Oliver Cloesoff’s Neighbour Part 2

"Oliver's adventure with his MILF neighbour continues. But, her daughter is now involved. And she's picked up more than a few tricks from her mom"

Font Size

Lisa’s eyes snap open.

For one millisecond, her facial expression is one of pure bliss. Before reality sets in. She gasps sharply, and looks down at Oliver in a panic.

Oliver freezes mid-motion. He’s still crouched in front of her, with his fingertips resting on the half-unzipped fly of her jeans. The delicate white lace of her bikini briefs hovers close to his face. His heart hammers so violently he’s convinced she can hear it. He tilts his head up, searching her expression for any sign that this isn’t about to end in disaster.

Lisa presses one finger to her lips in a swift, urgent shhh. Oliver nods. Message received.

She draws a long breath. Then, as steady as she can make her voice, she calls toward the hallway. “H-hi, Tori! How was your day, sweetie? I’ll be right with you… just finishing something up in here.”

From down the hall drifts Tori’s long, exaggerated sigh. “First, ew. Second, don’t bother. I’m grabbing a snack and disappearing to my room. You… er… keep doing… whatever that is.” A beat of silence, then she mutters, “Gross, Mom.”

For the next sixty seconds, Oliver and Lisa hold perfectly still, barely breathing, while Tori moves around the kitchen. The fridge door opens with a soft whoosh, closes with a gentle thud. Finally, her voice floats back one last time: “I’m putting headphones on, so don’t worry about me overhearing.” Her bedroom door shuts with a firm, unmistakable click.

Only then does Oliver let out a long, shaky breath and rise slowly to his feet.

Lisa meets his gaze, sheepish and a little giddy, and lets a quiet giggle escape. “So… that was Tori. She’s pretty great, right?” she whispers.

Oliver’s chest is still thundering. He rubs the back of his neck. “Uh, yeah. She’s… opinionated.” He hesitates, then adds in genuine bewilderment, “But if she already knows what you’re up to, why the whole ‘keep quiet’ thing?”

Lisa shrugs, and the motion causes her breasts to jiggle through her bra. “Obvious, isn’t it? She doesn’t need to know it’s you.” Lisa flashes him a small, conspiratorial grin. “She’s used to walking in on my solo… hobbies. I knew if she thought that’s all it was, she wouldn’t ask any questions.”

Oliver can’t help but smile in admiration. Lisa reads people like other people read street signs—effortless, precise, devastatingly effective.

It stings just a little that her entire plan hinged on him not opening his mouth and ruining everything, but he can’t argue with her logic. The absolute last thing either of them wants is Tori figuring out exactly who’s kneeling in front of her mother right now.

He nods, accepting the logic. “Guess that’s our cue to wrap up for today.” His cheeks burn as he glances down at himself. “Sorry she… interrupted you before you could finish.”

Lisa’s lips curve into something mischievous and a little embarrassed. “Well… actually, I got what you might call a mini peegasm.”

Oliver blinks. “A what?”

Her cheeks flush pink as she explains, voice dropping even lower. “The second I heard her voice, I panicked—thought she might actually walk in. Next thing I know, I’m… letting go. Right there in my panties.” She giggles softly, eyes sparkling with the absurdity of it. “So don’t feel too bad for me, okay?”

Oliver opens his mouth. And closes it. He has literally no idea what to say to that.

After a few seconds of stunned silence, Lisa tilts her head, studying him. “I can’t imagine it’s the same for you, though. You were literally tugging my jeans down, staring at my lacy floral undies…” She nods toward the obvious bulge in his pants. “Bet you’re still throbbing.”

She’s not wrong. Oliver feels fresh heat crawl up his neck as he nods. “Yeah. I’ll, uh… head home and take care of it.”

He starts toward the front door, but Lisa makes a small, quick sound.

“Wait! Before you go—give me one second.”

She turns and disappears down the hall in the opposite direction. Oliver watches the sway of her hips, until she’s out of sight. He stands there, pulse still racing, wondering what on earth she’s doing.

A soft thump—something landing on the floor. The unmistakable metallic squeak of a dryer door closing. A faint rustle of fabric. What the hell is she up to in the laundry room?

Moments later, Lisa reappears. And she has a triumphant little smirk on her face. Her breasts bounce gently with each step. Oliver notices immediately: her panties are now plain black. There’s something in her hand.

She stops in front of him, grinning, and presses the warm, damp scrap of white lace into his palm. “Here. Another pair just for you. Still hot off the press.”

Oliver stares down at the delicate floral lace she was wearing minutes ago. The fabric is impossibly soft. The crotch is still noticeably damp. And rising from it is that sharp, unmistakable, intimate scent of her pee.

