Cuckolding her Timmy Ch. 01

Author's note : This is the sequel to Cuckolded Cuties series, featuring the daughter of Louise and Ryan.

It's a brilliant Saturday morning. Timmy is just sitting in his bedroom, reviewing one of his old practice papers. The 18 years old high school boy feels like getting some sleep but doesn't want to become lazy. He can't let himself start napping for hours on end like he knows he would if he allows himself to. So the scrawny teenager forced himself to keep on reading the teacher's comments despite really needing to lie down.

Suddenly there is a knock at the door to his house. Getting up from the chair, he places the piece of sheet on a table and heads over. As he looks through the peephole, the boy is surprised when he sees Emilia Oliver, one of the hottest girls in their year, standing right behind it. Not only that but she is also the daughter of his parents' boss, Mrs Oliver. The two have known each other and been close friends for many years. He opens the door for her, nervously rubbing the back of his neck and smiling at her.

"Hi!" he chirps, flashing her a coy smile, biting his lower lip coquettishly. Emilia grins in return, making her way inside her childhood friend's home. She is six feet tall, with long, wavy brunette hair and hazel colored eyes. The teen's figure is extremely hot, with large C-cup breasts, washboard stomach and muscular thighs, a round, firm ass on top.

The girl loves the effect she is having on Tim, as he looks at his feet, blushing madly from her mere presence. It's no secret that both of the young people have deep feelings for each other. Everyone has always been teasing them about it for the past several years, including their own parents.

"Hello to yourself," Emilia responds suavely, swaying her hips, 'accidentally' bumping into Tim's thin legs with her muscular thighs, the product of playing volleyball for their school, being the team's captain and the most talented member. She is so good that she's actually been offered many scholarships from different universities to play for them. It delights the voluptuous athlete to see him turn red as a tomato from the light contact.

"Wanna study together and then watch TV and cuddle on the couch?" the girl's crush asks. She quickly nods as they get to his bedroom, where he retrieves his textbooks and brings it over to a table, where they proceed to sit and work through notes of what was covered in class. It really bores the teenage girl who has accepted an unconditional offer already, one which has been given to her since she is also academically gifted as well as great at sports.

Still, she agrees to be there to support him while he works at it, but also so that she could have some fun teasing him as well. The girl yawns and rests her head on his shoulder, smiling contently as he turns to gaze at her fondly. Without thinking about it, he raises his hand to brush aside a strand of her hair and cups her cheek gently, looking into her hypnotizing hazel eyes, mesmerized. His gaze falls down to her round, firm breasts, taking in the deep valley between the mounds.

Emilia smirks, looking straight at the tent pitched in his shorts. As soon as Timmy realizes what she is staring at, the boy flushes once more, quickly turning back to look at the notes like him as she giggles. Her hand comes to rest on his inner thigh, inches away from his groin, making him stiffen further still. Over the next half hour they continue diligently, before pausing to take a break. She quickly grabs his arm, leading him downstairs to the living room where they select a movie to watch together, cuddling on the couch like the teenage boy suggested earlier. It turns her on when the side of his arm brushes up against her tits and she can feel her panties getting wet. The teenager has started gotten an IUD inserted a month ago, right after turning eighteen, and is anxious for them to start dating so she can finally fuck her secret love.

But the buxom brunette refrains from saying anything about his boner, not commenting on it even when she is about to leave. She just wants to tease him until he is all fired up and ready to make the move. "Thanks a lot for coming over," her long-time crush whispers, leaning over and tenderly wrapping his arms around her in an embrace, making her feel butterflies in her stomach. She then exits the house, feeling delighted and one step closer to confessing to him.

Unfortunately, things do not go the way she planned. The very next day, she encounters Wade, one of the school's best footballers and a notorious player, at the campus. She hates the brute with a passion, being disgusted with the way he regularly uses girls as cocksleeves and tossing them aside once he is bored with them, especially since he has recently been trying to get into her pants as well

The curvaceous teenager is simply eating by herself in an empty classroom during lunch break. Emilia has observed when each room would be vacated at certain times of the day, and has often taken advantage of those slots, just as she is doing right now. Suddenly, there is loud banging on the door, confusing the girl as no one usually comes by at this time.

