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.