Matchmaing for the Shy

Matchmaking For the Shy

is a six-part chain story written by members of the Author's Hangout in the Literotica forums.

Today's episode sees Emma, exhausted single mother of four, and Zach, burned-out engineering graduate, find comfort and purpose in each other's arms. It contains themes of gentle, consensual female domination.

Thanks to my beta readers

mrs_mackenzie

and

TheRedChamber

for their feedback.

* * *

Zach stared at the matchmaker's form, lost. His personal information had been easy enough. Name. Preferred means of contact. Gender. Desired gender. It was the first of the free-form questions had stumped him:

What are you looking for? There are no wrong answers.

He could imagine a lot of wrong answers. Something casual? Get lost, fuckboy. Something serious? As if anyone would want to settle down with him.

And what was with this paper form? His handwriting was atrocious. He hadn't written entire sentences on paper since middle school.

At least that was a problem he knew how to solve. He scanned each page and carefully erased the few blanks he'd already filled in. A few minutes in a PDF editor got him a nice fillable form. Much better.

The same question stared at him, now with a blinking cursor.

What are you looking for? There are no wrong answers.

Just for fun, he typed, "Big tiddy goth gf." Even better, "Big tiddy mommy domme." Then inspiration really struck. "Big tiddy mommy dommy." He knew that wasn't how it was pronounced, but it rhymed too well to resist.

Select all, delete. Once more alone in a field of unbroken white, the cursor blinked patiently.

What are you looking for?

How was he supposed to know? His few forays into the dating world had been brief and unsuccessful. The best that could be said of them was that he'd had the good sense to recognize when he was being taken advantage of. Eventually.

Frustrated, Zach switched to a different tab. He'd figured out the name for what he'd seen his roommate Damon doing with Gabriela. It was called reverse pegging, and searching that phrase had led him to a constellation of other terms. Chastity, cuckolding, sissification, small penis humiliation. Some he'd come across before, others he hadn't. None of it sounded the least bit appealing.

At last, he landed on a video that seemed different. True, the woman still wore head-to-toe latex, complete with opera-length gloves and a severe leather corset. She posed on her bed like all the others, spike-heeled boots arranged just so. Next to her lay the usual tools of this trade: a dildo, a strap-on harness, a ruler.

It was the title that had set her apart from the rest.

You are worth more than your penis.

Zach clicked play.

"Hi, I'm Miss Petra, and we're going to do a cute little reverse pegging scene today. But, first, I wanted to take this opportunity to pull back the curtains a bit and talk to you candidly about small penis humiliation. You may have seen some videos of me saying things like..."

The video cut to the same woman, now with blonde hair in a crisp white blouse. "Pussy is for real men with real cocks, honey. Shrimp-dicked beta simps fuck my boots, if they're lucky."

She froze mid-sneer. Voice-over, Miss Petra said, "And..."

It took a moment to understand what he saw next. It was a close-up of a man's crotch. A shell of pink plastic enclosed his penis, secured by a small brass padlock to a ring around his balls. A chastity device. As Zach watched, a pair of hands clad in slick black latex appeared. From off-screen, Miss Petra cooed, "Let's see what you've got for me, little boy."

She unlocked the man's cage and pulled it off to reveal a perfectly ordinary looking penis, perhaps even slightly larger than Zach's. Miss Petra was less impressed.

"Are you kidding me?" she demanded, her voice flat. "Is that all you've got? Sad-sack micropenis piece of shit, I can't believe I even bothered to find your key again. You should be fucking ashamed of yourself."

She grabbed the man roughly by the balls and forced the cage back on.

"You should

not

be ashamed of yourself," Miss Petra said, leaning forward on her bed to look earnestly into the camera. "First of all, Bobby's penis is entirely normal."

She held up the ruler, pinching it between finger and thumb halfway along its length. "This is six inches. Most men are smaller than this. Bobby is right around average. He just likes being told he's a limp-dicked loser whose tongue is the only thing that will ever satisfy a woman. This is a

game

we play."

She paused to let that sink in, then tossed the ruler aside. "But, also? What's wrong with satisfying a woman with your tongue? Or your fingers? Or a toy? Most women can't even come from penetration alone. Think outside the dick!"

Miss Petra slid off the bed, landing gracefully despite her boots' extreme heels.

