Gay Femboy and His CEO Daddy

The city lights glittered like scattered diamonds beyond the floor-to-ceiling windows of the corner office, forty-seven floors above the quiet streets. Most of the building had emptied hours ago. Only the low hum of the HVAC and the occasional distant elevator chime broke the silence. Inside, the air still carried the faint scent of expensive cologne and the warmer, sweeter notes of the body wash Talia favored.

Talia sat perched on the edge of the leather visitor chair, tablet balanced on one slim thigh, stylus tapping lightly against his lower lip. At twenty-two he looked almost delicate under the soft desk lamp—narrow shoulders, a willowy waist cinched by the tailored waistcoat he wore over a silk blouse open one button too far, slender legs crossed at the ankle in slim-cut trousers that hugged the soft curve of his ass. His dark hair fell in a soft, artfully messy fringe across one eye; a touch of liner made the long lashes look even longer. He was every inch the personal assistant the board saw by day, and every secret inch the femboy who privately ached for the man across the desk.

Hugo lounged back in his chair like he owned the night as thoroughly as he owned the company. Forty-eight, broad-shouldered, silver threading the dark hair at his temples, the sleeves of his white shirt rolled to thick forearms. The top buttons were undone, revealing the strong column of his throat and a dusting of chest hair. Power sat on him the way the tailored trousers sat on his powerful thighs—effortless, absolute. For weeks the air between them had been electric. Lingering touches when Hugo handed over a file, fingers brushing Talia’s wrist a second too long. The way Hugo’s gaze would drop to Talia’s mouth whenever the younger man spoke. The low, rough chuckle whenever Talia called him “sir” with just a little too much breath behind it. Both of them knew. Both of them wanted. Neither had crossed the final line.

Tonight’s strategy session had run long—market projections, acquisition targets, the usual corporate chess. Talia had felt Hugo’s eyes on him the entire time, heavy and heated. Every time their knees brushed under the table, electricity sparked up Talia’s spine. He kept his voice professional, but inside he was already calling the man Daddy in the private theater of his mind, the word a secret prayer.

Hugo closed the final folder with a decisive snap. “That’s enough for tonight.” His voice was deep, gravel-rough from hours of talking. He stood, rounded the massive desk, and walked to the heavy oak door. The lock clicked with a sound that seemed to echo through Talia’s entire body. Hugo turned, leaning back against the wood, arms folded across his chest. The city light caught the silver in his hair and the hunger already darkening his eyes.

“I’ve been watching you for weeks,” Hugo said, no preamble, no corporate polish left. “The way you move in those tight little pants. The way you look at me when you think I’m not paying attention. You want this as badly as I do.” He pushed off the door and crossed the room in three long strides until he stood over Talia, close enough that the younger man had to tilt his head back. “I want my pretty little assistant on his knees. I want to hear you call me what you’ve been dying to call me. Say it.”

Talia’s breath left him in a shaky rush. Heat flooded his cheeks and raced straight down to his cock, already half-hard against the soft fabric of his trousers. He set the tablet aside with trembling fingers, heart hammering so hard he could feel it in his throat. This was the moment the flirtation had been building toward—the locked door, the open admission, the permission finally spoken aloud. He slid off the chair and sank gracefully to the thick carpet, knees parting, spine straight, hands resting lightly on his own thighs the way he’d imagined a hundred times. Looking up through his lashes, lips parting, he gave Hugo exactly what the man demanded.

“Daddy,” Talia whispered, the word velvet-soft and dripping with need. Then louder, clearer, eager: “Yes, Daddy. I’ve wanted this. Wanted you.”

Hugo’s low growl of approval rolled through the office like thunder. He reached down and cupped Talia’s chin, thumb stroking over the plush lower lip. “Look at you. My perfect little femboy. So pretty on your knees already. Those soft lips made for sucking cock. That tight little body made for taking whatever Daddy gives it.” His free hand went to his belt, the leather whispering as he unbuckled it. “Weeks of you teasing me with those lingering looks and accidental brushes. I’ve jerked off thinking about bending you over this desk. About how wet and open you’d get for me. About the sounds you’d make when I finally fuck that sweet hole.”

