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My Brother's Roommate

Sixteen

Ch. 16 / 23 Mar 31, 2025

Penelope

On a Friday night in Chicago, my neighborhood is the place to be.

It's part of the reason I chose an apartment in this area, just above the chaos of downtown while still being nice and close to the lake. With all the trendy bars, cozy coffee shops, and some of the best restaurants on the north side, I live right in the epicenter of every twenty-something's weekend plans.

Even November's plummeting temperatures can't keep away the swarms of people filtering in and out of bars for happy hour, toasting to the end of a long workweek. And on any other weekend, I'm usually among that crowd, a strong drink in one hand and a half-priced appetizer in the other. But tonight, none of that is on the agenda.

Actually, I have no idea what is on the agenda. What I do know is that when Wolfie texted me saying he had something to show me, I didn't ask many questions for fear of scaring him off again. More than anything, I was relieved to hear from him at all, based on how we left things last week.

Now I'm riding shotgun in his car, admiring Wolfie's seasoned city driving as he expertly weaves us through the traffic that Friday nights in Chicago are so famous for. Rush hour in the city always turns me into a white-knuckled stress bomb, but my chauffeur for the evening is seemingly unaffected by the chaos. It's a nice change of pace.

"This is insane," I mutter, motioning toward the shit show that we're bearing witness to.

When a nearby driver lays on his horn, I jump at least three inches out of my seat. Meanwhile, Wolfie seems totally unfazed.

"Tell me your secrets," I say. "How did you become such an expert in city driving?"

"Practice," he says matter-of-factly. "I grew up here. But the roads won't be so bad where we're going."

I pause, wary of pressing my luck with questions, but ultimately ask in a small voice, "And, um, where is that exactly?"

Wolfie takes his eyes off the road for a second, just long enough to offer me the slightest hint of a smile. "You'll see."

As we head west, away from the lake and past the more developed parts of the city, both the drinking crowds and the traffic dissipate. Whatever it is that he wants me to see, it sure is awfully far from either of our homes.

A full thirty minutes pass and we're still driving, making our way farther and farther away from any part of the city that's familiar to me. Soon, the streets we're traveling are lined with more old-school corner stores than trendy cocktail bars, and the sidewalks are roadside are a bit more cluttered with litter, shattered liquor bottles and plastic bags.

I've ridden the bus through this part of the city before, but I've never gotten off here. Never had a reason to. It's the kind of place you pass through without stopping, the city equivalent to a flyover state. It's not dangerous, per se, but it's not the kind of place where a girl should be wandering around alone.

Luckily, I'm not alone. I'm with Wolfie, who looks apathetic as usual as he turns away from the string of abandoned storefronts and down a more residential road.

"Did we make a wrong turn somewhere?" My teeth sink into my lower lip as I size up the run-down apartment buildings lining the block, each of them shedding shingles and siding like old skin.

Wolfie shakes his head, steering us straight ahead. "Nope. Almost there."

I shift in my seat, trying not to seem unsettled by our surroundings. Both the neighborhood and the anticipation have me feeling fidgety. I'm the type who likes to have a plan, the type who needs to know what to expect.

Two blocks later, he parks on the street between an old truck and a minivan that's held together with the power of duct tape. I blink at Wolfie, waiting for the admission that he took a wrong turn after all and didn't want to fess up. Instead, he frees himself from his seat belt and hops out of the car.

All-righty then. I guess we're doing this.

Whatever this is.

Deep breaths, Pen. You can be spontaneous.

I join him on the sidewalk. To my surprise, his fingers lace through mine, sending a warm rush of adrenaline prickling through my veins.

The last time we were together, things got pretty heated. I can't help but reflect on Wolfie's behavior that night and the things he said. Maybe he was so free because he knew nothing could actually happen between us-not with my brother right next door. It's an interesting theory, anyway.

But right now, I don't have time to analyze it because our palms are pressed together tight enough for me to feel his heartbeat, and all the uncertainty between us washes away. For now, it's just him and me, hand in hand, and I would follow him anywhere.

We fall into step, strolling down the sidewalk for half a block until Wolfie halts in front of an old brick four-story building.

"This is it."

He stares up at the building, his eyes full of every emotion. Pride. Sadness. Love. Anger. His reaction is far more interesting than the building itself, with its boarded-up windows and unremarkable brick exterior.

I try to take it in, to see whatever he's seeing, but I come up blank. It's just an old run-down apartment building that looks like it's set to be demolished.

"What is this place?" I ask.

Wolfie swallows, his eyes still locked ahead. "Something I wanted to show you."

It strikes me that this is Wolfie letting me in. I'm barely breathing, recognizing this is a big moment between us. "What is it?"

"This is where I grew up."

Suddenly, it feels like somebody planted a firecracker in my stomach. I knew Wolfie was a born-and-raised Chicagoan, but I've always figured he was from the suburbs or somewhere else on the outskirts of town. But this isn't suburbia. This is an urban hellscape. How has he never brought this up?

"It was me, my dad, and Maren," he says, pointing toward the top apartment on the left. "In that two-bedroom up there."

I glance up at the side of the building where he's indicating and squint, trying to picture him here. "You wanted to show me . . . where you grew up?"

He nods. "I know you've had a lot of questions."

I give him a small smile. "Your past is your business. And I'm happy to be patient. I just . . . want to understand you is all."

"I know," he says softly.

"What about your mom?" I ask on a whisper.

