Oliver and Tori exchange panicked faces.
Tori looks flushed as she whispers to Oliver, “What are we going to do? My mom’s home early!”
Oliver, having gone through a very similar situation the other day—except with Lisa’s and Tori’s positions flipped—is going through something akin to PTSD. But that also means he knows what to do in this situation.
He puts on a brave face and looks at Tori. Tori is much like her mom in how assertive she can be. But she’s also still a teenager. The minute something doesn’t go her way, her assertiveness disappears, and she freezes up. Oliver realizes he’s going to have to dig them out of this mess.
Oliver calmly whispers to Tori, “Tell her that pizza sounds great. But you can’t greet her yet because you just got out of the shower. Maybe casually ask her about her gig as well.”
Tori nods. She takes a deep breath to steady her nerves. “Hey… Mom. Yes, pizza would be nice.” She nervously looks at Oliver before continuing. “Don’t come in! I… just got out of the shower. How did your gig go?”
They hear Lisa giggle from the front door. “Wouldn’t dream of it, sweetie! I’ll just order the usual, so you can take your time.” They hear Lisa setting down her car keys. “As for my gig, it went well. There were so many sexy bras and panties! But I’ll tell you more about it later on.”
Tori noticeably calms down. “Sounds good, Mom. So… uh… instead of getting the pizza delivered, could we pick it up?” She turns to Oliver before continuing. “Besides, it’s probably cheaper that way.”
Lisa calls out in an exaggerated whine. “But, honey, I just got home! I’m beat.”
Tori glances nervously at Oliver. Is her plan foiled? Or is her mom just messing around?
Fortunately, it’s the latter. Lisa giggles. “Just kidding, of course. You know me; I live for not paying for things when I don’t have to. I’ll just go make the call.”
Tori flashes Oliver a thumbs-up. “Problem solved! You can leave while we’re getting the pizza.” She grins sheepishly. “Oh… sorry, I’d invite you to stay for dinner. But it’s probably better if my mom doesn’t know you’re over here.”
Oliver nods in understanding. “No problem, I get it. I prefer not looking for trouble.”
About ten minutes later, they hear Lisa picking up her car keys. “Shall we, then, Tori?”
Finally, a minute later, Oliver is alone. He gathers his clothes and looks down: he’s still wearing Tori’s skirt. Not only that, but he’s also still wearing her bra and panties. He sighs. Tori left in such a rush they didn’t have time to discuss what to do about her clothes.
Oliver looks at himself in Tori’s mirror. He’s sure he looks ridiculous. Guys aren’t built to wear girls’ clothes and underwear—especially not cute cotton bras and panties.
Oliver considers removing them and placing them back in Tori’s drawer. But he knows that doing so would violate her privacy. And, with her being as assertive as she is, Oliver doubts she’d ever let a guy near her underwear drawer. He doubts she’d keep it to herself either if he opened it.
While Oliver and Lisa have their own underwear game going on, Lisa is probably very protective of her daughter. She will not be okay with someone touching her daughter’s drawer—even if he’s only returning her stuff. Which would only invite more questions.
He sighs once again. For now, he’ll just have to put his regular clothes on over Tori’s.
Oliver pulls on his jeans while being careful not to get Tori’s cute skirt caught in the zipper. Once he gets over that hurdle, he pulls on his shirt. Oliver is grateful that the material is dark and thick enough that there are few telltale signs he’s wearing a girl’s bra.
Finally, he checks to see there are no bumps from the straps or clasp showing, or the cups showing at the front. Oliver leaves for his own house while being careful not to stretch Tori’s bra too much with his movements.
Later on, while getting a drink of water before bed, he sees a light coming from outside—or more specifically, from Lisa’s house. What is going on? He goes outside to investigate. He then peers over the fence and gasps out loud.
Oliver realizes the light is coming from Lisa’s bedroom. While this is more comfortable than if he had been looking into Tori’s bedroom, what he sees is still surprising.
Lisa is walking by her window and clearly getting ready for bed.
Oliver watches as Lisa pulls off her blouse. He watches the revealing of her bare skin, along with her bra strap. Because of the way Lisa is standing, Oliver can’t see the exact bra or colour she’s wearing. He sucks in air. And silently pleads that she turns, giving him a better view.
