The Halloween Milf Next Door

Writer: UndyingDevotion

Description: During A Delivery To His Stunning Next Door Neighbour, James Finds His Deepest Fantasies Might Just Become A Reality.

James swore when his knee collided with the wooden post of the front porch, cautiously making his way down the front steps despite having his vision obscured by the saran wrapped platter his mom had forced upon him. Once he felt his feet hit tue sidewalk he let out a relieved sigh, setting off in the direction of his nextdoor neighbour's home.

His track and field training came into sudden use as a small contingent of soon-to-be trick or treaters came barreling towards him, forcing him to leap back and forth between them to avoid an unwanted accident. Just about hopping out of the path of a pint sized Mandalorian, James continued on his way, casting his eyes down to the wide platter, just to make sure everything was where it should be.

A short walk brought him to the elaborate pathway that led up to the opulent bone white house that he had known for most of his life in Illinois, a three storey building that was one of the most eye catching homes in James's neighbourhood, with carved pumpkins of all shapes and sizes littering the steps of the porch. But just like many of his male peers at high school, it was less the building that became a fixation for him and more of the woman who inhabited it.

Carol Richards had divorced her ex-husband just after James hit middle school, long enough ago for him to forget what Mr Richards looked like entirely, not that he minded, remembering the man only by his grouchy demeanour. Mrs Richards had always been the complete inverse of her long dispensed husband, a woman who never failed to exude a feeling of warmth to anyone she came into close contact with.

Despite being in her early forties, James had been convinced for much of his life that Mrs Richards simply didn't age, possessing both a physical and emotional youthfulness that made her seem far younger than her true age. She was a mother to two twin boys, both of whom happened to be a good three years older than James, with the pair both into their second to last year at college. James could recall a number of occasions where he was invited over by the twins, acting as a pair of surrogate siblings for the only child, but their age difference eventually drew them apart as the twins reached college age, with their respective interests rarely converging.

Yet, James always found himself acting as a lightning rod of affection for their mother, something the twins were all too thankful for as they yearned for their own independence, happy to offer up James as the sacrificial lamb for their mother to smother. Even after the twins finally moved across states to their college in California, Mrs Richards still always found her way of plying James with a bit of her intoxicating warmth every so often, though much of her time after the departure of her sons was spent at her law firm in the city, with James's encounters with the woman becoming less and less frequent over the few years that passed.

It became a routine for James's friends to invite themselves around to his house whenever they could, with many hoping to catch just the tiniest glimpse of the chestnut haired beauty next door. Many feelings of guilt popped up whenever he recalled he and his friends spying on her from his bedroom window during the summer period, desperate to witness Mrs Richards sunbathing in her back yard, always clad in a bikini far too undersized for her stunning body. James could also remember with much amusement catching some of the married men around the neighbourhood doing their best to catch a surreptitious look at Mrs Richards, with one or two earning the evil eye from their wives.

No matter how infrequent his visits with Mrs Richards became as she kicked her career progression into full gear, he could always guarantee that he would see her during the various holidays throughout the year. Christmas and Easter were always times for her to show off her neighbourhood spirit, decking out her house with decorations and attractions that never failed to catch the attention and the imagination of both kids and adults alike, with James recalling one Christmas in particular where she had covered her front yard in enough massive inflatable mascots to cover up the usually immaculate lawn entirely.

However, it was Halloween above all that always whipped up the fervour within James. Even as a kid he could vividly remember sprinting over to Mrs Richards home, dressed in whatever elaborate costume his parents had stuffed him into. By far, she was one of the most generous dealers of candy in the neighbourhood, always amongst the first points of interest for any trick or treaters looking to fill their sacks with high quality chocolate. James was always the recipient of special treatment, always getting an extra helping of whatever Mrs Richards was dealing out.

James dashed up the the steps and swaggered up to the ornate front door, using the perfectly clean diamond patterned glass to ensure that not a hair was out of place. Reaching a hand out from beneath the large platter, James pressed against finger to the doorbell, taking a small step back as he waited for a reply. Barely half a minute passed before he heard the locks on the opposite side being clicked open.

