Chapter 1 — Trent
I woke up with a skull-splitting hangover, five women in my bed, and a mouth on my cock.
So.
Forty was going great.
For several seconds, I didn’t open my eyes. I stayed exactly where I was, flat on my back, one arm flung over my head, sheets tangled around my hips, and my pulse pounding like someone had hired a construction crew to remodel the inside of my skull.
Warm lips moved over me.
A soft hand dragged up my thigh.
Someone giggled near my left shoulder.
Another woman shifted against my side, naked skin sliding over naked skin, and the scent of perfume, sex, whiskey, vanilla, and expensive regret filled my bedroom.
Jesus Christ.
My bedroom.
That alone should’ve snapped me sober.
I never let women spend the night.
That was one of my rules. I arranged rides and made sure everyone got home safe.
Pleasure, yes.
Confusion, no.
Morning-after intimacy? Absolutely fucking not.
And yet there I was, in my own bed, with bodies everywhere and a woman’s mouth working me like she had woken up with a mission.
My cock was extremely interested.
My brain was not.
Fragments of last night crawled in, broken and bright. My fortieth birthday. Lucky’s packed wall-to-wall. Aaron grinning like the devil while ordering shots. Callum calling me an old bastard. Rory laughing into his drink. Women. Music. Whiskey. Angela in a black dress, smiling like she knew exactly how long I’d waited to finally have her under me.
Angela. Her mouth against my ear, and nails on my chest.
I huffed out a rough breath, and the mouth on my cock took me deeper.
My hips jerked.
“Fuck,” I muttered.
Someone laughed softly. “Still bossy in the morning.”
My eyes snapped open.
The voice didn’t belong to Angela.
The world sharpened in one violent second.
My bedroom was destroyed. Pillows on the floor. A bra hanging from the lamp. My tie twisted around the bedpost. A black heel near the bathroom door. Sheets tangled around bare legs and naked hips. Angela slept half on her stomach near the edge of the mattress. A blonde I vaguely remembered from the private room was curled near my left side. Another woman with red nails was draped across the bottom of the bed. Two more bodies shifted beneath black sheets.
And between my thighs, dark hair spilled over my stomach.
No.
The woman lifted her head.
Green eyes. Smudged makeup. Swollen lips.
Lilah McKnight.
Eloise’s sister. Callum’s sister-in-law.
Family.
Very naked.
Very much licking her lips while my cock still rested in her hand.
I shot upright so fast my head nearly split open.
“Fuck.”
Lilah blinked, startled, her fingers loosening immediately. “Wow. Good morning to you too.”
I yanked the sheet over myself like dignity had decided to crawl back into the room twelve hours late. My heart pounded harder than my headache now.
“What the hell are you doing?”
The second the words left my mouth, I saw her face change.
Hurt first.
Then anger.
Then that proud little lift of her chin that looked too much like Eloise when someone pissed her off.
“You invited me,” she said.
My stomach sank.
Around us, the other women began to stir. Angela lifted her head from a pillow, hair wild, mouth curved with lazy amusement.
“Birthday boy panic?” she murmured.
“Everybody up,” I said, voice rough.
The blonde groaned. “Already?”
“Yes. Now. Up.”
Angela rolled onto her back and stretched like a satisfied cat. “That is not how you talked last night.”
“Last night is currently under review.”
Red Nails laughed from the foot of the bed. “He’s cute when he’s horrified.”
“I’m not horrified,” I snapped.
Lilah arched a brow.
I looked at her and immediately regretted the lie.
Everyone in this room had known exactly what kind of birthday disaster they were walking into. Last night hadn’t been a mistake because bodies wanted what bodies wanted.
It was a mistake because I had let mine drag a family line into bed with it.
I swung my legs over the side of the mattress, keeping the sheet over my lap, because apparently my cock hadn’t received the moral crisis memo and was still half-hard.
Traitor.
“Clothes are wherever we threw them,” I said, rubbing a hand over my face. “Coffee is in the kitchen if you need it. My driver can take everyone home.”
Angela sat up, unbothered, the sheet sliding down to her waist. “Does this mean I don’t get birthday breakfast?”
“You got birthday dessert.”
She grinned. “Several times.”
One of the women laughed. Another cursed softly while hunting for underwear beneath the bed. The room shifted into a slow, naked, post-party scavenger hunt while I sat there wishing my skull would cave in and spare me the rest of the morning.
Lilah didn’t move.
She stayed kneeling on the bed, wrapped in nothing but tangled hair, one hand resting on the sheet, watching me like I had turned into someone she didn’t recognize.
That was fair.
I didn’t recognize myself either.
I owned The Night Lovers Club. I had built an empire on pleasure with rules.
I lived by lines and made other people respect lines.
