Louise eyed her daughter, one eyebrow raised, “That one? Seriously?”
Willow smirked a little, her white lipsticked lips raised in a playful smirk, “Yeah. Yeah, I think so.”
The two leaning against one wall, Willow with a coke in her hand and Louise with a glass of red wine stared across the party, past the various groups of people, talking, laughing, drinking and in costume to the the figure of Ms Williams, sitting alone, checking her watch as she too drank from a glass of red wine.
“Why her?” Louise asked, glancing back to her daughter, suspiciously.
“She used to teach me math,” she grinned, “she was a real bitch in school, I want to see if I can get a little bit of payback, you know?”
Louise shrugged, “Mm, alright. I agree, the first to persuade her up to the guest room to make out wins.”
Willow nodded in agreement, “Mm, but I get a go at her first…”
Louise paused and, with her little finger, dabbed at the corner of her ruby red lips, taking a spot of the lipstick and reaching out, dabbing it on Willows' cheek playfully.
Willow gasped and raised a hand to her cheek, knowing there would be a red smudge on her otherwise pristine angel costume.
“Mm, I think you need to go to the ladies room before you take your first swing at her, sweet pea.” Louise winked.
Willow stared mouth agape as her mom sauntered away, the woman dressed as the devil, wearing a cute red outfit that showed off her figure, a sweeping curved tail, pointed horns and dark makeup completing the effect.
Louise glanced back, noting the tiny head shake and smirk her daughter gave as she walked off towards the bathroom and she made her way through the Halloween party towards the woman.
She was in her late forties, Louise knew, with modest b-cup breasts and slim hips. She wasn't the sort of woman that she often chased, but she would do in a pinch.
“Heeey… Mrs Williams, right?” She said as she sat down opposite the teacher, she was dressed in a knee-length black skirt and an orange sweater, the glasses and the hairstyle giving her a Velma-esque look, likely the look she was going for.
The teacher looked up at Louise as she slunk into the sofa alongside the teacher, smiling plaintively as she crossed one red stockings clad leg over the other, reclining and putting an arm on the backrest of the chair, her other cradling the wine glass.
“Ah, you're Willows mother, yes?” She asked.
Louise, a little taken aback, smiled some and nodded, “Ah, you remember me?”
Mrs Williams nodded, “Mmhm, you've slept with maybe… Half of our school's single mothers, I think.”
Louise hesitated, she hadn’t considered that but she knew it was probably true. She decided to roll with it, given the only other circumstance was to go against the word of however many women had gabbed about their escapades.
“Well,” she smirked playfully, “I won't deny I bring a lot of women in this neighbourhood a little… Relief, from their pent-up needs. How is Mr Williams, anyway?”
She flushed a little and Louise had to hide a smirk, recognising the symptoms, Mr Williams was underperforming…
“He’s well, thank you,” she replied, frostily, looking away, eyes scanning the party, her cheeks still flushed, modestly crossing one leg over the other.
“You know…” Louise stretched out a hand, resting it on the woman's exposed knee, “If you want…”
She looked towards Louise and frowned, “I will not become just another notch on your bedpost. I suggest you bark up another tree.”
Louise hesitated, withdrawing her hand a little meekly, “I’ll uh… Go refill my glass.”
She said, standing with her still half full glass and walking away to where she and Willow had stood before, the girl waiting with a smirk on face. Her little angel, dressed as an angel contrasting nicely to her demoness vibe.
“Strike out?” Willow said innocently as Louise stood beside her, huffing.
“Yeees. She knew of my exploits… I never stood a chance,” she sighed, “at least not on my first pass.”
“Mmhm, watch how the pros work.” Willow traced a finger across her mom's cheeks, smirking as she strutted through the crowds, adjusting the cascading white hair of her wig as she moved towards her former teacher.
“Mrs Williams!” she said, voice dripping with glee as she sat down where her mom had been.
The woman looked at her with a soft well used smile, “Ah Willow, I just had a run in with your mother.”
Willow pursed her lips distastefully, “Oh dear… I hope she didn’t?”
“Ah… I’m uh, sorry. She can be quite a handful sometimes,” she bit her lip, then smiled to her, “But it’s nice to see you again, it’s been years, how have you been?”
The woman sighed a little then put on a tired smile, “Oh you know, work is work, the students are lovely, but…” she shook her head.
“But what?” Willow pressed, tilting her head and eying the slender built woman.
“I shouldn’t say, it’s hardly appropriate.”
Willow laughed a little, “Neither was what my mom probably said to you, but that didn’t stop her.”
The woman let out a soft laugh and shrugged a little, a smile on her lips, “That's true I suppose.”
“So, Mrs Williams?”
“Oh please, call me Heather.”
“Okay, Heather, what was it you were going to say?” Willow smiled.
“It’s just life has lost its spark in a way… I’m almost fifty, my husband doesn’t find me attractive anymore, I’m just… Waiting for retirement, I suppose.” she said softly.
