From Mother to Mare Pt. 01

This a complete work of fiction and any resemblance to any living or dead person is completely coincidental. All characters are above the age of 18.

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Part 1 : Being Modern

Liam Hall was a 6'3'' teenager with a well-built body; his mother Regina, a 5'7'' buxom brunette. But according to him, she was an old-fashioned woman in a modern world.

She was busty and had full, ripe breasts, yet her dressing sense was so out of date that, to Liam's dismay, the best of her womanly features were always kept hidden from his eyes, which brimmed with fierce lust.

Liam's taboo desires for his mother partly rose because her appearance was charming, like women from Greek sculptures. Even at 37, her face was a fusion of cute features: shy blue eyes and a crisp smile that exuded seductive sweetness. On top of that, she had a mole on her upper lip to adorn her beauty.

But his lust was fueled by the accidental sight of her naked back when he forgot to knock. This was the first time he had a glimpse of what she looked like beneath those layers of garments. She had a graceful, curvy physique, peach-toned legs, and a full plump ass. As he gawked at her shapely back, it made his mouth drool and filled his heart with the lust of fifty demons.

Following that, he was caught in a tug of war between the guilt of seeing his mother in a way no son should and his desire to own her; with time, his desire proved stronger. It became his habit to wank every night while imagining her naked body as vividly as he could.

Yet, to his utter disappointment, mostly at home, she wore those oversized maxi dresses that made a woman look ten years older. In public, her choice of clothing was mostly long dresses that hemmed near her ankles, sometimes shirtwaists that looked like 50's fashion, and even her notion of short summer dresses were the ones that edged several inches below the knees.

It all pained Liam to look at women his mother's age blatantly wear short clothes, while she, many times sexier, still resorted to such a dull approach. So, at last, he made up his mind to take things into his own hands and turn her into a modern, milfy mare.

Chapter 1

One night, in the middle of spring, Liam decided to give it a try to spark things up in their shabby two-bedroom apartment. It had a tiny kitchen and a good enough living room, where they spent most of their time. Following dinner, Liam and Regina reclined on the worn couch in their scantly lit living room, sipping cheap wine and chatting about casual things. While he was not of legal age yet, she still sometimes allowed him to drink with her.

They were down a few glasses, and her more or less drunk state was obvious from the blush, dreamy eyes, and beds of sweat that formed on her forehead.

"Have you decided on your college?" Regina asked, her speech slurring a bit.

"Nah, not yet."

"You're going to be nineteen soon. Now you're stalling," she sighed.

Liam sat upright. "I am not stalling. I'm looking for a way to make money; we haven't had a home we can call our own or any savings. I need to-"

"Lee, listen to me," she cut him off. "You need to study and work on your career rather than be around your mom to waste your life."

Liam wasn't enjoying the way this conversation was heading. He had something more steamy in mind. Taking a deep breath, he gazed straight into her eyes and, with a bold, commanding voice, stated, "I am not wasting it, and I am not leaving you like that old man."

Regina frowned while a gloomy look unfurled around her face. "Let's not talk about him, right?"

"Yeah, let's not talk about that loser."

"Well, I can't blame him," she said, giving out a sad giggle and gulping a few sips. "I'm such an odd old woman, and men want young chicks."

Liam tightened his spine and almost exclaimed, "That's bullshit. You are not ugly or old; it's just that you have always been so old-schooled. That geezer made a huge mistake leaving you, leaving us."

"Your dad made his choice." She laughed frantically, taking a mammoth mouthful of wine, and said in a solemn whisper, "Who would rather be with me than some young girl, huh?"

Liam looked away. "If I had the chance, I would be with you than anyone else."

Regina's face lightened as she laughed out loud at his compliment. "Huh! What was that? Are you trying to flirt with your mother, Lee?"

"I am not flirting; I'm just saying that you are not old or ugly. You are beautiful, and..." he paused for a brief moment, then continued, "hot. Hot enough to be a model in Hollywood."

This made her chuckle again. "Are you blushing? Aww, you're such a mamma's boy."

"I'm not," he screeched.

His mother leaned towards him and caressed his head, stroking her fingertips through the strands of his hair. "Calm down, baby. You're such a sweet boy. Thanks for all the compliments; it was all to make Mamma happy, isn't it?"