And somehow, on my fortieth birthday, I had woken up with Lilah McKnight’s mouth on me and no damn clue how to explain that to my brother without losing blood.
The women filtered out one by one, laughing, teasing, kissing cheeks, collecting shoes and phones from the locked tray in my entry because even in my own penthouse I didn’t play with privacy. Angela lingered long enough to kiss my jaw.
“Happy birthday, Trent,” she whispered.
A rough laugh escaped me. “Get out before I develop more consequences.”
She winked and left.
The bedroom door clicked shut and then it was just me and Lilah.
The silence was worse than the headache.
She climbed off the bed, grabbed a sheet, and wrapped it around herself. “You look like you’re about to throw up.”
“I might.”
“Because of me?”
I stood, found my boxers on the floor, and tugged them on with my back turned. I just needed three seconds where her face wasn’t right there reminding me what I’d done.
“No,” I said. “Not because of you.”
“Could’ve fooled me.”
I turned around.
She stood near the chair where her dress hung, sheet clutched tight, mascara smudged beneath her eyes. Beautiful. Wounded. Angry.
Goddamn it.
“Lilah.”
“No.” Her voice cracked like a whip. “Don’t say my name like I snuck in here and violated your precious bachelor sanctuary. You kissed me first and said if I thought I could keep up, I should prove it.” Her eyes flashed. “I proved it.”
Memory filled in the gaps now that panic had finished kicking down doors in my head.
Lilah outside Lucky’s with her friends. Me laughing, too loose from whiskey but not gone. Her teasing me about being old. Me telling her she couldn’t handle my kind of party. Her stepping close, eyes bright, mouth wicked, and saying, “Try me.”
The car.
The elevator.
Her kissing me like she had been thinking about it longer than either of us wanted to admit.
The bedroom. The laughter.
Hands.
Mouths.
Lilah on her knees, then under me, then beside me, then looking at me in the dark like this meant something more dangerous to her than it was allowed to mean.
I dragged both hands through my hair. “I know.”
“Do you?”
“Yes.” I exhaled hard. “I know you chose to be here. I know I chose too. I know nobody forced anything. That is not what I’m saying.”
“Then what are you saying?”
“I’m saying I promised Callum and Eloise I would keep my hands off you.”
Her mouth tightened. “I promised Eloise I’d keep mine off you.”
“Well.” I glanced at the bed. “We’re both shit at promises.”
A tiny, reluctant smile twitched at her mouth.
Then it vanished.
“Do you regret it?” she asked.
That question would’ve been simple to answer months ago.
I looked at the bed. The wreckage. The proof of the life everyone expected from me. Noise. Sex. No attachment. No strings. No feelings that couldn’t be washed from skin by noon.
“No,” I said.
Lilah went still.
I looked back at her. “I regret drinking that much. I regret letting the party end here. I regret waking up and making you feel like you were the problem.” My voice roughened. “I don’t regret wanting you.”
Her eyes shone.
I stepped closer but didn’t touch her. “That’s why this has to stop right here.”
She laughed, bitterly. “Because you wanted me?”
“Because you’re not just someone from a birthday party. You’re Eloise’s sister. You’re part of our circle now, whether any of us like how complicated that makes things.”
“I’m not a child.”
“I know that.”
“Then stop acting like I need a permission slip from my sister to make bad decisions.”
“I’m not worried about your permission.” My jaw tightened. “I’m worried about the fallout. Eloise loves you. Callum loves Eloise. I love my brother. And I’m not turning every family dinner into a goddamn crime scene because I couldn’t keep my dick out of one place it had no business being.”
Her expression softened, then hardened again. “Maybe I wanted it there.”
My cock twitched because the universe hated me.
For a moment, neither of us moved.
“Fine.” She dropped the sheet and grabbed her dress.
I turned around to give her privacy.
Fabric rustled. A zipper slid. The quiet felt heavy enough to bruise.
When I looked back, she was dressed.
“Please don’t tell Eloise details,” she said.
“I won’t.”
“Or Callum.”
I gave her a look.
She sighed. “Fine. He probably already knows.”
“Callum has a sixth sense for my bad choices.”
“Does it beep?”
“Usually it kicks my door open with a toddler.”
That got the smallest laugh from her.
She walked toward me, rose on her toes and kissed my cheek. Soft. “Happy birthday, trouble,” she whispered.
I groaned. “That was cruel.”
“You’ll survive.”
She stepped back, studying me with an expression I didn’t know how to hold. “You’re not as heartless as everyone thinks.”
I opened my mouth, but nothing came out.
Lilah gave me a sad little smile and left.
The door clicked shut.
My penthouse went quiet.
