Grate Sex - Cover

Grate Sex

by Jo-Anne Wiley

Copyright© 2025 by Jo-Anne Wiley

Fantasy Sex Story: INCLUDES TITLE ILLUSTRATION: Great sex is where you find it, sometimes right beneath your feet.

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Reluctant   Heterosexual   Fiction   Masturbation   .

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The thundercloud threatened, darkened the street and set the street lamps flickering.

“Damn,” Kelly swore and popped her umbrella as the skies opened and a deluge swamped downtown Manhattan. Torrents of water flooded the gutters, turning the catch-basins into swirling drains of filthy water clogged with discarded newspapers, cigarette packs and wrappers.

Kelly was only two blocks from the refuge of her office building but even so, it was hopeless. Her umbrella was quickly becoming ineffective and the damp was invading her expensive high-heels. Like others caught in the open, she looked ahead to any storefront where she might escape the downpour but was disheartened at the sight of bedraggled onlookers crowding into any space that might offer a bit of sanctuary.

The rain started in earnest, the spray passing down through the fabric of her designer umbrella and taking the curl from her hair along with it. She forged on, past the entrance to an alley and as she sidestepped a river of foul water, Kelly glanced up. Her eyes shifted, then focused.

It was a metal awning bolted to the side of a building that no one else had spotted. A mere thirty-foot dash down the alleyway was shelter from the storm. She hesitated a moment but a trickle of cold, tracing a line down her spine, spurred her forward.

Ducked-down, Kelly turned into the alley, jumped a puddle and landed with her back against a brick wall. The deafening rain hammered on the sheet-metal above her head.

She was standing on a cast iron street grate with the awning positioned to protect it. She spotted the hinges and lock and assumed the grid was actually a metal hatchway which allowed access to the basement of the building at her back. An old coal scuttle she thought, built back in the day when coal would be off loaded from a truck and shoveled down a chute.

Kelly closed her umbrella and propped it against the wall. Her foot skidded on the metal and the heel of her shoe caught in a slat, scraping the snake-skin. She cringed at the thought of ruining a pair of four-hundred dollar pumps and immediately lifted her foot and, crossing an ankle over the opposite knee, she inspected for damage.

She blew out a breath. Kelly had been lucky but now looked to find secure footing.

The access hatch had a wide metal frame cast around the perimeter, wide enough to safely support a shoe either side, but it meant widening her stance to straddle the iron grate. Kelly placed the sole of her left shoe down and, hiking her tight business skirt to mid-thigh, stretched out with the opposite toe.

With a hand on the wall behind and feeling smug, Kelly leaned back and watched the rain stream down from the edge of the awning. She was safe and dry with nothing more to do than wait out the weather.

And it didn’t take long. The storm passed as quickly as it had arrived leaving the air fresh and cool.

Kelly waited an extra minute, then swiveled her hips and as she reached for her umbrella she caught movement below her feet. Her imagination ignited: Rats.

They were everywhere in the City and Kelly dreaded the thought of them. She had visions of a filthy rodent, its teeth, yellow and gnashing, digging its claws into the skin of her leg and scurrying up under her skirt. The thought left her polarized.

With senses flipping and eyes circled in fright she attempted to pierce the shadows beneath her feet. But it wasn’t a rat that drifted into focus, but the contours of a man’s upturned face. And he was looking up her skirt.

Kelly couldn’t make her legs work and she stood frozen with her feet wide apart. Sure, she was wearing pantyhose and a pantyliner, but still, the guy was looking between her legs and Kelly was sure he was enjoying the view. Kelly swallowed hard and looked about to see if anyone had noticed her dilemma. But she still had the alley to herself, except for the man below the grate.

A brush against her ankle centered her attention. With a rush of panic, Kelly watched a disembodied hand squeeze out from between the slats like a cobra’s head and latch onto her ankle.

Kelly wanted to kick. Wanted to empty her lungs and scream– scream like she had never screamed before. She braced herself for the vice about her ankle to tighten– to squeeze the delicate tissues to the point of snapping the bone before dragging her hapless body down into the dark dank depths of the sewer where her blouse would be torn from her shoulders, her skirt yanked up to make way for probing fingers. Stripped naked, her vagina would open to the invasion of a filthy fat penis. And her breasts eaten by the wild scavenger from the New York City sewer system.

