Jill's Decision Ch. 02: Advanced Lessons

Story Info
Jill decides Scott has more to offer.
5.5k words
4.58
16.7k
29

Part 2 of the 7 part series

Updated 06/09/2023
Created 12/28/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
EroSteve
EroSteve
318 Followers

Note to readers: I am disparaged that low scores for content are being given by readers who ignore the "taboo" portion of this category, and presume that only "Incest" content is appropriate.

Please...show some patience, and just enjoy the build, o.k.?

EroSteve

*****

Chapter 2 -- Advanced Lessons

Jill gathered her thoughts, quietly, there in the dark. She knew she had these tendencies. Psychologists can self-diagnose, but kink is kink, and everybody has what they like. For Jill, it was a long, strong, hard cock, preferably full of cum. She tried to tell herself that she led a normal life, but that may very well be debatable. Well, mostly, at least, but this had been a bit too close to the fire. Her fire. Scott was young, and strong, and obviously well-endowed, but come on, Jill, Amy boyfriend? Seriously?

She was still panting from the release. Her left hand wrapped around her right breast now, coated in the sticky mixture of her pussy juices mixed with Scott's cum. Delicious, and she knew it. Her hand pushed her breast in and up, then down to the nipples, pinching them out. It still felt so good, post-orgasmically, and her mind hadn't quite cleared up. Fuck he has a nice cock. Fuck, he cums a lot. She licked her lips, savoring the taste again. So naughty.

She lifted herself up enough to gain purchase on the toilet seat, and with difficulty, sat, still bent forward, her left hand now joining her right over her swollen sex. Her right fingers were still pushing, prodding her clit in the post-orgasmic bliss, and she felt the warmth collect at her outer lips as Scott's cum began collecting.

It was instinct. Nature. Muscle memory that made her do it. Jill's left hand cupped itself just below her engorged pussy, and cramping her stomach slightly, she felt the fluids build, then ooze into her hand. Jill's memories stopped, and she saw Scott's cock now, at the tip of her mouth. She pictured his hands stroking the turgid shaft, his purple head throbbing just in front of her. She wanted it; she wanted to taste it warm from his source. His hand was on her head, now, pushing her back, opening her up.

Jill squeezed again, and two more sizable dollops of cum left her body, warm for her hand. Lifting it to her mouth, there in the darkness, Jill lowered her lips to it, feeling Scott's hands push her back, and like a drunk taking a shot of whiskey, she pressed her hand forward, throwing her head back.

Copious, smooth, sticky, musky, pungent. So much. It must have been another two or three teaspoons full, and her mouth filled with the pungent man-musk, salty and pheromone-laden. She felt her nipples stiffen and saw Scott's cockhead dilate and squirt it's thick seed directly into her womb. Jill's fingers were racing over her clit, and the orgasm that followed was simmering hot, her vaginal walls quavering as she swallowed the naughty mixture away.

She was sweating. The room smelled like sex. She knew it. Her mind was moving a mile a minute, and despite the orgasms still shaking her body, Jill had a small panic-attack trying to decipher what she had just completed.

The problem wasn't that she was afraid, or ashamed. The problem was that she was still amp'd. Still needing more. The problem was that her orgasm was only clitoral and labial, not full-on vaginal. Now, she had to return to a party in motion, and what, pretend to be the simple housewife?

A moment or two later, Jill was standing in front of the vanity, lights on, and lightly washed the cum from her face. "They must have some makeup here somewhere", she thought. Opening the rest of the drawers, she found enough. Some blush, mascara, and a dark shade of lipstick. "Perfect", she noticed, as the wax glossed each lip anew, her face seemed fresh and well, unfucked. "Actually, this is really nice. Think I'll keep it...as a souvenir", and Jill pocketed the tube inside her shorts.

O.k. New problem. Light blue shorts tend to darken when wet. This wouldn't normally be a problem, if say, she were in the pool, and the entire shorts had become wet, but she hadn't intended on swimming, and the wetness they were showing was directly over, or rather under, her crotch.

No way out of this. Not now. They were boy shorts, loose and comfortable, so she went without panties, but now, each step that she took pulled them closer to her mons, and wet as they were, they stuck there, clearly outlining the fact that she shaved, and more clearly outlining the fact that she was fresh-fucked, since dry-out as she may, enough residual "Scott" was still flowing from that swollen hole that the possibility of getting and keeping dry was remote.

Nice. Just lovely. o.k. Pool it is. Let's make lemonade out of this somehow.

