Matchmaking for the Shy Ch. 02

AUTHOR'S NOTE: This is a chain story written by several members of the Author's Hangout on the Literotica forum. Chapters will be published irregularly but hopefully around one per month. This is part 2 - the first being written by the talented Mrs_Mackenzie.

--- CHAPTER 2 ---

Heather kept clicking her pen over and over again. Click, click, click. The questions that Brianna had presented to her for the matchmaking ordeal seemed simple in nature, yet impossible to answer.

"What makes you happy?" one of them read. Happy? What kind of happy? A feeling of contentment? A momentary respite from worries? Being excited about something? Taking pleasure in an activity? Happiness was hard to define, at least when overthinking every question on the quiz. It was easier for Heather to determine what made her 'unhappy'. Eric, for one thing, was at the top of the list - and she was upset with herself for constantly wondering what he was doing. If 'he' was happy now, without her.

With a deep sigh of frustration, she pushed the paper aside and put the ballpoint pen down beside it. Why was she stressing so much about something so irrelevant? It wasn't like she expected to meet someone who would sweep her off her feet. But Brianna cared about the matchmaking service, and Heather cared about Brianna. So after a minute of silent contemplation, she picked up the pen again - and after only four clicks, she wrote down; "Reading a good book. Feeling listened to and understood. Enjoying one of my favourite dishes. Cuddles."

She stared at her answer - the neat handwriting feeling more satisfactory than the words chosen. But it would suffice.

For 15 years, Heather had been married to Eric - and for another six prior to that, they had been a couple. She tried to think back to a time before they met; about the less than a handful of dates she had been on during her high school years. Could those awkward evenings even be counted as dates? Dating as an adult likely included fewer moments playing video games together in some dank basement whilst the guy's mother kept checking in on them every five minutes, or going to Baskin-Robbins and awkwardly trying to avoid looking silly or sexual as you licked away at your frozen treat. No, Eric had been the first man that made her feel like she could relax a little bit - and then he had taken advantage of her trust and naivety.

With sudden focus, she turned the page and went through the next set of questions. Most were short. Succinctly presented. Others, far more challenging. "What are you looking for in a partner?" seemed particularly difficult. Besides, how could she truly know, with her experience being so limited? But she was done with overthinking every little question Brianna had provided, and she let her heart lead. It's not about trying to figure out how much or how little you 'deserve', she told herself - it's about stating your preferences, unfiltered, for once in your life.

It took her the better part of an hour, but as she slid the completed questionnaire into an envelope and sealed it shut, Heather felt strangely content. The weight of the task completed lifted from within, and her mind became playful - wandered to potential matchmaking scenarios. Not to the dates, or the awkward 'getting to know each other' phase, but to more intimate moments. Would she find someone that would cherish her? That would fulfil her wildest desires, and fantasies long forgotten, opening up her world to things she would never dare to speak out loud?

Catching her reflection in the mirror hanging on her closet door, Heather tried to imagine herself as a sultry goddess - as some modern woman with unbridled passion, who let herself be taken by lust. It was a difficult image to conjure, but not impossible. Submissive and kinky. She could be that. There was something there, buried deep within her subconscious - beneath layers of fear, shame and denial. For the briefest of moments, she imagined a man - young, handsome, lost to his own needs - put his vigorous cock up against her bottom, and.. and she did nothing to stop him. A shock went through her. A pleasurable shiver, that made her heart skip a beat and her breath catch in her throat.

One thing was certain; the type of relationship she had shared with Eric was certainly not what she yearned for. Regardless of whom she'd be paired up with, he would not be left wanting. So long as he'd treat her with love and devotion, she'd fulfil him in ways he didn't even know existed - and explore that new, intoxicating world together with him. Yes, she thought to herself, a shy little smile upon her lips. It was time for change. Time for a new perspective.

---

"Okay, spit it out. You're clearly distracted by something." Jake - Zach's friend and workout buddy - was a perceptive fellow, though Zach's inattentive mood during their training routine wasn't exactly subtle. The gym smelled like sweat and too many cleaning products, though their section was mostly empty, with just two old ladies gossiping whilst walking on the treadmills nearby.