With her heart hammering she held her breath and waited for the unavoidable consequences of the stupid risk she had taken by entering a deserted alleyway. Would she gamble her life and fight back? Or give in to him. Present him with her body and hopefully please him. At least long enough to keep her alive for awhile. As a young woman of little experience she wondered if she was capable.

But then his thumb moved.

His fingers held her delicately. Tenderly. And he traced the edge of her ankle bone, down and around. His hand rose to sooth the curve of a calf muscle. And then ... he was gone.

Kelly blinked. Looked to the street again and then back down at her exposed leg. She took a breath and her lungs froze. What was that? Oh, Lord– the faintest whiff of semen hung in the damp air. It seemed to cling, invading her nostrils. Kelly shuddered, shook off the feeling of despondency, reached for her umbrella and ran.

Back at the office, she tried to do something with her hair and, with her senses still dazzled, got herself seated behind her desk. Kelly opened the file she had been working on, looked at the column of tax assessments, and tried to focus. But trying to work seemed as hopeless as trying to fix her hair.

Her fingers trembled and Kelly struggled with her feelings. Should she call someone? Report it to the authorities? But then everyone would know what a dope she had been. I mean, nothing really happened, she tried to convince herself. It wasn’t like I was subjected to a real sexual assault.

Her insides were tumbled and she fought to settle herself. A sense of isolation rose in her chest and she let her head slump, closed her eyes, and tried to come to grips with tortured guilt. What was this strange feeling that had come over her, this cloak of loneliness? And then her chin slowly came up and her eyes opened in surprise. It was disappointment. Unbelievable.

Kelly was stunned by this new revelation. She was frustrated and disappointed– felt cheated, even. She had suffered through the shock and fear but in the end, nothing had happened. And strangely, that left her feeling empty and disillusioned.

“What’s up ... You okay?”

Stacy stood in front of Kelly’s desk, her eyes full of questions.

Kelly felt cold and exposed. “Oh-h ... nothing.” She looked away. “Just trying to figure out something for tonight’s dinner.”

“Oh sure. Always a quandary ... when you eat alone as often as you do.”

“Something you don’t spend much time worrying about,” Kelly shot back. “You’ve got dinner invitations lined up.”

Stacy grinned and tossed blond hair from her eyes. “My boobs are better.” And with a practiced shift of a shoulder her unfettered breasts rolled to one side and lifted beneath her soft, white sweater. It was a move she had perfected for those moments when she didn’t have money for the bartender or wanted to be treated to chateaubriand at Jason’s Restaurant.

“Very nice,” Kelly admitted, comparing Stacy’s healthy chest to her own diminutive orbs. Bitterly, she had to admit she didn’t have much there to offer a man but had read somewhere that some guys like small tits so she still held out hope. But at thirty years of age, she had begun to wonder when such an elusive man would enter her life.

“Okay.” Stacy straightened and parked hands on hips. “Don’t bullshit a bullshitter. Especially one who knows you so well. You’ve got something stuck in your craw and I want to know what it is.”

Kelly’s eyes fell and she turned as red as a brick.

“Ahh, see?” Stacy started in again. “Hit a nerve, did I?”

Kelly sagged. “I h-had an incident. At lunch,” she stammered, not looking up.”

“What kind of incident?” Stacy pressed for details.

Kelly let out a breath and looked about the office, but not seeing any interlopers she conceded. “It was at lunch. I was headed back to the office, along fourteenth, and it started to rain. Really hard. I stopped a moment. I was standing on one of those cast iron grates in the sidewalk, you know? And happened to look down...”

“Is this going to take long?” Stacy interrupted. “I got a shitload of paperwork...”

“Okay ... okay...” Kelly sniffed. “I was standing on this god-damned grate and when I looked ... well ... well there was a guy down there. Looking up. He was looking up my skirt.”

