sugardaddy!hollis X sugarbaby!reader
tags: hollis is freaked out fr, p in v, teasing, public touching, oral (both receiving,) cumshot, tons of orgasms, tons of sex in general, sugarbaby dynamic, dirty talk, toes in mouth, light smacking, idk there’s prob more
You had just turned nineteen and the world was already trying to swallow you whole. The first semester of college was a never ending revolving door of deadlines and caffeine, your shitty serving shifts were pure chaos, and the stack of bills on your kitchen counter grew taller every week. Rent was due in six days. You weren’t sure you’d still have a roof over your head by then, let alone tuition for spring.
So that random Friday night you sat on your tiny balcony, blunt pinched between your fingers, city lights flickering below like distant stars. The sweet smoke curled around you, warm and hazy. You thought about it. Stripping? Maybe. You had the body. A tight waist, full hips, tits that looked even better in low cut tops. But the idea that kept circling back was something your friend had mentioned weeks ago: being a sugar baby. Easy money. Older men. Disgusting, but… easy.
You let the thought marinate overnight. By morning you’d whispered “fuck it” to your empty apartment and made the account on Seeking Arrangements. Your photos were pure sin… seductive mirror shots in lace lingerie, breast-centered selfies that screamed touch me, lips parted just enough to promise everything. The responses flooded in almost immediately.
Most of them were exactly what you’d expected: wrinkled, silver-haired executives and lawyers with beer bellies and entitlement. Your stomach turned at the thought of their hands on you. You slammed the laptop shut and went to class, then work, letting the exhaustion bury the idea.
That night, back on the balcony with another blunt, your phone buzzed again.
Hollis would like to connect.
You tapped the notification out of boredom more than hope. Then your eyes widened.
He was young. Early twenties at most. Long, silky blonde hair that framed a sharp, almost angelic face. Smudged black eyeliner. Full lips. The kind of effortless beauty that made your thighs press together on instinct. His profile pictures showed him shirtless in designer pieces, taught V-line peeking out, eyes half-lidded like he’d just rolled out of someone’s bed.
What the fuck is someone like him doing on here?
You messaged first, fingers trembling slightly.
What’s a guy like you doing looking for a sugar baby? You could have any girl you want.
He replied in under a minute.
Because I have stupid money and I like pretty girls who know how to behave. Simple.
Very, baby. Prettiest little thing I’ve seen in months. Those lips… fuck. I already know how they’d look wrapped around me.
Heat flashed through you. He didn’t even pretend to be subtle. You kinda liked that.
For the next week the two of you texted nonstop. He sent you five hundred dollars every other day like it was nothing. “For your nails, baby,” or “Buy something that makes your ass look edible.” You never asked where the money came from. You didn’t care. He was funny, filthy, and strangely attentive. He remembered how you mentioned you hated mushrooms and loved the way your voice sounded on the phone when you were sleepy.
Then he suggested dinner.
Somni. Saturday. 8pm. Wear something I can slip my hand under if I get bored.
You agreed, stomach fluttering.
Saturday night you prepared like it was a ritual. Long shower, razor gliding over every inch of skin until you were smooth and soft. Hair mask, face mask, thick vanilla-coconut body butter that left you glowing and smelling edible. Your hair fell in loose, bouncy curls. Your makeup was soft but lethal. Smoky eyes, long lashes, glossy lips that were begging to be kissed… or fucked.
The dress you chose was perfect: sheer black lace hugging your tits and waist, flowing into a cheetah-print skirt that swished around your thighs with every step. Strappy heels. No bra. You looked expensive. You looked fuckable.
When he knocked, your heart slammed against your ribs. You opened the door and there he was… taller than his photos suggested, maybe 6’5, long blonde hair loose and shining under the hallway light. Smudged eyeliner made his hazel eyes look predatory. He wore an all-white outfit: cropped jacket open over his bare, toned chest, matching pants that hung low on his hips. A thin gold chain rested against his collarbones. He smelled like expensive cologne, cigarettes, and something darker… pure sex.
“Goddamn,” he said, voice low and raspy, eyes dragging down your body like he was already undressing you. “Look at that. My pretty little whore all dressed up for me.”
The word should’ve offended you. Instead it sent a pulse straight between your legs.
“Hi, Hollis,” you managed, smiling.