Willow bit her lip, she felt a little bad for the woman, but, the fruition of her competition could at least alleviate some of her worries.
“He doesn’t find you attractive anymore? Is he blind?” Willow said, raising her eyes.
She laughed a little and shook her head, “No no, It’s just I-”
“He’s an idiot then.” Willow interrupted, plainly, “You’re as beautiful as I remember being.”
Heather tilted her head a little, “You used to think I was beautiful?” she asked, voice soft.
“Used to?” Willow smirked, taking a sip of her coke, “Honestly Heather, I learned so much stuff in college, I’d love to show you some of it sometimes,” she winked.
Heather laughed a little, “Oh you’re so much like your mother.”
“Mm in a way, we both think you’re gorgeous and we’re both attracted to you…”
Heather looked at her, biting her lip a little, her cheeks with a red hue, “I hear there's a spare guest bedroom upstairs…”
Willow blushed brightly, feigning her surprise, “You… You really want that?”
Heather bit her lip, uncertain, but intrigued.
Louise watched as Willow, looking meek and guilty, glancing around, was led away from the party by the hand by Mrs Williams and she couldn’t help but roll her eyes, grinning.
She was disappointed she had lost but at the same time was proud of her daughter for scoring what she considered to be a difficult target. She would wait, fifteen maybe twenty minutes. Then she would join in.
Mrs Williams lay on her back, her hands desperately gripping at the bedsheets, a pillow gripped between her teeth as she moaned into it, her hips grinding and gyrating as Willow, arms wrapped around the woman's thighs lay between them, her mouth against the woman's smooth mound, licking and sucking at her juicy pussy, she had been pleasantly surprised, when Heather had stripped, to find just how fine her body was, slender and lithe, the signs of her age few and far between, her pussy smooth and shaved, her modest breasts with full nipples still proud on her chest.
Willow looked up at Heather's face over the swell of her breasts, enjoying as the woman smeared her lipstick across the white cotton of the pillows, displaying just how much pleasure she was in.
Willow expertly lapped at her core, teasing her clit with licks and sucks, pushing the woman to greater heights.
She squeezed at the woman's ass, pulling her up to meet her eager mouth, the teacher looking down at her former pupil, dressed as a sweet little angel, skillfully devouring her hot wet pussy.
She recognised as she started to draw close to her climax, noting the increased breathing, the faster-paced movements of her hips, but Willow wasn’t done with her yet, wasn’t done claiming her victory.
She pulled her lips from the woman and heard her whine in protest, freeing the spoilt pillow from her lips to speak in between desperate pants, the woman's hair messed against the bed from her movements.
“A-ah! Willooow!” she whined as the girl grinned, kissing up to the woman's stomach and across the soft swell of her breasts, “Why did you stop?!” she asked the advancing girl.
“Oh that's easy Mrs Williams…” she bit her lip and guided the tip of her slender cock into the woman's soaked pussy, “because I want you to cum on my cock..”
She lay down atop her, sinking her length inside her, the surprise causing Heather to arch her back, gasping out in pleasure as she was suddenly filled by the young girl's cock.
“O-oh my gosh!!” she cried out, wrapping her legs around Willow, her hands moving to grip the girls back as she grinned down at her, their breasts pressed together as she started to work her hips forward and backwards.
She kissed at her teacher's neck and throat as she worked into her with her slender shaft, the pleasure intense as with each thrust she brought pleasure to the mature woman, enjoying it far more than she thought she would.
She had thought it would be like her play sessions in college, seduce a girl, fuck the girl, ditch the girl, but seeing the expression of this mature woman, so long deprived of pleasure finally finding some joy in life and for once, feeling great about herself, warmed her heart as much as it heated her cock.
She picked up her pace, slamming her cock into the woman's hot core, the silken walls squeezing her as she fucked her, her small balls slapping against her with each thrust.
“W-willow! Gods you’re going to make me, I’m, I’m going to!!” she tilted her head to the side, once more biting the pillow as her voice, which Willow remembered being so stern and formal moaned out loudly into the pillow clenched between her teeth as she came around her cock, pussy milking and squeezing her.
Willow beamed brightly as she felt her former teacher cum around her cock, but she didn’t stop, she didn’t slow, she just kept going, forcing her teacher to ride the heights of her pleasure for longer.
Willow, unable to resist pressed herself down, catching Heather in a kiss and pushed her tongue deep into the older woman's mouth, tasting the red wine, as she made out with her, deep and passionate as her hips continued to meet with hers, fucking her hard and as deep as she could manage.
As the older woman's orgasm subsided Willow slowed, grinning a little as she broke the kiss.
“Mm… That was pretty hot…” Neither of them said.
Heather, eyes wide and face flushing looked over Willows' shoulder to see Louise standing in the doorway, grinning her hand wrapped around her thicker, longer cock, stroking it slowly as she eyed the two of them.
“Mm, roll over Willow sweetie, let mommy join in.”
“L-Louise we were-!” she started, but Willow put a finger to Heather's lips, shushing her.