Talia shivered hard, a full-body ripple of pure want. His cock throbbed, tenting the front of his trousers, a damp spot already darkening the fabric. He leaned into the touch on his face, nuzzling Hugo’s palm like a cat starved for affection. “Please, Daddy. I’ve been so good. I’ve waited. I’ve touched myself at night thinking about your hands, your voice, your thick cock stretching me. I want it so bad it hurts.” His own hands lifted, hovering near Hugo’s hips, waiting for permission, already desperate.

Hugo freed himself with deliberate slowness, shoving trousers and briefs down just enough. His cock sprang out heavy and thick, flushed dark, the head already glistening. It looked even bigger this close—veined, powerful, the kind of cock that would leave a man feeling it for days. He stroked himself once, twice, right in front of Talia’s face, smearing the bead of precum across the tip with his thumb. “Open that pretty mouth. Show Daddy how hungry you are. No hands yet—just that soft tongue and those fuckable lips.”

Talia’s mouth watered. He leaned in without hesitation, lips parting, tongue slipping out to taste the salty-sweet drop. The first contact made him moan softly around the head, eyes fluttering shut in bliss. He took more, slow and wet, sucking gently, swirling his tongue under the ridge the way he’d fantasized. The taste of Hugo flooded him—clean skin, musk, power. His own neglected cock twitched hard in its confines. Every filthy word Hugo spilled only wound him tighter.

“That’s it, baby boy. Such a good little cockslut for your CEO Daddy. Look how eager you are. Weeks of tension and now you’re on your knees sucking like you were born for it.” Hugo’s hand slid into Talia’s soft hair, not forcing, just holding, guiding with firm pressure. “Take more. I want to feel that throat work. I want to hear you choke a little on it because you’re so fucking desperate.”

Talia obeyed, sinking deeper, eyes watering slightly as the thick head nudged the back of his throat. He breathed through his nose, relaxed, took another inch, throat fluttering around the intrusion. Spit slicked his chin. The stretch burned in the best way. Interior monologue spun filthy and grateful—Yes, Daddy, use my mouth, claim me, finally—while his hips gave tiny aborted thrusts against nothing. He pulled back with a wet gasp only long enough to pant, “More, please—want all of you, want you to ruin me—” before diving back down, lips stretched wide, cheeks hollowed.

Hugo’s praise turned rougher, voice dropping into that commanding register that made Talia’s stomach flip. “Fuck, look at you. Pretty little assistant all wrecked already, makeup starting to smear, lips shiny with spit. You’re going to look even better bent over my desk with that tight ass up and your hole fluttering for my cock. I’m going to open you on my fingers first, get you dripping and begging, then fuck you so deep you’ll feel me in your throat from the other end. You’re mine tonight. Say it.”

Talia pulled off with a filthy string of spit connecting his swollen lips to the glistening cock. His voice cracked with pure submission. “I’m yours, Daddy. All yours. Please—use me, fuck me, make me take it. I’ve needed this. Needed you to stop holding back.” Tears of overwhelmed want pricked his eyes, but his expression was pure eager surrender. He stayed on his knees, mouth open, tongue out, waiting like the perfect toy he’d always wanted to be for this man.

Hugo stroked his spit-slick cock slowly, eyes raking over the slender young man at his feet—the heaving chest under silk, the obvious erection straining trousers, the way Talia’s thighs trembled with restraint. The air between them crackled, thicker than ever. Hugo’s free hand gripped Talia’s hair again, tilting that pretty face up. “We’re just getting started, baby. By the time I’m done with you, you’ll be dripping and marked and so thoroughly fucked you won’t walk straight tomorrow. But first…” He stepped back half a pace, cock bobbing heavy and ready. “Crawl to the desk. Get that perfect ass up high. Show Daddy exactly what you’ve been offering with every little tease. And keep those hands behind your back until I say otherwise.”

Talia’s pulse roared in his ears. He dropped forward onto his hands, then deliberately laced them at the small of his back as ordered, and began to move on his knees across the carpet toward the massive desk. Every shift of muscle, every soft sound of fabric, every shaky breath was a promise of the hard fucking still to come. The night was far from over.

Hugo watched Talia crawl the last few feet, the younger man’s slender body moving with deliberate grace, hands still laced tight at the small of his back, silk blouse riding up to flash a strip of smooth pale skin. The tailored trousers pulled tight across that soft, perfect ass with every shift of his knees. Hugo’s cock throbbed heavy and spit-slick as he stepped in behind him, one large hand settling between Talia’s shoulder blades and pressing him forward until his chest met the cool mahogany of the desk.