He stepped closer, fingers brushing your jaw before tilting your chin up. “You nervous, baby?”
“Good. I like when they’re a little scared.” He smirked, thumb grazing your bottom lip. “Makes it hotter when they’re dripping for me later.”
He took your hand, his grip firm and possessive, and led you down to the street. An orange Lamborghini Huracán waited, gleaming under the streetlights. The engine roared to life with a guttural growl that vibrated through your chest and made your neighbors’ windows rattle. He opened the passenger door for you, gave your ass a firm squeeze as you slid in, then winked.
The interior smelled like the finest of leather and his cologne. As he pulled into traffic, one hand on the wheel, the other immediately found your thigh, sliding under the hem of your skirt.
“Soft,” he murmured appreciatively, fingers tracing circles higher and higher. “You shave for me?”
“Yeah,” you breathed, voice catching as his fingertips brushed the edge of your panties.
“Such a good girl.” He squeezed your inner thigh, hard enough to leave a faint mark. “I can’t wait to see how pretty that pussy looks spread open on my fingers. Or my tongue. Or my cock… whichever I feel like using first.”
Your face burned. You pressed your thighs together around his hand, but he just chuckled darkly.
“Already squeezing? Greedy little thing. We haven’t even had appetizers yet.”
The drive to Somni was a blur of city lights, thumping bass from his speakers, and his filthy commentary. Every red light, his hand wandered higher. By the time the valet took the car, your panties were soaked and your pulse was racing.
Inside the restaurant the lighting was dim and intimate, the air scented with truffle and warm bread. The hostess led you to a private corner table. Hollis pulled your chair out, then sat across from you, legs spread lazily under the table so his foot could brush yours.
He ordered a bottle of wine that cost more than your rent, then leaned forward, eyes locked on your cleavage.
“So tell me, baby,” he said, voice velvet-rough, “how wet are you right now?”
You bit your lip, glancing around to make sure no one could hear. “Very.”
He grinned, slow and wicked. “Good. Keep it that way. I want you squirming through the whole dinner thinking about how I’m gonna bend you over later and fuck that pretty pussy until you cry.”
Your breath hitched. Under the table, his foot slid up your calf.
This was dangerous. This was exactly what you’d been fantasizing about.
And you couldn’t wait for dessert.
The sommelier poured the deep red wine into crystal glasses. Hollis raised his, eyes never leaving yours.
“To pretty girls who know exactly what they’re getting into,” he toasted, voice low.
You clinked glasses, the wine rich and velvety on your tongue, tasting of dark cherries. “And to sugar daddies who don’t look like grandpas.”
He laughed, a raspy, genuine sound. “Smart mouth. I like that. Means you’ll talk shit while I’m balls deep.”
Heat flooded your cheeks. You took another sip to steady yourself.
The tasting menu began arriving in elegant waves. First course: delicate scallop crudo with yuzu kosho, tiny edible flowers, and a smoky dashi foam. Then a dish of aged Wagyu tataki with black garlic and pickled cherry blossoms. Hollis fed you a bite from his fork, his fingers brushing your lower lip on purpose.
“Fuck, you look good eating off my hand,” he murmured. “Imagine how you’ll look choking on something much bigger.”
You nearly whimpered. Under the heavy white tablecloth, his foot slid up your calf again, then higher, pressing between your thighs. You parted them instinctively. The tip of his boot teased along the damp lace of your panties, rubbing slow, firm circles against your clit through the fabric.
“Hollis…” you breathed, gripping the edge of the table.
“Shh, baby. Just keep looking pretty and tell me about you. What’s a nineteen year old like you doing on Seeking? Be honest.”
You tried to focus as his foot kept its relentless pressure. “Bills. Rent’s about to kick my ass. College is expensive. I’m… tired of scraping by. Serving tables, stressing every month. This seemed like the only way out that didn’t involve dancing in a club.”
His eyes softened for half a second, then the wicked gleam returned. “Poor baby. I’ll take care of you. But I’m not some soft old man who just wants arm candy. I want this…” his foot pressed harder, making you bite back a moan “whenever I want it. I want you wet, obedient, and dripping down my fingers on command. Think you can handle that?”
“Yes,” you whispered, rolling your hips subtly against his boot. The waiter cleared plates without noticing a thing.