Lisa’s quiet giggle snaps him back. “I know you like these. And so do I. So do me a favour and bring them back when you’re done, okay?” She winks, voice dropping to a teasing purr. “With great panties comes great enjoyability.”

Oliver’s face flames. He manages a strangled. “I will. Thanks… I think,” before fumbling for the front door handle and stepping outside, the warm, scented lace still clutched in his hand like contraband.

Back in his room, Oliver sinks onto the edge of his bed, Lisa’s white lace panties still warm and crumpled in his fist. He stares at the delicate floral pattern, mind reeling from the sheer lunacy of the last hour.

She invites him over, just to model her bra and panties. Like it it’s the most casual thing in the world! Then her daughter bursts through the front door, and scared Lisa so badly she actually pissed herself.

And instead of mortification ending everything, Lisa simply peels the soaked lace off, and presses the still-damp piece of fabric into his hand with that devilish little wink. “Bring them back when you’re done.”

He lets out a soft, disbelieving laugh. Just another quiet afternoon in the suburbs.

Oliver glances down. The crotch of the panties glistens faintly, still holding the heat and the evidence of her accident. A slow smile spreads across his face. He closes his eyes, lifts the lace to his nose, and inhales.

The scent crashes into him like a wave: ammonia mixed with the sweetness of an aroused woman who’s just lost control. His cock jerks hard inside his boxers, swelling thick and fast, heat surging through his groin in a dizzy rush. He’s already aching, half-hard from nothing more than the memory of her grin as she handed them over.

He stands up, despite the unsteadiness in his legs. His fingers shake as they fumble with his zipper. The jeans slide just low enough. Then, he drops back onto the bed.

He slides one hand into his boxers, and wraps his fingers around himself. With the other hand he presses the damp lace directly to his face, the warm, wet crotch sealing over his nose and mouth. He breathes in slow and deep, filling his lungs with her.

The scent floods him again, richer now, more overwhelming. His mind replays the scene at Lisa’s house: his face just inches from her panty-clad crotch, with the thin white lace being the only barrier between them. He remembers the way her breath hitched, the way her eyes fluttered shut in that split-second of bliss before panic took over.

His hand moves faster. Pleasure twists tight and hot in his belly. He imagines Lisa’s voice purring right against his ear: “With great panties comes great enjoyability.”

Then the fantasy shifts—he pictures her sprawled on her own bed right now, legs wide, fingers circling lazily between her thighs, watching him through half-lidded eyes while she waits for him to finish and return her panties.

His balls tighten, with that familiar electric hum building at the base of his cock.

“Fuck—Lisa—” The words rip out of him.

He bucks into his fist once, twice—and then he’s coming hard, shuddering, gasping against the lace still pressed to his face as pulse after pulse spills over his knuckles. The orgasm rolls through him like thunder, leaving him trembling, breathless, and—for one perfect, filthy moment—completely lost in her scent.

The next morning, Oliver walks upstairs, still half-lost in the hazy afterglow of last night, Lisa’s damp lace panties tucked safely in the back of his dresser drawer. He steps into the kitchen and stops short.

His parents, Drew and Molly, sit close at the table, coffee mugs steaming between them, voices pitched low. They glance up as he enters. Drew clears his throat.

“Hey, bud,” his dad says, setting his mug down. “We were just talking. We haven’t even said hello to the new neighbours yet—the mom and her daughter, right? Lisa and… Tori, is it? Thought we could invite them over for dinner tonight. Nothing fancy, maybe around 5:30? Just a welcome to the neighbourhood. What do you think?”

Oliver’s entire body tenses up. His heart races, like it’s trying to escape his chest. Panic sets in.

They think he hasn’t met Lisa. They have no clue that he’s already been inside her house, kneeling in front of her while she stood there in nothing but a bra and those white lace panties.

He forces a casual nod, and mumbles his agreement. while his mind races with the implications of this invitation. What is he going to do?

After lunch, Oliver glances out his bedroom window and spots Lisa in her backyard, kneeling among the flower beds, tending to her garden.

He watches her for a second too long—jeans hugging her hips, black t-shirt clinging tight enough that her breasts strain visibly against the fabric with every slight movement. And feels himself instantly grow excited.

He swallows, forces himself to move. A few moments later, he’s at the fence, and he taps lightly to get Lisa’s attention.

Lisa turns, her face lights up with a warm, knowing smile. Her eyes sparkle with mischief as they lock on his. “Well, hello there, neighbour.”

