14. Jackson
Jackson
T he speakeasy hides behind an unmarked black door tucked into a quiet stretch of Fulton Market, the kind of place you only know if someone trusted shows you.
I guide Tarryn through the entrance with my hand at the small of her back, fingers splayed across the silk of her dress.
The heat of her skin bleeds through the fabric, branding my palm with memory and need.
My body buzzes with electricity at the connection. My mind fighting to stay focused on walking instead of letting it take me back to the memory of being inside her, her tits pressed against me as her pussy milked my cock and she moaned my name.
Inside the bar, everything softens. Amber light spills across leather booths and gleaming mahogany, the deep hum of jazz winding through the place. A hostess leads us to a half-moon booth in the corner, discreet and dimly lit. It’s intimate.
We slide in, and even though the space is wide enough to keep our distance, she leans toward me like she always did when we were teenagers.
"You know Chicago better than I would've expected," she says, her voice warm with a flit of amusement. “Discover this on one of your dates?”
“Hardly.” I roll my eyes, ignoring her attempt to find out if there’s been a string of women before her nestled next to me in this booth.
I signal the server, eyes never leaving hers.
"I spent two summers interning at Marshall & Gould. The senior partner was obsessed with speakeasies. Said the best deals were made when people felt like they were getting away with something.”
She laughs, and it hits me hard, deep and low in my chest, that familiar ache that’s never fully gone away.
"Sounds like something you'd say.”
I smile, not denying it. "Maybe I like the idea of getting away with something forbidden. Or maybe…" I lean in slightly, caught in the gravitational pull between us. "I just like the look on your face right now.”
Her brow lifts. "What look is that?”
"Relaxed. Open.” I lean back a touch, studying her features. “Like you're not at war with yourself.”
The light dances across her cheekbones, softening her features. She’s always been stunning but seeing her like this, unguarded, even for a moment, is pure bliss. I drink her in like it’s been years since I’ve allowed myself to.
Because it has been.
"Tell me something I don't know about you," she says. "Something from the last eight years. No resumes allowed.”
I let the silence stretch for a breath, then offer it to her straight.
"I lived on a houseboat after law school. Six months. No Wi-Fi, barely any reception. Just Lake Monroe, cheap bourbon, and solitude.”
Her eyes widen and she lets out a burst of laughter. "Seriously? You? Mr. Buttoned-Up Power Suit lived off-grid?”
"Pretty much." I shrug, but my chest tightens. "I needed to stop chasing things. I needed to be still for a while. Let the dust settle.”
She studies me, eyes narrowing like she senses more beneath the surface.
She's always seen through me quicker than anyone else.
"And I needed to stop looking for you in everyone I met.”
That makes her go still. Not flinching. Just quiet. The kind of quiet that leaves me nervous.
"Did it work?" she asks.
"For a while." I let the truth land. "But the second I saw you again”—I shake my head and smile—“it was like someone flipped all the switches back on.”
She doesn’t speak. Just watches me, lips parted slightly, like she’s not sure how to breathe around the weight of what I’ve just given her.
"Your turn," I say, voice quieter now. "Tell me something real.”
She traces the rim of her glass. For a second, I think she might dodge the question.
"I almost got married.”
Everything inside me pulls taut but I don't let it show.
"What happened?”
Her voice flattens, detached like she’s telling me someone else's story. "He was perfect. On paper. Harvard Law, junior partner, rich family, all of it. He proposed with a three-carat diamond in front of a hundred people.”
“And?”
"I said yes." Her eyes finally meet mine. "Then I spent months convincing myself that love would come later. That intimacy was a learned thing. I even went to therapy thinking I was the problem.”
I lean in. “But?"
Her voice dips low. Vulnerable. Raw. "But he wasn’t you. And I always knew that.”
The air between us tightens like a rubber band pulled taut. I reach across the table and take her hand, not to comfort her, not to make a move, but to anchor us to this moment that feels impossibly real.
“Tarryn.”
She looks at me like she wants to believe this could still be something. That maybe fate has finally brought us back together to fix that cruel twist of timing that I thought had wrecked us completely.
"Hayes? Jackson Hayes? I'll be damned!”
I look up, and just like that, the bubble bursts.
