Kat's Casual Encounter

Kat finished reapplying her lipstick -- Urban Decay Slowburn -, tossed it into her purse, and stood back from the mirror to get a good look. She liked what she saw -- in her jeans (not too tight), a dark-pink scoop-neck top, and a black velvet jacket, she looked both casual and pretty fucking cute if she did say so herself. The kind of get-up that would get her plenty of attention from whoever she was talking too, without showing off her goodies to everyone in the room. Speaking of which- she carefully adjusted her shirt, making sure it showed enough creamy cleavage without being outright slutty. Then she grinned to herself, hooked her fingers in the neckline and gave it a sharp downwards tug. Perfect. Kat had spent longer than she'd like to admit choosing which bra to wear -- in the end she'd gone for one of her slightly-too-small ones, to really put her assets front-and-centre. A little uncomfortable, but hopefully worth it by the time it was coming off. Now she was really showing some skin, but with the jacket over the top she wouldn't look too slutty. Probably.

That done, Kat pulled out her phone and checked the time -- her date should be out there by now. She blew herself a kiss for luck, then headed out of the ladies room to track him down.

She looked around the spacious room, hoping to recognise him from his photos on the dating app; her pictures hadn't been entirely accurate, so she couldn't rely on him spotting her. It was a pretty nice place, if kind of uninspired; yet another perfectly ordinary venue trying to chase the spotlight with Instagram-inspired décor and fancy cocktails. At least this one didn't have chalk-painted furniture and mason jars in every corner. Still, with Roxy Music playing on the jukebox and a scattering of other customers chattering quietly it felt pleasantly chilled out.

In his last message, he'd said to meet by the bar, so- was that him over at the far end? Alone, and he seemed to be periodically looking round for someone, so probably. Kat headed over, checking him out in what was hopefully a discreet fashion. Handsome Asian guy, not so tall but broad-shouldered in a flatteringly-cut suit -- he fit the bill alright. Well, there was only one way to find out.

"Dan?" He smiled and nodded. Damn, he was even better looking than she'd expected! Why were so many guys unable to take a decent photograph of themselves?

"You must be Katherine! How-" He gave a vaudeville-worthy double-take. "Wait, are you-"

"Yes, I am, and don't make a fuss about it." Kat looked him straight in the eyes as she said it, an unmistakeable warning in her tone.

"Uh, sure, sure." He blinked, and began a doomed if noble attempt to maintain eye contact. "You look," he looked back up at her face, realised she knew he'd been looking down her shirt, and looked away entirely. Cute, really. "You look, uhm-"

"Oh thank you!" Kat gushed in her most saccharine tone, "You look very, uhm too."

Dan grinned helplessly. "Hey, is the suit too much? I feel kind of overdressed."

"No, no" she said, reaching over to brush an imaginary speck of dust from the lapel, "Well, maybe a little, but-"

"Honestly, I just enjoy wearing it."

"Well, you should never pass up an opportunity to do something you enjoy."

"I'll drink to that!" Dan turned and signalled the bartender. "What would y-"

Kat looked right past him. "We'll have a whiskey and soda and a Cosmopolitan. Please."

"Coming right up!" As the man mixed and poured the drinks with practised ease, she realised Dan was watching him with interest. She tapped him on the shoulder and tilted her head quizzically.

"Oh, I like to watch people do things they're good at," he explained, "always a pleasure to see an expert at work."

"I wish!" he laughed, placing the glasses on the polished mahogany bar-top along with Kat's change; but as he withdrew to a polite distance, she could see him smiling broadly. Kat liked that.

"How did you know I liked whiskey?"

"Oh, it says so on your profile, remember?" Kat replied, handing him the cocktail glass.

"You know, I've actually never tried one of these?" He sipped the red-pink cocktail, then gave a small nod. "Cheers!" The two of them clinked glasses. "Like your jacket, by the way."

"Thanks, it's-" she took a sip of her own drink, "-ahhh- yeah, it's vintage."

"Ah, so what does that actually mean?"

"Umm, I think that the person I bought it from found it in a thrift shop?" She held her arm out to him. "Feel how soft it is!"

A little hesitantly at first, he stroked the black material with his fingertips. "Oh, that's nice . . ." Kat could read him like a book; so self-conscious it was adorable, clearly wanting to touch her more and not wanting to go too far. Damn right too; being overly forward was her thing.

As she pulled her arm away, she shrugged the jacket back a little to expose more of her chest, then looked over at the bar, pretending to read the cocktail lists so Dan could get an eyeful. Of course, since there was a full-length mirror on the wall, Kat could see him practically drooling. She had to bite her tongue to keep from laughing out loud; when she turned back he was visibly blushing. Wrapped around her- well, maybe not her little finger.