"For this next part, I'm going to bring out my lovely assistant." Bending at the waist, she pulled aside her bedskirts to reveal the bars of a cage built into the underside of her bed. "Hi, little boy! You ready? Let me get this door open for you."

Bobby came crawling out on his hands and knees. He wore nothing but a spandex hood that rendered his head a featureless black blob. Zach was surprised by how ordinary he looked. The man was a porn star, wasn't he? But he was soft all over, with a definite paunch. Even Zach had more muscle definition, despite his long hours at the computer and only a couple of workouts a week.

Nonetheless, there was no mistaking the affection between the two. Bobby pounced on Miss Petra's boot and began kissing it noisily. She was smiling as she kicked him away. Undeterred, Bobby grabbed her other boot. The scene reminded Zach of someone playing with a rambunctious puppy.

"All right, enough of that." Miss Petra clicked her fingers. Bobby settled into a kneeling position at her feet. She handed him the strap-on harness. "Put that on. Go."

Next, she flourished the dildo. It was a simple pink thing, barely more than a cylinder with a rounded end and a flared base. "$20 for the basic model, and it comes with a feature no man can match."

A squeeze set it vibrating. She cycled it through a few different modes before turning back to Bobby, now sitting on the corner of the bed with the harness buckled around his hips. Miss Petra cupped his balls underneath the pink cock cage.

"Bobby's really into extended chastity play," Miss Petra explained. "On the one hand, I do like how clingy and submissive he gets after a few days. It's sweet. At the same time, sometimes a girl just wants to hop on her man's dick! You know what I mean?"

Laughing, she slid the dildo through a big ring in the harness and snapped the ring back into place. The dildo jutted out from Bobby's hips above his own caged penis. She flicked it with her finger, leaving it bobbing.

Now Miss Petra swung a leg over Bobby's lap. They kissed, a quick peck that soon became more passionate. His hands began to roam her back and sides. She had her arms around his neck. Her fingers cradled the back of his head. Her other hand reached into his lap. Bobby twitched.

"I turned on the vibe," Miss Petra mumbled, her voice muffled by Bobby's mouth. "I'm kind of grinding on it right now. It's nice..."

Zach could see her hips rocking. She buried her face in Bobby's neck, hugging him tightly to her. Zach shifted in his chair. The couple on screen had an undeniable chemistry, and he found himself responding to that.

Bobby's hands drifted lower. He kneaded Miss Petra's ass, his fingers stark against the gleaming black rubber. He shifted her in his lap. She gasped, then sighed happily. His hand stroked her thigh, the hollow of her knee, her shapely calf. His thumb rubbed the patent leather of her tall boots.

"Fucking pervert," she said. Her giggle took the sting out of it. She folded one leg back to her ass, hooking the pointed toe of her boot over Bobby's knee. "Better?"

Bobby made an approving noise. His hand found her ankle, then her sharply inclined arch. He kissed her with renewed ardor.

"Open my fly for me, bitch."

Bobby reached obligingly under her ass from behind. So much was happening between them, obscured by their bodies. Zach had never before noticed how porn stars contorted themselves to accommodate the camera. This felt...real. Cozy, despite her fetishwear and Bobby's hood.

Miss Petra half rose, then slowly lowered herself. Her head tipped back, ruby-red lips parting to reveal the tip of a tiny pink tongue. Bobby laid a line of kisses up her neck and along her jaw, ending behind her ear.

Zach was straining at his shorts. He glanced over his shoulder. His door was closed. Damon wouldn't be back until late anyway. He'd have a happy hour thing, or plans with Gabriela.

Scooting his chair back, Zach tugged at his fly. His other hand found the lube in his desk drawer.

Miss Petra was gyrating slowly in Bobby's lap. Her eyes were closed. Her mouth was open. She looked lost in her own world.

Zach stroked himself, trying to match Miss Petra's languid rhythm. With his other hand, he tapped his touchpad. Five minutes left. Could he last that long?

For Bobby, it wouldn't matter. The strap-on would let him keep going as long as Miss Petra needed. Zach found the idea strangely comforting.

Giving up on the idea of matching his orgasm to Miss Petra's, he pumped his hand up and down his shaft. Soon he felt the telltale tingle at the base of his balls. His pleasure surged. He grunted once, twice, then sighed.