"No ma I mean it. You are hot."

"Then how come your dad left me? How come no one ever asked me out?" She sadly whispered as her head drooped down with quivering lips.

The question his mom asked seemed like an opportunity. "It's cuz you have a poor sense of fashion. You still dress like you're living in the fifties."

Regina rolled her eyes. "We've talked about this before."

"No, we haven't; you avoid this conversation or you just nod and act like you understand, then the next morning it's all the same as ever again. You asked, how come no one ever asked you out? Here's what I'm going to tell you, if you start dressing like a modern woman, men will follow you like puppies."

She smiled, "Lee! I don't wanna be followed by men like puppies."

"Then do it for yourself. People call you strange, stupid, and all kinds of stuff; it hurts me to hear such things about you."

She rolled her eyes again. "Do what? Wear a bikini and roam the streets."

Liam slapped his forehead and shook his head.

"Then what do you want me to do?"

Liam leaned back and the tattered couch creaked under him. His heart raced pendulously as he mused about what he should say so as to make his dart hit the bullseye. Taking sips bigger than the cavity of his mouth could hold while gathering enough nerve, he blurted out whatever his mind could gather in the heat of the moment. "Here's the thing: we go shopping. I buy you some clothes of my choice; you dress up the way I want, and then we go out somewhere, to some pub or club. If no one asks your number, then you go back to wearing anything you want; I will never bother you about your clothing again."

"Lee dear!" She sighed with a tinge of discomfort in her eyes.

"Come on, ma, it's just a night. One single night is all I am asking."

She shook her head from side to side and said, "No one will ask for my number; I know you will choose some of those mini pants or short skirts, and I will look very stupid in those. Everyone will laugh at me."

"What if everyone gawks at you? What if somebody actually asks you out?"

She smiled nervously. "Then you win!"

Liam smirked, "Bingo! And what do I get if I win?"

"Name it!" his mom shrugged.

"Okay, here's the deal. If you are right, you get to go back to your way of dressing, and if I win, you will start wearing clothes that's on par with today's fashion."

"You have a deal. But I have a bad feeling about this."

Liam put his glass on the table. Leaning close to her, he held her face between his palms, then gently kissed her forehead. "I shall make you feel beautiful; trust me."

She smiled as he looked into her eyes. Liam could smell the alcohol in her breath; his heart was blaring inside his chest as he fought back the carnal urge to kiss her luscious, wine-coated lips.

"So when do we go shopping?" Regina asked to break the silence.

"How about tomorrow?"

She gulped. "Tomorrow?"

"Why not? The sooner, the better."

His mom giggled with her face still between his palms. "You always have your way with me."

"Not always, only sometimes." Liam smiled and kissed again, this time on her cheeks. Then, licking his lips, he said, "Goodnight; you have had enough wine for one night; also, we need to wake up early tomorrow."

His mother smiled, completely oblivious to his ideas.

"Goodnight love." Hic!

***

The following day, Liam noticed his mother was nervous. Her gait was more reserved, and her dress more rigid as ever. A strange shadow of bleakness hanged about her face as if something deep had poked its nose out through the open faucets of her mind, and it confused him.

Spending a night where sleep barely met his eyes, Liam felt a bit tired yet boldly hopeful. He kept pestering her to finish the chores quickly, but she, it seemed, consciously or otherwise took a slow, lingering demeanor. She acted similarly to when one is about to meet an unpleasant authority or enter some unknown, perilous territory.

When she finished, it was almost afternoon. Liam glanced at her as she came out of her room and pursed his lips. The way she dressed herself was more than modest: a plain-looking, full-sleeved turtleneck gown, the hem of which clutched her ankles so low that her sandals could barely be seen.

"Lee, are you sure about this?" Her shy, worried expression only spoke of reluctance.

"Yeah, of course."

"Can't we just-"

"You promised!" He cut her off as she started to say something to change his mind. Before she could say anything else, he spoke in a commanding tone, "Let's go," to which she acquiesced with a nod.