She goes to open the door, groaning as she sees Wade standing there. "What do you want?" the athletic girl demands, hands on her hips as she glares at the smirking asshole. The teen has never had much patience for the likes of him, and now that he has disturbed her little peace and quiet, she is even more upset by his presence, her tone curt and indicating that he should leave.

Wade doesn't answer but quickly shuts the door and locks it behind him, before grabbing hold of her and smashing his lips down on hers in a violent kiss. Startled, Emilia tries to push him away. Against an average guy, the toned girl would have no problem, but Wade is extremely strong and she couldn't break his grip as he forces her backwards and shoves her onto the ground. He starts pawing at her breasts, squeezing the globes of flesh with his hands.

Before Emilia could react, he has already yanked down her miniskirt and is rubbing her pussy through the cotton underwear. To her shame, the rough handling and aggressiveness has made her drenched. Wade smirks as he realizes this too, running his fingers over her soaked panties, making her gasp as he slips a couple of them in. She tries to wriggle free as he keeps her pinned down but fails.

"Please stop this," the teenage sports star begs as Wade expertly removes her underwear, exposing the hairy bush above her glistening cunt. He scoops up some of the dripping pussy juices, bringing it up to his lips, sucking on it. The boy shakes his head mischievously, now inserting the same fingers back into her molten hole, causing the flames of passion to spread through her loins.

"If you cry out, people will come and see you like this. Will you be able to face Timmy after he finds out?" the muscular guy sneers. He is now lewdly thrusting deep into her sex with his fingers, loosening up the vagina enough to put in his entire hand after spreading the labia apart. Emilia moans, thrashing about, squirming from the pleasure of being fisted, trying futilely to dislodge his hand from inside her cunt.

"Wade, I'm begging you. Stop. I don't want this," the girl insists, desperation evident in her voice, even though the throbbing pussy is now leaking a lot, creating a massive mess on the aggressive teen's fingers with the clear, sticky liquid. He begins to unzip his pants, pulling it down with his boxers, revealing a huge cock. Even flaccid, it is at least seven inches. "No! Wade, no!" Emilia sobs, attempting to stand up but pushed back down again.

He tugs on the meaty appendage in front of her, looking at her toned legs as he jacks off. Within minutes, the already large tool swells up even further, reaching its full ten inches. The girl can only stare at the anaconda in shock. It's a monster, obscenely huge and veiny, pulsating with arousal as it just out towards her. The boy then approached her menacingly, gripping the tool by the base, encircling it with his fingers.

"Please don't do this to me Wade!" Emilia once again pleads, despite finding herself getting even more aroused at the sight of his powerful rod, still wanting to save her virginity for Tim. He doesn't listen, placing his muscular body between her thighs, spreading them apart and then pushing past her labia with the tip of his hard cock. She tries to struggle more but is pinned and cries out slightly from his size as he penetrates her.

Her vagina is stretched out, expanding to accommodate the impressive girth as he drives into her warm tunnel. Wade revels in being the first to enter her tight, little pussy, getting to deflower the most beautiful girl in school. That bastard gets off knowing that he is fucking her before Tim, that little pissant who Emilia loves and loves her back, ever could. She has to bite her lower lip to muffle a scream, shocked by how it feels to have something this large embedded in her cunt.

Emilia has used dildos before, but none remotely as big as this. It hurts so bad at first, but once he begins pistoning in and out, the pain starts to disappear, replaced with pleasure instead. She finds herself letting out soft moans, grinding up unconsciously. The girl arches her back, lifting up her hips to meet his thrusts. It just feels so wonderful to be filled up perfectly by Wade's humongous cock pounding her right now.

As the shaft seesaws in and out of her slippery orifice, her insides gripping the erection, the pretty teenager feels guilty for enjoying sex with another boy other than Tim. However, she reminds herself that Wade is taking her against her will and she and her friend aren't dating yet. That dork hasn't asked her out. The constant drilling of her pussy brings her back to focus on the massive tool sliding in and out of her snatch. It's making her sight go hazy as the blissful friction suddenly pushes her over the edge, making her climax with a shriek.

