First Date Jitters

Charlie looked at the time on her phone and bit her lip, wondering when her date would arrive. She'd gotten to the pub early, and so he wasn't late, but she felt anxious all the same. It was her first time meeting someone off of Reddit so she was extra on-edge, and had decided to take a shot of whiskey when she first got to the bar to try to calm her nerves. The bartender smiled at her affably and poured her a double.

Back at her table, Charlie opened the camera on her phone and gave herself a quick once over. She'd worn her long dark hair down in waves and stuck to fairly minimal makeup: just mascara and a matte red lipstick.

She had no idea that in a matter of hours the lipstick would be smeared around her mouth, the mascara would be streaking down her cheeks, and cum would be dripping out of her asshole.

***

"Charlie?"

Charlie looked up from her phone, embarrassed to be caught checking her makeup. Her date, Oliver, stood before her. She'd worried she might be catfished, but Oliver looked just as he did in his photos: handsome, tall, and slim, with red hair.

"Hi," Charlie said with a smile. She stood up and gave Oliver a hug. After they grabbed a couple drinks from the bar, they returned to the table and started chatting.

Charlie and Oliver had met on Reddit about a month earlier, after she'd posted in a travel sub looking for things to do on her vacation in London. He lived just outside the city and commented with a few ideas, then messaged her privately. They were both in their mid-twenties and hit it off pretty much right away. It wasn't long before they moved the conversation to Kik and got flirty with each other, sending the occasional racy photo. (Charlie refused to send nudes, opting instead for pictures of herself in cute lingerie.)

The week before her trip Charlie had asked her if she wanted to meet for a drink while she was in London. She agreed, and checked out the area she was staying in on Google Maps and found a bar a block from her Airbnb, figuring if she wanted to end the date early she wouldn't have to travel too far.

***

After Charlie told Oliver how her trip was going and he suggested a few more places she should visit, she began to relax a bit more. The beers they'd ordered definitely helped, making her feel more flirtatious than usual. She playfully swatted him on the chest a few times when he teased her and at one point grabbed his hand to pretend to read his palm, tracing the lines with her finger.

"Are you staying around here?" Oliver asked once they'd finished their second round.

Charlie nodded. "I'm in an Airbnb nearby."

"Cool." He paused. "Do you want to go hang out there for a bit?"

"Um," she said, trying to buy herself some time. She didn't really know Oliver that well, but she was having fun and would be lying to herself if she said she didn't want to at the very least make out with him.

"Okay, yeah," she finally said, smiling.

Oliver settled their bill at the bar, and after they stopped inside the small market next door to grab a six-pack of beer, they made their way up the street to the Airbnb.

Once inside, Charlie put on one of her Spotify playlists and they settled on the couch with their beers. They were talking about the places they'd traveled and where they'd like to go when Oliver suddenly took the beer can from Charlie's hand and kissed her. She was a bit surprised at how abrupt he'd been but kissed him back. He stroked the side of her face, his hand traveling down her neck, squeezing her arm for a moment before moving to her breast.

Charlie began to protest but Oliver kissed her more deeply, circling her nipple with his thumb through her shirt and holding the back of her head with his other hand. She shuddered a bit, enjoying the sensation.

Oliver moved his mouth from her lips to her neck, slowly kissing it and making her softly moan. He took this as a sign that she wanted more, so he hoisted her up over his shoulder and carried her into the bedroom, despite her cry of alarm.

It wasn't until he laid her on her back on the bed that Charlie realized she was drunker than she'd thought. She'd forgot about the double shot she'd had at the bar before Oliver arrived. The alcohol, combined with the growing pull she felt between her legs, was making it hard to tell Oliver to slow down as he unbuttoned the top half of her shirt and lifted her bra, exposing her breasts.

Oliver ran his hands and tongue over Charlie's bare tits, causing her pussy to clench. She longed for him to move his hand inside her panties but also desperately wanted him to stop. It was all too fast.

"Maybe we shouldn't—" she managed to say.

"Relax," Oliver whispered, gently pinching her nipple before licking it. He slowly dragged his fingers under her skirt and up her thigh until they reached her panties, gently prodding her hole through the damp fabric.

