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His parents are right infront of the door, talking to who seems like his new babysitter, another new one to torture. Dennis thought to himself. He always terrorizes his babysitters away so that explains why they’re talking to another new one.
His new babysitter was having a really long conversation with his parents, he cannot see if it was a boy, or a girl babysitter — or maybe a non-binary one? Not that he thought it wasn’t possible, nor weird anyways. He cannot even see the babysitter’s face, just a really intimidating height.
“Thank you so much, Mr. Robinavitch.. for really accepting this opportunity to babysit Dennis… though he’ll be bit too much to handle, please call us if anything goes badly” Dennis heard his mother finally ending the conversation. Well.. he assumed it was finished since She looked at Dennis with a sharp look
Dennis had always thought he was a bit too old to have a babysitter at his age. He’s 16, turning 17 in 2 months — that’s the issue. Being a teenager was a liability to being very naive to drugs, alcohol, sex.
His mom walks to the living room, where Dennis was resting with a phone on his hand.
Dennis looked at his mom as she sat beside her with a serious look on her face. “Dennis, Can you please just behave for once. We’ll be sure to bring home some berries for you.” She was basically pleading, not that Dennis would actually behave. It’s ridiculous enough that they think he still needs a babysitter at such a grown age.
“Hello, I’m Michael Robinavitch.. you can just call me “Robby”. I’m your new babysitter.” The sudden voice stood in-front of him. Robby extended his arms for a handshake towards Dennis. Dennis’ whole demeanor changed silently as he stared at the man in front of him, who looked like he was in his mid 30–40s. This guy was totally his type.. Dennis wasn’t openly gay towards his parents, but his friends do know.
Dennis hesitated for a moment before taking Robby’s hand with shaky hands.
His parents stared at the two’s introduction for a moment and smiled before saying their farewells. “See you in 3 days, behave yourself Dennis Whitaker.” then they left the front door, leaving the two of them alone.
Dennis felt too oddly tense, fuck. He’d never seen anyone fitting his ideal type besides his new babysitter. The idea is too highly inappropriate.
“So.. what do you do for fun, Dennis?” Robby broke the suffocatingly awkward atmosphere in the air around them. It wasn’t helping Dennis though, Robby was looking at him. It was too much for Dennis.
Dennis just looked at his own hands, fidgeting. Trying to come up with an answer that doesn’t sound too boring.. he can’t just fucking say “Oh, nothing! Jerking off to old men, specifically twice my age!” That’d make it too weird.
“Watching movies.. reading books– uh.. comics.” Dennis decided to come up with whatever first came up to his mind. Which was a relief.
Dennis turns to steal a glance at him for a second, then looked away immediately.
Robby noticed the tense demeanor in Dennis, and he just let out a rumbling chuckle. “I like watching movies too, what’s your favorite movie?” Robby stood up and went to the kitchen, probably getting them something to eat while talking.
“Mysterious.. Skin.. – I uh.. maybe, Fight club.”
Robby returns to the living room with 2 plates of carbonara for the both of them, handing one of the plates to Dennis. Their hands brush for a moment.
„Fuck, fuck, fuck!„ Dennis thought to himself as he felt a bit turned on, fucking teenage hormones.
“Thanks.. I– kinda.. like Carbonara..” Dennis tried his best not to look too awkward as he looked at Robby already slurping the pasta up.
His dick twitched just at Robby slurping the pasta up.
Dennis snaps out of it. He can’t think of his babysitter like that. It’s unprofessional at his part — and it’s illegal, he’s simply twice his age. That’s weird enough..
“Are you not hungry?” Robby looked at him, as he said in between his enjoyment with the food
Dennis looked at him with a slight blush, trying his best to retain his composure. “Oh.. I’m so sorry, I just.. —Nevermind.” He then starts eating his Carbonara. Noticing the fact that Robby was looking at him with confusion.
After they both finished the Carbonara, Robby took their plates and went to the kitchen sink to wash the dishes up.
Dennis couldn’t take it anymore so he secretly went inside the bathroom to jerk his unnoticeable semi-hard on. Pulling his sweatpants down as he stared at the wet stain on his underwear, an evidence of his pre-cum.
He wraps a hand around his shaft and starts to slowly stroke his hard erection. Dennis covers his mouth to suppress any embarrassing noise that may come out of his lips.
“Fuck.. Uhm.. uh..” Dennis felt his legs shaking as he starts to slowly reach the edge, following a slightly faster rhythm with his talented hands. Pre-come ejaculating slowly on his hands making it slick and wet as he strokes it.
