.
Chapter 2
A couple of weeks have passed by since me and Will met up to discuss some opportunities and as I was packing for my trip to Chicago for the week, I got a call from Sierra. I answered it and we exchanged pleasantries and she asked what was I doing. I told her nothing much just packing because I’m going to be heading out soon for a week. She asked what would I be doing in Chicago and what was my schedule like while I was on. I told her basically eight hours a day I’m gonna be busy training and learning about the program that I’m going into and then after that it’s free time however I’ll probably be spending that meeting up with someone folks that’s in town for the seminar also. Her asking questions like this kind of confused me because I did not know what her intentions were especially since it’s been a few weeks since we met at the coffee shop. Now I understand why she was making small talk now because after I left for Chicago, I will be heading back home for the month and then packing up everything to go to LA for the rest of the summer and stay at my uncle‘s house. Because it’s only a 2 1/2 hour drive to Chicago compared to the hour long flight it would take instead. She asked that I plan on driving or flying there and I told her I already have my plane ticket purchased and I’m actually leaving out first thing in the morning. She asked if she could come over just so we could catch up before I left and as much as I wanted her to, I already have plans with my parents. As I’m leaving out to meet my parents for dinner I get a call from other than Alex. I hop in a car as I’m driving. I ask Alex what does she want and she tells me that she’s coming back in town to catch up with her parents.
Chapter 3: Nights by the Lake
Saturday in Chicago was electric, the city buzzing with life as the weekend took hold. Sierra had spent the day soaking in the energy, and I’d enjoyed playing tour guide—showing her the highlights like Millennium Park, the Magnificent Mile, and a few hidden spots that weren’t on the usual tourist map.
By the time dinner rolled around, I could tell she was craving something more personal.
“You’re quiet,” I said as we left the restaurant, the city lights glittering above us.
“Not quiet,” she replied, her voice soft but teasing. “Just thinking.”
“Dangerous habit,” I joked, earning a playful roll of her eyes.
“Maybe. But I think you’ll like where my thoughts are headed.”
That caught my attention, but before I could ask, she turned the conversation back on me.
“You’ve got another spot in mind, don’t you?” she asked, slipping her arm through mine like it was second nature.
“Maybe,” I said, tilting my head toward the lake. “Come on.”
The sun had set by the time we reached the waterfront, the horizon fading into deep blues and purples. A soft breeze rolled off the lake, carrying the scent of water and the faint hum of distant laughter.
Sierra kicked off her heels and walked barefoot beside me, her movements effortless, graceful. “This is what I needed,” she murmured, glancing out at the water.
We found a quiet spot near the edge of the lake. I spread my jacket on the ground for her to sit on, and she accepted it with a small, appreciative smile.
“You do this for all the girls?” she asked, her tone teasing but her eyes searching mine.
“Only the ones who kick their shoes off and drag me to the lake,” I replied, matching her tone.
She laughed, a soft sound that settled into the quiet night around us. “Smooth answer.”
The conversation flowed easily after that, dipping into deeper topics—her family, my plans, the risks we both felt we were taking in our own ways. At one point, the playful glint in her eyes faded, replaced by something softer.
“Can I ask you something?” she said, her voice quieter now.
“Sure.”
“Do you ever think about what you’re leaving behind? Like… do you ever wonder if it’s worth it?”
I hesitated, watching the way her fingers absently toyed with a loose thread on my jacket. “Sometimes,” I admitted. “But I think about what I’d regret more—staying or going. And for me… staying just wasn’t an option.”
She nodded, her gaze fixed on the rippling water. “I get that.”
For a moment, we sat in silence, the weight of her thoughts hanging between us. Then she turned to me, her eyes catching the moonlight in a way that made my breath hitch.
“You’re a hard guy to figure out, you know that?”
“I’ve been told,” I replied, keeping my tone light even as her gaze pinned me in place.
She leaned in slightly, her voice dropping to a near whisper. “I think I’m starting to, though.”
And just like that, the air shifted. There was no overthinking, no hesitation—just the pull of the moment as our lips met.
Her kiss was tentative at first, testing, like she was unsure of her own boldness. But when I deepened it, she responded with a hunger that caught me off guard, her fingers tangling in my shirt as if anchoring herself.
When we finally pulled apart, her forehead rested lightly against mine, her breath warm against my skin.
“This is… complicated,” she said, her voice trembling slightly.