“Ass up,” Hugo ordered, voice thick. “Chest down. Keep those hands where I put them.”

Talia obeyed instantly, arching his back, presenting himself, cheek turning to rest against the polished wood. His breath fogged the surface. Hugo yanked the slim trousers and the soft briefs beneath them down in one rough motion, baring the smooth cheeks, the tight pink hole already clenching in anticipation. He spat into his palm, slicked two thick fingers, and pressed them in without preamble. Talia moaned loud and shameless, pushing back onto the intrusion, taking them deep.

“Fuck, Daddy—yes—”

Hugo worked him open hard and fast, scissoring, curling, stretching that greedy little hole until it fluttered wet and ready. Then he pulled free, lined up the thick head of his cock, and slammed home in one long, possessive stroke that buried him to the hilt. Talia’s cry bounced off the glass walls. The desk creaked. Hugo set a ruthless pace immediately—deep, grinding thrusts that forced the younger man up onto his toes, every stroke bottoming out, balls slapping softly against Talia’s smooth sac.

“That’s it, take it. Take every fucking inch of Daddy’s cock. You’ve been begging for this with those pretty eyes for weeks.” Hugo’s hands clamped hard on Talia’s narrow hips, yanking him back to meet every thrust. “Listen to that wet little hole swallowing me. So tight. So fucking perfect for me.”

Talia pushed back greedily, moaning with every impact, the silk of his blouse rasping against the desk, fringe sticking to his damp forehead. Interior heat coiled tight and filthy—Yes, ruin me, claim me, make me yours—while his own small cock bobbed untouched, leaking steadily onto the wood beneath him. “Harder, Daddy—please—want to feel you tomorrow—want everyone to know you fucked your little assistant stupid—”

Hugo gave it to him harder, pounding deep and possessive, the thick shaft dragging over Talia’s prostate on every stroke until the younger man’s thighs shook. Spit and precum slicked the way, filthy wet sounds filling the quiet office. Hugo leaned over him, chest to back, mouth at his ear. “My pretty femboy. My cockslut. You’re going to walk into that board meeting tomorrow still feeling me dripping out of you. Say it.”

“I’m your cockslut, Daddy—your pretty little femboy—only yours—” Talia’s voice cracked on a particularly deep thrust that shoved the air from his lungs. He rocked back harder, chasing it, hole clenching desperately around the thick invasion.

Hugo growled approval and fucked him through several more punishing strokes before pulling out abruptly. Talia whimpered at the sudden emptiness. Strong hands flipped him easily onto his back across the wide desk, trousers tangled at one ankle, legs shoved wide and up. Hugo hooked them over his own broad shoulders, lined up again, and drove back in to the root in one brutal thrust that made Talia’s back arch off the wood.

Missionary. Face to face. Hugo’s powerful body covering him, silver-threaded hair falling forward as he planted his hands beside Talia’s head and started pounding in earnest—deep, relentless strokes that shook the desk and forced broken moans from Talia’s throat with every slap of skin. One of Hugo’s hands dropped between them, wrapping around Talia’s small, leaking cock, stroking in time with the hard thrusts.

“Look at me while I breed this hole,” Hugo demanded, eyes dark and locked on Talia’s. “Tell Daddy how good it feels having your CEO stretch you open like this.”

Talia’s hands finally came free, clutching at Hugo’s forearms, nails digging in. His legs trembled high and wide, hole fluttering around the thick cock slamming into him. “So good, Daddy—feels so fucking big—filling me up—please don’t stop—stroke my little cock, make me come on you—” His voice went high and needy, filthy praise tumbling out between gasps. “Love being your good boy. Love taking Daddy’s cock so deep. Use me. Fuck me until I can’t think.”

Hugo’s fist worked faster over the slim shaft, thumb smearing precum across the sensitive head while his hips never slowed, pistoning hard and deep. The dual sensation wrecked Talia—prostate battered relentlessly, cock stroked with rough affection. Heat built white-hot and unstoppable. Dirty talk spilled between them in a constant stream, both men feeding it.

