Keira's Journey Ch. 01

Story Info
Keira finds a new dating app, and a new date.
7.9k words
4.83
5.8k
13

Part 1 of the 3 part series

Updated 04/12/2024
Created 12/31/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
EllySing
EllySing
38 Followers

"I'm telling you, it's dire out there," Keira said, stabbing her straw at the ice in her glass. "Dating apps are pointless, and every first date is the same." She pushed her empty glass away before sighing and leaning back against the wall, propping her heel on the edge of her seat. "It's all about what-do-you-do-for-work and where-did-you-grow-up and what-do-you-do-in-your-free-time... Dinner and a movie, drinks and dinner, coffee and a walk, you name it, I've done it, all the possible first dates. At some point, you hit diminishing returns."

"I'm telling you babe, you're better off without guys," shrugged the woman next to her. "Or at least that's what I tell myself. Goodbye Sheila-the-woman, hello Sheila-the-single-mother," she chuckled, rummaging through her bag for her phone. "No emergencies from grandma, so I have time for one more, then I have to get home before she brings the kids back. Got a date of my own, with the only dick I'll ever need.. spoiler alert, it's a dildo. Fancy another?"

"Go on, then. But I can't be bothered to go to the bar," Keira said, sliding her own phone out of her back pocket to scan the table's QR code. "What's the world come to," she muttered, "even goddamn pubs aren't immune to technology. I miss the good old days where you had to go up and figure out the complex social phenomenon that is queuing at the bar to order a drink, don't you?"

Sheila noisily slurped the last of her own drink and shrugged again. "Also why I don't date. There's a thousand dating apps, I'd have no idea where to start."

"Don't bother, they all suck."

Keira slid along the bench next to her friend. "You actually have a folder called dating?" Sheila snorted. Keira nodded, opening up an app at random, and flicking through the introductory messages she'd received recently.

"Check these out," she groaned, "this is the level of creepiness that is online dating nowadays: 'Hi tasty', now that one's actually fairly mild. Here's a good one: 'How do you look so innocent, and yet so wild?' And this one just says 'Do you like your ass licked?' which, I guess, is upfront..."

Sheila laughed, taking the phone off Keira to scroll through herself. She smirked and shot her friend a side eyed glance. "Well, Keira, do you like your ass licked?"

"That's neither here nor there," Keira sputtered, "the point is—"

She gasped as a waiter tried to inconspicuously set their drinks down, though she was sure she spotted a repressed smile as he took their empties away. His quick glance at her before he turned to walk back to the bar confirmed her suspicions, and she groaned as she slumped on the table, burying her face in her crossed arms. "I hate you," she mumbled to her laughing friend.

***

Keira laid in bed, aimlessly switching from one dating app to another. They really do all suck, she thought to herself, opening up the playstore. She scrolled through the apps in the Dating category, looking for one she might not yet have tried, one which might hold the key to breaking her out of this hellish cycle of first dates.

Even when first dates progressed past that, and turned into a sort of relationship, they all grew stale eventually. Often sooner rather than later. Once the honeymoon phase passed, Keira always realised something was missing. She got on with people well enough, had a fairly high tolerance for bullshit, but one thing she'd learned as she approached her thirties was that sex formed a big part of her needs. And sex was just... boring. Even one night stands, with no strings attached, which TV had promised her would be wild and satisfyingly sexy, were disappointing.

A new logo caught her attention, and she clicked on it without thinking much. The description was pretty short and basic, oddly devoid of any of the typical SEO-buzzwords. There were shockingly few reviews and ratings for the stated number of downloads. Ah, what the hell, can't be worse than the rest, Keira thought as she installed the app.

She quickly signed up, filled in the bare minimum to get her profile live - oddly, it did not require a photo, or a bio, but instead asked a number of seemingly unrelated questions, promising high quality matches through a proprietary algorithm. Keira answered without thinking too much about it - yes, her job required a fair amount of executive decision-making; no, she did not mind confined spaces; and she figured in the game of tag she'd rather be chased than the chaser. Unconvinced by how any of this related to dating, Keira finished up the questions, then set her phone to do-not-disturb and went to sleep.

***

NEW MATCH: DEVIN (D).

Match score: 96%.

Confirm?