Stepping down the stairs carrying a towel in front, Jill made a bee-line for the pool. "Hey, Honey, I, uh, I, um, didn't think you wanted to shwim". It was Jim. More correctly, it was a toasty Jim, all liquored up with his buddies smiling like a pack of hyenas around him. Jill smiled, too, heavy in his own fog. Jill faced away from him; approached the group in the pool. The lights from the balcony shone just enough to light everyone up, but still gave a twilight glow. Besides, those lights were behind her, and the 3 or 4 kids in the pool would only see silhouettes.

"I changed my mind. Join me?" she asked, knowing full well he may not even have heard the question. Jill arched her back, and in one smooth leap, entered in a graceful arch with hardly a splash. She surfaced only a few feet away, coming up to sweep her hair back, and opening her eyes, found herself in 5 feet of water, directly behind Scott.

"Uh..Hi, Mrs. Curtis." Scott had moved to the ceramic-lined side, his arms on the pool's edge as she swam up to his left.

"Hi, Baby boy. You still o.k.?" Her hips brushed his as she turned slightly to face him, pulling her hair back over her shoulders.

"Uh, yeah," Scott was looking for anyone near "I'm good. Uh, I really like that with you" and for the first time, Jill saw his smile light up. Unfortunately, she also saw where his eyes lowered, and knew this game was still afoot.

"Well, Handsome," Jill's right hand smoothed over his back and pulled him in front of her slightly, facing the deepest water with no one there "you and I may have to complete some additional education soon. I mean, "if" you're willing to participate in a meaningful way?" and her left hand snuck forward on Scott's abdomen, lowering easily into his shorts as she wrapped her hand around his slightly rigid member.

Scott exhaled, then stopped. Jill's hand lowered further still, cupping his full, round ball sac under the water, and squeezed slightly, pulling up just enough to feel his rod jerk. "The night's young, Scott. Don't you think?"

Jill smiled at him, pushing herself away in the water, performing a backstroke that easily lifted her C cups above the water for his gaze as she swam away.

Jill paused to look past her feet, Scott's eyes glued to her form in the water. "Naughty boy."

Scott coughed, surprised. She swam to the edge, and lifting herself out, wrapped up in a towel. 2 minutes later, she was sitting with the adults, conversing again.

20 minutes later, Scott was still in the pool, trying to swim it off.

As the evening progressed into midnight, it was Amy who pulled out the stereo for the younger generation to dance. There, under the moonlight, in the din of the house lighting, the few older teenagers met and danced to the tunes alongside the pool.

Jim was beyond hope now. Between the stories of his travels and his inability to hold his liquor, he was a puddle in the chair facing his buddies, near the grill, furthest away from the pool and the activities. Jill and her neighbor, Sondra noticed when the quiet discussion turned to raucous laughter. "There they go, Sondra. Jim's onto his new toys now. I guarantee that they'll head into the rec room in the garage next."

"Well, Jill, it could be worse. At least they're not driving, right?"

"True, but what does that leave us ladies to do?"

Sondra smiled slightly "Whatever we want, darling. Whatever we want." Swirling the cherry around her Tom Collins, she slumped back in the chair, inebriated herself. This woman was not motivated past her drink, it seemed, and any further conversation with a drunken neighbor was, well, hardly inspiring. Her silk cover-up draped across her legs hid her long legs somewhat, but her ample bosom slumped with her as she closed her eyes. "Are we seriously the only adult ladies left here? What happened to the rest of the neighborhood?"

Jill looked things over "I think everyone else boogied home. Too much party for them."

Over her shoulder, Jill saw Amy and Scott dancing near the back, right where she'd have to cross into the house, and her words paused, maybe too long for Sondra. "Whatever we want, hmm? Hey, Sondra, I think I'll refresh my wine, girl. Be back in a moment." Amy had her arms over Scott's shoulders, her head resting quietly on his chest. Amy's small-ish breasts pressed into him at the angle, concealed too well by the ample padding of her one-piece. It was age-appropriate, if you were, well, 60. Amy got her long legs from her mother, though, and the deep "V" cut of her swimsuit showed them off well.

Through the slight fog in her head, Jill couldn't help but wonder if he was aroused. That cock. Mmmmmm. Who knew? She found herself staring. Lifting herself up, and crossing the terrace in front of the dancers, embraced in a slow song now, she strolled past them on her right, between her and the pool, and headed towards the kitchen entrance. She didn't have to, but there was a certain deliberate sway in her hips now, and though her bottom shorts were still wet, in the summers heat, now relenting, it felt nice stuck to her pubes. As she neared them, Scott had moved Amy's back to her. Interesting. He was watching every step, and Jill noticed. She did the unthinkable for a mother not wanting to make a scene.