Oliver’s pulse kicks up. He tries to play it cool, but his voice comes out a little too high. “Hey, Lisa. So… uh… my folks and I were thinking. Would you and Tori like to come over for dinner tonight? Around 5:30? Just, you know, a welcome to the neighbourhood.”

“That would be lovely,” she says, nodding enthusiastically. “I’m sure I can bribe Tori with dessert or guilt her into coming along.”

“Great.” He forces a grin, then scratches the back of his neck, cheeks warming. “So… about the other day. That was pretty nerve-wracking with Tori showing up, huh? You two… okay?”

Lisa lets out a soft, delighted giggle. “We’re fine. She was just weirded out. Honestly, she’s convinced I was just… taking care of business solo.” She leans a little closer to the fence, voice dropping conspiratorially. “She has zero idea you exist, let alone that we’ve already met.”

Oliver exhales, tension easing a fraction. “Yeah. That’s… actually what I wanted to talk about.” He takes a deep breath. “Dinner. My parents have no clue about… us. Any of it. And if we act like we already know each other—like, too friendly—they’re going to get suspicious fast.”

Lisa tilts her head, playful but reassuring. “Easy fix. You pretend it’s the first time we’re meeting. I’ll follow your lead. We’ll be polite, awkward strangers. No problem.”

He nods, grateful for her calm. But there’s another worry. “Okay. But there’s… one more thing.” His face flames as he gestures vaguely toward her chest. “What if dinner’s chicken? And my brain immediately goes to… you know. Those. And I end up… reacting. In front of my parents. And Tori.”

Lisa bursts out laughing. “Oh my god, I’m flattered. Truly.” She wipes a tear from the corner of her eye, then flashes him a devilish grin. “But there’s a simple solution.”

He raises an eyebrow, wary.

“If chicken is indeed what we’re having, and your mind goes straight to my tits,” she says, giving her chest a tiny, teasing shimmy, “just think about your mom’s boobs, instead.”

Oliver’s jaw drops, in horror and disbelief. “Are you insane? I’m not going to think about my mom… oh.” The lightbulb flickers on. “Wait. That’s… actually genius. In the most fucked-up way possible.”

“Exactly.” She smirks, crossing her arms under her breasts so they lift just enough to torment him further. “If you’re worried about getting… titillated… there are worse kill-switches than picturing her melons.”

He groans, eyes squeezing shut as he shakes his head. “This is the worst plan I’ve ever heard. And yet… it might actually work.”

Lisa’s smile softens, triumphant but kind. “It’ll work. Promise.”

Oliver sighs, shoulders dropping. “Alright. Dinner’s at 5:30. But you and Tori can come over earlier. Hang out. Whatever.”

“See you then,” she says, voice warm.

He turns away, then freezes mid-step. His hand flies to his pocket. “Shit—wait. I almost forgot.” He spins back, with a sheepish grin, and says. “Your… um. Panties.”

Lisa’s eyes gleam. She waves her hand. “Don’t worry about them right now,” she murmurs. “During dinner, excuse yourself to the bathroom. Leave them on the counter or tucked somewhere discreet. I’ll collect them later.”

She chuckles, low and suggestive. “And who knows… I might have one too many glasses of wine and suddenly need the bathroom myself. Right after you.”

The doorbell chimes at exactly 5:15, a bright, cheerful sound that sends Oliver’s heart into overdrive. He practically sprints down the hallway, smoothing his shirt, forcing his face into something polite and neutral before he swings the door open.

There they stand: Lisa and Tori, framed in the golden late-afternoon light.

Oliver flashes his rehearsed smile. “Welcome! I’m Oliver. And you must be… Lisa and Tori, right?”

Their eyes meet for the briefest, most electric second—warm, amused, utterly in on the game—before she extends her hand. “Good to meet you, Oliver. Yes, I’m Lisa.” She glances sideways at her daughter. “And this is Tori.”

Tori offers a small, awkward wave and a half-smile, cheeks faintly pink. She looks younger than Oliver expected, almost shy, her long blonde hair spilling over her shoulders in the same shade as her mother’s. Side by side, they could easily pass for sisters rather than parent and child.

Both wear slim jeans and soft blouses, the top buttons casually undone to reveal just a hint of collarbone and the gentle swell beneath. Oliver’s gaze lingers—first on Lisa, whose fuller curves fill out the fabric in ways that make his pulse stutter, the shadow of cleavage hinting at the lace bra he’s already seen up close.

Then, traitorously, his eyes drift to Tori. At her slender body, the same golden hair catching the light. What kinds of bras does she wear? He wonders. He snaps his gaze away, heat crawling up his neck. Jesus, stop. She’s a kid, compared to you. Get it together.

