Three Dinner Dates

Copyright © November 2022 by CiaoSteve

CiaoSteve reserves the right to be identified as the author of this work. This story cannot be published, as a whole or in part, without the express agreement of the author other than the use of brief extracts as part of a story review.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. It goes without saying that all sexually active characters in this story are over 18

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Chapter One

Dinner Date #1 - Anna meets a stranger whilst waiting for her sister to arrive

As day turned to dusk, the city took on a different vibe. What hit you the most? Maybe your eye was taken by the way those futuristic office blocks started to sparkle, as the glow of interior lights was soon met by the reflection of those down at street level. Perhaps it was the way the streets suddenly came alive with city slickers at the end of their day, some rushing back home to family, and others intent on enjoying just a few more hours before the night ended. If neither of those grabbed your attention, then for sure you'd be taken in by the abundance of bars and restaurants, some subdued and sophisticated, others bright and buzzing, all popular, all rapidly filling up.

It was to one of said bars, a softly lit sophisticated cocktail lounge come restaurant, that Anna was heading. She kept herself to herself as she weaved her way through the masses, ignoring the occasional call outs from over-enthusiastic city workers. Don't get it wrong, the twenty-six-year-old blonde noticed the gestures towards her, and even took a little self-satisfaction that she was pretty enough to be noticed, but they were not why she was here. The only thing on Anna's mind was reaching her destination, and meeting up with her sister, Chloe.

For all she may have blended in, especially in the dimming light of dusk, Anna didn't belong here. The city was the haunt of her sister, but not of Anna. Oh yes, she enjoyed herself every time she came into the city, but she never felt at one with the place nor, sister apart, its people.

Anna and Chloe may have been sisters, but life had taken them in quite different directions. The worlds they lived in were like chalk and cheese. Chloe had one of those brand-new swanky apartments overlooking the river, perfect for her and whoever was the latest in a line of executive boyfriends. Anna, on the other hand, lived out in the suburbs, her tiny two bedroomed terrace being functional rather than flashy, yet still more than big enough for just the one of her. Sometimes Anna wondered what it would be like to switch places, even if just for a few hours, but that was all it was... an idle fantasy.

The one thing Anna knew was that the city was out of her league. You might not have noticed from appearances. At five foot eight, slim build, and with her blonde over-the-shoulder length hair down rather than being up in its usual pony tail, it was no surprise that Anna got herself noticed, especially when she dolled herself up as she had done that very night. Even her outfit wasn't so out of place, unless you glanced closely at labels--Anna was much more high street mass produced, than the designer brands that most went for, but, as far as Anna was concerned, she looked just as good.

Her latest ensemble was a figure hugging, bodycon dress, V-necked, with a lace covered bodice and short lacy sleeves. The midi style came down to just above the knee, the fabric stretching against her every step, a short split at the back allowing some ease of movement and a tantalising glimpse of bare leg. The outfit was finished off with a pair of black heels, nothing near as extreme as the stilettoes most seemed to be wearing, and a black clutch bag. A touch of make-up, warm red lipstick, smoky eye shadow, and just a hint of foundation, gave a facade to hide behind. Even the earrings, tiny clusters of sparkling diamantes, were pretending to be something they weren't.

It was a far cry from what Anna usually wore. She was usually much more casual when out and about, and as for work, Anna was much more comfortable in her uniform. It gave her a sort of certainty to life, a comfortable predictability. Anna didn't like to stand out in a crowd, nor be put on a pedestal. She just liked to be... well, Anna liked to fit in, to get the job done, to avoid creating waves, to avoid being the centre of any occasion.

You see, that was it. Anna was an imposter. For all she could doll herself up and look the part, she didn't belong here. Anna didn't have the education. Anna didn't have the gift of the gab. Anna didn't have the desire, nor even the possibility, to be flashing the cash. Anna didn't even have the confidence to think she could ever live this lifestyle.

Deep inside, Anna hoped one day to meet her Prince Charming, to meet the guy who would take her out of her mundane world and set her free. She knew though that her Prince Charming would be somewhere else, not in this world of smart suits, designer dresses, and cash in abundance.