Stacy gawked, her eyes bugged. Then a wide grin split her face. And displaying a line of perfect teeth, the pride of her over-priced oral surgeon, she began to laugh. “A guy looking up your skirt ... oh my ... alert the media.” Her eyes glistened, “You wearin’ underpants? Or was today the one day in your life you decided to go commando.”

Kelly watched Stacy pull a tissue from the sleeve of her sweater. “Commando?”

Stacy dabbed at the corner of an eye.”Yeah, yuh know. Panty-less. I mean, how much of an eyeful did the dude get?”

“Not much,” Kelly mumbled. She wasn’t getting any sympathy from her friend and felt betrayed.

“Well never mind.” Stacy turned to go. “Next time you’ll know to leave your panties in your desk drawer.”

“You mean go back?”

“Well sure. Why not? Be naughty for once and give the guy a little something. It’ll be fun...” Stacy stuffed the tissue back into her cuff and disappeared down the hallway leaving Kelly to contemplate her hurt feelings.

Kelly was left unsettled by her friend’s feckless attitude but Stacy’s words still rang clearly inside her head: Be naughty for once.

Later, after work, Kelly made a slight detour on her way to the car-park. She had spent the afternoon struggling with a nagging sensation– between her legs, mostly, and now stood at the opening to the alleyway. It was almost surprising to see that the grate below the tin awning was still there. That it really did exist. Go commando, she thought, and resisted the urge to rub her thighs together.

During the midnight hours, Kelly had an insane dream. She was crawling through a sewer, madly trying to escape whatever was following behind. She was crawling through human excrement– her hair was soaked with piss. Her naked body smeared in shit. She raced forward on hands and knees but the sewer narrowed, the space became tighter as she moved forward until finally her shoulders jammed against the concrete.

With a cry of panic Kelly realized she was stuck, not being able to move forward nor back out. She heard the scurry of claws and the feel of its fur. The giant rodent mounted her from behind, sunk its curved incisors into her lower back and holding her, it pried open her buttocks.

Kelly was suddenly torn from sleep. She found herself face down on her pillow, her knees tucked up and sweat ran in rivulets across her ribs.

She rolled onto her back and stared at the ceiling. She had never experienced anal sex– she ran a hand down between her legs, searching for the elastic of her underpants– and here she was, dreaming of it. Her fingers brushed her swollen clitoris and she bit her lower lip.


Kelly checked her desk clock. By eleven, she was in such a state, she could hardly work. She recalled the odor clinging in her nostrils and moisture gathered beneath her tongue. No!

Her hands went limp and her chin sagged. Kelly couldn’t believe she was actually contemplating going back. I’m not really, she told herself over and over. Just going to pass by, on the way to the lunch counter, and look. So that’s the reason I wore a loose dress today? Instead of my usual skirt and jacket?

She was fooling herself. Who was the man beneath the grate? Kelly needed to know more. They shared something, now. Had history, as insignificant as it might seem.

“And besides,” she said out loud to herself, “it was a random encounter. He won’t be there this time.”

“Who won’t be there?” Stacy stuck her head through the door.

Kelly’s chin came up, her eyes bugged. “Ahh, t-the guy who’s cleaning my gutter. I’m supposed to pay him.”

“Gutters? But you live in an apartment.”

“Yeah. Well I asked the landlord but nothing ever gets done. So I hired someone but he won’t be there. It’s almost lunchtime.”

“Humm.” Stacy shrugged. “Oh, and I checked with the records department, about the building with the awning.”

“You checked?”

“Well sure. You’re interested, aren’t you?”

“No-o-o,” Kelly lied.”

“Back in the late eighteen-hundreds, it was a tavern. Paddy Green’s to be exact. Your grate in the alley was used to roll kegs of beer into the basement.” Stacy spun on a heel. “Got a lunch date. See yah.”

Kelly slumped back into her chair. “Fascinating...” And she was left to contemplate the empty void in her doorway, along with the one in her stomach.

At quarter to twelve she went to the lady’s room, pulled off her pantyhose and contemplated her ratty white pants. There was nothing wrong with them except they drooped in the bum and looked like something a prepubescence school girl would wear. I just can’t, she thought. Kelly told her supervisor she had a dental appointment and went shopping.