The two of them finished their drinks, ordered another round -- a Black Russian for him and a White for her -- then went to sit down. Kat steered him towards a table in a secluded corner, where they'd have a little privacy, and for a while they made amiable small talk.

"-no, I mean I love acting, but there's so much downtime, for every ten minutes of actual acting there's like hours and hours of just waiting."

"Funny, my dad says something similar."

"He was in show business?"

"No, the 82nd Airborne."

Another ten minutes or so, and Kat was sure she'd swiped on the right one. Fuck it. Time to commit.

"Hey, Dan?"

"Yeah?"

"My boobs are down there."

He looked immediately guilty, like a puppy that's chewed your slipper. "I, uh, . . ."

Kat rolled her eyes theatrically. "I know you wanna look at them! You practically dove face-first into my cleavage the moment I walked up to you!" Twisting the knife a little.

"Well-"

"Seriously." She arched her back a little, pushing her ample assets out at him. "Take a good look." He did, obviously relieved to not have to pretend any more, leaning in until she half-thought he was going to just bury his face in them right then and there. The moment stretched out in silence, until Kat burst out laughing. A couple of seconds later Dan was too.

She let him finish, then said "You finally stopped blushing! I guess the blood has gone somewhere else, huh?" and was rewarded with a helpless goofy smile. "Oh no, there it is still. Maybe I should have flashed you?"

Dan downed the last of his drink, shook his head in disbelief. "Do you do this a lot?"

"What, trawl dating apps for anonymous sex?" She made a see-saw motion with her hand. "Not a lot, but you know, I get bored easily."

"What's anonymous about it? I know who you are!" He picked up his glass, apparently hoping he might have missed some. "Actually, when I saw your pictures on the app I did kind of think you looked like- well, you."

"Amazing how different a girl can look just by tying her hair back and wearing glasses."

Dan held up the empty glass, and in a surprisingly-decent Humphrey Bogart drawled "Why Miss Dennings, you're beautiful!" She drained the last of her own drink, briefly cursing herself for not having 'accidentally' spilled a few drops on her chest.

"You know you're actually much handsomer in person? You should really get better pictures." She settled for wiping the last few creamy drops up on her little finger and licking it clean. "Although at least none of your pictures were of your cock."

"Is that as bad as people say?"

"Dozens of the fucking things every time I use the app. And I mean, I love cocks and all, but that's not the point." A waitress materialised over her shoulder, picked up the empty glasses, and glided away. "Oh, she was right behind me, wasn't she?"

"When you were talking about loving cock? Afraid so." Dan's smile just failed to turn into a smirk. "Why, are you going to start blushing?" Kat looked at him. "Awww, guess not." He shuffled in his seat. "Want me to go to the bar?"

"Nah, my round." She leaned forward and lowered her voice. "There is something you can do for me though?"

"Sure?"

"Send me a picture of your cock?"

Dan blinked. "Wait, what?"

"Oh, I think you heard me."

He looked so confused, it was delicious. "I, uh, don't have any?"

"That's no problem, the restroom's over that way." Kat gestured across the bar.

"I don't-" his expression changed "wait, are you fucking with me?"

"Yeah." Kat let him relax for a second before continuing, "But I do want you to do it."

Dan swallowed. "Seriously?" Was he going to?

"Seriously." He closed his eyes for a few moments, then opened them and started to get up. He was! "Hold up a sec, let's just make sure it's looking at it's best." Kat grabbed his wrist and pulled his hand onto her left tit. Apparently he wasn't so confused he couldn't start feeling her up, squeezing her gently through the fabric. She let him cop a feel for a few seconds, then firmly removed his hand. "Off you go."

After one final pause, Dan got to his feet and walked off quickly towards the men's room, with the awkward posture of a man who has both an erection and the unshakeable conviction that everyone knows. Kat giggled softly to herself, leaning back in her chair to wait. The minutes ticked by, until she heard the telltale ding on her phone.

Kat pulled it out, checked behind her, opened the message, muttered "ooh, nice!". It wasn't anything spectacular, but it was pretty good looking. The drop of pre-cum glistening on the tip was a nice touch. Mostly though, it wasn't the picture itself that made her feel all warm and naughty inside, it was the fact that she'd gotten him to do it.