"Is that James?" Mrs Richards spoke flirtatiously as her head appeared between the crack of the door, displaying her face which had been perfectly made-up, deep red lipstick highlighted her ivory white teeth, with a dusting of blush that accentuated her aristocratic cheek bones. "I was wondering when you would arrive."

"Oh, I'm not too early, am I?" James asked, swallowing as he received a calming smile in return. "It's just that mom wanted me to give you a bunch of these cookies, I'm not sure why though."

Mrs Richards replied simply by opening the door completely, revealing a sight that instantly sent the blood in James's body rushing down to his groin, causing him to harden against his constricting jeans.

She posed without a hint of shame, showing off the gladiator costume that adorned her body, baring the figure she had worked incredibly hard at maintaining over the years. A faux leather corset sat snugly around her waist, decorated by a series of plastic ornaments made to resemble brass fixtures. Thin Roman style pteruges of the same faux leather made up the skirt section of the outfit, with each small movement of her legs granting a full view of her alabaster thighs. She wore a pair of black pleaser heels, with diamond shaped straps that stopped just short of her knees. To finish off her costume, a dark grey thick replica fur cloak rolled from her shoulders down to her feet.

"James, you know that there's no such thing as being too early or too late in my home, especially for you," she replied with a quick wink, gratefully taking the wrapped platter from James, "in fact, you couldn't have arrived at a better time. Come in, I don't want you standing out in the cold."

James did as he was asked, stepping inside of the massive home where he was immediately glad to feel the warm heating wash over him. He closed the front door and followed the lady of the house through the highly modern hallway, listening to her heels clicking against the decorative white tile flooring along the way.

The pair swept into the large dining room, with Mrs Richards skipping over to he marble top kitchen island to place the platter down beside a row of at least three dozen white paper bags. James glanced out of the windows that looked out to the expansive garden, letting him see the perfectly curated flower beds and lawn, along with the sun lounger that never failed to bring up memories of his summers of trying dutifully to not get caught during his extended staring sessions.

The sound of rustling caught James's attention, drawing his eyes back over to the island. He spotted Mrs Richards unwinding the transparent wrapping from the tray, bending over the edge of the marble top as she inhaled the scent of the freshly baked cookies.

"Perfect, as always," she said, delicately lifting the Halloween themed cookies up one by one, gently depositing them into each of the open paper bags, "your mother's skill with an oven will never cease to amaze me."

"I guess so," James shrugged, having benefited significantly from his mom's decade long career in bakery, "but what are you doing with the bags. Are you going to be handing them out to the trick or treaters?"

"Not tonight, I'm afraid," Mrs Richards admitted, letting the final few cookies slide into their respective bags, brushing the crumbs off her hands, "the firm is having a little Halloween get together, and I promised to bring the party favours. I couldn't have thought of anything better to hand out other than some bespoke gifts and a sample of your mother's baking."

"So you're not going to be here for the evening, Mrs Richards?" James asked in surprise, unable to recall a Halloween where the stunner hadn't featured in the neighbourhood festivities in some capacity.

"I'll still have a bucket of candy on the front porch for anyone wanting to give their sweet tooth its fix, but I'm going to be in the city for much of the night," she replied, sealing each bag with a small, colourful sticker, "and how many times do you have to be reminded? You know you can call me Carol. Besides, are you going to miss me tonight?"

"Sort of," James answered with a cherry red blush when he looked into her sparkling hazel eyes, "it's not quite Halloween without knocking on your front door."

"Ahh, but you won't need to worry about my door soon. College is just around the corner for you, and you'll have more than enough scantily dressed girls eager to throw themselves at you," Carol grinned, resting her hip against the island top, "if you think my outfit is a something worth looking at, you should just wait until you're living in the college dorms during Halloween. Sexy nurses and barely clothed women will be in abundance."