For the first time after a birthday party that should have left me smug, sore, and proud of my stamina, I stood in my bedroom surrounded by proof of excess and felt absolutely fucking empty.
The kind of empty no amount of sex could fill because sex had never been the problem. I loved sex. I loved women. I loved pleasure, skin, mouths, hands, fantasy, performance, surrender, dominance, the moment someone let go because I made the world safe enough for them to do it.
But this?
This was not pleasure. This was noise.
The party after the party after the party. And somehow, at forty years old, the silence afterward had gotten louder than the music.
I showered until my skin turned red. Brushed my teeth twice. Put on sweatpants. Made coffee strong enough to reanimate the dead. Then stood in my kitchen staring out at Lake Michigan like the water had answers.
It didn’t.
Forty years old.
Rich. Free. Desired. Untouched by commitment. Unburdened by wife, children, schedules, school plays, family calendars, bedtime routines, or the slow domestic suffocation I had joked about for years.
I had everything I claimed to want.
So why the hell did I keep picturing Callum walking into family brunch with Everett on his hip while Eloise rolled her eyes like she was annoyed and in love at the same time?
Why did I keep seeing Rory’s hand at Isabelle’s back?
Aaron looking at Sloane like she had turned every wound in him into something worth surviving?
Why did all their chaos suddenly look less like a trap and more like a door I’d been pretending not to notice?
I lifted my coffee and my front door opened.
“I’m changing my locks,” I called.
“You say that every time I enter,” Callum answered from the foyer.
A tiny squeal followed.
Then the slap-slap-slap of little feet against marble.
Everett rounded the corner, his dark hair sticking up.
“Uncle!” he shouted.
My chest did something stupid.
I set my coffee down and scooped him up before he could destroy the decorative bowl on my table. “My favorite sticky menace.”
Everett immediately grabbed my goatee.
I winced. “Why are children always sticky?”
Callum walked in carrying a diaper bag and wearing the expression of a man who had arrived not to visit, but to investigate. “Because they’re honest about being disasters. Adults hide it under expensive sheets and worse decisions.”
I glared at him over Everett’s head. “Subtle.”
“Wasn’t trying to be.”
Everett slapped both hands on my cheeks and babbled something that sounded judgmental.
“See?” Callum said. “Even he knows.”
I kissed Everett’s forehead because he was impossible not to love, even while assaulting my facial hair. He smelled like baby shampoo, crackers, and something sweet.
“What are you doing here?” I asked.
“Checking on my elderly brother after his birthday.”
“I’m forty, not a museum exhibit.”
“You looked rough through the peephole.”
“You looked through my peephole?”
“No. I lied. But you do look rough.”
I shifted Everett on my hip and moved toward the kitchen because Callum’s stare was getting too sharp. “Coffee?”
“No. I brought a child into your post-orgy crime scene. I need both hands and a clear head.”
“It wasn’t an orgy.”
Callum looked around the penthouse.
One black heel still sat near the hallway. My tie remained on the lamp. A lace bra had somehow made it onto the back of the couch.
Callum lifted a brow.
I sighed. “Fine. It was adjacent.”
Everett pointed at the bra. “Hat?”
“No,” Callum and I said at the same time.
Everett giggled.
Callum set the diaper bag down and leaned against the counter. “Eloise saw Lilah get into your car last night.”
I looked down at Everett, who had begun patting my chest like he was checking for structural integrity. “I figured.”
“She’s upset.”
“I figured that too.”
“She’s not just upset with you. Lilah made her own choice. Eloise knows that.” His voice hardened slightly. “But you promised.”
“I know what I promised.”
My temper sparked. Fast. Defensive. Useless.
Everett laid his head on my shoulder and just like that, the spark lost oxygen.
I swallowed and looked away. “I fucked up.”
Callum’s expression changed.
“Did you hurt her?” he asked.
“I would never hurt Lilah.”
The fact that he said it without hesitation almost made this worse.
“I panicked this morning,” I admitted. “Made her feel like I regretted her.”
“Do you?”
“No.” I met his eyes. “I regret the situation. I regret breaking my word. And I regret letting birthday chaos turn into family fallout but I do not regret wanting her.”
Callum nodded slowly.
“She and I agreed it doesn’t happen again so Eloise can keep her kitchen shears away from my dick.”
Callum didn’t smile. “Is that what you want?”
“What I want is irrelevant.”
“That’s new.”
I gave him a flat look.
He crossed his arms. “You’ve been weird lately.”
“I turned forty yesterday.”
“You were weird before that.”
“Maybe your face is weird and I’m reacting appropriately.”
“Deflection.”
“Sibling abuse.”
“Trent.”
I set Everett down near the basket of toys I kept in the corner for visits.
“What’s going on with you?” Callum asked.
“Nothing.”