Despite clicking around a bunch, Keira could not figure out how to access more details about this Devin, or what the D next to his name meant. Still, she figured this was what she'd downloaded the app for, so she tapped 'yes'. Within minutes, the app proposed a time and place to meet up later that same day. Keira tapped 'yes' again, the app chimed a confirmation, and left it at that. She had no clue how she'd identify this "Devin", but figured that was a problem for... 10 hours later, and got ready for her day.

***

Keira tugged up her dress's neckline, regretting her choice. She'd looked up the bar online to plan her route, and realised it was way fancier than she was used to. Unfortunately, her dressiest dress also happened to have a deeper decolletage than she remembered, and fit close enough to her body that she had to wear a thong.

This is officially the weirdest date I've been on, and it hasn't even started, she thought to herself as she walked up to the hostess stand. "Hi, I have no idea if he's here yet, but I'm supposed to be meeting someone called Devin? Sorry, I don't know his last name," she asked the hostess. Or even what he looks like, she carefully refrained from adding.

She was guided to a table off in a corner. Keira felt increasingly out of place; this was definitely not her usual kind of establishment. Every table was ensconced in its own booth with privacy curtains, and the plush fabrics absorbed the sound, masking any conversations around her as Keira crossed the bar to her table.

A man - Devin, presumably - was already seated. Keira thanked the hostess and slid in across from him, breathing a tiny sigh of relief as the hostess left the curtains opened when she walked away.

"Good evening, Keira."

Devin was... ridiculously handsome. It was as if he'd taken all the traits from all the men ever rated as 'sexiest man' by magazines like People and Heat, and mashed them all together. Then he smiled - a slightly crooked smile, with only his left cheek dimpling, the asymmetry of which was immensely pleasing - and Keira suddenly felt more nervous than she'd been on any of her dozens of first dates.

"Hi—" she cleared her throat and tried again. "Hi. Devin, I presume? It's nice to meet you... I think. Not gonna lie, I've never done a blind date before, and it's... weird." Keira paused for a second that felt like an eternity. "Weird in that it's not what I was expecting. Though I guess I wasn't expecting anything in particular, I guess I just didn't know what to expect. I guess I don't know much about you at all, really. It is Devin, right?" Jesus, Keira, shut the fuck up.

Devin chuckled and drummed the table with his fingers, slowly, in time with the mellow jazz music playing in the background. "Yes, that's me. I agree, it's a bit odd. To be honest, I've never been on one of these, either. So we can both be awkward together," he smiled again, and Keira's insides did a bit of a flip.

"Is my awkwardness that blatant, then?" she asked, feeling herself blush and hating herself for it. She was immensely grateful to the waitress who chose that moment to come place water on the table and hand them drink menus. Keira raised an eyebrow as she noticed hers contained no prices. "Ah, is this one of those places that's so fancy it's turned misogynistic?"

Immediate regret, she thought as she froze and raised her eyes to see Devin's reaction. Absolutely not first date talk - and definitely not first-five-minutes talk! She was relieved to see he simply laughed and took a sip of water. "Yeah, it's kind of rude to just assume I'll be paying. But," he winked, "I'll be paying. We're non-traditional enough as it is, don't you think?"

Keira frowned, unsure how to respond to that. She closed her menu and set it down on the table. "So, Devin, tell me something about yourself. Literally anything." She brought the glass to her lips, mentally placing bets with herself on whether he'd start with his current job or where he grew up.

"I like strong women, and I have a feeling I'm going to like you, Keira. You strike me as the upfront and headstrong type who likes a good argument." He looked straight at her, setting his elbows on the table and leaning towards her. "And I like winning those arguments," he added, holding her gaze until she chuckled and looked away.

"Well, that's not what I thought you were going to say," she murmured. She crossed her legs and tugged down at her dress. "I was more thinking about how many siblings you have, or where you're from, or something like that."

Devin sighed and leaned back. "That might have been what you were expecting, but I don't think it's what you're looking for. Either you and I click, and we can learn all of that later. Or we don't, and there's no point in learning it now."

Keira cocked her head. "I... actually agree. But isn't that what 'clicking' is? Talking about trivial nonsense to see if there's a spark of something more?"

The waitress interrupted their conversation as she arrived to take their orders - Keira ordered a red wine, one she'd picked based on the name sounding kind of nice, as opposed to her usual method of picking whatever was cheapest, and Devin asked for an Old Fashioned.