“Come for me first,” Hugo ordered, voice gravel. “Milk my cock when you do. Show Daddy how much this pretty hole loves getting wrecked.”

“Yes—Daddy—I’m gonna—fuck, I’m coming—” Talia’s body locked up hard. His small cock pulsed in Hugo’s fist, stripes of cum striping his own soft belly and the silk of his open blouse. His hole clenched rhythmic and desperate around Hugo’s thrusting length, milking him, pulling him deeper.

The tight fluttering drag shoved Hugo over the edge immediately. He slammed in to the hilt with a guttural groan, cock swelling and kicking as he flooded Talia’s ass in thick, hot pulses, grinding deep to pump every drop inside. “Take it—take Daddy’s cum—fucking fill you up—” He kept rocking through it, slow and deep, making sure every spurt painted the younger man from the inside.

They stayed locked like that for long heartbeats, chests heaving, Hugo still buried full and thick inside the wet, marked heat of Talia’s body. Cum already began to leak around the base of his cock with every tiny shift. Talia’s legs stayed draped over Hugo’s shoulders, trembling, eyes glassy with aftershock and lingering hunger. Outside the glass the city glittered on, indifferent and endless. Hugo’s thumb stroked absently over the corner of Talia’s swollen mouth, but neither man moved to pull free. The night still held hours, and the locked door guaranteed no interruptions. Talia’s fingers curled tighter around Hugo’s wrist, already testing the weight of what might come next, body still open and dripping and quietly begging for more.

Hugo stayed buried deep inside the trembling heat of Talia’s body for another long stretch of heartbeats, chest rising and falling against the younger man’s silk-damp torso, the thick pulse of his cock still twitching out the last lazy spurts of cum. The desk lamp threw soft gold across Talia’s flushed face, the smudged liner, the open mouth that still shaped silent aftershocks. Outside the glass the city kept glittering, distant and irrelevant. Hugo’s thumb traced the corner of Talia’s swollen lower lip one more time, then he finally eased his hips back.

He pulled out slowly, inch by thick inch, watching the way Talia’s used hole clung and fluttered, reluctant to let him go. The heavy shaft slipped free with a wet sound that made both of them groan. Immediately a thick rivulet of creamy white cum welled up and spilled from the stretched pink rim, sliding down over Talia’s smooth taint and dripping in slow, filthy strings onto the polished mahogany between his spread legs. Hugo’s dark eyes stayed locked on the sight, greedy, possessive. He dragged two fingers through the leaking mess, scooped a glistening strand, and pushed it gently back inside the fluttering entrance, watching Talia’s belly twitch.

“Look at that,” Hugo murmured, voice still rough from climax. “My pretty little femboy dripping Daddy’s load all over the CEO desk. Perfect. Fucking perfect.”

Talia’s legs were still hooked loosely over Hugo’s shoulders, trembling hard now that the thick stretch was gone. His small cock lay soft and spent against his own sticky belly, the silk blouse ruined with cooling stripes of his own release. He made a soft, broken sound when Hugo’s fingers teased the sensitive rim, hole clenching instinctively around the digits as if trying to keep every drop. Interior heat still glowed low and satisfied; the deep, thoroughly fucked ache already blooming into something he wanted again tomorrow, and the day after, and forever.

Hugo withdrew his fingers at last, wiped them absently across Talia’s inner thigh, then scooped the slender young man up as if he weighed nothing. Strong arms gathered the trembling femboy carefully off the desk, trousers still tangled uselessly around one ankle, and settled him sideways across Hugo’s powerful lap in the big leather chair behind the desk. Talia curled instinctively into the solid warmth of that chest, bare ass nestled against Hugo’s still-half-hard cock, cheek pressed to the open collar of the white shirt where silver-threaded chest hair tickled his nose. The scent of sex and expensive cologne wrapped around him like a second skin.

Hugo’s mouth found his immediately—deep, claiming kisses that tasted of salt and shared breath. One large hand cradled the back of Talia’s head, fingers sliding through the damp fringe; the other spanned the narrow waist, thumb stroking idle circles over the soft skin just above the curve of that used ass. He kissed like he owned the air in Talia’s lungs, slow and thorough, tongue sliding deep, nipping the plush lower lip, then soothing it again. Talia melted into every press, hands fisting weakly in the front of Hugo’s shirt, still shivering with aftershocks while the leftover cum continued its lazy trickle down his thighs onto Hugo’s trousers.