“That’s a lie.”
“I’m hungover.”
“Still not the answer.”
I stared out the window. The lake glittered beneath morning light.
“I woke up this morning,” I said slowly, because apparently the hangover had damaged the part of my brain responsible for shutting the hell up, “and before I realized who was in my bed, I liked that someone was still there.”
Callum said nothing.
“I liked not waking up alone.” I laughed under my breath. It sounded wrong. “Pathetic, right?”
“No.”
“Spoken like a married man.”
“Spoken like your brother.”
I looked at Everett. He had abandoned the dinosaur and was now trying to place a block into my shoe.
“Sometimes I watch you,” I said.
Callum went very still.
“Not in a creepy way. Don’t flatter yourself.” I rubbed a hand over my jaw. “You and Eloise. Everett. Rory and Isabelle. Aaron and Sloane. All of you used to be a wreck in some unique, exhausting way, and now you have families.”
“We had people before.”
“Not like that.”
Callum softened.
“I tell myself all the time I don’t want it,” I continued. “Marriage. Kids. The whole domestic trap.”
“Are you sure about that?”
I smiled.
“I don’t know anymore.”
Everett toddled back over and lifted his arms.
I picked him up without thinking. He tucked his sticky little hand against my neck and rested his head on my shoulder again.
Something in my chest pulled tight.
Callum watched my face and, because he’s an annoying bastard who knew me too well, saw too much.
“You want it,” he said.
I looked at him sharply. “Don’t you dare go there.”
“You do.”
“I said don’t.”
He lifted both hands. “Fine.”
But his face said not fine.
His face said he had just learned something he would absolutely tell Eloise later while pretending he was not gossiping.
“I’m not telling anyone,” he said.
“You better not.”
“Eloise will know by lunch.”
“Callum.”
“She reads me like a children’s book.”
“Develop mystery.”
“I married a smart woman.”
“Clearly a mistake.”
He smiled. “You’re allowed to want a family, Trent.”
I shifted Everett on my hip and looked away. “Everyone would laugh.”
“No, they wouldn’t.”
“Yes, they would.”
“Okay, Aaron would.”
I huffed out a laugh.
“And Rory would smile like an idiot. Eloise would cry. Isabelle would start planning something. Sloane would say something gentle that makes us all uncomfortable. I would mock you once and then help you figure out what the hell you’re doing.”
“Terrible sales pitch.”
“Honest one.”
Everett patted my cheek again. “Unca.”
My chest tightened.
“Yeah, little man,” I whispered. “I’m here.”
Callum’s voice softened. “Maybe that’s the point.”
I looked at him.
He nodded toward Everett. “You’ve always been here. For me. For Aaron. For everyone. Maybe wanting someone to be there for you doesn’t make you weak.”
I swallowed.
Outside the window, Chicago moved like any other morning. People going places. Starting days. Living lives.
Inside my penthouse, I stood half-hungover, emotionally ambushed, holding my nephew while the wreckage of my fortieth birthday still sat in corners of the room.
Something had shifted.
I felt it now.
A crack in the old story I had told about myself.
The eternal bachelor.
The sex-club king.
The man who fixed everyone else’s love life and went home alone because alone was simple. Except simple had started to feel a hell of a lot like empty.
Callum picked up the diaper bag. “I should get him back before Eloise assumes I let you teach him inappropriate words.”
“I would never.”
“You absolutely would.”
Everett waved the dinosaur at me. “Bye!”
I kissed his forehead. “Bye, sticky menace.”
Callum took him, then stopped near the door. “Trent?”
“What?”
His gaze held mine. “Don’t pretend this morning didn’t mean anything if it did.”
I looked around the penthouse. The sheets. The clothes. The evidence.
Then the toy basket in the corner.
The ache in my chest.
The want I had no idea what to do with.
“It meant something,” I said.
Callum nodded, then he left.
The door closed behind him.
I stood alone in the quiet, surrounded by money, sex, regret, and a toy dinosaur Everett had left lying upside down on my marble floor.
I picked it up.
For some reason, that ridiculous little dinosaur made my throat tight.
Forty years old. Billionaire. Club owner. Eternal bachelor. And for the first time in my life, I looked at the silence in my penthouse and wondered what it would sound like full.
A wife laughing in the kitchen. A kid yelling down the hall. Someone’s shoes by the door because they planned to stay.
The thought was terrifying, and impossible.
The thought would get me mocked into an early grave by every person who loved me.
I still wanted it.
And that was the real disaster waiting for me after my fortieth birthday.
Not Lilah, the women, or the hangover.
Not even the blowjob that nearly gave me a heart attack.
The disaster was that I had finally admitted the truth to myself.
I didn’t want another night.
I wanted someone who stayed.