His imaginations went wild as he strokes himself. It was drifting to him getting satisfyingly fucked by his babysitter roughly. He sped up his hand, it was getting a bit more harder to suppress his moans.
As he slowly reaches the edge, Robby’s voice echoed outside the bathroom.
“Dennis, what are you doing? Your parents are asking me.” Robby’s voice was a bit commanding and rough. He wondered if his voice was also like that during sex.
Dennis starts speeding up the rhythm of his strokes, letting out silent moans. He was great at keeping his voice quiet, as far as he knows.
His legs starts shaking, and his eyes were losing focus on what’s happening as he came. “Shit..ugh..! Oh my fucking ..” Dennis slowly tries to catch his breathe, resting for a couple minutes before finally leaving the bathroom.
Robby easily spots him leaving the bathroom. “Sorry, I was.. just peeing.” Dennis smiled awkwardly and returns to sit on the couch in the living room.
“All good, I thought you were taking a shower” Robby chuckled as he returns his attention to the TV, which he didn’t even notice was playing an obviously R-18 show.
Dennis’ cheeks were still slightly visibly flushed from his embarrassing masturbation, and imaginations.
“Hey, do you have a girlfriend? Some.. girl was calling your phone earlier” Robby looked at him with a smirk.
Dennis looked at him, his cheeks painted pink from earlier made it look like he was blushing from the question.
“What?! No — I don’t have any girlfriends–?” Dennis quickly explained as he was fidgety. “who was- calling anyways?” Dennis tried to make himself look “calm”.
Robby looked at him with a smirk, slightly leaning closer, just to tease him with the so-called “Girlfriend”.
“Amy..” Robby lets the name curl out of his mouth, as he continues. “You have her contact saved as .. Amy with 2 hearts, that’s something friends don’t do” Robby chuckled as he took sip of what looked like Dennis’ father’s beer.
“it’s not what it looks like” Dennis grunts as he tries to avoid Robby’s obvious teasing smirk.
Dennis’ eyes landed onto the movie that was then playing a sex scene. Fucking hell, this babysitter was unreliable. Dennis thought to himself, it isn’t like he doesn’t mind it— his parents were just really protective and wants Dennis to avoid these topics.
“Ooh.. why? Are you imagining sex with Amy?” Robby’s attention turned to the movie too, smirking and it’s obvious that he loves teasing Dennis.
Dennis’ cheeks were now flushed visibly red with embarrassment. He looked at him with furrowed brows, and tackled him.
They both laugh hysterically as the two of them were tackling each-other, and play-fighting.
Dennis was now straddling Robby’s hips as they were tackling each-other. Dennis wasn’t hard to pin down as he was smaller compared to Robby.
They stop tackling each-other, as Robby realized that they were in a very sexual position. It was exactly the position Dennis was imagining earlier in the bathroom when he stroked himself.
Dennis looked at him with parted lips, breathing heavily. His mind spins around as he tries to gain some composure. Robby was below him. He was straddling his hips, he can either try to get fucked by this guy.. or stand up.
They both know how bad this looks, especially Robby. It was a bit too awkward to have a teenager on top of your hips. It was unprofessional of him, and inappropriate.
It took both of them by surprise when Dennis placed his lips against Robby’s.
Dennis broke the kiss and looked at him with watery eyes, and with flushed cheeks.
“I’m so fucking sorry.. shit.. I’m so sorry.” Dennis looked at Robby, his words sounded desperate for forgiveness.
Dennis’ was obviously hard, it was hard to ignore since it was bulging on his pants.
Robby looked at him with an unreadable expression, it was making Dennis anxious. „What is Robby thinking of? Is he gonna tell my parents? Fuck„ Dennis’ mind crumpled with negative possibilities on what Robby could do.
Dennis stood up and ran upstairs to his room, slamming the door shut. He was having a huge panic attack at this point — it wasn’t hard to distinguish the anxiety in Dennis’ eyes when he was staring at Robby with watery eyes.
His anxiety attacks aren’t usually this bad. He wants to call his best friend, Trinity. She would know what to do — or, maybe she’d think it’s weird and he’ll lose his best friend. He tries to tolerate his anxiety attack. It wasn’t his first one after all.
Robby still laid there on the sofa; stunned and immobile, as he decides if he should call Dennis’ parents, or check up on Dennis upstairs.
He sighed slowly as he slowly went upstairs, towards Dennis’ room.
“Dennis?” Robby called softly, knocking on his door. Slightly worried that the Anxiety attack was more serious than it looks.