As the girl squirts all over his dick, Wade begins cumming, spraying his ejaculate inside her warm, soft cunt. His semen coats her womb as he keeps on pumping the teen full of his white, hot cum. He then lies down next to her, breathing a little ragged yet miraculously still hard. Now Emilia can just get up and put her skirt and panties on. She could simply leave right now. Yet getting away from Wade is now the last thing on her mind.

Staggering to her feet, his jizz leaking from her used cunt, she says "Let me clean you up" before kneeling down to lick from his glans down to the base. The girl kisses all over the glorious package, admiring his equipment as she runs her tongue all over into, lapping up her own juices. He smiles at her depraved actions as she wraps her lips around the tip, before sliding them down until half his cock is inside her mouth.

It takes her some more time but eventually the still horny girl manages to stuff his entire thing in, taking the upper part down to her throat. She then gives him a very sloppy blowjob, deepthroating the large guy for a few minutes. Cock is now her favorite taste. Once done fellating him, the teen detached her mouth from his groin, moving up to straddle his lap this time. "Want another round, baby?" Wade asks her.

Emelia doesn't answer but lowers her body, allowing his massive weapon to penetrate her cunt once more. This time it is much easier and she takes him in to the hint, resting on top of him before starting to ride. She bounces up and down on his pole enthusiastically, yelling out in bliss as she repeatedly impales her pussy with his spear. It is making her feel ecstasy as he drives his tool deep inside her canal.

Wade grips her large, muscular ass, thrusting his cock in her searing cunt, making her feel blissful friction with the large fuckstick as he fucks her nonstop. He pulls her up and down on his lap with his powerful arms, shafting the cunt aggressively. Suddenly, he flips over, rolling her onto her back as he gets on top again, before brutally fucking her much harder, making her shout suddenly as she has her second climax.

"Tell me what you what," he growls in a feral tone, slamming his hips into her, wrecking the tight box, tearing apart. His equipment is pillaging her, ravaging the curvy girl as he rams in deep into the confines of her fleshy channel. The teen enjoys the folds bunching around his turgid shaft as he keeps on doing her on the floor in the classroom, making her spasm with incredible sensation.

"Y Y You," Emilia cries out, thrusting upwards, desperating taking as much of the tool inside her snug cunt as she can, hands running up and down his strong back, clinging on to him.

"You want my big, fat cock, don't you?" Wade hisses.

"Yes! Oh, yes!" she groans.

"Say it!"

"I want it! Arggg! Please give it to meeeee!"

"Say that you want my big cock in your slutty pussy!"

"I want your big cock in my slutty pussy! Ahhhhh! Make me your slut! Fuck me, fuck me, fuck me!" Emilia cries almost hysterically as he flexes his hips, ramming the shaft entirely into her gaping hole. Eventually, he starts spewing many ropes of semen into her cunt again, spraying the inside walls of the tunnel like a firehose, triggering another orgasm from her as her pussy juice gushes out all over the floor.

Seconds later, the girl is astonished that Wade is still hard. She doesn't have time to think of it before he resumes drilling her pussy, pistoning in and out of the soaking cunt with his massive weapon. The beautiful athlete screams as he fucks her to her fourth orgasm, quickly followed by a fifth, making her squirt everywhere. Wade finally has his third climax, spewing the last strands of his ejaculate into her womb.

As she quickly mops up the juices from the floor, Wade tucks the giant snake back inside his pants. "So are you going to be my sweet girlfriend from now on?" he asks, confident of himself. "Gonna ditch that pathetic little wimp and have him masturbate thinking of you while we are banging each other senseless." He is certain she'd happily agree and is shocked by her response.

The female athlete just gives him a smirk. "Hell no. I can differentiate between love and lust. Timmy is still my only love. You are just a fuck buddy. We'll be friends with benefits and keep on fucking on the side, even after I've asked Time out, which is going to be soon," she replies, leaving him flabbergasted at her flippant, nonchalant tone as she leaves the room, heading outside.

Over the next several weeks, the two proceed to fuck like rabbits, with Emilia sneaking Wade to her house when her dad isn't around, knowing that her mom wouldn't mind it, as long as she doesn't find out it started with rape. From what she's heard, her mother actually philandered quite a lot back in the day, cheating on her dad all the time before stopping once it's clear that he wouldn't put up with it for much longer.