Through suddenly heavy-lidded eyes, he saw Miss Petra pull Bobby to herself. She buried her face in Bobby's neck again and shivered violently. Her breath came in harsh, syncopated gasps. Then it evened out. She melted into Bobby's arms. He cradled her like a massive doll.

Seconds ticked by. Zach watched them, mesmerized. There was something here that he wanted, but could not quite name.

At last, Miss Petra stirred. She pressed a tender kiss to Bobby's shoulder, then lifted herself off the toy. She stood over her partner for a moment, steadying herself with a hand on his shoulder.

Then she walked toward the camera. Her boots were loud on the floor. She didn't speak. Zach was treated to a close-up of her breasts in shining black latex before her hand blotted out his view and the video ended.

The website wanted to move on to the next video.

Bubbly teen in stiletto heels DESTROYS his worthless balls!

Zach closed the tab.

His hand was sticky with cum. He wiped it clean and started to put himself away, only to discover he'd gotten cum on his shorts. When he stood and shucked them off, he found more cum on the floor. He had made a real mess this time.

And doing what? Sitting in his room, masturbating to a video, when he could be out doing anything else. Going for a walk, picking up a hobby, even grocery shopping. How long had it been since he'd had a proper meal?

Zach's eyes fell on the matchmaker woman's questionnaire. It was still on his desk, next to an empty granola bar wrapper and a bill he'd paid weeks ago. He had been filling that out. He had been taking a concrete step toward meeting someone whom he could hold in his arms instead of looking at on a screen.

Methodically, he used his shorts to wipe the floor under his desk. He tossed them into his hamper, along with a few other pieces of clothing that lay around his room. He used the bathroom. With clean hands, he put on a fresh pair of shorts. He cleared his desk, tugged his sheets into some semblance of order, and went out again to dump his little trashcan into the big bin in the kitchen.

Returning to his room, he logged back into his laptop.

What are you looking for?

"Someone to come home to. Someone to cook for, someone to eat with. Someone to share my life with."

* * *

Emma was having a bad day, again. She had caught Etta trying to discreetly drop her glasses down a sewer grate. Apparently, 'none' of the 'other girls' wore glasses. This was news to Emma.

"Really?" she asked, squatting down in front of her third-grader. "Not even Christine or Amy or Mei Lin..."

She trailed off, realizing what all of these girls had in common. They were all Chinese.

"I'm not like them!" Etta snapped, stamping her foot. It would have been cute if it weren't so horribly sad.

She was not qualified for this. She wanted to crawl back into bed and pull the sheet over her head. Instead, she was alone on a busy Manhattan sidewalk with three small children.

She didn't even have Shu Fen with her. Her au pair was twenty blocks in the other direction with her eldest, Callia. Never again would she have the luxury of all her children going to the same school in the morning.

Thinking fast, she dug out her phone. "Jonas, want a little screen time? Sit against the wall there and play some Sesame Street for Caleb. Can you do that for me?"

Of course he could. Jonas would do anything for a little screen time. Emma felt guilty about not doing something about that, but she had no idea what she would do, and it was so convenient so often. At least she only played them downloaded media. She'd spent too much time in the belly of that beast to let any algorithmic feeds near her own kids.

With two now semi-stable, she turned her attention back to the third. Some pieces were falling into place. Jonas and Callia took after her, not quite platinum blonde and blue-eyed but at least fair-skinned and sandy-haired. Caleb was a bit darker. With his curls, people usually took him for Mediterranean or Latino. Only Etta, with her round face and stick-straight black hair, got regularly clocked as Asian.

That was much too big a conversation to have on the sidewalk. As she so often had to do, Emma triaged ruthlessly. "Etta, we can talk about this tonight. For now, you have to wear your glasses. You need them to see."

"I do not, and I will not, and you can't make me."

It was moments like this that she saw her late husband peering out through her child's dark eyes. Wei Wei too had had a stubborn streak, under that mild, smiling facade. Etta had yet to develop the facade.

Unfortunately, she was right. Another thing she'd inherited from her father, a keen sense of the actual. Unless Emma wanted to duct-tape Etta's glasses to the kid's head---and somehow convince every mandated reporter at school to go along with that---she could not make her daughter wear them.

Time to change tack. "Edna Mode wears glasses. Mirabel. Um, Velma. Ooh, Sadness. Didn't you want to be Sadness for Halloween?"