“It doesn’t have to be,” I replied, my hand brushing a stray strand of hair from her face.
She pulled back, just enough to meet my eyes. “But it will be. You’re leaving, and I’m… I don’t even know what I’m doing.”
I searched her expression, catching the flicker of doubt mixed with something deeper—something she was clearly trying to fight.
“We don’t have to figure it out right now,” I said, keeping my tone steady. “Let’s just… see where this goes.”
Her hesitation lingered for a moment longer before she nodded, her lips curving into a faint smile. “Okay.”
Back at the Apartment
The walk back to the apartment was quieter, the unspoken tension between us simmering beneath the surface.
Once inside, Sierra wandered to the balcony, her arms resting on the railing as she stared out at the city. I watched her from the doorway for a moment, taking in the way the light danced across her features, softening the guarded edge she usually carried.
“You’re quiet again,” I said, stepping outside to join her.
“Still thinking,” she replied, her voice laced with both vulnerability and determination.
“About what?”
She turned to me, her expression unreadable. “About how I didn’t expect this. Any of it.”
I nodded, leaning against the railing beside her. “Neither did I.”
Her eyes met mine, and for a second, I thought she might say something else. Instead, she closed the distance between us, her hand brushing lightly against my arm. “This is new for me,” she admitted softly.
“What is?”
“This… letting myself just feel. No plan, no overthinking. Just… this.”
I reached for her hand, intertwining our fingers. “You don’t have to have it all figured out, Sierra.”
She exhaled a shaky laugh, her fingers tightening slightly around mine. “That’s easy for you to say. You’re good at this.”
“Good at what?”
“Making me want to take risks I’m not sure I’m ready for.”
Her words hung in the air between us, heavy with meaning. But instead of pulling back, she leaned into me, resting her head on my shoulder.
For the rest of the night, we stayed like that—quiet, close, letting the city’s hum fill the spaces between our words. And as I held her, I couldn’t shake the feeling that whatever this was, it was only the beginning.
Chapter 4: Crossing Lines
The city lights painted the balcony in warm hues, their golden glow soft against Sierra’s skin. She still leaned into me, her head resting on my shoulder, her fingers tracing lazy circles on my arm. “I never realized how quiet the city could feel,” she murmured, her voice barely above a whisper. “Quiet?” I smirked. “This city is anything but quiet.” She tilted her head to look up at me, her lips curved into a teasing smile. “Guess I’m just distracted.” “Good distracted?” I asked, watching her eyes as they locked with mine. “Depends.” Her tone turned coy, her fingers slipping lower to rest against my chest. I reached for her hand, holding it in place as my heart thudded beneath her touch. “On what?” “On how this ends tonight.” The subtle challenge in her words made my breath hitch, but I wasn’t about to let her take full control of the moment. I shifted, turning to face her fully. “What do you want it to mean, Sierra?” Her hesitation was brief but telling. She searched my face, her expression softening before she closed the gap between us. This kiss wasn’t tentative like before—it was deliberate, her lips parting slightly as her hands slid up to my neck, pulling me closer. I didn’t fight it, couldn’t even if I’d wanted to. The spark between us burned hotter now, my hands instinctively finding her waist, holding her steady as the kiss deepened. When we finally broke apart, her breath was uneven, her lips slightly swollen. She stayed close, her forehead resting against mine, her fingers tangling in the back of my hair. “I don’t usually do this,” she said, her voice trembling with honesty. “You think I do?” I replied, brushing a strand of hair from her face. Her laugh was soft, almost nervous, but it didn’t stop her from taking a step closer, pressing her body against mine. “You’re good at making it feel natural.” I pulled her back inside, the warmth of the apartment replacing the chill of the night air. The city hummed outside the window, but all I could focus on was her—her scent, her touch, the way she looked at me like she was trying to decide whether to run or stay. She reached for my shirt, her fingers brushing my chest as she unbuttoned it slowly, deliberately. “Tell me to stop,” she said, her voice almost daring. “I won’t,” I said simply, my hand trailing along the curve of her jaw. Her hesitation was brief. She let the shirt fall to the floor, her hands roaming over my skin as her lips found mine again. Each kiss grew hungrier, more urgent, as we stumbled toward the bedroom. But just as I was about to pull her closer, she stopped, her hands pressing lightly against my chest. “Wait,” she whispered, her breathing heavy. I froze, my hands still resting