Because Robert Callahan, senior counsel for Netcom Industries and one of Westfield's most important clients, is approaching our table. I release Tarryn’s hand, but not fast enough.
Callahan’s eyes sparkle with mischief. His presence here—in this deliberately chosen, out-of-the-way location—feels like cosmic mockery of our attempt at privacy.
"Robert." I rise, handshake automatic while my mind races through implications. "What brings you here?"
"Monthly poker game in the back room." His attention shifts to Tarryn, curiosity evident in his expression. "And who is this lovely companion?"
Professional necessity overrides personal desire. "This is Tarryn Wells, one of Blake Financial's finest attorneys. We're discussing the Westfield contract revisions."
Understanding dawns in Robert's eyes, followed by something knowing that makes my jaw tighten. "Over craft cocktails in Chicago's most romantic speakeasy?” He winks at me knowingly. “That's dedication to client service."
Robert's amusement is poorly concealed. "Well, I won't keep you from your… professional discussions. Oh!" He snaps his fingers as if suddenly remembering something. "I'm hosting the Bulls game in my box next Friday. You should both come—perfect opportunity for informal relationship building."
When he's gone, Tarryn exhales slowly, tension vibrating through her body. "So much for keeping this away from professional circles."
"He doesn't know anything," I assure her, though the words ring hollow even to my ears. "We're colleagues having drinks. It happens every day."
"In hidden speakeasies where the lighting makes everyone look like they're having an affair?" She shakes her head, the movement sending dark waves cascading over her shoulder in a way that makes my fingers itch to tangle through them. "We're not fooling anyone, least of all ourselves."
Before I can respond, my phone vibrates against the table. My mother's name illuminates the screen, unusual for this time of night. Concern immediately overrides all other emotions.
"I should take this," I say, already sliding from the booth. "It's my mother."
I step into a quieter hallway near the restrooms, pressing the phone to my ear.
"Mom? Everything okay?"
Her voice comes through clear but strained. "Everything's fine, honey. Well, mostly fine. Your father had his follow-up with Dr. Kowalski today."
My pulse accelerates, memories of hospital corridors and beeping machines never far beneath the surface even though he hasn’t had another heart attack since the first one. "What did he say?"
"The good news is his condition is stable." She pauses, the weight of unspoken words evident in her silence. "The less good news is there's a specialized surgical procedure that could significantly improve his quality of life. Something about a valvular intervention."
I lean against the wall, free hand pressing against my eyes. "I'm sensing a 'but' coming."
"But insurance will only cover about sixty percent of the cost." Her voice drops, embarrassment coloring her tone. "It's elective, technically speaking. Not immediately life-threatening."
"How much?" I ask simply.
"Jackson, your father forbade me from asking you," she confesses, maternal worry transcending pride. "He's so proud of what you've accomplished. Says watching you argue a case is better than any medicine."
The unexpected vulnerability in her description of my stoic father—a man who once viewed asking for help as weakness rather than wisdom—creates a tightness in my throat that makes it difficult to respond. "Mom. How much?"
She names a figure that would decimate my savings but remains within reach—especially with the signing bonus the junior counsel position would provide. The position I'm competing for against Tarryn. The position that suddenly carries implications beyond professional advancement.
"I'm transferring the money tomorrow," I tell her, decision instantaneous and absolute. "Tell Dad it's an investment in future fishing trips that he's not allowed to refuse."
Her relief is palpable but she still tries to deny accepting it. "He'll protest."
"Let him. I'm still going to do it." I glance toward the booth where Tarryn waits, her profile illuminated by the table’s candlelight. "How is he, really?"
"Stubborn as ever." Affection warms her tone. "The chest pains have been worse lately, but he won't admit it. This procedure could make such a difference, Jackson."
After assuring her the money will be arranged, I end the call and stand motionless in the hallway, absorbing implications that ripple outward like stones dropped in still water.
The promotion, already professionally significant, now carries my father's well-being in its wake.
The competing presentation against Tarryn, originally a showcase of complementary talents, transforms into something more fundamentally opposed to my instincts—a direct competition against the woman who's reclaiming territory in my heart with frightening efficiency.
When I return to the booth, Tarryn reads my expression with the uncanny perception she's always possessed. "What's wrong?"