It never stopped Anna from dreaming though.

The dinner, the once every couple of months get away from it all, was Anna's sister's idea, and Chloe never asked for a penny in return, nor did she ever stand on ceremony or rub Anna's face in it. Their lives may well have been different, but they still loved each other, as only sisters could.

Sisters?

As Anna reached her destination, a single thought filled her mind.

Where was her sister?

Anna glanced up and down the street, but there was no sign of Chloe. She peered in through the window of the Manhattan Cocktail Lounge, but again there was no sign of Chloe.

Anna glanced at her watch. It wasn't quite seven, so she was a little early. Rather than going inside, Chloe waited on the street. It had only been a few minutes, but felt like an eternity, especially for a young woman who felt uncomfortable being amongst the city gentry.

The two sisters had their routine, and this was breaking from it. They were always on time, and they always met outside. They would arrive. They would exchange pleasantries. They would go in together, Anna picking up her confidence from that of her older sibling.

It was as Anna waited, that her phone burst into life, a tell-tale ping announcing the arrival of a text message. She pulled the phone out of her black clutch bag and stared at the words.

'Hey Sis, running a little late, grab a drink while you wait. Be with you soon,' the message read.

Of all the days to be late, why did Chloe have to pick this one? It wasn't so much the tardiness that Anna was concerned about. She knew that her sister had some high-powered job in the city, and work came first. What made Anna worried wasn't so much the what, or the when, but more the where. As she grabbed hold of the long metal pole which functioned as a door handle, Anna's feeling of being an imposter intensified.

This was the sort of place her sister frequented.

This was the sort of place where her sister felt in her element, with the business clientele, splashing the cash, having a whale of a time.

This was the sort of place her sister blended into, dressed to impress with her sharp outfits and high heels.

This was the sort of place Anna loved to visit, but not the sort of place she felt she belonged.

There was nothing else she could do. She could hardly wait on the street, could she? That would just encourage more cat calls, or even make her look like she was on the game waiting for her next client. Anna pulled the door open and slipped inside. She stood in the doorway, glancing around what was already a very busy cocktail lounge.

"Good evening," came a cheery, but rather camp welcome from one of the waiters. "Do you have a reservation?"

"Errm... yes... Warren... Chloe Warren," Anna replied.

"Warren... yes, here we go... table for two," the waiter replied having checked his list of bookings. "Are you on your own?"

"Yes, just me... I came alone," Anna immediately replied, wondering why it wasn't obvious that there was only one of her.

"I'm sorry, Ms Chloe. I meant... will you be eating alone?" the waiter corrected himself.

Anna smiled. He was being apologetic when really it was her misunderstanding.

"No... no... I thought you were asking if I came alone. My sister will be joining me. Oh, and she is Chloe, not me. Chloe said she was running late and to grab a drink while I waited."

This time it was the waiter who smiled.

"Perfectly fine," he replied. "You can wait at the bar, and when your sister arrives, you can switch to your table. Have you been here before?"

"No... no... first time," Anna responded.

"Worry not," the waiter responded. "Dino will take good care of you, and, if you don't mind me saying, his cocktails are to die for... especially the chocolate martini if you fancy something sweeter."

"Mmmm... sounds great," Anna replied, restraining the need to lick her lips as she imagined just what a chocolate martini might taste like.

Moments later it was something else which occupied her mind. The journey from entrance to bar wasn't far, but as she walked through the busy cocktail lounge, Anna couldn't help but sense that she was being watched. In her mind, it was like her every step was being scrutinised, the young blonde now becoming the centre of attention. Reality couldn't have been further from the truth. Yes, one or two had their eyes fixed on the blonde in the little black dress, but most were occupied in their own conversations.

If the cocktail lounge was busy, the bar itself was quiet. Of the dozen or so high stools, only two were occupied, and not for long. No sooner had Anna reached the bar, than the seated couple were greeted by a waiter and led off towards their table.

"Grab a seat... and a menu... be with you soon," the bartender called out to Anna in a thick Italian accent, at no time breaking away from the drinks he was enthusiastically preparing.