"Maybe, but I doubt that they'll hold a candle to you," James smiled shyly, "you've always been the talk around school. I can't even begin to count the number of times where guys would talk about... well, you can sort of guess what the topic was."

"Believe me, James, I've always been aware of the lustful ways of the twins's friends. I even had to stop attending their soccer games because I kept distracting the dads, and the coaches occasionally," Carol replied with mischief in her eyes, "did you ever take part in such riveting debates?"

"Well, I might have said some things," James coughed, looking back to the sun lounger sat upon the decking beyond.

"Did you put in a good word for your favorite neighbour?" Carol smiled, resting her elbows upon the island, propping her head on her hands. "Perhaps something relating to my hours of sunbathing during the summer periods?"

"Y-you knew?" James stammered, horrified by the idea that his best attempts at covert oggling had not only failed, but that Carol was fully aware of just what he and his friends had spent large chunks of their time at is house during the summer break doing. "Mrs... Carol, I'm really sorry about that."

Carol shook her head, amused heavily by the ever developing blush on James's face. "Don't worry about it, James, if I had a problem with it I certainly wouldn't have kept it a secret for all this time. In fact, I was always quite flattered whenever I spotted the curtains of your bedroom window shifting every few minutes or so."

"So much for discretion," James sighed, reminding himself to provide his clumsier friends with a bit of payback, "I couldn't help it. There's not many women in this town that stir up as much talk as you."

"Interesting," Carol said, sauntering around the island, dragging her nail across the marble as she brought herself directly in front of James, "tell me, was it just talking that you did? Or did you imagine yourself ever wanting something more?"I

"I, er," James swallowed again, fighting to keep his eyes fixed on hers, not wanting to cave to his desire to explore the sexy gladiatrix outfit.

With his the outline of his shaft becoming more prominent by the second, James struggled with his train of thought. One part of him believed without a doubt that she was simply teasing him, playing on his childhood crush in a kind way before letting him down gently. But another, significantly louder voice in his head took her question at face value, a sign that every dream he had ever conjured up over the years could be within reach, just as long as he had the will to make the daring next step.

"Earth to James, are you still with me?" Carol laughed, making James suddenly aware of his extended pause. "This isn't me messing with you, I'm genuinely asking if you've ever considered... acting on these thoughts of yours?"

"I-is that something you would be open to? If I did have such ideas that is?" James asked, reluctantly throwing caution to the wind.

Without warning, Carol slid her hands beneath the skirt of her costume, taking a few moments before she had what she wanted. James's eyes became as wide as saucers as he bared witness to the sight before him, not a breath left his body as Carol slowly slid her red thong across her thighs, allowing them to freefall to her ankles. Gracefully balancing on one foot, she lifted the other up to her hand, grabbing the thong as it dangled from the narrow spike of her heel.

Carol leaned over and stuffed the lace garment into the pocket of James's jeans, letting a sultry expression grow on her beautiful face as she stared back at his absolutely frozen body. "Does that answer your question?"

James let his hand crawl up to his pocket, brushing his fingers against the thong sticking out of it, just to make sure that it was truly there. "I guess it does," he breathed in awe.

Carol dropped her hands down to the buckle of James's belt and quickly opened it, struggling to get the zipper to slide across the bulge. But within a few seconds, she successfully wrenched his jeans down his legs, stepping back to let him finish the job concerning his black boxer shorts.

"My word, I had no idea you were so big, James," she cooed, turning on her heel to face away from him, leaning her upper body over the top of the island, parting her feet as she prepared for the inevitable, "the thing I want to know now is whether you know how to put it to good use? Are you ready?"

"More than you can imagine!" James rumbled with unconstrained enthusiasm, rushing to drop his boxers out of position. As soon as the band dropped down, his rock hard organ shot out, springing until James neatly caught it in his hand.

Shuffling across the tiled floor, carefully enough to not mark the individual tiles with the rubber soles of his sneakers, James brought his cock within three inches of Carol, licking his lips as the reality of the situation pumped adrenaline through his veins. Reaching a shaky hand out, James grabbed the wire holding the individual flaps of the skirt together and gently hiked it up, not stopping until the sight of Carol's bare pussy consumed his vision, ready and more than waiting for him.