Oliver’s prayers are answered. Lisa turns slightly, and it’s just enough for Oliver to get a good look at Lisa’s bra.
She has on a pale pink t-shirt bra with an underwire. The cups themselves, while not excessively detailed, are girly and look amazing next to her breasts. The perfect colour, the simplicity, etc. Is this something she got today at her gig? Oliver wonders.
Oliver also stares at and admires how the bra cups contain Lisa’s soft, pillowy breasts in a loving embrace and give them the support they need. This is art. Forget the museums, art shows, etc. He is witnessing one of the actual wonders of the world. His busty neighbour, apparently unwittingly, is giving him a private modelling show.
After a few minutes, Oliver feels himself grow excited. After adjusting his pants slightly, he glances back. He is now watching Lisa pull off her skirt. Is she wearing matching underwear underneath? Oliver wonders with excitement.
To his joy, Lisa is indeed wearing pale pink briefs. Oliver watches as Lisa tantalizingly reveals her matching undies and the shape of her butt as they stretch over them. Oliver smiles. Lisa must be quite popular with the photographers at her modelling gig.
Suddenly, he feels the familiar sensation building in his groin region. Oliver’s penis throbs, giving him a pleasurable feeling. Knowing what is about to happen next, he then grasps the fence and holds onto it as he releases. Between gasps, he yells out as quietly as he can. “Holy shit! I needed that.”
Satisfied, Oliver walks towards his house. He smiles to himself, grateful that he had the foresight to remove Tori’s underwear earlier. His boxers might be a mess now, but her underwear is safely inside his drawer.
Tomorrow he’ll figure out how to return Tori’s stuff.
Waking up the next day, Oliver can’t get the image of Lisa stripping by her window out of his head. Even if Lisa does not know he was watching her, he is grateful for the satisfying orgasm the sight of her in her underwear gave him.
He goes upstairs and looks out the back window.
Lisa is already busy tending to her garden outside in a casual t-shirt and jeans. Oliver sighs. On one hand, he’s happy to see Lisa. But, with Tori in her classes now, he’ll have to wait until later to return her skirt and underwear.
Oliver leaves the house and taps on the fence between his parents’ and Lisa’s house.
Lisa looks at him with a big smile. “Hey, Oliver! How’s it going today? Thanks again for having Tori and me over the other night.” She giggles. “Hopefully, Tori wasn’t too much of a pain. She’s been going through an ‘everything is stupid’ phase lately.”
Oliver smiles. “My parents and I were happy to have you two over. And don’t worry about Tori.” He laughs. “Honestly, I’m just grateful there weren’t many breast-related puns. Otherwise, I’d be the one dying of embarrassment.” He gestures to his crotch.
Lisa giggles and then shifts to her trademark sly grin. “Speaking of breasts, my ladies got the royal treatment yesterday at the shoot.” She leans over to whisper in his ear. “I’m wearing the bra I modelled underneath. Want to see?”
Oliver nods enthusiastically. “Yes! Need you ask?”
Lisa smiles and grasps the bottom of her t-shirt. She tantalizingly pulls her shirt up her torso before stopping just below her breasts. She then looks at Oliver and smirks before pulling the t-shirt the rest of the way off her body.
Oliver gasps. Lisa isn’t wearing just any bra; it’s the same one she was wearing last night. The same pale pink t-shirt bra that Oliver had seen Lisa walking around in last night. The underwire lifts them high and proud, the delicate fabric hugging every curve of her figure.
He feels himself grow excited as he inspects it. He didn’t notice last night but right on the centre gore sits a tiny red heart. Such a cute detail, sitting right between her cleavage like a secret invitation.
Oliver’s gaze stays locked on the bra, his breathing quickening. The simple yet feminine design looks even better up close—the smooth cups, the subtle lace trim along the edges, the way the straps sit perfectly on her shoulders without digging in.
Lisa’s giggle breaks him out of his trance. “I take it that my bra meets your approval, then?” She winks at him. “How does this compare to last night’s viewing?”
Oliver opens his mouth in shock. Does she know he was watching her? “Y-yeah, your bra is pretty cute. More cute than outright sexy. It looks great on you.” He panics. “But how did you know?”