He came back out of the restroom while Kat was at the bar, with the same they're all looking at me posture and a slightly manic expression. As she waited for their drinks to be poured, she saw him walk over to the jukebox and drop some coins into it. He made it back to the table first, and instead of sitting opposite him this time she slid onto the banquette alongside him.

"Was it- was it alright?" He was grinning helplessly, that charmingly goofy smile plastered across his face.

"Mmmm, better than alright!" Kat purred in his ear. "Nice length, good shape, maybe not quite as thick as I'd like but . . ." She winked. "Well, I like girth."

"Is that your expert opinion?" Kat nodded with mock seriousness as Dan tried not to look smug. The music in the background changed to a vaguely familiar New Wave track and he perked up, softly singing along. "If I had a photograph of you, something to remind me . . ." he broke into a fit of giggles, lolled his head back on the headrest. "Ahh fuck, if I didn't know better I'd think you spiked my drink."

"Nah, it's not booze doing that to you, it's adrenaline." Kat put her hand on his chest so she could feel his heart beating. "It's the thrill you get from doing something naughty and getting away with it."

"I guess you'd know, huh?"

"That's right, I would." Carefully she slipped her right hand down under the table, under the waistband of her jeans. "Makes me feel all warm and gooey and excited inside, it's the best!" Dan was humming along with the synthesisers. "You do need a drink though." She handed him a tumbler. "Shot-" he took the hint and downed the amber contents, gave a satisfied sigh "-and chaser" she slipped her hand out from her jeans and pressed a couple of glistening fingers against his lips. They slipped into his warm mouth and Kat smiled wickedly as he tasted her on them.

"Mmmmmmmm-" She slipped her fingers back out, now wet with spit instead. "-you taste nice."

"I do, don't I!" Kat leaned in and kissed him on the mouth, hard, tasting whiskey on his tongue. Her hand slipped down his chest and onto his crotch, feeling the bulge under his pants. She gave it a squeeze. Her lips moved to his ear. "I could make you cum right here . . ."

His eyes widened. "Please don't!"

"Oh, I'm not going to." Rubbing it gently. "I'm just saying I could."

"I wish I had your confidence in my self-control." He took her hand and pulled it away from his lap.

"Well, I guess it's time we got out of here anyway." Kat checked her purse, stood up, and straightened her jacket. "Right then. Back to my hotel room so I can fuck you senseless?" She took a couple of steps, then turned back to Dan. "Unless you've got a better idea?"

"Ah, no-" Dan got up, "-no, that sounds good. So do we need to call a cab, or-?"

"Nah, it's just a couple blocks from here." As they headed for the door, she looked over and saw the bartender grinning at them. Kat caught his eye and winked.

"Good, maybe the walk will cool me down a little."

A little while later they were falling through the door of her hotel room in a giggling tangle of groping hands and half-shed clothes. Kat closed the door firmly, locked it, smiled to herself in anticipation.

Behind her, Dan's happy laughter cut off abruptly. "I uh, I see what you meant about girth . . ."

Kat turned around, midway through pulling her shirt over her head. "What are you talking ab-" She saw what he was looking at on the on the perfectly-made bed. "Ohmygod-" Sitting neatly on one of the pillows was her dildo, all ten fat inches of it. "I used it in bed this morning- and then I was going to clean it and put it away- but I got that phone call and I must have forgot about it and left it there and then the maid must have-"

"Whoa, are you blushing Kat?" Dan was obviously finding this very amusing. "You are! After everything you're embarrassed!"

"I'm not- it's not the same- it's isn't funny!" She threw her shirt at him.

"It is kind of funny, though?" He was right, damn it. Well, there was one thing that would shut him up -- Kat reached back, unhooked her bra, and let it fall to the floor. As her magnificent breasts were finally released she was rewarded with both a feeling of relief and an audible sigh from her date. Who also looked pretty fucking good with his shirt off.

She trailed her hand across his muscular chest as she kissed him, gave a little "ooh" of surprise as he put his arm around her and held her tightly against him. Her soft breasts squashed up against him as they shared a long, deep kiss. Kat broke the kiss, a little reluctantly, pulled back a little, and let Dan do what he'd been wanting to all evening.

He ran his hands over every inch of her double-D's, cupped them and felt the weight of her beautiful big naturals. Squeezed them gently, then not-quite-so-gently, tweaked her nipples, and generally felt up every inch of Kat's big boobs.

Soft giggling interrupted Kat's heavy breathing. "Hey, what's so funny?" he asked, still fondling her funbags softly.

"Sorry, it's just, the look of concentration on your face!"

"Hey, this is serious business!" He didn't look very serious, not with that silly grin.

