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First Date Jitters Pt. 02

Story Info
Charlie's date with Oliver takes another unexpected turn.
1.8k words
4.52
30.3k
57

Part 2 of the 2 part series

Updated 06/09/2023
Created 11/22/2019
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"Don't tap out on me now, darling," Oliver said with a wicked grin. "I'm almost ready for round two."

He climbed off the bed and made his way toward the bathroom. Charlie closed her eyes and listened as the water ran behind the closed door. She thought she heard the sound of his voice and, thinking he must be talking to himself, let herself fall asleep.

***

Charlie woke again to Oliver taking off her shirt and bra. She whimpered as she felt him licking and pinching her nipples. He put his hand back between her legs, alternately rubbing her clit and slipping her fingers inside her.

"Still so wet," he murmured. "Do you want my cock again, darling?"

When Charlie felt a tongue against her clit it took her a moment to realize there was still a tongue against her nipple. She opened her eyes with a start and was horrified to see a complete stranger sucking and tweaking her nipples while Oliver licked her pussy.

"What the-who are you?" Charlie could barely get the words out. She tried to wriggle away but her body wasn't cooperating.

"Relax, gorgeous," the stranger said, kissing her neck and earlobe. "I'm Jack."

Charlie suddenly remembered what Oliver had said about bringing a friend.

"I could tell how much you wanted two cocks when you let me play with your arsehole," Oliver said, grinning at her from between her legs. "Don't pretend you don't want both your holes filled."

"No, I-"

Jack kissed her hard on the mouth just then, cutting her off, while Oliver continued licking her clit. Charlie realized they were both stroking their cocks.

"Don't worry, darling, we'll do all the work," Oliver said. "You just lie back and enjoy it."

As they fondled and teased her Charlie had a difficult time convincing herself she wasn't enjoying it. It felt wrong for two strangers to be touching her like this, but part of her liked the sensation of being used and having so many hands and mouths all over her body. It didn't hurt that Jack, dark-haired and a little taller than Oliver, was just as handsome as his friend.

Oliver began fingering her harder and Charlie knew it wouldn't be long before she came. Jack seemed to notice her breathing quickening and sat up and climbed up onto her chest, straddling her face.

"I want to feel you moan on my cock," he said as he brushed her hair out of her face. He pulled her mouth open and slid his cock inside, muttering "fuck" as he thrust in and out.

Charlie lay there as Jack fucked her mouth, thankful he was at least being gentle. She could feel his cock growing along with her orgasm as Oliver's mouth pushed her over the edge. Jack's cock moved deeper down her throat as she moaned.

"Let's switch," Oliver said suddenly. "You've got to feel how tight she is."

Oliver and Jack swapped places, the former sliding his cock into Charlie's still open mouth while the latter pushed his inside her pussy. Charlie hadn't realized until now but Jack's cock must have been at least an inch longer and around than Oliver's.

"Fuck, she is tight," Jack said, groaning as he fucked her.

Oliver's cock wasn't stretching her mouth as much as Jack's had but she was still having trouble not gagging, especially since he seemed determined to get as deep into her as he could.

"I told you, mate," he said to Jack, holding Charlie's head in place by her hair with one and groping her tits with the other. "Wait 'til you feel her arsehole."

Alarmed, Charlie tried to object but was held firmly in place, her body's only movements caused by the cocks plunging in and out of her.

Oliver pulled his cock out of her mouth, leaving her gasping, a stream of spit falling from her lips. He reached over to the table next to the bed and picked up what appeared to be a small glass of water.

"Here you go, darling, drink this," he said, handing it to her. Jack stopped fucking her for a moment to let her drink.

Charlie, who hadn't had any water all night, downed the glass in one go - realizing a split second too late that she'd been given not water but vodka.

"That's a girl," Oliver said, setting the empty glass back down as Charlie sputtered. "You want to keep the party going, don't you?"

The vodka hit Charlie hard and quick. Her head spun as she fell back onto the bed, limp, and barely registered it when the men flipped her onto her stomach. Oliver stood next to the bed and pulled her over so her head was hanging off of it, making it easier to fuck her mouth once more, while Jack slid his cock into her pussy as she lay prone. Moments later he put his thumb into her asshole, pushing deeper until it disappeared from view. He fucked her ass with his thumb for a bit, Charlie involuntarily moving back against, wanting to feel it deeper inside her. After swirling it around to try to stretch her out, Jack pulled his thumb out and replacing it with the head of his cock.

Charlie groaned against Oliver cock, unable to cry out.

"Fuck yes, drool all over my cock," Oliver said as she gurgled.

Jack reached down to her pussy and put his fingers inside to cover them in her juices, which he used to lubricate his cock and her asshole. He pushed into her slowly, enjoying the view of his cock stretching her out.

"Fucking hell," he said once he was fully inside her. "Her arse feels incredible."

It took a while of him thrusting in and out of her while rubbing her clit, but eventually Charlie's pain subsided and she started to enjoy the feeling of being fucked in the ass.