"It seems like you're enjoying it," he breathed into her ear. He pulled her panties to the side and ran his finger along her slit. "You're all wet for me."

Charlie whimpered. She was enjoying it, but also didn't know if she wanted to have sex with Oliver, and it seemed like that was the direction they were headed.

"I just don't know if we should do this," she said, pushing his hand away from her pussy.

"I think you know," Oliver said softly, bringing his finger to her mouth and spreading her wetness over her lips. "I can feel how much you want it. It's okay, just let it happen."

He put his hand back between his legs, this time sliding two fingers inside her. Charlie's back involuntarily arched as she moaned.

"See, look at that? You're so wet I was able to just slide right in." Oliver kissed her neck again. "Let's see how easily I can slide my cock in, hmm?"

"Wait—" Charlie said, but Oliver was on his feet, unbuttoning his jeans and dropping them. He was already hard. He pulled off her skirt and panties and kneeled in front of her, spreading her legs and holding them open.

"Condom!" Charlie gasped as he positioned the head of his cock against her hole.

"Don't worry darling, I won't cum in your pussy," Oliver said, and pushed into her.

Charlie couldn't stop herself from moaning, just as much out of pleasure as pain, as he pumped in and out of her pussy. His cock wasn't huge but it was bigger than average, and it had been a good while since she'd had sex.

Oliver breathed hard as he thrust into her. He let go of her legs to pull off his shirt and discard it on the floor.

"God, you're so tight," he said, moaning and running his hands over her tits. "I knew you wanted this from the moment I set eyes on you. I could tell what a slut you are from those photos you sent me."

Charlie could barely take in what he was saying. She was panting by now and could feel the pressure of an orgasm building deep within.

Oliver suddenly pulled out of her and flipped her over, lifting her ass into the air. He plunged his cock back inside of her and gripped her shoulders with both hands. She didn't have the energy to prop herself on her elbows so she just lay there, one side of her face pressed into the bed, her tits swaying as he pumped in and out of her.

"Fuck, my cock looks so good thrusting in and out of you," he said, quickening his pace. He moved his hands to her ass and spread her cheeks apart.

Charlie jumped when she felt his spit hit her asshole, followed by what had to be one of his fingers.

"Don't—" she began to say, but he'd already sunk his thumb inside her.

"Oh god, yes," he gasped. "You like having both your holes filled, don't you? Such a good little whore, taking me in your pussy and arse at the same time. I should have brought a friend along, we could have each taken a hole."

Charlie couldn't deny that it felt incredible and both hated and loved how dirty she felt in that moment. She barely knew Oliver and yet here he was, fucking her raw with his thumb in her asshole, talking about double-teaming her with someone even more of a stranger to her than he was. Her pussy began to tighten and she knew she was about to orgasm.

Oliver could tell too. "Fuck, yes, cum on my cock, you filthy little slut, cum for me. You love the thought of taking two cocks, don't you?"

Charlie clutched the bedspread in her hands as she came, juices pouring out of her and onto Oliver's cock.

"Yes darling, that's it, that's it," Oliver moaned. "Squeeze down on my cock, make me cum, whore."

Charlie's pussy continued to pulse as Oliver pulled out of her pussy one more time and pushed the head of his cock into her asshole. She cried out and tried to move away but he held her in place as cum spilled out of his cock into her.

"Fuck," Oliver said when he'd stopped cumming and rolled over onto his back. "That was incredible."

Charlie, exhausted and feeling both violated and more turned on than she'd ever been before, toppled over to her side. Oliver's cum began to leak out of her and onto the bed.

"Gorgeous," Oliver said, and when Charlie looked at him she realized he had his phone out and was filming his cum dripping from her asshole. She couldn't even bring herself to protest and vaguely wondered if he planned to post the video to Reddit.

Oliver snuggled up behind her and began spooning her. The combination of being drunk and post-sex sleepiness was too much for Charlie. She began to doze off just as Oliver started running his hands over her body. He rolled her over onto her back and gently sucked on one of her nipples.

"Don't tap out on me now, darling," Oliver said with a wicked grin. "I'm almost ready for round two."