"Spark isn't trivial nonsense, Keira. Trivial nonsense is easy to connect on. Spark is deeper, more foundational to who we are, to what we are." Devin lowered his voice, and an edge creeped in. "Spark isn't brains, Keira, it's blood; blood screaming inside you to work its will."

Keira had been taken in, leaning forwards, but that last sentence shook her out of her focus. "That's... that's a quote from Buffy the Vampire Slayer," she smirked.

Devin smiled and laughed, the edge leaving his voice instantly. "Yes it is - but you see! Trivial nonsense connection achieved."

"Let's say I agree," Keira said, setting one elbow on the table and leaning her chin in her hand. "How do you measure spark, if not by shared knowledge of TV show trivia?"

"That's easy," Devin replied, sitting up straighter and holding on to his glass of water with both hands. "Two easy steps. Step one is first impressions. Do we find each other attractive?" He leaned forwards, his hand barely grazing Keira's elbow. "I think you are absolutely gorgeous."

Keira's breath caught in her throat - she wasn't used to this level of openness. This didn't feel creepy like those messages on the apps, this felt... genuine. She was sure there was an agenda to it, but hell, she was here already, might as well go with it. "Well, obviously you're attractive too. Have you seen your face?" she asked, chuckling to dispel some of the awkwardness she felt.

"So, step one complete," Devin continued in the same tone, unfazed. "Step two is putting those first impressions to the test. We go home, and we have the best sex of our lives."

Keira felt her face instantly heat up, her heart speeding up at the idea, and looked off to the side, suddenly conscious of the open curtains by their booth. Devin kept his gaze on her, his fingers still resting lightly on her arm. She spotted the waitress approaching with their drinks, once again thanking her lucky stars for her perfect timing.

Devin finally took his hand away, taking his drink and gently swirling it around, making the ice clink on the glass. "Still, I'm not a complete animal," he said. "We can have one drink, and talk about anything you'd like. And then I'll escort you outside, and whether you get in my Uber or yours is up to you," he smiled, holding up his glass to her.

Keira looked him over thoughtfully. She grabbed her own glass and held it up to his. "Cheers, then," she smiled lopsidedly, and took a sip. "So, what other TV shows can you quote?"

***

Keira stood in front of Devin's open door. This was it, point of no return - or, well, not really, she could always leave at any point. The thought bolstered her and she stepped through, shutting the door behind her. She turned around, surprised at how normal Devin's apartment felt. She'd assumed it would be big and empty, kind of sterile, with brushed steel shelves filled with empty oddly shaped vases.

Before she could look around more, Devin stepped up to her and set a hand on her hip to pull her in to him. His other hand rested on the back of her head, fingers in her hair, and he gently angled her face up towards him. God, he really was gorgeous, especially up close. She let her eyes take his face in, his intense eyes boring into hers, his high cheekbones, following the curve of his jawline, and those lips... She leaned in, suddenly desperate for a kiss.

Devin responded instantly, his fingers tightening on the back of her head, the hand at her hip sliding to the small of her back to pull her in more. Keira's own hands found her way to his body, feeling the muscles in his back shift and tense under her touch, finding herself melting into his embrace.

She tentatively parted her lips, and once again he responded, reading her mind, flicking his tongue out to meet hers. His hands gently slid along her body until he found her dress's zipper, and pulled it down in one smooth movement. Without breaking their kiss, he slid it off her shoulders, and she helped him push it past her hips to let it pool at her feet.

Finally he stepped back, both of them panting slightly, and he looked her up and down. Keira blushed and took a step forward, wanting to close the distance between them, but he shook his head. "No... let me look at you, Keira. You are beautiful, this is a body that deserved to be admired."

She scoffed and stepped forwards again, and this time he let her, as her lips found his once more. One more step and she had his back to the wall, her fingers working to undo his buttons. She wound her hands inside his open shirt, fingers brushing his chest, feeling every ridge and edge, feeling his muscles contract as he groaned and pulled her in to him again.

Within seconds, his hands had found the clasp of her bra and undone it, and she let it fall to the floor. Devin groaned and picked her up. She kicked off her shoes and wrapped her legs around him, her arms holding on to his shoulders. He carried her through to the bedroom without breaking his pace and laid her on the bed.