Next courses came: Hokkaido uni with caviar and gold leaf, then a molecular take on duck breast with blood orange and smoked chestnut puree. Every bite felt decadent, luxurious. Hollis kept the conversation flowing… light on the surface, filthy underneath.
He told you he made his money through music, producing, and some “other ventures” he wasn’t ready to detail yet. “Let’s just say I get paid stupid amounts to do what I love and I don’t like being bored. Pretty girls keep me entertained.”
You asked about the eyeliner. He smirked. “Makes my eyes pop when I’m looking up at you from between your legs.”
By the time dessert arrived… a deconstructed chocolate soufflé with tonka bean ice cream and gold-dusted hazelnuts, you were throbbing. His hand had replaced his foot under the table, fingers slipping under your skirt, pushing your panties aside. Two long fingers stroked through your slick folds, teasing your entrance but never quite pushing in.
“Oh princess, you’re fucking soaked,” he whispered, leaning across the table like he was sharing a secret. “This little pussy is crying for me already. You gonna let me ruin it tonight?”
You nodded quickly, biting your glossy lip.
“Yes, Hollis. I want you to ruin me.”
He grinned, dark and satisfied, and finally sank two fingers deep inside you. You gasped softly, clenching around him. He pumped them slowly, curling against that perfect spot while his thumb circled your swollen clit. The restaurant hummed around you with soft conversations, clinking silverware, while he finger-fucked you under the table like it was the most normal thing in the world.
By the time he had paid an obscene amount, and pulled his hand away, you were trembling on the edge, thighs sticky.
The valet brought the orange Lamborghini around. Hollis opened your door again, but this time he pressed you against the side of the car for a moment, kissing you hard. His tongue claimed your mouth possessively while his hand squeezed your ass.
Once inside the roaring car, the city lights streaking past, he rested his hand high on your thigh again, fingers still glistening from your arousal.
“So here’s the deal, baby,” he said casually, voice cutting through the bass-heavy music. “Every time I make you cum tonight… doesn’t matter if it’s on my tongue, my fingers, or my cock, I’ll give you five grand. Venmo, Zelle, cash, whatever you want. Think you can handle how hard I’m about to wreck you?”
Your eyes widened. Five thousand dollars per orgasm. You were already nervous, his energy was intense, his kinks clearly on the slightly extreme side… but the thought made your pussy clench.
“That’s… a lot,” you said, voice shaky with arousal and disbelief.
He laughed, low and dark, squeezing your thigh hard enough to bruise. “I know. I’m a freak, sweetheart. I like making pretty girls fall apart. I like hearing them beg and cry and squirt all over me. And I’ve got more money than I know what to do with.” He glanced over, eyeliner-smudged eyes gleaming. “You scared?”
“A little,” you admitted, shifting in the leather seat, still aching from his fingers. “But… I want it. I want you.”
“Good girl.” He slid his hand back under your skirt, two fingers plunging back into your soaked heat without warning. “Because by the time I’m done with you tonight, you’re gonna be addicted to this dick and my money. Now spread those legs wider. I want to feel how excited you are for me to ruin that tight little cunt.”
The Lamborghini purred beneath you as his fingers worked faster. You moaned openly this time, head falling back against the seat, the city blurring past while Hollis smiled like the devil himself.
You knew you were about to have the night of your life.
The Lamborghini roared into the underground garage of a sleek, modern mansion in the Hollywood Hills. Hollis barely gave you time to breathe before he pulled you out, pinned you against the car, and kissed you like he was starving… tongue deep, hand fisted in your curls, grinding his hard cock against your stomach through his white pants.
“Been thinking about this tight little body since the second you messaged me,” he growled against your lips. “Gonna fucking ruin you for anyone else, baby.”
He led you inside. The house was all glass walls, low lighting, expensive art, and the faint scent of incense. He didn’t even make it to the bedroom.
In the living room, he shoved you onto the massive sectional couch, hiking your skirt up around your waist. He dropped to his knees, ripped your soaked panties down your legs, and buried his face between your thighs like a man possessed. His tongue was relentless… long, flat strokes over your clit, then spearing inside you while his lined eyes locked on yours.
“Fuck, you taste so sweet. This pretty pussy is mine now,” he moaned into you, sucking your clit hard. Two fingers plunged deep, curling viciously. You came in under two minutes, thighs shaking around his head, crying out his name.
