Entry 2: The Lonely CEO
Tonight, I met power wrapped in loneliness.
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He called himself David — early fifties, sharp suit, sharper jawline, the kind of man who built empires with a pen stroke and a cold stare. Still handsome, still broad-shouldered, the kind of masculinity that carries itself even when the body starts to soften at the edges. His hair was steel-gray at the temples, which only made him look more distinguished. His eyes, though — deep, dark, restless — betrayed what the rest of him tried so hard to hide.
David is a CEO. Married, of course. Children grown. A public life that demands control. But tonight, behind the locked door of his penthouse, control was what he wanted to surrender. Not loudly, not theatrically — but quietly, desperately.
He poured us whiskey, expensive and aged, though his hands trembled as he handed me the glass. I could tell it wasn’t the drink that made them shake. It was me. Or rather, what I represented: the one thing he couldn’t have in the light of day.
“I don’t usually… do this,” he said, which I’ve already learned is a phrase almost every client utters. But the way he said it, soft, almost ashamed, told me he wasn’t trying to impress me. He was confessing.
So I slipped into Christian. Confident. Smooth. I let my hand brush his, deliberate, grounding. “Then tonight doesn’t have to be usual,” I told him.
His laugh was small, pained, but genuine. And when he looked at me again, it was like I’d given him permission to breathe.
What he wanted wasn’t rough or wild. It wasn’t the performance of sex. What he wanted was touch — the weight of a body against his, the warmth of lips on his neck, the reassurance that he was still desired as a man, not just respected as a figurehead. He melted slowly, like ice breaking under heat, until the mask of the CEO slipped and left only David.
In his arms, I felt the ache of years of denial, the hunger of someone who had given everything to the world and kept nothing for himself. He clung to me as if I were a secret he couldn’t bear to lose, even though he’d already paid for me to be there.
When it was over, he whispered, almost to himself:
“I wish I could have met you twenty years ago.”
I didn’t answer. Christian never does. But Nick felt the weight of it, heavy in his chest.
The truth? I think David wasn’t paying for sex. He was paying for a moment of honesty. A night where he could be the man he’d always wanted to be, if only behind closed doors.
And I gave him that.
David greeted me in his penthouse like a man used to commanding every room he entered — but I saw it in the small details. The way his voice caught for half a second. The way his eyes lingered too long on me before snapping back, as if afraid I’d noticed.
He was handsome, no question. Early fifties, tall, shoulders still broad from the gym, with just enough softness at the waist to betray the years. His hair was dark but silver at the temples, cut immaculately. The kind of man you’d see on the cover of a business magazine, shaking hands with politicians. Masculine, powerful, but with a loneliness in his eyes that no suit could disguise.
We sat in leather chairs across from each other. He poured two glasses of whiskey, a vintage I’ll probably never taste again unless another client offers it. His hand shook as he handed mine over.
“You don’t have to be nervous,” I told him, letting Christian’s voice pour smooth and steady.
“I’m not,” he said quickly, then smiled, almost embarrassed. “Or maybe I am.”
There it was. The crack in the armor.
I leaned back in my chair, let my legs part slightly, an invitation without words. “Nervous is fine. I just don’t want you to feel like you have to perform. Tonight is about you.”
His eyes flickered down my body, then back up. He swallowed hard. “It’s been… years. Since I’ve—” He stopped himself, shook his head, and downed half his whiskey.
I set mine aside and leaned forward, closing the space between us. My hand rested lightly on his knee. His thigh tensed under my touch, but he didn’t pull away.
“You don’t have to explain,” I whispered. “I understand.”
And in that moment, I could feel him surrender, just a little.
The moment my hand touched his knee, David exhaled — not a sigh, not a groan, but something caught between relief and fear. It was the sound of a man stepping over a line he had drawn for himself decades ago.
“Christian,” he murmured, my name awkward in his mouth, like he wasn’t sure if he had the right to say it.
“Yes?” I kept my voice low, steady, patient.
His eyes searched mine, as though trying to find judgment, but there was none. Only invitation. When I leaned closer, the faint scent of his cologne — cedar and leather — mixed with the warmth of whiskey on his breath.
I touched his jaw, the roughness of his stubble under my fingertips. He closed his eyes at the contact, like a starving man tasting food again. His body went still, waiting, bracing.
I kissed him first. Slow. Gentle. Testing.
At first, he didn’t move. His lips were frozen, his hands gripping the arms of his chair as if he might fall. But then, slowly, he kissed me back — hesitant, careful, like a man relearning a language he had once been fluent in.
I deepened it, my tongue brushing against his lower lip. That broke him. He groaned softly and leaned forward, his hand finally rising, trembling, to touch the back of my neck. The kiss became hungrier, needier, the years of repression melting into heat.
When I pulled back, his eyes were wet, though he blinked the shine away quickly. “God, I’ve wanted this,” he confessed, voice raw.
I smiled, letting Christian’s confidence cloak the tenderness I felt as Nick. “Then take it.”
He did. His mouth claimed mine with a sudden force, teeth grazing, tongue pressing, all the restraint gone. I slid from my chair onto his lap, straddling him. His hands gripped my waist hard, fingers digging in like he was afraid I’d vanish. I could feel him stiff beneath me, pressed against the fabric of his tailored trousers.
I rolled my hips, deliberately slow, and he broke the kiss to groan into my shoulder. “Fuck,” he whispered, almost angry at himself.
“It’s okay,” I murmured, lips against his ear. “You don’t have to hide here.”
His reply was a desperate pull of my shirt, his fingers clumsy as they worked at the buttons, hungry to see what lay beneath.
David’s hands shook as he fumbled with my shirt buttons, and for a moment I thought he might give up altogether. But I caught his wrists, steadying them, guiding his fingers down until the fabric parted. His eyes followed the reveal — the line of my chest, the dark hair scattered across it, the toned stomach beneath.