"She wasn't in the picture. It was just us and Dad. Well, and his revolving door of girlfriends. And there was one . . ." Wolfie's voice tightens, then trails off into a long, tense silence. "There was one who was especially bad," he finally says, like he's finishing a memory he would rather not face.

I draw in a slow, shaky breath, releasing it through my teeth.

What do I say? What questions are the right questions? Am I overstepping?

There's no way of quieting all the questions overlapping in my brain. All I can do is trust my gut and remember what Scarlett said. Just be your usual supportive self, and the rest will come.

God, I hope she's right.

It's only now that I realize Wolfie and I are still holding hands, and I give him a quick, reassuring squeeze, then drag my thumb along the expanse of his palm. "We don't have to talk about it if you don't want to."

"I do want to," he says firmly, his voice gruff and sure. "I want you to understand." His chest rises and falls in quick, measured breaths, his gaze still fixed on the front window of his old apartment.

His eyes are wild and worried, but I don't want him to be anxious. "It's okay," I say, tightening my hand around his. "You can tell me anything."

After a long, uneasy moment, he pushes back his shoulders and speaks, as emotionless as if he were reading from a phone book. "She came into my room one night. My dad's girlfriend. Her name was Janine. I was sixteen. It was late. The room was dark. But I felt her sit down on the edge of the bed. And then," he pauses, drawing another slow breath, "she touched me."

My heart lodges in my throat, and it feels like there's no oxygen left. I can't catch my breath. She touched him? His dad's girlfriend? This poor, broken man. I had no idea. He's been living with this pain all this time?

"I am so, so sorry, Wolfie," I whisper after a long, pain-filled silence. It's the only thing I can think to say. But no amount of apologies could ever be enough. Not for what he's been through. Once the initial shock wears off, a second thought rises to the surface. "Does your dad know?"

Wolfie nods somberly, his jaw clenched. "Told him the next morning. He brushed it off, said I probably just dreamed the whole thing and Janine would never do something like that. I thought I was doing the right thing by telling him, but I guess-"

"You were doing the right thing," I say quickly, interrupting. "I'm so sorry he didn't take you seriously."

"It was a long time ago. But it . . . you know. Complicated a couple things."

I bite my cheek, my head bobbing in a slow, sympathetic nod. "Of course it did. And that's not your fault." I mean every single one of those words.

My chest aches for him. For this truth he's been burdened with for so many years, not feeling comfortable to share this horror with anyone. How would he ever feel comfortable opening up if his own father didn't believe him? But Wolfie felt comfortable with me, and that makes my heart soar.

Maybe this step out of his comfort zone was to bring me understanding, or maybe it's part of him healing. I'm not sure, but I am grateful.

Realization shoots through me.

Wolfie has secrets that he doesn't want others to know. He has childhood pain and trauma. And as a result, sex can be difficult for him.

My throat is tight and my stomach is knotted. I wish I could fix this for him, but I know I can't on my own. It's his to endure. All I can do is be here, stand beside him, support him.

We stand wordlessly for a good long while, taking in the apartment building and all the old haunted memories that live there. When Wolfie finally breaks the silence, it's with a low chuckle of disbelief.

"I can't believe this place is still here. Thought they would've torn it down by now." His mouth curls into a small, sad smile, his hand gripping mine extra tight. "But I'm glad it's still here. So I could show you."

He turns to me, his bottomless gray eyes locking with mine. He doesn't have to say another word. Just the way he looks at me, like he's staring straight into my soul, says it all.

In a lot of ways, Wolfie is a lot like the building he grew up in. Worse for wear, but still standing strong despite everything it's endured.

"Thank you for telling me," I say in a small voice as the weight of his admission still rocks through me. "It means the world to me, and I will do whatever I can to help you. Whatever you need, Wolfie, please know that you can always count on me."

After a few more moments, we leave in silence. On the drive back to my apartment, it's like the fog of tension has lifted and Wolfie is a whole new man.

He points out the parks he went to growing up, the corner stores where he and Maren used to pool their money and buy bags of chips and packs of gum. For as broken as his childhood was, there were brighter memories too, little golden moments shining through the cracks in the concrete. And he's all too eager to share them with me.

By the time we pull up in front of my building, I feel closer to him than ever. Like his chipped edges all make sense. I want to keep driving with him, to learn this whole city through his eyes. I want to know every story and every scar. And it seems like he's finally brave enough to show me.

"Thanks for coming with me," Wolfie says as he shifts the car into park. "For letting me share that with you."

"You don't have to thank me," I say, correcting him. "I want to know that stuff. To learn everything about you."

And I realize my words are true. Things didn't start out this way between us, but they're changing. I want to be here for him, to help him work through his hang-ups. It's no trouble at all, despite what he thinks. It's a privilege to know that he trusts me with this stuff.

I reach over the console, taking Wolfie's hand in mine. He doesn't flinch away, just lets me trace the lifeline of his palm with light, reassuring strokes.

"Well, if you'd like to keep learning. You know. Stick around." He pauses, wrapping his fingers tight around my thumb and treats me to a gentle smile. "I think I'd really like that."

"Yeah? I think I'd really like that too."

I'm not quite sure who makes the first move. All I know is that moments later, we're sharing the sweetest, softest kiss I've ever known, each touch of his lips to mine more grateful than the last. There's something about the way this man kisses that's unlike anything I've ever experienced before. His earthy, masculine scent coupled with the tender strokes of his tongue against mine is the most perfect thing.

When I break away from our kiss, I trail my fingers along his scruff and breathlessly ask, "Maybe you should come inside?"