“That’s one,” he grinned, wiping his glistening mouth. He stood, shedding his white jacket, revealing his toned chest. His cock strained against his pants… long, thick, and already leaking. “C’mere, pretty. On your knees.”
You slid off the couch obediently, but shot him a bratty little smirk. “Only because I want to.”
He laughed low. “Brat. I like it. Makes me wanna fuck the attitude right out of you.”
You sucked him eagerly in the living room, taking him deep, gagging softly as he guided your head with a firm hand in your hair. “That’s it, good girl. Look at those pretty lips stretching for me. Fuck, you were made for this dick.”
He pulled you up before he came, bent you over the back of the couch, and slammed into you in one thrust. The stretch burned perfectly. He fucked you hard and deep, one hand gripping your hip, the other reaching around to rub your clit.
“Fuckin’ take it, baby. Take every fucking inch. This pussy is gripping me so tight, such a greedy little whore for my cock now, aren’t you?”
“Yes…fuck, Hollis!” You came again, walls fluttering around him. He didn’t stop, just fucked you through it until your legs shook.
He carried you… still impaled on his cock, to the kitchen island, laying you back on the cool marble. Legs over his shoulders and his arms gathered around your knees, he pounded into you, watching your tits bounce with every thrust.
“Uh uh. Eyes on me,” he ordered when your lashes fluttered shut. You obeyed, but when they slipped shut again in overwhelming pleasure, he lightly smacked your cheek… just enough sting to make you gasp and refocus. “Good girl. Keep those pretty eyes on me while I wreck this cunt.”
He made you cum twice more like that. Once on his cock, once when he dropped down to suck your clit again while fingering you.
From the kitchen he took you to the bedroom, stripping you fully finally and tossing you onto his massive bed. Missionary, slow and deep at first, then brutal. He hooked your legs over his shoulders, folding you in half, and sucked your toes into his mouth while slamming into you, tongue swirling, eyes dark with lust.
“Fuck, even your toes taste good,” he groaned around them, hips snapping relentlessly. “Gonna make you cum so many times you forget your own name, baby. This pussy was made for me.”
You came again…shaking, even squirting a little onto his chiseled abs, while he worshipped your feet. The brat in you surfaced: “You’re such a fucking pervert,” you moaned with a smirk.
He grinned wickedly, thrusting harder. “Your pervert, princess. And you fucking love it.”
Hours blurred by. He took you against the floor-to-ceiling windows overlooking the city lights, your tits pressed to the glass while he railed you from behind, fingers in your mouth for you to suck on. “See how good you taste? Suck them like you suck my cock.”
Another orgasm. And another.
In the luxurious shower now, hot water cascading, he had you braced against the tile, fucking you standing while he rubbed your clit. Then he sat on the bench and made you ride him reverse cowgirl, spanking your ass lightly and praising how beautifully you bounced.
Back on the bed, he went down on you again until you came on his tongue, then flipped you into doggy, pulling your hair just right. Every time you came he’d murmur filthy praise. “That’s my good girl, creaming all over me again, makin’ that fuckin’ money.”
By the time you were both exhausted and sweat-slick, you’d lost count… definitely ten orgasms, maybe more. Your body felt boneless, glowing, utterly used in the best way. Hollis finally let himself go, pulling out and painting your tits and stomach with thick ropes of cum, groaning your name like a prayer.
He collapsed beside you, pulling you into his chest, kissing your forehead tenderly despite how rough he’d been.
“Fuck, baby… you’re perfect.” He grabbed his phone, tapping quickly. Your phone buzzed on the nightstand with multiple notifications. “That’s fifty grand for tonight. Five for each time I made you cum. Keep being this good for me and I’ll take care of everything. Rent, tuition, whatever you need.”
You curled into him, bratty spark still there even as you drifted off. “Only if you keep sucking my toes and fucking me like that.”
He laughed, pulling you closer. “Deal. You’re mine now, pretty girl.”
The next morning you woke up in Hollis’s massive bed, sunlight pouring through floor-to-ceiling windows, his long blonde hair splayed across the pillow. He was already awake, tracing lazy circles on your bare hip while scrolling on his phone.
“Morning, princess,” he murmured, voice still raspy from last night. He leaned over and kissed you slow and deep, tasting like mint and last night’s sin. “I already paid your rent for the next six months. And your tuition is handled… don’t argue. Good girls get taken care of.”