"Just thinking about stuff," Zach muttered, letting go of the barbell as he finished his set. His upper body was screaming at him, but he tried not to show it.

"Uh-Huh?" The pressing tone in Jake's baritone voice made Zach sigh, then break out into a smile.

"Don't laugh, okay? There was this girl.. No, sorry, woman.. And she gave me some kind of form to fill out. A weird survey thing." Zach straightened up and wiped his face with his towel, casting a glance across the gym floor, making sure none of the other patrons was paying attention to their conversation. "It's for some dating experiment or something. Finding an ideal, well-suited partner. That kind of thing."

"Oh?" Intrigued, Jake's smile grew even wider. "Sounds old-school, but that might suit you. Did it seem legit?"

"I think so, yeah." Zach was surprised by Jake's enthusiasm. It felt odd; especially because Zach himself found the whole thing baffling - and he hadn't decided on how to approach it yet. He ran a hand through his auburn hair and stepped away from the weights, reaching for his water bottle and taking a sip. "You really think it's a good idea? For me, I mean. I struggle to put myself out there." Somehow, with the blood pumping and the sweat dripping down his torso, he found it easier to open up about topics he was insecure about.

Picking up on Zach's concern, Jake took on a contemplative look. "Yeah, man. If you're cautious, what do you have to lose? Better than sitting at home, levelling your Warlock, right?"

"I guess so," Zach admitted, letting a chuckle slip.

"I know you don't believe in it, but sometimes the universe looks out for us," Jake told him as the duo moved over to the free-weights. "The dating apps are full of fake accounts and people using photos from the Jurassic era. And everyone feels lonely sometimes, man. Sometimes we just need a little help taking the right steps towards finding someone, you know? Then - boom! - you're handed a survey by a random woman, asking if you wanna participate in some dating thing? It feels like fate." The grin on Jake's face made it hard for Zach to decide if he truly believed what he was saying, or if the whole thing was meant as a nudge; perhaps to prompt him into action. Sometimes he did need a push.

He ignored the muscle's complaining and resumed his lifting routine, picking up a pair of dumbbells and squaring off with the mirror image staring back at him: freckled skin, unblemished save for the faint scar above his left eye from falling off his bike when he was a kid. Talking to women was not his strong suit, and he was horrible at picking up on subtle cues. Several times, Jake had insisted - afterwards - that a woman had been flirting with him, but Zach had not noticed at all. But even if he had, he didn't have the experience necessary to see it coming and gauge the right reaction. But if matched with a woman? Then the rules were much clearer. Both of them would be there because they were single, looking for love, and paired up by whichever matchmaking algorithm the service might use. Hopefully, they'd be a decent fit. It just seemed easier.

"I might as well fill out the form," Zach conceded as he pushed himself through his repetitions, wincing at the dull ache in his muscles. "No harm in trying."

---

It was a slow afternoon, the Coffee Pages nearly empty except for two upper-class women who sipped tea from cups whilst holding out their pinkies, and the usual 'I'm going to be a famous writer one day' middle-aged man on his laptop, working on his latest novel. As she worked, Brianna kept her eye on the door; the streets of New York being pelted in rain outside the large glass panes - the sound both soothing and a tad melancholy.

Drenched from head to toe, but with a smile on his lips nonetheless, a man walked through the front door of the shop. A well-groomed man in his 20's, with a scruffy stubble that highlighted his lean jawline. His hair fell past his ears, as wet strands of it framed his face. "Hey," he said, with a pleasant voice, warmly greeting her. "Charles Gold sent me." He wiped some of the water away from his forehead with the sleeve of his coat. "Said something about a secret mission..?"

Although she tried not to judge people based on their appearance, she wondered if Charles had sent the wrong man. This was the 'Sparks of War' expert? He looked more like a gym rat than a nerd, and she'd expected someone who looked the part.

"Hi," Brianna replied cordially, "Thanks for stopping by. Don't mind Charles; he can be quite dramatic. I just wanted to talk to someone with some Science Fiction expertise. The usual?" She nodded towards the coffee machine by her side, and the man responded non-verbally, procuring a list from his pocket with the order on it, penned in her husband's handwriting. "What do you know about 'Sparks of War'?" She watched the man as his expression shifted between surprised, puzzled, and pleased.