“Let us make you feel good,” Willow said, voice soft, encouraging.
Heather bit her lip, but, after what Willow had just given her, wasn’t going to deny she wanted more.
Heather nodded and Willow grinned, slipping her hands under the woman's shoulders and rolling, Heather letting out a soft squeak as she was moved, finding herself suddenly on top, Willows cock buried in her pussy.
She blushed, looking down at the angel who winked and then felt the devil place a hand on her ass.
Heather blushed and started to turn but Willow took her chin in her hand and tugged her head back, “No you look at me, Mrs Williams… I want to see the pleasure on your face…”
Heather swallowed and blushed, feeling Louise behind her, the woman's thicker and fuller cock rubbing between the cheeks of her ass.
Willow smirked, she could see the fear in Heathers expression, it was likely this conservative woman was a virgin when it came to anal and, given the size of her mother's cock she could understand her fear, but it was unjustified, she knew her mom would know too and she wouldn’t be that cruel.
Heather’s eyes rolled back as she felt Louise’s cock spread her labia and push into her pussy, so soaked that Louise didn’t need to prepare her cock in any way, simply pushing it in, slow and careful, stretching the woman's now incredibly tight pussy.
Heather in all her life had never had more than one cock in her, now she had two in her pussy, the mother-daughter duo dp’ing her pussy, spreading and filling her, making the pleasure more intense for the three of them.
“O-oh, oh my… Oh my god…” Heather breathed and Willow knew she must be experiencing some very intense sensations to have gone from an ‘Oh my gosh’ to the infinitely more severe ‘Oh my god’.
Together in unison mother and daughter, angel and devil began to move, their cocks pressing in and out of the tight mature teacher, on her hands and knees between the pair, her breasts hanging as she leaned on her hands and knees.
Willow and Louise moved with practised motions when Willow was withdrawing Louise was pushing in and vice versa, the pair of them ensuring that at any given moment Heather was full of one of their cocks, either Willows long slender shaft or Louise’s more substantial member.
Heather had her eyes closed, her lips parted, her tongue lolling slightly as she panted and moaned, her whole body shaking a little as both women pumped their cocks into her needy pussy.
She could already feel her climax mounting again and had no idea what to expect, she had never cum more than once in any singular experience before and she felt desperate to experience it, to achieve a brand new high.
The room was filled with the sounds of bodies slapping into bodies, of Willows soft light gasps, Louise’s deeper groans and heathers suppressed but desperate moans.
It hit her all at once, without warning or build up, just a sudden eruption of pleasure that overwhelmed her. Unable to support her weight she collapsed on top of Willow, their bodies pressed together as the woman came, the changed position doing nothing to discourage Willow or Louise and they continued to buck their hips into her, fucking her hard and without pause.
Heather was silent, unable to find the air to cry out to the pleasure that wracked her body, the climax high and unyielding, unable to taper off as thrust after thrust renewed the pleasure in her body, keeping her in a state of pure bliss.
Willow grinned, kissing and nipping at the woman's neck as she came around their cocks, milking the shafts of their pending load.
“A-ah mom, mom I’m gonna cum too!” Willow panted, having spent more time in the lush confines of the teachers pussy than her.
Louise bit her lip and nodded some, “Y-yeah, me too, this is really fucking hot…” Louise may have been late to the party, but the lewdness of the underside of her cock constantly rubbing against her daughters was quickly pushing her over the edge.
Willow grinned and tilted her head back, closing her eyes as they continued to force pleasure upon Heather, not allowing her respite from their shafts, which were growing steely, both their efforts becoming sharper, less on pace and more erratic.
Willow gasped and bit her white painted lip, hilting her length inside teacher's pussy, her orgasm peaking, Louise too only lasted a few more pumps before she slammed her hips forward, sheathing her fatter cock inside the mature woman's core.
Willows and Louise’s cocks pulsed against each other as they released their load inside the wet heat of the milf sandwiched between them, Louise leaning forward, resting her heavy breasts on Heather's back even as her heavy balls rested, twitching on Willows own smaller sack.
Heather’s whole body tensed as she felt jet after jet fire into her body, the lewdness and pleasure making her feel loved, grateful and incredibly satisfied.
Her throbbing hot pussy milked the cum from the two women, who were more than happy to oblige and spent every drop of seed inside her that they could, even as Heather lay limp across Willow, embracing her, finally starting to come down off the high of her climax, her body exhausted, a lethargy coming over her with the body wide satisfaction.
Louise looked down over Heather's shoulder at Willow and grinned, winking playfully as her climax started to subside, Willow already completely spent.
Willow winked back and breathed hard, her hands caressing over her teacher's body possessively.
“Mm… So, how was that… Mrs Williams?” Willow said in a soft, whispering voice as she lay content under the two women.
Mrs Williams panted hard, her voice weak and exhausted, an undercurrent of lust and desire in her words, “A-ah… B plus… I think… I think you need some homeschooling…”
Louise laughed and Willow grinned, “I think you’re right…”