Robby waits outside for what felt like an eternity. (5 minutes lol) “If you don’t answer the door, I’ll burst this door open. I can’t tell if your anxiety attack is getting to you, or you’re just ignoring me.” Robby called out for him.
The door slowly opened as Dennis was sitting on the bed, his erection still visible from his sweatpants.
Robby slowly went inside and sat beside Dennis, the atmosphere has never been this thick before. It was more suffocating than from earlier when they just met.
“Look, you can’t just kiss me.. I’m dating someone. I also won’t tell your parents about it. They might sue me too.” Robby looked at him; as if the last sentence was a joke, but it really didn’t sound like a joke at all.
Dennis looked at him. Those words struck his chest so hard. “I’m dating someone ..” it felt like all his hopes and dreams crushed,, fuck it.
He leaned in again for a kiss, more possessive, more desperate. Robby tries to push him away, but Dennis just continued kissing him.
Robby pulled away for a bit. “Fuck..! Stop, we cannot do this.” Dennis looked at him with tears threatening to fall down his eyes. He decided to pull away, but not because he wants to stop.
“Please..” Dennis looks up at him as he kneels down in-front of Robby in between his legs spread open. Dennis was doing this intentionally for Robby to be turned on.
Dennis slowly brings his mouth up onto Robby’s waistband.
„I’ll let you do anything to me, anything at all„ Dennis thought to himself as he noticed Robby look at his eyes, He grips onto his own erection trying to relieve some pressure in his sweatpants.
Dennis smirked as he saw Robby’s dick twitch a bit. It was unintentional on Robby’s end, but it was still suggestive.
He starts to pull Robby’s pants down as Dennis sniffs Robby’s manly musk dick scent. He was incredibly insane for this — Dennis looks up at Robby, and licks his semi-hard on bulge.
Robby hissed at the feeling of Dennis’ wet tongue brushing against his semi-erection.
“Stop.. we cannot do this, you’re too young..” Robby grunts as he tries to remain his composure, his dick was fully hard now.
Dennis pulls down Robby’s underwear, smirking as he moans at how thick it actually is — his mind cloudy already with imaginations of the dick fucking his insides.
“You’re so big..” Dennis stood up slowly, as he looked at Robby again with a hunger for lust.
Their lips crushed against eachother once again. This time, they’re both willingly giving in to the soft passionate kiss. It started slow — until it was accompanied by their tongues fighting for thirst.
As they pulled away from the kiss – Dennis’ eyes looked glassy, and so innocent. It made Robby snap back to reality. He is kissing someone twice younger his age, a fucking teenager.
“No.. don’t think about it..” Dennis said, as if he instantly read the panic between Robby’s eyes.
He slid down between Robby’s legs, wrapping his lips around the thick head. Making Robby’s head roll back slowly — Dennis was like.. so familiar with blowjobs.
Dennis looked up at him, and moans on his dick. Sending jolts of vibration up Robby’s shaft.
“Fucking hell.. you’re insane..” Robby looked down, seeing Dennis’ lips stretching around his thick manhood. Swallowing his dick like a fucking veteran at blowjobs.
His hands finds its ways to the back of Dennis’ hair, gripping tightly at it as he slowly thrusts up. Enough to draw a gag from the boy.
Dennis’ eyes were watery, a few tears running down his cheeks as he takes Robby’s cock deep — as far as he could take it. Robby was my forcing him to take it all in his throat yet.
Robby tries to push Dennis down on his dick, but Dennis pulls back immediately before he starts choking.
Dennis tries to catch his breathe, his eyes watery with tears. His mouth slightly wet with pre-cum and spit. “you’re insane.. I can’t take all of that in my throat.. it’s too big..”
“if you cannot take it in your throat, how can I fit it in you?” Robby looked at him, his hands are still gripping behind Dennis’ hair.
Dennis cannot even fathom if Robby was saying that as a joke. His dick was veiny, and thick. His mind already spiraling if Robby fucks roughly — or gently with care.
He looked at Robby with lust, lowering himself down again between his legs, getting on his knees.
Taking all his length up slowly, trying to relax his throat.. Dennis was so fucking horny, he cannot tell if it was hormones, or if he’s actually like that.
Robby wipes off the tear that ran down Dennis’ cheeks, trying to suppress his gag reflex from acting up
“Such a.. fuck– good boy..” He slowly thrusts his hips in Dennis’ throat slowly, enough to not hurt him.
Dennis’ starts to suck his dick faster, the praise really railed him up to perform better.
The room was surrounded with wet slurping from Dennis, and deep grunts from Robby’s lips. They were so lost in the feeling of trying to pleasure each-other.