Walking down the worn, rugged stairs, both of them moved out of their tarnished apartment--a brick-walled, two-story house whose window panes had turned gray like an old woman's lens. In the brine-kissed air of the city, the sun hung lowly over the horizon, the light almost mellow, contrasting to their shabby neighborhood with homeless men smoking cheap tobacco, trash cans chocked full of rotting heaps, and crisp leaves from the surrounding trees littering over the streets until rustled away by an occasional breeze. It was one of the poorest suburbs in Providence, RI. Liam's dad ran away when he was just five years old. After that, he and his mother moved to this apartment, especially because of its cheap rent. They had been through hard times, with Regina in and out of several low-paying jobs to make their ends meet as well as pay for his expenses.

Taking a cab, they rode to a cleaner part of the city, garnished with restaurants, bakeries, and shopping malls. It's cobblestoned pathways were lined with a hint of salt mingling with the smell of cakes and freshly brewed coffee.

Mulling over several outlets, most of which were extravagant, Liam decided to go to The Pristine Plaza, an all-in-one shopping complex for all kinds of things. Nothing too fancy, but good enough for what he had in mind. After walking about the complex for some time, he came across a store that showcased some mannequins wearing mini skirts and bandage dresses. He smiled because this was the particular kind of store he was looking for. When he turned back, his mother had a deep blush across her cheeks, clutching the purse close to her chest. She looked like a little girl who had been called to the principal's office.

Regina looked at Liam and quivered, "It's...I don't know, I don't feel confident about it."

Liam leaned his head playfully, "It's going to be fun. Come on."

"Please don't make me!" She pleaded like a puppy, her chest rising and falling with her anxious breaths, her teeth biting down upon her lips.

"Hey, hey, remember the deal; also, we don't have to buy anything; lets just have a look around," he chimed, clutched her wrist and rushed inside, tagging her along.

The inside of the store was even more salacious than the outside decor. The walls, painted red, were covered with pictures of smutty models. The music, the dingy lighting, and even the scent had an erotic feel to them.

A salesgirl appeared and asked in a welcoming tone, "How can I help you, mam?" slightly frowning as she eyed Regina from top to toe, perhaps thinking she might be in the wrong shop. As a reply, Liam intervened, stating, "We are looking for party wears," plainly but boldly.

Her narrow eyes conveyed confusion, but as if pushing that aside, she asked in a professional voice, "One piece?"

"That'd be great," Liam replied.

They followed the girl to a section where the shelf was stacked with sexy outfits. Searching for some time among this rack or that, Liam found a sequin burgundy bodycon dress and he lit up with a satisfactory expression. It had a low neckline, was completely backless, and by the length, he assumed the hemline would stay above her midthighs.

In a swift turn, he asked the salesgirl, "I assume you have a trail room?"

"Of course," she smiled, pointing to a door yonder. Carrying the dress in his hands, Liam beamed, "Let's go," and started walking with enthusiasm. After him, Regina followed in short, reluctant steps.

As she entered the trial room with puppy eyes, Liam instructed her how to wear the dress and while she was inside doing whatever she was doing, Liam stood there deep in imagination and gave his dick a swift rub.

When she opened the door, Liam's jaw dropped. She did wear it exactly as instructed. The burgundy dress tightly gripped her curves along her busty chest and shapely hips. The neckline was low, showing off the depth of her milky cleavage, while the hemline, standing a few inches higher than her mid-thighs, flashed her healthy, long legs. Liam eyed his mother, and her blush reddened to a darker shade. While she stood there tensed, head lowered, crossing an arm partially across her belly, the sequin twinkled in the light.

"Damn!! Looking hot. See, I told you."

She pushed a strand of hair behind her ears, looked at him, and murmured, "You're just making it up."

"I am not; trust me, you look fabulous."

"The dress looks good on you, mam," the salesgirl added. Amidst all the compliments, her shyness eased up a bit as her nervous face transformed into something a bit more relaxed. Her curled lips turned to a smile as Liam winked at her upon hearing the girl's compliment. Following the procedures afterwards, Liam had it packed. Paying in the register, they left the store side by side, his mother still holding him by the arm. Once outside, she playfully pushed him on the chest and exclaimed, "I still can't believe you talked me into it!"

He laughed as he pulled her close, giving her a gentle hug. "Thank you, ma, really, for doing this."

She shrugged. "What choice did I have?"