Placing her hands inside her cover-up, gripping the thin material of the boy shorts at the waistband at her sides, she pulled up, then back, and let the wet fabric not only cling to her swollen mound, but now dug softly into her own crease as she pulled the material off her back thighs into her crack, highlighting her pussy in front, and bearing the completeness of her ass underneath the coverup, if only she were to slide it aside. She was ruthless. Pure slut, and she knew it. She was hunting now, plain and simple. What she didn't know, or more likely, want to admit, was why, or maybe what she was hoping to accomplish? She reasoned it was just the alcohol, but she had never before been "in competition" with her daughter. Not like this, but it felt so good while also feeling so very naughty, and she felt her pussy swell with anticipation.

Jill spun slowly on her heels, allowing her cover-up to conceal it all still. She never stopped looking at Scott as she neared the couple in embrace. She felt her pussy ooze it's liquid out, knowing it added to her wetness deliberately. His gaze captured each moment of her advance as he danced with Amy, her eyes closed; his wide open and staring. As Jill neared the couple, still locked together, she pursed her lips, pulled out the tube of lipstick she had so innocently pocketed, and looking at "no one in particular", set her hips back slightly, lowered her breasts, lifted her head up slightly at the moon, and slowly applied the gloss to her lips. Innocent, my ass. It was a scene from a porno flick, and she knew it. She may as well have been Jessica Rabbit in the bar at that moment, she oozed such sexuality. Capping and pocketing the tube, her eyes locked with Scott's, and she blew him a slight kiss, winking.

Scott felt the inevitable begin.

Jill continued. Three more steps, and she made the slight left turn towards the doorway in front of the veranda and out of line-of-sight to everyone else BUT Scott. Turning slightly to her left, her head over her left shoulder, staring directly into his eyes again, she used her left arm and hand to slide her robe to the side, behind her, exposing the flesh of her left ass-cheek, while highlighting her left breast, captured perfectly inside the bikini top.

Scott froze. More of the inevitable was growing in his loins. He couldn't stop what was starting, nor could he look away, nor did he want to. Raising both hands over and behind her neck, Jill reached back and untied the bikini top, holding the strings now with only her right arm, lowering her left, resting it on the mound of her ass for Scott to see, daring him to look away. She raised her left leg onto the chair adjacent to the doorway, highlighting the muscles in her calf and thighs, stretching the expanse towards her wetness only slightly into view. As she again pursed her lips in a kiss, Jill looked down, at her own left breast to watch the material slip over and down from it as she released the string. In what took forever to occur, almost in slow-motion her breast bounced slightly from the unrestrained weight which allowed it a more natural poise, as the areola tightened and then lewdly displayed her nipple's profile to him. There could hardly be a more sexual beckoning.

For Amy, Scott's developing erection was uncalled for, and something they had talked about repeatedly. Scott knew that look in her eyes the moment she backed up slightly and peered up at him. "You're a pig, you know that Scott? Seriously? Can't we just dance a slow dance for 5 minutes without your horn dog showing up? Jesus Fucking Christ, you ass."

And Amy walked off.

Scott didn't want to explain to her why, or how, he just wanted to crawl into a hole in frustration. What the fuck, Mrs. C? His arms dropped to conceal the growing bulge that Amy had already felt, and he looked back at where Mrs. Curtis had entered the house. Through the screen door, barely lit, he could make out the figure of Jill standing just behind the door, laughing slightly at Amy's rejection. He could also see her outstretched hand with her pointer finger making the "come hither" motion.

So he did. Scott glanced to see Amy chatting up her friends in the far corner, nearer the garage, and decided it wasn't worth a public fight, and that this night wasn't going anywhere positive except with maybe Jill. Stepping through the door, he was met with a fully re-clothed Jill. "Come on, Scott, we need to talk a bit."

Jill led them up the stairs, around the corner, and into what she believed was a spare bedroom before she spoke again. "Looks like you aren't getting anywhere with Amy, the same way I'm probably not going to get anywhere with Jim tonight. So maybe we should continue your lessons here, o.k.?"