She broke the kiss and looked at him leaning over her, the hunger in his eyes an exact reflection of the fire inside her. He smiled, and her fingers brushed that left-cheek dimple as she responded in kind.

Keira went to pull of his shirt, wanting to see more of him, wanting to see all of him, and he tutted. "Not yet, not yet..."

His hand brushed her hair out of her face, and he kept his lips tantalisingly just out of reach as Keira buckled to try to kiss him again. She could feels his breath on her, ragged and uneven, and his hand trailed down her face, her neck, brushed her exposed breast, followed the curve of her waist and found its way to her hips. He hooked a finger in her thong and tugged at it.

Keira lifted her hips, and Devin growled. "Fuck, I want you, now."

In a flash he pulled her thong down and grabbed her hips to pull her to the edge of the bed. Keira gasped and tried to sit up, but he set one hand on her chest and firmly pushed her back down, his other hand resting on her inner thigh, guiding her legs open.

His fingers brushed her pussy and she flinched, surprised at the intensity of the feeling shooting up inside her. "Shh, it's okay baby," he whispered, the hand pinning her down softening and brushing gentle circles on her stomach. "Just relax," he looked up at her, and she nodded, letting her head fall back onto the bed.

Devin gently spread her lips and moaned. "Beautiful inside and out, you are," he murmured, then leaned in to kiss the crease of her thigh. He slowly worked his way inwards, spiralling every closer to her pussy, his breath sending shivers up her spine.

Finally his tongue lapped at her entrance and she moaned, crossing her arms over her face. "Fuck, Devin," she groaned. His only response was to push his tongue in further, tasting her, feeling her pussy respond to his touch. He slid his tongue up, between her lips, finding the small nub of her clit and giving it a slow lick.

Keira gasped and bucked her hips, causing Devin to grab them with both hands to pull her in close to his face. His tongue circled her clit, slowly, carefully, until she relaxed and melted back into his arms. He rested her back on the bed, one hand finding its way back to her pussy.

He teased at the entrance to her pussy with a fingertip, carefully judging her reactions, feeling her wetness. She moaned softly, gently grinding her hips in time with his tongue, and he pushed his finger in further. "God, yes," she murmured, her voice still muffled by her arms covering her face.

Devin slowly fingered her, shifting and turning his finger inside her, feeling every part of her. When he inserted a second finger, Keira gasped loudly, extending her arms out to grab fistfuls of the bedsheets.

He smiled into her pussy, and started licking her clit faster, flicking the tip of his tongue over it as his hand worked in and out of her. He felt her pussy clench around his fingers and kept up the pace.

Keira's thighs clenched and tightened around his head, and still he continued, his fingers pumping in and out of her, his chin coated in her juices as he kept his tongue pressed to her.

"Oh God—" Keira moaned, her breath catching in her throat, her eyes flying open. She could feel it building. She could feel the rhythmic contractions of her pussy, gripping Devin's fingers, she could feel the tightness building in her core. She glanced down.

There he was, looking up at her, his face buried between her legs but his eyes locked on hers. The wild hunger in his eyes sent her over the edge, and she felt herself tipping over, the tightness inside her suddenly releasing and sending waves through her body.

She threw her head back and a low growl escaped her throat.

And still he continued.

Keira didn't know if this was one long orgasm or several in a row. When one wave of pleasure ended another immediately took over. Her body begged her to continue, wanting more, but every part of her was on fire. "I... I..." she stuttered, unsure even what she was trying to say. "S—stop," she managed to get out, "Stop."

She gasped as all feeling retreated immediately. Devin lifted his head, breathless, and slowly removed his fingers from inside her. He stood over her, looking down at her naked form, all trace of the wildness she'd spotted earlier gone from his eyes.

He slid an arm under her shoulders and one under her hips, shifting her up on the bed to come rest on the pillows, pulling a soft blanket over her and lying down next to her. "Are you okay?" he murmured into her hair as he pulled her close.

"Yeah," Keira breathed out, feeling her heart return to a semi-normal rhythm. "Just... give me a minute, then I'll do you," she mumbled, shifting to fit her body to the shape of his.

"No baby, not today," Devin chuckled. "You said 'stop', and until we've agreed on other words, that one is sacred." He brushed her hair and softly kissed her ear. "You relax, now."

EllySing
EllySing
38 Followers