They sauntered around the complex, looking at a few more stores. Taking her to a saloon, he had her wavy hair trimmed to shoulder length. With her dimpled, glittering smile, her hair now gave out a tantalizing lure. Afterwards, from a store that advertised trendy footwears, he chose a red-laced heel to match her dress. From a small store he bought a few cosmetics like, lipstick, eyeshadow etc. It was mostly because, in addition to her cautious clothing, he never saw her using makeup. Although she would have looked gorgeous in that sequin wrap without any cosmetics, he chose to buy some to enhance her beauty even more.

Liam bore all the expenses from his own wallet to Regina's utter surprise at how her son has become so independent as to pay such expensive bills. Every time she inquired with a curious question, he didn't really give his secrets away; rather, he made some dubious case about how he saved money from high school or some other story, and thus successfully kept his petty drug deals a secret from his mother.

Although the weather was beautiful and Liam wanted to goof around a bit more, they decided to call it a night because it was already time for dinner. Hence, they booked a cab to ride back to their dry, dull apartment.

***

It was before when Liam started dressing his mother up, with detailed instructions, regarding what she should do and what she shouldn't. By all means he wanted to ensure that the dress flashed a lot of her skin. Although he wasn't present in her bedroom while she was in the process of wearing his chosen attire, he very much wanted to.

Liam's manual efforts began especially after she opened the door to call him in for inspection. The way she wore the cloth was perfect expect for the fact that she tried to pull the hemline down as much as the elasticity of the fabric allowed, which to some extent spoiled its purpose. So he adjusted it by slightly pulling it up to its usual position and when she tried to protest, he calmed her down by stating, "this is the way it should be worn."

Making a few adjustments here and there, Liam went on to apply some makeup. By watching a few videos on YouTube about how to wear makeup, he followed the steps, of what he could learn in such a short time. He added a few sprays of aromatic perfume from her closet and lastly worked his hands at her feet, gently wrapping the straps of the red heel.

When he stood back to put an inspecting eye on her, he saw a goddess bewitching her spectator. A smoky pair of eyes sat seductively on her garnished face; her vermilion lips looked succulent and the bold and beautiful dress twinkled, explicitly mimicking the sexy shapes of her curves as if like jelly on her glossy skin.

"Do I look stupid?" she pouted.

"Are you kidding?" he replied still eyeing her up and down.

"Eh?"

"I mean the way you're looking I'm definitely winning the bet."

Regina grinned and blushed. Liam then went to his own room to get himself ready for the evening. He didn't wear anything fancy, just his usual.

Down the same rugged stairs out into the street, when they walked and waited for a cab to show up, all eyes of strangers were fixed on her. She leaned close to him, clutching his arm strongly as she walked or rather stumbled in her heels, showing her obvious discomfort to the situation.

Riding a cab, Liam took her to the very club he used to go to with his high school friends. Velvet Lounge, was written over it in strong purple neon, along with a martini cup. As they entered, Liam was welcomed with sizzling music, familiar blue pink lights and the strong smell of liquor. It was not one of the too fancy clubs but rather the ones frequented by people with a scanty pay check.

Liam choose this one in particular because, apart from being familiar, it was also known as the 'hook-up' club. As obvious from the name a lot of people especially men who visited there, were horny as goats and in search of some ass to hump. So he had a surer chance of winning the bet.

Into the thrilling atmosphere of the club, Liam saw his mother taking a couch table in the farthest corner as he went to order their drinks. From the bar counter he noticed a lots of hunks eyeing his sexy mother; both teenagers and grown ups.

Back to the table where his mother sat with her rigid posture while they sipped the chilled beer, he teased her, "you are raising a lots of heart beats," took another sip and added, "seems like its time for the next part of the plan."

Regina furrowed her brows, "what plan?"

"Okay here's what I'm gonna do; I shall leave you alone here on this table and see if some fish entangles in my mother's trawl."

A concerned look sat on Regina's face as she eyed the place around. Teenagers dancing on the floor, couples kissing and all around there were hungry eyes transfixed on her.

"Stop being nervous, let loose; people come here to enjoy they ain't bite you"

His mother turned her gaze back to him, "I don't like the way some guys are ogling; by the look on their eyes, it seems like they want to rape me!"

"Oh! I'm sure some of them are already doing that in their head," Liam teased. She gasped and punched his shoulder playfully, "you have become a very naughty boy. How long are you planning to leave me here?"

"Um, how about till I finish a bottle of beer?"