on her hips. “What’s wrong?” Her eyes searched mine, uncertainty flickering across her face. “This is... fast,” she admitted, though she made no move to pull away. “Then we slow down,” I said, my tone steady. “You set the pace, Sierra.” Her lips curved into a small smile, the tension easing from her shoulders. “You’re too good at this.” “Good at what?” “Making me want more.” I leaned closer, brushing a featherlight kiss along her jawline. “And what do you want?” Her breath caught, and for a moment, she didn’t answer. Then, with a resolve that seemed to surprise even her, she whispered, “You.” Her confession sent a jolt through me, but I kept my touch gentle, my hands moving up to cup her face. “Then let me show you,” I murmured, kissing her again—slower this time, savoring the way she melted into me. The night stretched on, the lines between restraint and desire blurring with every touch, every kiss. And though we didn’t rush, didn’t leap into the unknown without thought, the connection we shared grew stronger, leaving no doubt that something had shifted between us. By the time the first hints of dawn painted the sky, Sierra lay curled against me in the bed, her fingers tracing idle patterns on my chest. She still hadn’t said much, but the soft smile on her lips told me everything I needed to know. “This is going to get complicated,” she murmured, echoing her earlier words. I kissed the top of her head, my arm tightening around her. “Maybe. But it’s worth it.” She tilted her head to look up at me, her smile growing. “You’re dangerous, you know that?” “And yet, here you are,” I teased, earning a quiet laugh. For now, the complications could wait. Tonight, we’d taken a step neither of us could undo—and neither of us wanted to.
Final Chapter: Crossroads
The morning sunlight filtered through the curtains, casting a warm glow over the apartment. The city outside was already buzzing with life, but inside, everything felt still. Sierra shifted against me, her hair spilling across my chest as she let out a soft sigh.
“Morning,” I murmured, running a lazy hand down her back.
She tilted her head up, her lips curving into a sleepy smile. “Morning.”
For a moment, neither of us moved. It was easy like this—wrapped up in each other, with no expectations and no weight of reality pressing down. But reality had a way of creeping in.
“We should probably get up,” I said eventually. “I did promise you breakfast.”
Sierra groaned but sat up, stretching her arms above her head before slipping out of bed. “Fine, but only if they have pancakes.”
I smirked, watching as she padded toward the bathroom. “You’re easy to please.”
“Sometimes.” She glanced over her shoulder, eyes glinting with something unreadable before disappearing inside.
Breakfast was at a quiet café near the lake, the kind of place that served strong coffee and let people linger. We sat by the window, watching the water shimmer under the late-morning sun.
“So,” she said, stirring her coffee. “Big changes coming up for you.”
“Yeah. Orientation starts soon. After that, it’s a whole new world.” I leaned back in my seat, studying her. “What about you? What’s next?”
Sierra hesitated, tapping her spoon against the rim of her mug. “Honestly? I don’t know.”
I waited, giving her space to find her words.
She sighed. “I thought I had everything figured out before I met you. I was just going through the motions, playing it safe. Now… I feel like I’m at a crossroads.”
I nodded slowly. “And what do you want?”
“That’s the thing,” she admitted. “I don’t know if I want a relationship, just fun, or if I need to take time to figure myself out first.” She met my gaze, searching for a reaction.
I took a sip of my coffee before answering. “You don’t have to decide that right now.”
Her lips parted slightly, as if my words caught her off guard. “I don’t?”
I shook my head. “We don’t have to label anything. We just keep moving forward, see where it takes us.”
Sierra exhaled a quiet laugh, shaking her head. “You make things sound so simple.”
“Maybe they are.” I reached across the table, brushing my fingers over hers. “All I know is, I like having you around.”
A pause. Then, slowly, her fingers curled around mine.
“Me too,” she admitted.
The next few days passed in a blur of late-night conversations, spontaneous outings, and stolen moments that neither of us tried to define. But then, it was time for her to head home.
We stood by her car, the city humming around us. Sierra leaned against the door, biting her lip. “So… I guess this is where we say goodbye?”
“Or see you later,” I corrected.
She smirked. “Confident, huh?”
“Just hopeful.”
She hesitated, then stood on her toes, pressing a soft kiss to my cheek. “See you later, then.”
I watched as she got in her car and drove off, knowing that whatever happened next was up to her.
And maybe, just maybe, this was only the beginning.
To be continued…
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