He steps back, gesturing to come inside. “Come on in. Uh—this is my mom, Molly, and my dad, Drew.”

Molly beams, wiping her hands on a dish towel as she steps into the hallway. “Welcome, welcome! So glad you could make it. I hope everyone’s in the mood for chicken!”

Oliver feels the word land like a punch. Of course it’s chicken. Of fucking course. His face flames; he ducks his head and busies himself closing the door while the adults exchange pleasantries.

They settle around the dining table soon after, with their plates steaming with food. The conversation flows easily—light, harmless, the small talk that should be safe. Oliver keeps his eyes mostly on his plate, forcing himself to breathe normally, to laugh at the right moments.

Then Drew leans back between bites, fork in hand. “So, Lisa, what do you do for work?”

Oliver’s fork freezes halfway to his mouth. The hair on the back of his neck stands straight up. He keeps his expression blank, but inside, he’s screaming.

Lisa smiles serenely, unfazed. “I model with a local agency. Mostly clothing.”

Tori snorts softly beside her, unable to help herself. “Yeah, Mom. Underclothing.”

Oliver chokes—hard. Chicken catches in his throat; he coughs violently, eyes watering. Perfect excuse. He pushes back from the table, waving a hand. “Sorry—wrong pipe. I’ll just… be right back.”

He flees to the basement, with his heart hammering. First stop: his bedroom. He yanks open the dresser drawer, snatches the neatly folded white lace panties—still faintly scented with her—and stuffs them into his pocket.

Then he ducks into his bathroom, sets them carefully on the edge of the sink, hidden just behind the hand soap where only someone looking would notice.

When he slides back into his seat, he catches Lisa’s eye across the table. He gives her the tiniest, most subtle wink. She returns it—quick, conspiratorial, gone in a blink—then waits a polite three minutes before dabbing her mouth with her napkin.

“Excuse me for a moment,” she says smoothly, rising. “That wine’s going right through me.”

Molly waves her off with an understanding smile. “Down the hall, first door on the left—or there’s one downstairs if you prefer.”

Lisa’s lips curve. “Downstairs sounds perfect. Thanks.”

Eventually, dinner ends.

Lisa yawns, then stretches her arms. Turning to Tori, she says. “Well, kiddo? We should head home. I have a modelling gig to get ready for tomorrow.”

Tori nods and pushes out her chair. She turns to Oliver and his parents, and says in a sweet voice. “I guess we’ll be leaving. But thank you for inviting my mom and I over for dinner. It was yummy.”

Lisa pushes out her chair as well, and nods. “Thank you, Cloesoff family. It was delicious. The breast was so tender and juicy.” She subtly winks at Oliver.

Oliver feels his face grow hot. He appreciates the fact that Lisa didn’t make any boob-related jokes during dinner, but he supposes getting one in was always inevitable.

Tori suddenly looks at Oliver and says. “Could I… uh… use your bathroom before we go, Oliver?” Tori talking directly to him surprises him. But he nods his head and tells her it’s downstairs.

A few minutes later, Tori returns and joins her mom by the door. As they head out the door, both Tori and Lisa call out. “Thanks again for dinner!”

Later on, Oliver heads to the bathroom one last time before bed, flicking on the light and stepping inside.

As he stands at the toilet, something catches his eye: a small, crumpled white shape shoved into the far corner of the windowsill, half-hidden behind the little potted succulent his mom insists on keeping there. Curiosity prickles at the back of his neck.

He finishes, flushes, washes his hands—slowly, methodically—yet his gaze keeps sliding back to that pale scrap. Finally, unable to ignore it, he dries his hands, steps closer, and reaches out.

His fingers close around soft cotton. Warm cotton.

Oliver’s breath catches. He pulls the item free and unfolds it carefully. Plain white panties. No lace, no floral patterns, no frills—just simple, everyday underwear. The fabric feels soft against his palms, the elastic waistband slightly stretched from wear. His pulse kicks up, thudding in his ears.

Did Lisa…? The thought flashes hot and immediate. Another pair? A surprise handover? But these are smaller—noticeably smaller—than the lacy ones she’d pressed into his hand over the fence.

He turns them over, heart racing now, and spots the tag stitched neatly into the waistband.

Tori.

The name stares back at him, small black letters on white, unmistakable.

Oliver’s mouth falls open. A shocked exhale escapes him. Not Lisa. Tori.

His mind reels, scrambling to piece it together. Dinner replays in fast-forward: Lisa excusing herself mid-meal, just as planned, slipping downstairs to retrieve the lace he’d left for her.

And then… Tori. Right before they left, she’d mumbled something about needing the washroom. She’d been down here alone for a couple of minutes.