Jack made a flipping motion with his hand to Oliver, who helped him maneuver himself onto his back while keeping Charlie on his cock. She laid against his chest, her head resting over his shoulder as he continued to fuck her from below.

Oliver kneeled in front of them, spreading open her legs and sliding his cock along her slit, slapping it against her clit. She moaned softly.

Jack stayed inside Charlie but remained still for a moment so Oliver could sink his cock into her pussy. They quickly found a rhythm; as Jack pulled out, Oliver pushed in, and vice versa.

"God, she's still so wet," Oliver moaned, rubbing her clit with his thumb. He leaned down to whisper in Charlie's ear. "See, I knew you wanted this," he said, caressing her tits with one hand and holding her throat with the other. "I knew you were just a horny little slut who wants nothing more than to lay back and have her holes filled."

Oliver's words and thumb, moving more and more quickly against her clit, and his and Jack's cocks moving in sync inside her were too much for Charlie. She felt yet another orgasm rising, more powerful than the previous ones.

"Going to cum again, darling?" Oliver whispered, his breath hot as he kissed her neck. He and Jack started fucking her faster. "That's it, cum all over our cocks like a good little whore, let us feel your pussy and arse tighten on us, you fucking slut."

That was it for Charlie. A wave of drunken bliss washed over her as her pussy squeezed down on Oliver and Jack's cocks.

"That's a good girl," Oliver said, sitting back up and holding his cock inside her to enjoy the feeling. "Fuck yes, keep cumming, slut."

When Charlie's body had finally stopped writhing, Jack and Oliver pulled out of her holes and turned her over so she was on her knees straddling Jack. He lowered her onto his cock and spread her ass cheeks. Oliver didn't waste any time thrusting his cock into her asshole.

"Christ," he breathed. He couldn't believe how tight it was, even after taking Jack's cock just moments before.

The men began fucking Charlie in rhythm again. She couldn't hold herself up, so Jack held her up, his hands on her tits, while Oliver pulled her arms back.

"You look like such a good little whore, taking our cocks," Oliver said, watching his cock slide in and out of her. "What do you think, Jack, maybe we should we post our little video to Reddit?"

Charlie must have managed a small noise of confusion because Jack took her face in his hand and turned it so she could look at the table next to the bed. Oliver's phone was propped up and facing them. Charlie had no idea when he'd turned the camera on.

"No," she whispered, even as her pussy clenched at the thought of people watching her be fucked like this.

"Don't you want everyone to see you letting us use your holes?" Oliver asked, as if reading her mind. "Just imagine all the men you'd make cum as they watched you get fucked over and over. In fact, let's give them a close-up, shall we?"

Jack let Charlie drop onto his chest and grabbed the phone off the table. After handing it to Oliver he put his hands on Charlie's ass and spread her cheeks while Oliver recorded their two cocks filling her.

"Oh god," Jack said, fucking Charlie's pussy faster. "Fuck, I'm going to cum."

"Fill up her fucking pussy," Oliver said, in turn fucking her ass faster. "I'm going to cum in her arsehole again. That's what you want, isn't it, you fucking whore, to be dripping with cum?" he asked Charlie, who was panting like a dog by now, a small line of drool hanging out of her mouth.

In a matter of moments the men were both gasping and breathing hard, and Charlie could feel their cocks throbbing and leaving ropes of hot cum inside her.

They were all still for a minute, breathing hard, until Jack pulled out of Charlie's pussy and headed toward the bathroom. Oliver pulled out of Charlie's ass and slid out from beneath her. He laid beside her, reached down between her legs, and dipped his fingers into the cum seeping out of her holes, recording it all with his phone.

"Sorry about that, love," he said, slipping his cum-drenched fingers into her mouth. "To be fair I told you I wouldn't cum in your pussy, but I didn't say anything about Jack."

"The video-" she mumbled, making a feeble attempt to grab the phone.

"Oh, don't worry, we're not really going to put it online," Oliver said, grinning at her again. "It's for our private collection, to watch and wank to whenever we please. I'll send it to you so you can see just how much of a slut you've been."

Charlie closed her eyes, her head was still spinning. She couldn't let herself think about this; she needed to sleep. She didn't know how much time had passed by the time she started to nod off and suddenly felt Oliver and Jack's hands on her again.

"Come on now, darling, the night's still young," Oliver whispered in her ear, and she moaned as Jack put his cock inside her yet again.

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5 Comments
merrySMmerrySMabout 1 year ago

What a slice of heaven. Need to read more of your stories.

AnonymousAnonymousalmost 2 years ago

I love a good fuck wear the guy talks dirty. It's surprisingly hard to find. Thanks

AnonymousAnonymousabout 2 years ago

I can tell that this will be one of my go-to guaranteed to make me cum stories. Loved it and all of your stories and hope you will write more. Thank you!

AnonymousAnonymousover 4 years ago
Chapter 3 please!

Awesome writing. Don't stop!

AnonymousAnonymousover 4 years ago
Chapter 3?

Do you plan to continue this story? I love it! One of the best nc out there

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