Lisa shrugs her shoulders and shoots him a playful grin. “Why do you think I kept my light on while I gave you a brief show? I wanted you to watch me.”
Oliver nervously nods. “But how did you know it would be me who saw you?” He gulps. “What if my parents saw instead?”
Lisa lets out a warm, throaty laugh that makes her full breasts bounce softly inside the pale pink t-shirt bra. “Sweetie, I checked the driveway first. Your parents’ car was long gone, and I know exactly which bedroom window belongs to my favourite peeping neighbour.” She shoots him a sly grin. “I left that light on just for you.”
Oliver does not know how to respond. He opens and closes his mouth several times. There’s being observant, and then there’s this. Lisa even knows when Oliver’s parents leave the house. But despite being taken aback, Oliver feels himself growing excited. His boxers feel tight.
Lisa’s sly grin widens as she enjoys Oliver’s reaction. She traces one finger slowly along the top edge of the left cup, right where her breast swells against the fabric. “Mmm, the photographers at the gig went crazy for this set.” She giggles as she playfully snaps her bra straps. “Pretty sure that at least one of them needed some alone time afterwards. Both men and women.”
She smirks at Oliver. “So did I, admittedly. Having all those eyes on my girls; my undies didn’t stand a chance. I was so wet!” She then leans over to whisper in his ear. “But I saved the full reveal for you. Want to see how the panties match?”
Without waiting for an answer, Lisa glances left and right to confirm the fence hides them and turns around. Bending forward slightly, she hooks her thumbs into the waistband of her jeans.
She tugs them down just enough to expose the top half of the matching pale pink briefs. The soft cotton sits low on her hips, stretching snugly over the generous curve of her ass. Lisa twirls around and gives Oliver a 360 view, a tiny red heart placed on the front waistband, mirroring the one on her bra.
Oliver stares at Lisa and admires her amazing body in her cute lingerie set. He doesn’t doubt for a second how excited the photographers were becoming as they watched Lisa. Without thinking, Oliver asks, “Do you want to pick up where we left off the other day?”
Lisa smirks. “I thought you’d never ask.” And with that, Lisa’s hand drifts up to her shoulder. She hooks two fingertips under the thin bra strap—simple and pale pink—and slides it downward in one smooth, deliberate motion. The elastic gives without resistance; the strap glides off the curve of her shoulder and settles against the top of her arm.
Suddenly, they hear a nearby shrill voice that makes both of them jump. “Mom?! What the fuck are you doing!” Tori peers over and notices Oliver on the other side of the fence. “And with Oliver?!”
Oliver’s face goes red. Nothing could’ve prepared him for this—Tori catching him and Lisa. He can only open and close his mouth.
Lisa, however, is all smiles. She’s lost it, or she’s too horny to care anymore. She then turns around to face Tori, while nonchalantly fixing her bra strap. “Hi, honey. I guess it was only a matter of time before you caught us, huh?” She giggles.
Tori crosses her arms and rolls her eyes. “Yeah, no kidding.” She glares at Lisa then Oliver. “I knew that something was up during the dinner. I couldn’t quite put my finger on it, but it’s obvious this has been going on longer than the other night.”
Oliver, still unable to speak, can only look away sheepishly. Not only because Tori now knows of his involvement with Lisa, but because he knows he’ll also likely have to reveal his involvement with Tori. The question is: who will admit to it first?
Tori notices Oliver’s nervous expression and softens her accusatory tone. She then moves her fingers through her hair and sighs. “But I’m one to talk, aren’t I?” She looks at Lisa directly. “Mom… Oliver and I have been, well, doing stuff together as well.”
Lisa gets a shocked look on her face upon hearing this revelation. She turns around to confront a nervous Oliver. “Oh, really? Care to elaborate, Oliver?” Then, suddenly, her expression changes to one of amusement. “I’m not a young grandmother, am I?”
Oliver looks back at Lisa. “N-no! Nothing like that at all.” He sighs heavily. “She just makes me try on…” He looks away awkwardly before quietly finishing his sentence. “…her underwear.”