Somehow, she talked Etta into putting her glasses back on. She pried Caleb and Jonas off her phone. She got all three of them to school, on time no less. She even remembered to message Etta's teacher, warning her to keep an eye out for any further attempts to lose the glasses.

Emma was desperate for her fix by the time she made it to Coffee Pages. Brianna took one look at her and said, "Oh, good. You can tell me what you think of this. It's new."

She held up a cake pop the size of a tennis ball. "Chocolate sponge cake dipped in ganache and sprinkled with shavings of dark chocolate. I call it Triple Happiness. On the house in exchange for your honest opinion."

It sounded like diabetes on a stick. Emma took it eagerly.

Diane was sitting at her usual table in the corner, filling out a form Emma recognized.

"You too?" Emma asked, surprised. Diane always seemed to have her life so well in order. It was inconceivable to Emma that someone like her would need such help.

"You know what they say. Sauce for the goose is sauce for the gander. Or vice versa, as the case may be."

"Her brother talked her into signing up with him," Brianna explained, handing over her Americano. "Speaking of which, I have a date for you."

Emma's stomach lurched. "Already?" she stammered.

"Yeah, why not? You got a minute to talk about it?"

She had six precious hours before pickups. In that time, she needed to schedule two appointments, contest a bill, submit another for reimbursement, research summer camps, shop for groceries, clean the bathroom, unpack the kids' spring clothes (two months late, astronomically speaking), run some laundry, figure out what to do about Etta's glasses...

The idea of adding another thing to her to-do list was overwhelming. She hadn't thought through what it would take to squeeze a date into her schedule.

"I don't know. Now's not a great time." Even as she spoke, she heard the rebuttal: when would be? It'd be four years before Callia went off to college, a dozen before Caleb left the nest. And that was assuming none of them boomeranged back.

"Well, you have to drink your coffee, right?"

Emma looked at the mug in her hand. She had forgotten to ask Briana for a paper cup to go. She forced a smile and pulled out a chair. "Right."

Briana took the chair across from her. "Okay, so, this guy? He's in a very different stage of his life. I'll be up front about that."

"A different stage? What does that mean, larval?"

"He just graduated college."

"So he's twenty...two?" Closer to Callia than to herself. Hell, closer to Caleb than herself.

Briana must have heard the skepticism in her voice. She made a placating gesture. "I know. I know. That's why I wanted to talk to you about this first. But listen to this."

She pulled a printout from her apron pocket. "

What are you looking for?

Someone to come home to. Someone to cook for, someone to eat with. Someone to share my life with."

Briana looked up expectantly, smiling. Emma had to admit it sounded more mature than the frat boy she had been imagining.

"Well, I will certainly be home," she said begrudgingly. "And he's welcome to cook for me."

Eating with her might be a bit of a stretch. She ate most of her dinners off her kids' plates after she put them to bed.

That reminded her. She'd have to find time to eat her own lunch, and it had to happen before she went shopping or she'd buy out the entire bakery aisle.

"Have your coffee with him tomorrow," Briana said, snapping Emma out of her reverie. "Fifteen minutes. If there's no chemistry, we'll call it there."

"Okay." She scraped the last of the cake pop off the stick, savoring the dense, moist sponge. "Yeah, okay. I can do fifteen minutes."

She looked down at the dregs of her coffee. Her break was over. She smiled at Briana as she pushed her chair back. "I'm sorry. I don't mean to sound ungrateful. I do appreciate what you're doing."

They exchanged a few more pleasantries before Emma made it out the door, already thinking about the rest of her day.

* * *

Emma told herself she wasn't going to get excited about this coffee...meeting. She refused to call it a date. Nor was she going to fuss over her hair and makeup. She was too old and too busy for that nonsense, especially for a guy who was only going to run screaming the other way. Just a minute with the brush getting the tangles out, then her everyday sunscreen, eyeliner, blush, tinted lip balm.

She would at least put on a dress. The day had dawned ten degrees warmer than yesterday, with clear blue skies. After weeks of dreary grey, it only made sense to take advantage. She reached for an old favorite, a belted maxi dress in deep Klein blue poplin. It had pockets.

As she pulled it off the hanger, the bold floral print behind it caught her eye. Nothing quite screamed, "Spring!" like a skater dress with a massive fuchsia tulip by your hip.