But why?

Why would a high school girl—shy, awkward Tori—slip out of her own underwear, and leave them behind? In his house. For him to find.

A dark, forbidden thrill coils low in his gut, warring with confusion and a sharp spike of guilt. He thinks of her at the table: long blonde hair falling over her shoulders, the undone top button of her blouse, the way she’d smirked at her mom’s “modelling” comment.

He glances toward the closed bathroom door, half-expecting someone to barge in. But the house is silent. His fingers tighten around the cotton.

Oliver stuffs the briefs deep into his pocket, his pulse hammering. He closes his eyes, rubs his temples.

This situation was already weird enough, and now it’s like the passing of the torch. But with panties!

Next afternoon, Oliver is determined to know what Tori was thinking when she left her underwear in his bathroom. And, despite the situation, he can’t help but feel a sense of déjà vu. This is eerily similar to what Lisa and him have going on.

But how does he approach the topic with a high schooler, without coming across as a total pervert? He sighs and leaves the house.

Walking over to the fence, he looks over. And, fortunately, sees that Tori is outside. She is sitting on a patio chair, while catching some rays in a pair of shorts and a bikini top. He takes a deep breath; here he goes. This could easily be a dirty look on his part, and it would be tough to explain if another neighbour overhears.

Leaning over, Oliver lightly taps on the fence. She looks over and waves to him. Tori then gets up and starts walking over to him.

Oliver awkwardly says to her. “Hi… uh… Tori. Could we talk for a sec?”

Tori gives him a confused look, but then nods her head. “What about?”

Oliver sighs, before he awkwardly tries to avoid looking at Tori’s breasts in her top. “It’s about… yesterday. After our dinner… you sort of left your…ahem…” He trails off.

Tori’s expression changes from one of confusion, to a sly grin. “You can say panties, you know. I didn’t leave them in your bathroom for no reason.”

Tori’s forwardness takes aback Oliver. When she and Lisa came over last night, Tori seemed quite shy. At least compared to Lisa. And, it’s because of that, he didn’t expect she would then leave him her panties. And be so open about it now.

“But why, though? You realize our age difference doesn’t make this okay, right?” Oliver asks.

Tori shrugs her shoulders, with a bored look on her face. “I guess I just thought you were cute.” She then shoots him a sly grin. “Besides, that didn’t stop you from trying to check me out all night. Both of us.”

Oliver gulps. She has him there. He sighs; he’ll have to work on being more subtle in his leering. Or just not leer. He apologizes, before Tori raises a hand.

Tori sees the worry in his eyes and continues. “I’m not offended, okay? I just didn’t know for sure if you were only interested in me and my mom’s bodies. I couldn’t tell if you were just interested in our boobs. Or our underwear.”

She shoots him a sly grin. “That is until I saw you watching me when I was picking a wedgie. And it hit me.” She laughs. “You deliberately looked, didn’t you? At my white undies?”

She and Lisa really are mother and daughter! Both of them are scary-observant. And apparently, neither of them take offence.

Oliver nods. “It’s true. I have a thing for… pretty bras and panties.” He sighs, looking her in the eye. “So… what happens now?”

Tori gives him a shit-eating grin. “We are going to go to my room. And you are going to try on some pieces for me.”

Tori has now taken control of the situation.

She has led him to her bedroom, and tells him to sit on her bed. Oliver obeys. She then goes to rummage through her bra and underwear drawer.

With her standing in front of her drawer, Oliver can’t see which pieces she’s selecting. All he knows is that he’s going to be wearing teen girl underwear in less than five minutes. He sighs, and wonders how he got himself into this mess.

Tori overhears him, and turns around. “If you’re concerned about me telling my mom, don’t be. I have no intention of getting her involved.” She shoots him a toothy grin. “She doesn’t need to know. This is just going to be a fun game between you and me.”

She finishes pulling out a couple of her plain t-shirt bras and cotton briefs, and starts bringing them towards him with a smile on her face.

She sets them in a pile beside him and says. “Pick the order. I’m also going to select one of my old skirts for you to try on, and then our fun can begin.”

A few minutes later, Oliver stands in Tori’s bedroom. He sighs. How did things come to this? He likes women’s underwear, but this is next level.

Oliver glances down. Not only is he wearing Tori’s black t-shirt bra and matching panties; he’s also wearing one of her cute skirts. And it’s surprisingly comfortable.

Suddenly, without warning, the front door swings open.

An older but still young woman’s voice calls out cheerfully.

“Hey, honey! Today’s shoot went well! There were so many beautiful pieces. How about we just order a pizza tonight?”

Published 5 hours ago

Leave a Comment