"Oh, how can I resist that smile?"

"Wha-" Kat put a hand on the back of his head and pulled it down into her fulsome cleavage. "-mmmph . . ." Dan took the hint. He slurped, sucked, kissed, licked, all over her tits, nursing on them greedily.

Kat threw her head back and enjoyed the oral breast-worship she was receiving. "Mmmm, guys like you, I-" she felt his teeth against her nipple "-gently! Oh, not that gently- I don't know if you were breastfed too much or too little."

"Hey, you leave my mother out of this!" Dan laughed, lifting his flushed face out of Kat's thoroughly-licked cleavage. He went to unfasten his belt, and Kat followed suit, quickly slipping her jeans off and kicking them into a corner. She was totally naked, and totally aware of his hungry gaze on her.

Dan was still wearing a pair of silk boxers which sported a very promising looking bulge; he went to pull them down, but Kat stopped him. "No, I wanna unwrap it!" She got down on her knees, put her hands on the waistband, and pulled it down slowly. When finally freed, his straining prick sprang up, slapping Kat on the cheek. Dan gave a moan of relief. Finally seeing it in the flesh, Kat took a good, long look at his good, long cock. "Ooh, that's nice!" She gave it a wet lick from base to tip like the world's yummiest lollipop, and was rewarded with a big droplet of pre-cum. "Tastes pretty good too!" Kat rubbed her face against his cock, nuzzling her mouth against his meat, smearing it with lipstick traces, until she was face-to-face with an unexpectedly big pair of balls. "Oh, where'd you hide these beauties?" She took each one into her mouth and giving it a gobstopper-suck before letting it free with an audible pop.

"Hey, remember what I said in the bar about self-control?" She gave his wet cock the lightest of kisses and sat back on her heels. "There's no way I can hold out long like this!" an apologetic tone in his voice.

"Yeah, that much is obvious!" She held up a forefinger, trailing a strand of pre-cum. "This thing's like a bottle of lube with a leak!" Kat stood up and stretched. "Don't worry! I'll make you cum, take the edge off. Then we can fuck properly." She cupped her tits and squashed them together. "I've got a pretty good idea how to do it, too . . ."

"Umm, Kat?" She looked at him. "Would you, uh, do something for me?" Ooh, whatever could it be?

"Well, maybe . . . "

"Would you put your glasses on?" Huh.

"Really?" He nodded. "Sure, I guess so."

"Thanks!" Oh fuck, that smile! "I have kind of a thing for girls in glasses." he confided.

"Well, alright. Turn around a minute and I'll do it." Dan looked a little confused. Kat made a circle motion with her finger. "I mean it! No-one has ever looked sexy taking contact lenses out." He thought better of whatever he was going to say, and obediently turned his back on her. Fuck, he had a nice ass too! Kat carefully removed her contacts, popped them into the case, and put on her glasses. "Alright, you can look now."

Dan turned around eagerly, and he obviously liked what he saw. His prick twitched visibly, yet more pre drooling from the tip. Kat put a hand on his shoulder and guided him to sit down on the edge of the bed, then knelt in front of him. "Hey, remember what you said at the beginning of our date? About liking to watch experts?" She grinned. "You're going to want to watch this very closely."

Kat was pretty sure there was a bottle of oil somewhere in her stuff; but fortunately between drool and pre-cum there was enough lubrication that she didn't need to look for it. She spat on his cock for luck, then wrapped her big soft tits around it and started to give him what he so obviously craved. Squeezing them around his hard meat, Kat felt her own soft flesh spill through her fingers; she was more than a handful alright.

Now and then she let the head pop out the top so she could drool on it in a very un-ladylike manner, then smother it in her hungry cleavage once again. Dan really was watching her intently, a look of unrestrained pleasure on his handsome face as she expertly tit-wanked him. Kat made sure to gaze up at him with the cutest expression she could muster, biting her bottom lip in that special way that drove some guys crazy for no explainable reason. The glasses must help, she mused, relentlessly milking his big cock with her epic jugs. She should wear them more often for sure.

"Ohh, fuck, Kat I'm gonna-" Dan groaned. And then he did. Kat felt her cleavage flood with liquid warmth as his cock erupted between them, she waited a second or two then pulled it free, grasped it firmly and gave it a few good pumps. Fuck, it was still cumming, pulsing in her hand as hot, creamy jizz spurted out onto her big slippery tits, splattering her with heavy ropes of cum. Fortunately she overcame her initial surprise in time to take full advantage of this epic load, aiming his cock up and moving her head down to take the final spurts on her face.