Chapter 111. Olivia Rodrigo (Various Females X Reader)

November 30th - 11:41 pm

"Come on Liv, can't you wait another twenty minutes to do this?" Y/N asked his girlfriend Olivia, who had decided that this was the time to get all hot and bothered. He was shut up again by a hot and wet kiss though, and he wasn't exactly helping the situation by continuing to lock lips with her.

"No, I'm horny right now, it won't be the same if you make me wait twenty minutes." Olivia told him once their kiss broke once again. "I'm not even wearing underwear beneath this." She gestured to the cheerleader outfit from her good 4 u music video that she had shot several months ago, even going as far as to put on the latex gloves that went passed her elbows. "Come on, you know you want me baby."

Now that was the truth that she was speaking, he wanted her so badly, he had ever since he'd taken the No Nut November pledge for the Movember charity, having raised hundreds of thousands over the last month for the cause, and he had promised to triple the amount raised if he failed the No Nut November challenge, so one could see why he wanted to wait a little while before letting Olivia have her way with him.

Unfortunately for him, his body disagreed with his mind, having popped a huge tent as soon as Olivia had put her hands on him, and she had indeed noticed, because she'd moved a hand underneath his boxers and grasped onto his cock, loving the sharp gasp coming from him as she began pulling him.

"God Liv, did you have to wear the gloves as well?" Y/N complained, the friction between latex and his cock creating the sensation of a very rough handjob.

"You didn't mind the last time I used the gloves when giving you a handjob." Olivia reminded him. "I recall you blowing your load before I stopped teasing you that day."

"And I recall you used a load of lube that day." He reminded her with a grunt, placing his hands on her shoulders as she continued to rub his cock within the confines of his boxers. "Can you at least take it out of my boxers please?"

Olivia obliged his request, fishing his cock out, continuing to give him a rough handjob with her right hand, but now using her left hand to fondle his balls, running her latex covered fingers over every crease and surface of his ballsack, while her right hand stroked his cock up and down, feeling his veins pulse with every small squeeze she gave him.

Y/N wasn't going to last another five minutes, let alone twenty at this rate, he needed to distract her somehow, and what she said about not wearing underwear gave him a brilliant idea. He used his right hand to slide down her stomach and beneath her blue cheerleader skirt, wasting no time in burying two of his fingers inside of her, curving them and pressing them against her inner walls until he felt her physically shudder next to him.

"My god Y/N..." Olivia trailed off as she looked into his eyes, biting her lip as her grip loosened on his cock, her mouth hanging open as he continued to finger her relentlessly while standing with her until she was a puddle in his arms. "How are you so fucking good at this?" She questioned as she clenched her walls around his magical fingers.

"Because when I'm interested, I learn what to do." He whispered to her. "And you're so fucking interesting to me."

Suddenly, Olivia yanked his hand out of her skirt. "Lie down on the bed Y/N." She ordered him. "I'm going to sit on your face and you aren't going to stop until I get off." She informed him in such a commanding tone. "I might even suck you dry if you're doing a good job."

His mind had gone at this stage, he was sure he could last anyway, even if he burst at exactly 12am, that was considered successful. He lay down on the bed as he was told, with Olivia placing her thighs either side of his head, straightening out her skirt so that as she lowered, he was trapped without any light, the only thing he had to go off was experience in the way of having had Olivia sitting on his face before.

Y/N wasted no time in getting started, using his hands to grab Olivia by the hips and pull her into him even further, opening his mouth and letting his tongue drag across her wet slit, licking from her clit all the way down, moving his lips to drag across the sensitive bundle of nerves while his tongue licked her folds, moving up and down until he got the urge to stick his tongue inside as deep as he could, swirling it around on the inside while his hands gripped tight to pull her onto him, almost to the point where he could hardly breathe.

Meanwhile, Olivia had placed both her hands on his abdomen as she settled atop his face, allowing herself to let loose with her moans as he ate her out, head back and eyes closed as she let the heavens know how he was doing with his tongue. When his tongue went deep inside, her eyes shot open, her hips being forced down upon him, she helped out by grinding on his face until she noticed his throbbing erection almost staring at her.

Grinning deviously, Olivia leaned forwards as she grabbed a hold of his cock with her latex gloved hands, using both this time as she stroked him, using a twisting motion this time with both hands as they moved up and down his dry cock, just waiting to get wet and enduring the roughest, yet hottest handjob of his life. He bucked his hips with each twist of the hand Olivia made, almost beginning to fuck her hands in a way.