Her mother Louise confronts her about it one day. "Honey, you know I don't mind you being sexually active but aren't you in love with Tim?" Emilia snickers at this, making Louise frown. "Or was me and your father mistaken? We just assumed that you two have feelings for each other, but perhaps you only see him as a little brother. That'd be understandable as well, of course."

"No, mom, I don't see Timmy as a little brother," the girl sighs exasperatedly. "In fact, I love him and want to spend the rest of my life with him. I just find it funny when you are giving me heat for fucking one guy I don't love when you actually fucked multiple guys you don't love. Plus, I'm not Tim's girlfriend yet because he didn't ask me out, so I'm not cheating on him. You, on the other hand, cheated on dad by sleeping around after getting together with him."

Louise now smirks a bit, making her less experienced daughter frown. "Well, the thing is, sweetie, that's why he is with me today," she begins. "I fucked your dad as soon as we were old enough, before banging other guys. Once I fucked the shit out of him, he became addicted to it. He couldn't leave me even when he wanted to. But you are spreading for another guy even before you get together with Tim, which couldn't be good for you. He could find out and try to leave. You need to pussywhip him first, so that he will stay with you even after you've cuckolded him."

"I'll just fuck Timmy later," Emilia waves the concern aside dismissively, supremely sure of herself. "Don't worry about it. Even if he tries to reject me after this, I will simply remind him you own the company his parents work for. You stopped sowing your wild oats when you settled down with dad and had me though. So it's not like he is still a cuckold. Right?" To her surprise, Louise starts cracking up loudly at this.

"Actually I'm still banging other guys but he doesn't know about it. I really tried to stop but the temptation was too great. Even if your dad finds out he still wouldn't leave me though," she says, astonishing her daughter. "He loves me and I love only him. And one more thing," Louise calls out as her teenage daughter is about to leave the room. "You are a rich, beautiful girl. Just grab Timmy by the balls. He would let you." Emilia rolls her eyes. As if she needed being told to do that. The perverted teenage girl was already planning on cupping that oblivious boy's genitals anyways, even if he doesn't consent to it.

Emilia keeps on enjoying getting screwed by the powerful boy, letting him fuck her senseless for another couple of weeks before coming to a decision.

"I want you to give me a creampie before I go ask Timmy out this afternoon," she tells Wade as they have sex on Saturday lunch. Wade is driving his massive schlong deep into her tunnel, as her pussy strokes the tool, squeezing around it. She pumps his rod with her insides, the fleshy linings caressing his erection as he stuffs her with the spear. Her naughty request soon ends in a huge eruption from him as he unloads a batch of semen deep in her womb, filling up her vagina with his warm seed.

An hour later, she is at Tim's house. "Hey, Tim!" the girl greets him, her legs still trembling from getting fucked hard. With another boy's cum leaking out of her freshly fucked pussy, she asks "Would you like to go on a date with me?" He squeals excitedly, grinning as he leaps towards her, wrapping his arms around her tightly in a massive hug. Emilia is delighted by his response. The teenager now has everything she could ever want. Both the love of her life in her arms and passionate fucking with a hot guy.

"I love you Emilia," Timmy suddenly says, making Emilia gasp. "I've been in love with you for a long time now. But I never had the courage to say it." He looks at her with a smile, almost expectantly. It occurs to her that she should say the same thing back, but the girl couldn't find her voice. Emilia knows that she loves Timmy but is also feeling guilty about how she is going to keep on sleeping with another guy, and that she might not deserve the boy in front of her because of that. Of course, she could stop opening her legs for Wade, but she doesn't want to give up on those massive orgasms. Guess she'll have to try out Tim's cock first.

"Honey, you're so sweet. I, um, can't really say the same at the moment. But don't worry! All I want now is to spend a lot of time with you," she tells him earnestly. He is still giving her a shy smile, not looking too upset by her unwillingness to say those words. At least he can call himself her boyfriend now, and that is all that he needs. Timmy has absolutely zero idea that the girl he is now dating just had a creampie dumped in her snatch.

"That's okay. Come on. Let's go to have lunch at your favorite place today." The boy holds her hand, making her feel warm all over. She happily heads out with him, getting into the Aston Martin her mother bought for her birthday and driving off with Timmy sitting next to her. She is finally in a relationship with the boy she loves, even if she isn't ready to tell him she loves him yet.