You blinked, heart racing. “Hollis… that’s like… a lot of money.”
He smirked, smudged eyeliner from the night before still faintly there. “It’s nothing to me. You’re mine now. That means no more stressing about bills while I’m busy stretching that pretty pussy every chance I get.”
True to his word, the dynamic shifted fast.
He had you bent over the marble kitchen island again, your college laptop open in front of you while he fucked you slow and deep from behind. One hand gripped your hip, the other reached around to rub your clit in tight circles.
“Focus on your assignment, baby,” he teased, thrusting just hard enough to make the screen blur. “Tell me what you’re writing about while I’m balls deep.”
You could barely form sentences, moaning between words. When you came… shaking, clenching around him, he pulled out, spun you around, and set you on the counter to finish on your stomach.
Afterward, while you were still catching your breath, he tapped his phone. “Another five grand. That’s for making you cum while you tried your hardest to be a good little student. So fucking hot.”
He started sending you money constantly: random $2,000 “just because you looked cute in the pic you sent,” $10,000 after particularly rough nights, and automatic monthly transfers that covered your car note, utilities, groceries, and even a fat allowance for “looking expensive.”
Hollis flew you to Miami for a long weekend. Private jet, of course. You spent the days on a yacht.. him in designer swim shorts and nothing else, you in the tiniest bikini he’d bought you. At night he’d pull your bottoms to the side and rail you on the deck under the stars, making you ride him while the ocean rocked beneath you.
“Fuck, look at you,” he groaned, hands squeezing your ass as you bounced. “My perfect little sugar baby taking every fuckin’ inch. This pussy owns me as much as I own it, I swear.”
He bought you whatever you looked at twice. A new wardrobe full of designer pieces. Skimpy dresses, lingerie that barely qualified as clothing, heels that made your legs look endless. One afternoon in Bal Harbour he took you shopping and dropped $18,000 without blinking, then fingered you in the dressing room until you had to bite his shoulder to stay quiet.
Back in LA, he paid off your remaining credit card debt and bought you a sleek black Mercedes so you didn’t have to rely on uber after late shifts at your serving job. (which you quit shortly after. He insisted).
He remained an absolute pervert, but the care underneath it made you melt. He’d text you during class: “Thinking about how you looked crying on my cock last night. Be wet when you get home.” And you would be.
Some nights he was rough and filthy for hours… fucking you in every room of his mansion, making you suck his fingers while he pounded you in missionary, lightly choking you making your breath catch, sucking your toes while buried deep, edging you until you were begging and bratty.
“You’re such a freak,” you’d gasp with a defiant little smirk, even as you were shaking from what felt like your hundredth orgasm of the night.
He’d grin, hair messy, eyeliner running. “But I’m your freak. And you love creaming on this freak dick, don’t you?” Then he’d fuck you harder until you admitted it, screaming.
Other days he was softer…lazy morning sex where he’d hold you close, whispering praise while slowly grinding deep. “You’re doing so good, baby. Taking everything I give you. So proud of my pretty girl.”
He loved when you got bratty. It made him laugh and then pin you down to “fix” the attitude. You learned exactly how to push his buttons… teasing him with pics while he was in the studio, or pretending to be too “tired” to suck him off just so he’d manhandle you onto your knees with that wicked smile.
One random Tuesday he showed up at your old apartment, though your rarely slept there anymore, with flowers and a black card.
“Rent’s paid through next year,” he said casually, pulling you against his chest. “And I added you to one of my accounts. Use it. I want you spoiled and soft for me.”
You looked up at him, fingers tracing his bare chest under the open shirt. “Why are you so good to me?”
He tilted your chin up, thumb brushing your lip. “Because you make me feel alive. And because every time this tight little cunt squeezes me, I want to give you the whole fucking world.” His voice dropped. “Now get on the bed. I need to taste my favorite pussy before I head back to the studio.”
The relationship felt dangerously addictive. He wasn’t just paying your bills.
You were falling hard. And from the way he looked at you… like he’d burn the world down to keep you wet and happy, he was too.
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I LOVE THIS I NEED SUGAR DADDY HOLLIS TO BE REAL SO BAD UGHHH
Also I think I’m going to write the nerd!hollis x nerd!reader fic as well since both of these ideas are running close in the poll i posted hehe
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