"Oh, just about everything!" he beamed, sounding excited.

For the next twenty minutes, the man went on and on about the book, explaining in detail how many different layers it had to it, and how it was something so much more than it seemed at first glance. With sparkling eyes, he kept talking even as other customers entered the shop, with an enthusiasm that she had only seen once before; when Charles's brother got started with Star Trek lore. This guy must really love his stuff, she thought. Eventually, she had to cut him off.

"I appreciate your incredibly thorough explanation, but the coffee is getting cold." She offered him a polite smile. "Oh, but before you go.. You wouldn't happen to be single, would you?" A moment of shock swept over him, misunderstanding Brianna's intention, until she pointed to the little sign on her counter advertising her matchmaking service.

"No, I'm married, but.. Wait.." The cogs turned in his head for a moment. Then his expression turned quizzical. "You wouldn't happen to be the same matchmaking service that handed a survey to my buddy Zach?" He sounded very interested in that fact.

"Long, auburn hair? Kind of looks like a Viking?" The man nodded, his eyes lighting up. "Yeah, that was me!" Brianna replied with a big smile. "Small world."

"Wow. Small world, indeed. I was just talking about it with him at the gym this morning." He paused for a moment, contemplating something. "You know, I moonlight as a personal trainer down there, and I run into a lot of guys that are either too shy or awkward to approach women the classic way, and that aren't fond of the dating apps. But they're good people. If you want, perhaps I could pass your survey on to them?"

And there it was. A potential solution to her problem of getting men to sign up for her matchmaking program, and hopefully without feeling embarrassed about it. And to cater to the shy? It seemed like an untapped market. "That would be great!" she enthused, feeling relieved and excited. "Sorry, uhm.. What was your name again..?"

"I'm Jake. Jake Donners," he replied. "And if you promise to match my buddies up with good women, we have ourselves a deal, because they're all great guys."

---

"Cassian, are you in the parlour?" Diane shouted from the foyer of their family home in the Tribeca district of New York City. Her younger brother had spent the last two years in England, overseeing a London branch of their father's business - and although she didn't admit it openly, Diane had missed him terribly. Therefore, every opportunity she got, she'd drag him out for lunch or for drinks with old friends, or even to the theatre when she could get away with it. As Cassian appeared at the top of the stairs, she beamed at him. "There you are. Are you ready?"

"For what?" he asked. He wore the same frown that their father used to wear when Diane and Cassian were growing up, and they interrupted his important work. For the briefest of moments, she wondered if she wore the same cheeky expression as she did back then in response.

"Your secretary, the lovely Miss Highland, has informed me - with certainty! - that you do not have any plans this afternoon, and therefore I am going to take advantage of the opportunity and force you to spend time with your dear sister." Diane put a hand on the bannister and leant against it, peering up at her brother with an overly impish face.

His cufflinks caught the sunrays that were breaking through the curtains as he ran a hand through his almond curls, and for the briefest of moments, he stood there as if contemplating whether to argue or to acquiesce, until he sighed and said, "And where are you taking me?"

Ignoring his question, Diane made a clicking sound with her tongue and beckoned Cassian over. "Put your coat on," she said. "It's rather chilly out." For being late spring, there was a sharp edge in the air, as if the last remnants of winter still had claws burrowed deep into it.

Cassian obliged without a fuss, but as he slid his arms into the sleeves, he looked at her with a face that said he was far from excited. "You know I don't like surprises."

"We've talked about this. Your need to always be in control of every miniscule detail is not healthy." She smiled at him, but there was a hint of concern in her tone. And of sympathy. "And besides, you're hiding from the world. We're in the most marvellous city this side of the Atlantic Ocean, and you're locked up in dad's old office like you're on house arrest. It's time for some fresh air."

The tall man snorted. "Fresh air? In New York City? Right." He walked right past his sister, grabbing the keys from the antique rack on their way to the door.

"Stop being a sour puss," Diane chastised lightly as she followed him, her heels clicking on the tiles of the entranceway. But she smiled at him and said; "Thank you," as he held the door open for her. He was a proper gentleman, and she adored that about him. The way he'd always stand up whenever she entered a room, or grabbed her hand whenever they were walking down stairs - not only for safety's sake but out of courtesy. Whenever they strode down the street, he'd always stay closest to the road, to ensure he'd be able to protect her should a vehicle ever drive a little too close to the pavement. And he was dapper - no one could wear a black suit like Cassian did.