Anna did just that, climbing up on a stool towards one end of the bar. She readjusted her dress, pulling it down slightly from where it had ridden up. Still though, in a seated position the hem was now around mid-thigh. Anna crossed her legs, picked up the menu and quickly glanced through the myriad of cocktails on offer. It was no more than a cursory glance though, as Anna already knew what she would be having. She returned the menu and sat there, watching.

Dino was in his element. He filled shakers with ice, followed by spirits of all possible colours. Then the performance began. At first, he shook, vigorously mixing the hidden contents, the sound of breaking ice clearly heard. If that wasn't enough, he would toss the shaker into the air, somersaulting the shiny metal container before catching it once more. Another shake. Another toss. Then, with a loud tap, he placed the shaker on the counter, removed the lid, and decanted the most wondrously captivating drink.

With a performance like that to watch, Anna didn't even mind her sister being a little late. She was so engrossed in what Dino was up to, that she no longer thought about Chloe, nor did she register that she wasn't alone any more.

"Dino's good, isn't he?" a man's voice broke Anna out of her almost transfixed state.

"I don't know how many times I've been here," he continued, "but always I come to the bar and watch. Are you the same?"

Anna turned in the direction of the voice. There, a couple of stools further down the bar, was a man... god, what was she thinking... a man? There, a couple of stools further down the bar, was the most gorgeous man Anna had ever cast her eyes on, and what's more, he was talking to her.

For a moment, Anna simply stared. He was your stereotypical business man, dressed in the smartest of charcoal black suits, with a blue striped shirt, the top button of which was casually undone. He was stereotypical, yet so different. There was none of the extreme self-confidence, the appearance which often presented itself as arrogance. His eyes were fixed on hers, his gaze never deviating down over her body, nor towards her bare legs. He simply sat there, a smile on his face, as he politely waited for a response.

Anna though couldn't help herself but run her eyes across this stranger. His hair was short and dark, with just a touch of natural curl. He was well built, more in the mould of working out than being overweight. His face was so well defined, rectangular rather than oval, with the strongest chiselled jawline, and piercing blue deep-set eyes. How old was he? Anna was never so good at guessing, but she did so all the same... imagining this tall dark and handsome stranger as being in his early thirties. Without thinking, she even flicked her eyes down to his hand, looking for any tell-tale band of gold, even if it was the ghostly impression of where a ring once sat.

Then it hit her... he was talking to her, and he would be expecting a suitable reply.

"I'm... I'm sorry," Anna replied, not even realising what the question was. "You were saying?"

"No... no... I'm the one who should be sorry," the stranger responded, a genuinely apologetic tone to his voice. "So rude of me..."

"Rude?" Anna responded, confused.

"Yes, rude. I broke you out of your thoughts with some idle comment to the effect of do you come here often. God, so corny... anyone would think I was trying to chat you up, and without the decency to even introduce myself," the stranger continued, before adding. "I'm Simon, by the way."

"Anna," Anna responded, smiling back before answering in the shortest possible way. "No... first time... you do... often... and yes, he is..."

In the end Anna stopped trying, and simply burst into giggles. How was it she couldn't even put together a coherent response? Her mind was awash with such a heady cocktail of emotions, that rational thought was becoming clouded.

Here she was, talking to a stranger and one who quite obviously had a much more professional career than she did. She was nervous. She was scared. What if she said the wrong thing? What if she showed herself up for who she really was? Then there were the counterarguments, the interest in knowing whether he was just passing time or whether he had something more on his mind, the excitement in thinking that the most gorgeous man she had ever met might actually be trying to chat her up.

Her mind told her to turn and run, to avoid the obvious come down.

Her heart though, told a different story.

Anna was never one to follow her heart and was already thinking up her excuses. Taking a deep breath, she started again.

"I'm sorry. I meant to say it was my first time here, and yes, Dino is fantastic. I really like it, you know."

"Fantastico... I like it too..." Dino announced as her drew within earshot of the conversation. "Now... what can Dino be making for such a sweet couple?"

"Oh, no... we're not a couple," Anna quickly corrected.