But this wasn't him in control, she was on top, his head was between her thighs and under her skirt, and his cock was in her hands, she was most definitely in control and in charge of this situation at hand. However, Olivia decided to be nice this time around, peeling her gloves off and tossing them to the side as she fully leaned over, placing her head right next to the tip of his cock, opening her mouth to blow a hot breath to make him shiver, and she felt it beneath her alright.

Olivia opened her mouth and letting her tongue hang out, she moved to the base and gave him a long and slow lick to the tip of his cock, then licking from the tip to the base on the other side, getting a taste of the balls that had been in her mouth on previous occasions.

Had this been any other man, she was sure that they would've blown their load all over her by now, but a combination of having done this before and Y/N's ungodly stamina from being an athlete made their sex lives so much better. It allowed Olivia to tease and edge him without the fear of him cumming too early and ruining the night, and it allowed her to open her mouth and take the head of his cock into her mouth, swirl her tongue without the fear of her choking on a sudden burst of cum.

As soon as her lips wrapped around his cock, his hips bucked slightly, his hands keeping a firm grip on her lower back and hips so that her wet lower lips couldn't escape his constant assault on her sensitive parts, and with this constant pleasure, she would hum her approval on his cock, her moans vibrating and giving him an even greater sensation, and in turn he would moan into her, the vibrations bringing her closer to climax and the circle of pleasure continued between them.

The harder Olivia went down on Y/N, using all her previous experience with him to suck, lick and attempt to drain his balls of every last drop of cum, the harder that Y/N worked to make her cum on his face and drench him in her juices.

The two of them worked perfectly in tandem to pleasure the living daylights out of each other, neither of them was willing to cave until Y/N cheated, inserting his fingers into her while he used his lips and tongue to pleasure her clit, with the pleasure forcing her off his cock and to straighten her back as she felt the full force of an orgasm built up.

"Y/N! Fuuuck..." Olivia let out a staggered groan as she came all over his face, rubbing herself all over his face as she ground out her orgasm atop him, not forgetting that he was still throbbing leaning over somewhat to jerk his cock furiously, feeling his veins pulse and throb as she gave him no mercy, expecting him to hold out.

"Fuck... Liv... please, I can't hold on..." Y/N begged her.

"You can baby, just hold out for me." Olivia told him, her soothing voice a stark contrast to what her hands were doing to him. "Just a little longer, I believe in you baby."

Y/N gripped the bedsheets as he desperately tried to hold on against her vicious pumping of his cock, he could feel himself about to burst until the alarm he set a month ago sounded and saved him, with Olivia immediately ceasing her stroking, leaving his cock pulsing and throbbing.

Y/N though, wasted no time in sitting up and moving Olivia off his face, instead moving to pull her atop of his lap, penetrating her with one quick movement as he pulled her down onto him so they were face to face.

"God you're so fucking hot Olivia." Y/N told her as he gripped her skirt to hold her down against him, keeping his cock buried deep inside of her. "I just wanna eat you up, every inch of you."

"I want you to fuck me baby." Olivia t0ld him straight up and she removed the top part of the cheerleading uniform she was wearing, pulling his head in to suck on her nipples, loving the way he ran his tongue over the sensitive nubs. "I'm feeling rather submissive and breedable after the way you ate me out and made me cum all over your face." She whispered into his ear.

"Are you sure?" He asked her carefully.

"I'm sure." She nodded. "Fuck. Me. Hard."

Y/N instantly connected their lips as he immediately began helping her bounce up and down on his shaft, grabbing fistfuls of her skirt as he practically threw her up and down his long and thick cock, the built up feeling of almost cumming beforehand not leaving as he bust a huge load into her within a minute of her riding him.

"Fuck Olivia." Y/N groaned as he kept her in place, grinding against him as they both came. "I'm going to fuck you so hard, all night, you won't be able to walk in the morning."

"Make it a week, and I'll let you put a vibrator in me in public." She challenged.

The rest of the night was a blur, he had fucked her in so many positions, missionary, doggy, standing carry, mating press, she squatted on his cock, and he pounded into her ferociously in the prone bone position.

The only two constants that remained throughout the night was that the two of them didn't stop cumming, and the cheerleader skirt remained on the whole time, he found it so hot to fuck her in that skirt, and he was definitely going to ask her to wear it more often during sex.

Safe to say, Olivia spent the next nine days walking with a limp as a result of the unrelenting pounding she received, and she was verbally obligated to have the vibrator inside of her until Y/N had gotten twelve minutes of use out of it in public.