"Where's Morgan?" he asked, a small wrinkle in his brow betraying concern.

"We're walking today," Diane replied simply, with a wave of her hand. The tall skyscrapers and glinting glass shone in the spring sun, making the streets of New York City gleam. They started walking towards the crossing of Franklin and North Moore, where the firestation used in the Ghostbusters movies was situated. A few tourists took photos of it as they passed by.

"Enough secrecy," Cassian said once they'd crossed the street. "What are we doing? Where are we going?"

Diane knew she was playing with fire, but there was an overwhelming desire to push Cassian out of his comfort zone - for his own good - yet she approached the subject cautiously nonetheless. "It's been months since you broke up with that dreadful woman. You can't stay in mourning forever," she said, her brisk pace leaving her brother trailing slightly behind. "When are you going to start dating again?"

"I'm not in mourning." The curly-haired man drew level with Diane. "I'm just focused on work, and-"

"You're a catch by any standards," Diane said, cutting him off with a sharp look and tone. "Ever since father got sick, you.." She let the words fade to nothing, before taking a deep breath, coming to a halt on the sidewalk. "Cassian, please listen to me. I am worried about you. You spend all day working from home, you don't go outside, and you hardly engage with your hobbies anymore. Please - talk to me." Her eyes pleaded with him.

The two of them stood in silence for several moments. Cassian stared down at the cracks in the concrete underfoot while Diane observed his every move. Then he sighed, giving her that same sigh of exasperation she knew so well. "Diane," he began to speak, but then stopped again abruptly, a look of uncertainty on his face.

"There's this dating service," she blurted out, deciding it was now or never. "A matchmaking ordeal. A friend of mine who own this quaint little coffee shop runs it. You'd answer some questions, and then you'd be paired up with someone that would match your preferences for a blind date. Simple and effective." She tried to keep her face neutral and voice casual, but a hint of an expectant smile couldn't be kept at bay.

As they were blocking the sidewalk, people continued to stream past them on either side, but Diane hardly paid any mind to them as she waited for her brother's reply. When it finally came, the disappointment she felt was instantaneous. "Are you mad? I am not signing up for some dating agency!" His voice was raised a little more than usual, which indicated his inner struggle.

"Just hear me out over lunch," she pleaded. "There are many advantages to dating this way. I mean - think about it! You'll be matched with someone that actually has similar values. A woman you could build a meaningful relationship with. Plus, nobody would know what you do for work, so you'd be able to weed out the gold diggers and people with the wrong intentions." She could tell it would take convincing, and that he'd need some time to process what she was suggesting. There was hope, however. That look in his eye that said he might come around to it, or at least lack the willpower to fight her on the topic for long.

With a defeated sigh, Cassian nodded his assent, and they resumed walking towards Little Italy.

---

It had not been Zach's intention to listen in on Damon's and Gabriela's intimate moment, but the volume at which they went at it was inappropriate at best, and more than loud enough for Zach to overhear every moan and grunt as he laid in bed - eyes closed, but mind wide awake, creating images out of the noise which danced through his brain. This was so wrong, he thought. Yet his loins ached from within, desire coiling like a snake around his body, squeezing him tight and leaving him breathless and frustrated. Twice, he had to remove his wandering hand from the front of his boxers - ashamed of himself for being turned on by the sound of their passion-filled moans.

His cock begged him to indulge himself, to free it from the restraints of the flimsy material of his boxers, but there was no way he was going to jerk off to the sounds of his friend going at it. Not to Damon - his roommate and eternal confidant - as that seemed uncomfortably homo-erotic for Zach's liking; nor to his partner, which would be a clear violation of the Bro-code.

Still, sleeping was not an option, and his libido fought to take over his mind, whispering wicked thoughts into the darkness: vivid visions of Gabriela and her curves writhing against Damon under the covers. With a frustrated motion, Zach threw the blanket back and rose to his feet, setting course for the kitchen. If they heard he was still awake, then perhaps they would keep the noise down, he reasoned.