There was a twinkle in Dino's eye as he placed two cocktail shakers on the table, before addressing Anna and Simon.

"Well... from where I'm standing, you should be. Anyway, ladies first... what'll it be?"

"Chocolate Martini," Anna responded.

"And for you, Simon?" Dino asked.

"Moscow Mule," Simon replied, "heavy on the ginger."

"You got it, Simon," Dino announced. "Now, sit back and enjoy the show."

"He knows you by name?" Anna asked.

"Well... I did say I'd been before," Simon replied, smiling.

Strangers or not, Simon had to admit that he liked Anna. She was a few years younger, of that he was sure, and most definitely different. There was a nervousness about her, a timidity to her words which came across as being so honest and tender.

He had to admit that of all the women he had been set up with--the lads with their directness had arranged many--this casual encounter was the one which had him wondering. Could Anna be the one? Could they really be as well matched as Simon hoped? The only question though was how to slip the subject into idle conversation without it looking like he was fishing, or worse still, chasing after the young woman.

It was Anna though who helped break the ice.

"Do you work nearby?" she asked.

Simon smiled. It was a natural question, and with Anna asking, it wouldn't look like he was prying.

"You could say so," Simon quipped. "Did you see the big glass one on the corner?"

"What... the bank?" Anna asked.

"Yep, that's me... banking's in my blood. As for this place, well it's on the doorstep and it does fantastic food... oh, and Dino's cocktails aren't half bad either. How about you, Anna? What profession are you in?"

For a moment Anna just sat there, staring. When she asked the question, she never really imagined it would be coming right back at her. What was she going to say? Banking? Well, how could she follow that up with working in a supermarket? Anna took a deep breath, before answering.

"Who, me? Well... I guess it's a mix of retail and finance," she commented, happy in the way she had made a very mundane job appear just a little interesting.

"Sounds exciting," Simon immediately replied. "Who do you work for?"

Luckily for Anna, at that precise moment, Dino took the limelight.

"One sweet silky Chocolate Martini for the young lady, and one Moscow Mule for my good friend, heavy on the ginger. Shall I charge to your tables?"

"Yes pl--" Anna started to reply.

"Put them both on mine," Simon got in first.

"Simon... no... no... you can't," Anna started to protest.

"Well... I can... and I just did... think of it as my way of saying thank you," Simon responded.

"Thank you for what?" Anna asked.

"Thank you for... for... for just being Anna. It's not every day I get to pass the time with such a beautiful lady, so please let me buy you the drink. It's the least I can do."

Why was he so nice? Anna felt a warmth in her cheeks. Was she blushing? There was nothing she could do. Her only hope was that Simon hadn't noticed. Whether he did or not, he didn't comment, well at least not about her reaction.

"You know, Anna," Simon asked, "and please don't take this the wrong way, you'd be welcome to be my guest if you're on your own. The lads, well they can be a bit loud, but they mean well."

Once more, circumstances manifested themselves to avoid Anna needing to answer. It was just as well, as this time she wasn't sure what she wanted to say. Without the lads as part of the offer, and against her better judgement, Anna may well have accepted. That said, the arrival of Chloe put pay to any thought of an evening with the dashing Simon.

"I'm sorry, Simon," Anna responded. "I'm meeting somebody... and I can see she's just arrived."

The look on Simon's face must have said it all. For a moment he thought he'd found the one. He so wanted to get to know Anna better, and for her to get to know him. Yes, being there with the lads wouldn't have achieved the same, but he could always have offered to walk her home, to have some quiet time together. Now though... well, had he really read it wrong? Did Anna have a girlfriend of her own?

"Chloe, so good to see you," Anna greeted her sister with a kiss on the cheek.

"I'm so sorry, Anna," Chloe responded. "I hope you've haven't been waiting too long."

"Oh no... not at all. Simon here, has been keeping me company," Anna explained.

"Ladies," a waiter interrupted. "Would you like to follow me to your table?"

As Chloe followed the waiter towards a table at the far side of the restaurant, Anna turned back to Simon.

"Thank you so much for the drink, Simon. I enjoyed chatting to you, but I must join my sister. Maybe we'll meet again some time."