Exhaling the breath he had been holding for a good minute, James took a couple of small steps forward, just enough to put in in the optimal position for entry, a subtle reminder to himself that there would be no turning back, not that he would have considered doing so. A brief feeling of guilt struck him as he observed Carol bracing the palms of her hands against the marble top, worried about the idea of betraying the twins by fucking their mother right in their own home. But such feelings disintegrated when Carol carefully pushed her presented pussy backwards, causing it to make contact with James's shaft as it throbbed heavily.

"Are you having second thoughts?" Carol purred, deliberately rolling her hips, rubbing the lips of her womanhood against the head of James's cock, coating it with her leaking fluids. "Just one push, that's all it'll take."

A fog fell upon James, shrouding him with a blanket of pure lust. Any reluctance that still remained was pushed aside, his deepest fantasy was within his grasp and he had no desire to let it slip through his fingers. Shutting his eyes, James drove his hips forward, easily breaking through the soft barrier of Carol's wet slit.

"Nggh!" James grunted, unable to cope with the sensation of feeling Carol's warm, tight tunnel hugging his shaft with every centimetre he fed into her. "You're really tight!"

"Surprised?" Carol asked, with a light hearted glimmer in her voice. As James fought to keep his momentum steady, she decided to speed up to process, conscious of her lack of time before she absolutely had to depart. "I may be a 'milf' as your friends would so kindly say, but I'm still selective about who I get into bed with."

A sense of pride shot through James's chest as he listened to her, realising that he was among the few men his neighbour had chosen to engage in a sexual relationship with. Thrilled by the idea, James let his ego power him. A sudden surge sent his the rest of his cock plunging into the chestnut haired woman's hole, planting his feet on either side of hers as he quickly searched for his rhythm.

Tracing his hand along the length of her thigh, James soon ejected his cock from her pussy, then sent it barreling its way back inside, feeling Carol gradually stretching out with every injection of his twitching member, until he was able to saw in and out without much difficulty. Emboldened by the indecent, throaty moans that left Carol's lips, James snatched his hand out and grabbed the back of her neck, pushing her head down against the cool surface of the marble, letting his more domineering side take over.

"Hmmph, I never knew you could be so controlling," Carol gasped out, kicking her leg back into the air as James pummeled his cock into her at a near vicious rate, "I don't know how any of your former girlfriends could cope."

"They didn't, but maybe you can keep me satisfied?" suggested, shocked by his own sudden boldness, grabbing her leg as it hovered in mid air.

"Oh my, already fucking your friends' mother on the kitchen countertop, and even that's still not enough," Carol giggled, turning her head just enough to look back at James, "I might just have to consider your offer."

"I think I might be close," James hissed out loud, pounding against Carol at rapid speed, the sound of their colliding bodies filled the kitchen. "Where do you want me to finish?"

"Inside! I want to feel you filling me up!" Carol cried out, tossing her head around as her own climax struck.

With a final trio of blows, James felt the throbbing of his cock reach its highest intensity. Grasping her leg tightly in the air, James exploded deep inside her, jerking involuntarily as steaming hot ropes of seed were shot straight into the womb of the older woman. With stars in his eyes, James stumbled back, pulling his softening cock free from the depths of her addictive tunnel, unconcerned by the droplets of cum that fell to the floor.

"Carol, I don't think I've ever cum that hard before," James blinked his eyes in an attempt to regain his vision, providing her with enough space as she rose back up, "that was incredible!"

"Mmm, and you weren't too shabby yourself," Carol grinned, squeezing her thighs together as she shifted her skirt back down. Walking back to the other side of the island, Carol scooped up about half a dozen of the bags, sliding her arm through the loops of the handles. "Now, would you be so kind as to help me get these into the trunk of my SUV? If you do, I might just have to reward you for it when I get back."