A block away, there was a small boutique that specialized in women’s undergarments. Kelly was halfway-inside the door when she saw the display of personal vibrators and realized her mistake.

But it was too late to turn back. “Shopping for something sexy?” The woman straightened from behind the display and smiled.

“Ahh, just looking...” Kelly replied, the nervousness telling in her voice causing her to blush.

The woman behind the counter stretched to her full height. She looked like she should be an airline stewardess– tall, self-assured, slim and very attractive. She shot Kelly a reassuring smile. “I’m Mattie,” she introduced herself. “Could you narrow things down a little? I carry a lot of stock.”

Kelly felt her insides cave. “P-panties,” she stammered.

“Oh, well sure...” the woman stepped from behind the counter, “I’ve got an extensive collection. Come look.” And she led Kelly to a display unit with rolling shelves. “I import most of my undergarments from Europe,” she continued, sliding out a shelf. “Mostly from Paris and Milan.”

Kelly looked over colorful, neatly stacked panties in assorted fabrics. Silk, satin, lace. “Oh my...” Kelly exhaled. “How ever do you choose?”

Mattie laughed and reached for a lower shelf. “And I have these, for when you’re feeling a bit randy.” The shelf displayed even more panties but when Mattie held one up to the light, the crotch parted to reveal an opening large enough for a man’s hand.

Kelly felt a lump grow in her throat. “But...”

“Yes, Mattie continued. “Crotch-less panties. Cute, aren’t they? I get these from Italy,” she said with a cagey smile. “The Italian women are so forward in their thinking. And I just got this number in, special.” Mattie reached for a scrap of black lace. “I’ve already tried a pair and I can’t tell you how wicked they made me feel.”

“Wicked?” Kelly repeated, feeling a bit inept.

“Oh yes,” Mattie replied. “Look here.” She separated the opening. “Each side is lined with spandex and it causes your pussy-lips to bulge through. I wore a pair around town yesterday and it felt like I had a mushroom squeezing out from between my legs.”

Kelly’s eyes circled. “You went out in public?”

“Of course, silly,” Mattie’s smile deepened, “it’s so much fun. I love being naughty in a crowd. There’s a gentleman’s club a block over and the waitresses are naked to the waist. I go in, from time to time, wearing heels and a man’s sport coat ... nothing underneath ... to chat with the guys. It’s a blast. They can’t decide whether I own the club or I’m in there, hooking.”

“And you like that?”

“Yeah,” Mattie confessed. “It makes me feel dirty, yah know? But it never leads to anything serious ... except once in a while when I let a guy cop a feel and he gets off under the table.”

Kelly took a breath. “You do that? In public?”

Mattie smiled to herself. “Sometimes. But usually I’m satisfied with my Earth-Mover. It only takes a moment.”

“Earth-what?”

“The vibrator.” Mattie pointed. “The one with the spatula-shaped tip. It’s great. I get those from the Netherlands.”

“I see...”

“So you buying for a special guy?”

Kelly felt beads of sweat breakout across her forehead. “No. Not really.”

“Oh. A woman, then...”

Kelly felt cornered. “Y-yes,” she stuttered. “I have a ... a girlfriend.”

“Lucky girl,” Mattie cooed. “C’mon back and let’s us try these baddies on.”

Let’s us? Kelly thought.

“Your girlfriend will love you in them. Guaranteed.”

Kelly stepped into the booth and, as she feared, Mattie followed her in.

“Off with the old ... on with the new...” Mattie chimed.

Kelly swallowed hard. Running her hands up under her dress, Kelly dragged her panties down, off over her shoes. Mattie reached for them, frowned but didn’t say a word. She discretely balled up the graying cotton and dropped them outside the change room door.

“Here.” Mattie held out the crotch-less panties for Kelly to step into.

Kelly pressed her dress to her thighs and fighting to retain her modesty, she stepped into the undergarment. But modesty wasn’t a word found in Mattie’s vocabulary and as soon as Kelly started to straighten, Mattie hoisted the panties up, the elastic snapping across Kelly’s bum.

 
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