Robby rushed to pull him off of his cock, but Dennis tried to chase the feeling of something heavy resting on his tongue.
He smirked down at Dennis’ anxious looks, as if Dennis was communicating with him through Robby’s eyes „Why? Did I hurt you? Did I perform badly?„. Robby immediately shuts down those thoughts from Dennis. “You’re Incredible.” He strokes Dennis’ curly brown mullet.
“Fuck me, please..” Dennis looked at him, standing over him. Those deep blue eyes were wandering with lust in them — Dennis was unbearably pretty and horny.
Robby brushed a hand on Dennis’ sensitive skin. Gripping on his chin softly. “You’re really a spoiled brat, huh?” Robby looked at him with the similar look of lust — identical to what Dennis’ really wants right now.
They both are now on Dennis’ bed.
Robby was lying on the bed, as Dennis was above him. Straddling his hips — feeling the hard dick pressing on his bare ass.
“I– I don’t have lube.. or condoms..” Dennis’ cheeks flushed red, embarrassed to even name the two essentials for safe sex.
Robby looked at him, as he rummaged inside his wallet. pulling out a condom wrapper, and at least 5 lube packets — „does he really bring those everywhere he goes?„ Dennis thought when he saw Robby pull those out of his wallet.
As if reading Dennis’ confusions, Robby sighed and looked at him seriously.
“I have a boyfriend, his name is Jack.. Abbott.” Robby answered, seeing the color in Dennis’ eyes drain. “that’s why I bring these everywhere.” Those simple yet harsh words stabbed right in his heart. Dennis looked at him with an even more furiously confused look.
Dennis straightens his clothes. “Then, you’re cheating on him—?” still obviously confused.. is he just a side-chick to Robby? He certainly doesn’t like that.
Robby ignores his question, as he quickly opens a pack of lube — letting it cool down on his fingers.
“Try to relax for me.” Robby slowly pushed one finger inside of him – stretching him open. Dennis could manage. It isn’t like he hadn’t played with himself before .. just not a finger this thick, and deep.
Dennis was whimpering as Robby starts to grab the lube packet, emptying the first packet to his 2nd finger – pressing the 2nd finger inside Dennis slowly.
His body trembles at the cold feeling of lube touching his skin. He wasn’t used to this feeling.
The feeling of 2 fingers scissoring his insides open was making him want the dick in him – he doesn’t know how people find anal fingering so good.
That was his thoughts before Robby suddenly curls his fingers, hitting his prostate in the perfect spot.
Dennis buckled his hips as his whole body jolts like it was shock with a ton of lightning bolts.
“Shit…” Dennis hissed, feeling utterly screwed as Robby continued fingering him open.
Robby curled his fingers up — hitting Dennis’ sensitive prostate. He could tell Dennis was getting sexually overstimulated when he heard Dennis was reduced to a series of “oh.. oh.. oh..”
“Are you gonna cum for me, Whitaker?” Robby continued penetrating his prostate, bringing Dennis to the edge.
Dennis arched his back, his eyes rolling from the back of his head — Robby smirked as he saw the overstimulation in his face.
“I wanna come.. please..” Dennis was begging for release, he was at the very edge of his orgasm when Robby immediately removed his fingers.
Dennis furrowed his brows as he glared at Robby for leaving him on edge.
Robby looked at Dennis’ adorable expression.. his cheeks were flushed from almost edging himself to orgasm.
He ripped the condom wrapper open while staring at Dennis, seeing his embarrassed and nervous reaction when he started to roll the plastic in his dick.
Dennis gasped an air — the condom perfectly fitted Robby’s cock. It stretched from the tip down to his base.
“This is what you want, right?” Robby looked at him with predatory lust. He cannot register this reality — he’s so fucked.
Dennis just stared at the enormous size of the man in-front of him, He cannot tell if he’s either excited, nervous, or scared.
Robby was just staring at his eyes, ignoring the fact that his hard dick was scaring the boy below him. “Baby, I need a verbal consent from you.”
Dennis felt his throat dry up — he doesn’t know how to answer. It was like uttering a word could lead into a miracle or disaster.
“Yes, please.” He glazed at Robby’s lustful look at his soft body. Dennis doesn’t really work out that much — only work out he’d probably participated in is in Gym class.
Robby leaned into the small creak of Dennis’ hypersensitive neck, and placed a soft kiss there, Making the younger boy gasp a breath.
He sunk his teeth to the soft flesh on Dennis’ shoulders. Hard enough to leave a dark mark — soft enough to not leave a trace of blood or scar.