“Beautiful,” he whispered, the word escaping him like a prayer.
I kissed him again, harder this time, and slid his suit jacket off his shoulders. It dropped to the floor with a sound far too casual for a garment that probably cost more than my rent. He didn’t care. He only cared about touch.
I pressed my lips to his jaw, then down his neck, tasting salt and cologne. His breath hitched when I licked lightly at the hollow of his throat. His hands clutched at me like I was something he had no practice holding.
When I tugged at his tie, he stilled. For a moment, the CEO returned — the man who second-guessed, who feared being seen.
“Hey,” I murmured against his ear, soft but certain. “You don’t have to be him here. Just be David.”
Something in him broke. His chest rose and fell sharply, then he nodded. I loosened the tie, slid it free, and tossed it aside. My fingers made quick work of his shirt buttons, and soon he was bare-chested before me — strong, solid, with a light dusting of dark hair across his pecs and stomach.
I ran my hands over him, slow and deliberate. He shuddered.
“You’ve been starving,” I whispered.
“Yes,” he admitted, almost too quiet to hear.
I kissed my way down his chest, tasting the salt of his skin, the roughness of hair against my tongue. When I sucked lightly at one nipple, his whole body jerked. The sound that left his throat was raw, surprised — and it lit a fire in me.
I trailed lower, kissing down the center of his stomach until I reached his belt. My fingers paused there, teasing, tracing the leather strap. His cock strained against his trousers, the fabric stretched tight.
I looked up at him. His eyes were dark, pleading.
“Do you want me to stop?” I asked.
“Don’t you fucking dare,” he growled, and in that moment, the CEO returned — but this time not as armor. As need.
I smiled and undid his belt.
The buckle came loose, the zipper sliding down with a sound that felt louder than it should in the silence of that penthouse. I slipped my hand inside, brushing against the heat straining beneath his briefs. David’s whole body tensed, his breath catching sharp in his throat.
“Fuck,” he whispered again, more desperate this time.
I freed him from the confines of his trousers, pushing them down enough for his cock to spring free. Thick, hard, flushed — the body of a man who hadn’t been touched like this in far too long. He tried to cover his face with his hand, as if ashamed of wanting this so badly, but I caught his wrist and guided it back to my hip.
“Look at me,” I told him.
He did. His eyes locked on mine, wide and vulnerable, as I lowered my head.
The first brush of my tongue against his tip made him gasp, his hand tightening at my waist. I took him slowly into my mouth, savoring the weight of him, the taste of pre-come already slick on my tongue. His hips jerked up instinctively, but I pressed my hand to his stomach, steadying him, setting the pace.
“Christ—” His voice cracked, deep and rough, like he wasn’t used to letting anyone hear him this raw.
I bobbed my head, hollowing my cheeks, my tongue tracing every vein. The more I gave, the more his carefully built walls crumbled. His free hand found my hair, gripping tight but not forcing — just anchoring himself, like he couldn’t believe this was real.
When I pulled off him, saliva glistening on my lips, he looked like a man undone. His chest heaved, his eyes wet again, though he blinked it away.
“Please,” he said, and the word carried more than lust. It was a plea for release, for permission, for freedom.
I stood, stripped the rest of my clothes away, and guided him back into the chair. I straddled him again, our cocks pressed together, slick and hard between us. Grinding slow, teasing him with friction, I leaned in close, lips brushing his ear.
“You want me, David?”
“Yes.” It was a broken sound, but true.
I reached down, spreading lube over him, over myself, slick and ready. His hands shook on my hips as I positioned us. His breath caught — half anticipation, half fear.
And I sank down onto him.
The moment he slid inside me, David froze — like he couldn’t quite believe it was happening. His eyes squeezed shut, his jaw clenched, every muscle in his body taut as a bowstring.
“Breathe,” I whispered, sinking lower, inch by inch, until he was fully buried in me. I let my hands rest on his chest, feeling the frantic beat of his heart beneath the light dusting of hair. “Look at me.”
He opened his eyes, and what I saw there was more than lust. It was hunger, yes — but also grief, longing, decades of silence breaking open all at once.
“Jesus Christ,” he muttered, voice trembling, and thrust his hips upward.
I moaned, rolling my hips, taking him deeper. His hands clutched at me, fingers digging into my waist as if he was terrified I’d vanish if he let go. He moved slow at first, careful, then faster, needier, years of restraint snapping with each thrust.
I rode him, grinding down hard, our bodies slick with sweat. His mouth found my throat, teeth scraping, sucking, leaving marks he probably didn’t even realize he was making. The CEO was gone. All that was left was David — desperate, raw, human.
Every thrust pulled another groan, another gasp, another broken sound from his chest. I kissed him through it, swallowing his moans, tasting the salt of his sweat.
“I can’t—” he stammered, voice shaking.
“Yes, you can,” I told him, grinding harder, clenching around him, my own cock slick and throbbing between us. “Let go.”
That did it. He thrust up hard, once, twice — and then he shattered. His whole body convulsed beneath me, a strangled cry tearing from his throat as he spilled inside me, clutching me like I was salvation.
The sound of him undone, the sheer weight of his release, pushed me over the edge. I stroked myself hard, fast, and came across his stomach, thick ropes marking his chest as I gasped into his mouth.
For a moment, neither of us moved. His arms wrapped around me tight, holding me against him, his face buried in my shoulder. His body shook, not from pleasure anymore, but from something deeper. Relief. Grief. Both.
When his breathing finally slowed, he whispered, so quiet I almost missed it:
“I’ve never felt like this with anyone.”
I didn’t answer. Christian never does. But Nick — Nick felt that ache sink deep.