“You took me so well,” Hugo breathed against his mouth between kisses. “My perfect twenty-two-year-old cockslut. Walking around this office all day looking soft and professional, and now look at you—wrecked, marked, full of me.” Another possessive kiss, deeper. “This is only the beginning, baby boy. Many more after-hours sessions. Locked door. Desk. Floor. That big couch over there. Whenever I decide I need my pretty femboy assistant bent open and dripping again. You’re mine now. Say it.”

“Yours, Daddy,” Talia whispered back, voice wrecked and blissful. He nuzzled closer, kissing the strong line of Hugo’s throat, tasting sweat and skin. “All yours. I’ll stay late every night you want. I’ll wear the tightest pants. I’ll drop to my knees the second the last elevator leaves. Fill me again and again. I want to feel you every time I sit at my little desk outside.” His hole gave a soft, reflexive clench at the memory of that thick cock, a fresh bead of cum slipping free to wet Hugo’s thigh. Interior thought spun warm and greedy—Yes, more nights like this, more of that voice calling me baby boy, more of that stretch until I can’t walk straight—while his body stayed pliant and trusting in the older man’s lap.

They stayed like that for long, quiet minutes, simply breathing together. Hugo’s hand drifted lower, cupping one soft cheek, fingers dipping lightly into the slick mess still leaking from Talia’s hole, not to fuck, just to feel the evidence of what they’d done. Talia sighed into the touch, legs shifting slightly so Hugo could explore freely. The HVAC hummed. Distant traffic murmured forty-seven floors below. Satisfied silence stretched between them, broken only by the soft wet sound of another slow kiss, the quiet catch of breath when Hugo’s fingertips circled the tender rim again.

Hugo’s free hand stroked up and down Talia’s spine under the ruined silk blouse, mapping the slender muscles, the way the younger man arched into every caress like a cat. “Tomorrow morning you’ll come in early,” he said, voice low against Talia’s temple. “Bring coffee the way I like it. Wear that soft gray waistcoat that makes your ass look so fucking biteable. And when the door closes, you’ll bend over this desk again so I can check how well you’re still holding my cum. Maybe I’ll add another load before the board meeting. Keep you plugged full all day so every time you stand up you feel me.”

Talia’s cock gave a weak, interested twitch against his own belly at the promise. He lifted his head enough to meet Hugo’s eyes, dark lashes still clumped with liner and exhaustion. “Yes, Daddy. I’ll be wet for you. I’ll leave the briefs at home if you want. Anything.” He kissed the corner of Hugo’s mouth, soft and adoring. “I already can’t wait. My hole feels empty without you. Stretch me again soon. Please.”

Hugo growled approval and claimed another deep, lingering kiss, hand squeezing the soft ass possessively. They simply held each other after that, chests rising and falling in matching rhythm, the sticky mess cooling between them, the locked office wrapping them in private, post-fuck quiet. Talia’s fingers traced idle patterns over Hugo’s forearm, memorizing the strength there. Hugo’s chin rested lightly on top of the younger man’s head, breathing in the sweet scent of Talia’s body wash mixed with sex.

Eventually Talia’s breathing evened into something close to drowsy contentment, but his mind was already turning forward. He shifted just enough to feel the thick line of Hugo’s cock still semi-hard under his bare ass, and a slow, private smile curved his kiss-swollen lips. He was already scheming the next time—Friday night after the quarterly numbers locked. He’d stay late under the excuse of finalizing the acquisition deck, wear the pale pink blouse that clung when he sweated, leave the door cracked just enough that Hugo would hear the soft click of heels or the deliberate rustle of fabric when Talia deliberately bent to pick up a dropped stylus. He’d text a single photo of his bare hole already glistening with lube from the private bathroom, captioned only with “waiting for Daddy.” Then he’d be on his knees under the desk before Hugo even finished locking the door, mouth open, ready to suck the CEO hard again so that thick cock could breed him over the guest chairs this time, or maybe bent double against the cold glass of the windows with the whole glittering city as witness while Hugo fucked another load deep and told him he was the best investment the company had ever made. Yes. Friday. He would make it perfect.