Robby pulled back from his neck, and starts to line up his cock to Dennis’ entrance. He slowly dip himself inside Dennis.
Dennis instantly felt the horrid stretch of the big dick — it felt like he was getting ripped apart, feeling the manhood pulsating in him. He felt overwhelmed as he felt the corner of his eyes swell up in tears from painful it feels.
Robby stopped pushing, as he starts to pull back. He realized that Dennis was clenching — making a conclusion that maybe he wasn’t used to it.
Robby leans down to whisper something softly in Robby’s ears. “Relax for me, it might hurt a bit.”
He left soft trails of kisses on Dennis’ earlobe, nibbling his ears a bit to release the tension in Dennis’ body.
“Good boy, Dennis.” Robby felt Dennis relaxing his body, as he slowly pushed his length in again — Robby almost pulled his entire dick out before sliding down again, waves of unexpected pleasure entered Denis’ body when he felt his dick rubbing his insides.
Dennis gripped tightly onto the sheets — letting out a soft groan when Robby finally bottoms out his whole length inside Dennis’ perfect ass.
Robby softly slaps his ass cheeks. “Your ass is so fucking perfect with my dick inside of you..” Dennis couldn’t help but release a soft whine from that lewd compliment.
“You like that? Getting praised, or complimented?” Robby heard the soft whine coming from Dennis when he slapped his ass, and praised his ass.
„This is one kinky son of a bitch„ his mind runs with lewd imaginations with this boy.
Dennis rolled his hips, trying to push down on Robby’s dick — impatient to be edged.
Robby noticed Dennis silently whimpering, the desire in his eyes was driving him fucking insane. He can’t tell if Dennis wanted to be punished, or just really horny right now.
He holds Dennis’ hips, in order to stop him from grinding his hips down to Robby’s dick. “tsk.. tsk.. So needy already..” his grip tight on Robby’s hips – there’s no doubt that it would leave a mark later
Robby starts to slowly thrust his hips, gripping on Dennis’ hips as he slams the boy’s hips down to meet his slow–rough thrusts. The younger boy was reduced to an overstimulated moaning mess — his hands grips onto his own bedsheets.
“Faster..” Dennis tried to utter in between his slurred moans. Robby smiled at his tone. It was barely comprehensible from the moans he was letting out.
“what was that?” Robby leaned down as he starts to thrust deeper, hitting that sensitive spot that makes Dennis see a universe he had never seen before.
Dennis threw his head back, his mouth falling slightly open — his pre-cum was dripping onto his own belly.
Robby whispered softly in his ears. “Beg for it.. say „please„..” his thrusts were even more deeper now — however, his slow pace was still torturing Dennis’ insides.
“Harder.. please..!” He struggled to let those words out — but it rolled out of his lips perfectly. The mix of desperation and desire was present in those words.
Robby grunts as he starts to pick up the pace.. Dennis’ room was now audibly filled with skin slapping, and the mix of their vocal pleasure.
The scent of sex, and hormones were probably in the air surrounding the two of them — it just kept getting heated, and more warmer. Each thrust Robby was delivering to Dennis made his eyes blurry.
“You’re so fucking.. good for me..” Robby groans as he left a visible hickey on the younger boy’s neck.
The two of them were edging closer to their own climax — Robby could already sense his phone flashing with messages from Dennis’ parents. Asking him “how is Dennis?” .. “is he behaving well?” ..
He’ll definitely let his parents now how much of a „Good boy„ their child was under his “professional” guidance.
“Fuck.. I’m coming.. I– hmph..!” Dennis arched his back, his ass clenching on Robby’s dick which was still thrusting inside him. He slowly release ropes & strings of come. The hot white fluid painting his bedsheets a bit white, and covering both of their bodies with it.
Not soon after a few thrusts, Robby came undone inside of him — Dennis felt heavy, as Robby pulled out with the cum-filled condom.. he grinned at Dennis when he saw the young boy glancing at it with a blush.
Taking off the condom, and wiping the white fluid excess with some clean wipes — the atmosphere in Dennis’ room was steamy and hot.. indubitably, the room had the scent of after-sex.
“Wanna clean up?” Robby chuckled as, slapping Dennis’ thigh softly. He leaned in for a soft kiss on the young boy’s lips.
Dennis grinned at the older man.
“Yeah, also.. I think my parents are calling.” Dennis glanced at the call notification from his parents. Luckily, they were finished fucking each other when they decided to call.
Robby nodded, as they both get dressed up before answering the call.