Jill didn't advance, just put her hands on her hips, standing close enough to Scott, and waited for a response. Unless Scott agreed, this was going nowhere, and a professional Psychologist has a lot on the line to lose with accusations of aggressive, sexual behavior.

Scott was quiet, but the dim lighting from the outside foyer made clear the sizeable constraint his pants were attempting. "Um, Mrs. Curtis, I don't know what to say. Amy just doesn't want anything to do with me like this."

Good enough, and Jill's pussy throbbed in anticipation of what she was formulating. "Scott, I'm going to ask you once and once only. Have you EVER been with a woman, sexually?"

"No, Ma'am."

"Good boy. Still waiting for Amy, are you?"

"Yes, Ma'am."

"Would you like to be more prepared for Amy, Scott?"

Long pause. But then, "Yes, Ma'am."

"Good boy. If you do exactly what I tell you, no one will get hurt, and you might just learn a thing or two tonight, understand?"

"Yes, Ma'am."

Jill advanced the two steps to Scott and wrapped her arms around his neck, pushing her hips into his groin, capturing his erection firmly against her mound. He was thick now, erect, and she was priming his pump. She pushed him backwards, slowly, until the back of his legs met the bed. "Stand here, and don't move a muscle unless I tell you to." Her lips were wet inside his right ear, and both her hands were gliding over his shoulders, down his arms, and ended up hooked in his shorts as she lowered herself to her knees

"Do you have something for Mommy, Scott?" Jill whispered, kissing his abdomen as her tongue trailed wetly down his stomach, pausing at his pubes as her hands began lowering his shorts. "Something thick and hard and full of your baby-making sperm for me?"

Scott's breathing paused as Jill's knees hit the floor and the band of his shorts clear the bulbous head, now spring up slightly, relieved of the downward pressure. Her mouth was already at the tip. "Something warm I can taste?" and she kissed it softly, causing him to jerk before her mouth captured the crown inside her lips.

"MMMMmmmmm..."and Jill's mouth drew well over half of Scott's erection into her mouth on the first stroke in. Backing out now she remarked "Good boy, Scott...just what Mommy wanted." Her second stroke, with her head angled slightly back and her body forward, took nearly the entire length, save for a few fingers that separated her red lips from his groin. She held it there, and Scott threw his head back, his hands instinctively finding her head, and a low, guttural groan left his lips. His breathing stopped again, and his hips thrust out in response just enough to stroke his cock inside her mouth.

Jill relented, and slowly his manhood emerged from her mouth, the veins thickening, the shaft pulsing with his heartbeat, her tongue gently playing with the crown until her lips kissed the underside fully down to his balls.

And, oh, were they were full again. Tight, and so very, very warm. Jill's hand made an "O" around them at the top, where they connected to his core, and slowly began to tease them down and away from his body, like pulling an apple off the tree with just your thumb and forefinger wrapped around the stem. At first, they spasmed and rolled inside his sac, and pulled up again, but her grip tightened, and as her fingers massaged the two orbs from below, they slowly descended. Jill's lips were wrapped tightly around the head of his cock again, her tongue flicking the base.

She moved back slightly, stood, and pressed her body into his again, all the while pulling his sac lower. Her mouth was again in his right ear "I'm going to show you a few things that Amy has no clue about, Scott, and I hope you'll remember them the next time you encounter them. " Scott could feel the heat in her breath. He could smell his sex on her mouth as she kissed his chinbone down to the tip of his chin, then down his throat and over to his shoulder.

Jill squatted again. "Let's start with my mouth, o.k.? Ready, Stud? I want you to watch." Without waiting for the answer, Jill took the head of his meat into her mouth, made one small loop with her tongue, and crouching forward, angled her head back so that her throat straightened out beneath him. She released his testes, and put both hands on Scott's exposed cheeks. Scott looked down as slowly, ever so slowly, in the twilight, he watched his inflamed rod sink into the depths of Jill's mouth. She was breathing through her nose, then stopped, swallowed, and in the silence, pulled his ass cheeks forward until his pubic hair was rubbing against her lips.

Scott was in awe, and every nerve on his cock and balls was firing. Jill, for her part, gently swallowed, again and again, massaging the entire length of his stick, feeling the pressure building in them both.

He was near it; too near it, and he said so "Mrs. Curtis. Mrs. C. I'm gonna cum if you...if you..." but she quickly backed off, leaving a sloppy wet trail of saliva streaming off his cock. "Oh, no, you don't, Mr. Not yet. I'm not done with you by a long shot."

EroSteve
EroSteve
318 Followers
12