Lisa stares at him for a moment before bursting out laughing. “Are you serious?! That is priceless!” Her breasts jiggle in her bra every time she laughs. Despite the awkward situation, Oliver can’t help but enjoy the sight in front of him. He feels himself grow excited.
A few minutes later, Lisa calms down. She wipes a tear from her eye and turns around to face Tori again. “Like mother, like daughter, huh?” She shoots Tori a sly grin, which earns a confused look from Tori.
Tori does not know what is going on. Is her mother implying what she thinks she’s implying? She awkwardly glances at Oliver, then back at Lisa, before saying, “I do not know what is even happening anymore. But can we continue this discussion inside? The neighbours might overhear and get the wrong idea.”
Lisa nods her head. “Agreed.” She turns back to Oliver. “Why don’t you come over and we can continue the conversation inside?”
Oliver nods.
A few minutes later, Oliver arrives at Lisa’s front door. He knocks on the door and awaits either Lisa or Tori to greet him.
He looks down at the plastic bag he is carrying and sighs. Before leaving his house, he grabbed Tori’s bra and panties she had made him wear the other day, as well as the cotton undies she left for him in his bathroom during their dinner.
A few moments later, Tori opens the door. Her eyes stare menacingly at Oliver. Oliver grins sheepishly as he feels a great sense of awkwardness. Aside from dinner on the weekend, his only other interaction with Tori had been when she made him wear her bra and panties.
And just a few minutes ago, she found out Oliver and her mom have been secretly engaging in activities together for some time. He doesn’t blame her for feeling some animosity towards him.
After a few awkward seconds, she steps aside and says to him, “Well, come in…” Her tone is all business.
Oliver cautiously steps inside the house. And almost immediately, he feels her looking down at the bag Oliver is carrying. Oliver’s heart catches in his throat.
Tori then looks back at Oliver with a confused look on her face. “What’s in the bag?” she says to him, her voice and tone sharp and accusatory.
Oliver nervously turns to Tori and sees her glaring daggers at him. “Uh… I brought back your underwear from the other day. Remember when you had me cross-dress? But then we had to act fast when Lis—er, your mom returned from her gig?” Oliver sets the bag down and gives Tori an apologetic smile. “Sorry, I didn’t get the chance to return them until now.”
Just then, they hear Lisa burst out laughing. She appears from the living room. “Oh my god! You mean this actually happened? I thought you were kidding before.” She turns to Tori as she tries to keep a straight face. “You actually convinced him to wear your underwear? Bra too?”
Tori shrugs her shoulders. “It was a spur-of-the-moment.” She sighs. “Anyway… are we going to do this? I have homework to do.”
Lisa smiles at her daughter and nods. “Of course, honey. Why don’t we adjourn to the living room, and Oliver and I can tell you how this began.” She leads Oliver and Tori into the living room before turning to Oliver with a shit-eating grin on her face. “And I cannot wait to hear what happened with you and Tori. It sounds like a real doozy!”
Lisa and Oliver tell Tori everything that has happened in the last couple of weeks.
When Lisa tells Tori about Oliver showing an interest in her laundry, Tori looks over at Oliver. “Perving on my mom’s body, huh?” She rolls her eyes as Oliver grins sheepishly. “And at least they weren’t my undies, that would’ve been all kinds of fucked up.”
Lisa smiles at Oliver before looking back at Tori. “It wasn’t completely his fault, Tori. I was the one who deliberately brought out my bras and underwear, while he was mowing his parents’ yard.” She smiles sympathetically at Oliver. “And being a red-blooded male isn’t a crime.”
Then Lisa brings up the time when Tori came home from school early. “…Oliver and I were in here. Oliver had just pulled down my jeans, and I ended up getting a little excited. That’s when you walked in…”
Tori interrupts her mom’s story. “Hang on! I remember this. I had called out, and you had answered in this strained voice.” She then looks at Oliver with a look of bewilderment. “It was you! You made my mom cum! I thought she was getting herself off!” Oliver’s face turns bright red.
The speaker soon shifts to Oliver, as he explains their underwear game over dinner. “…like with you, I needed to return your mom’s underwear. So we devised a plan where I’d use the bathroom to drop off the pair, and then your mom would collect it a few minutes later.”
Tori laughs as she looks at both Oliver, then Lisa. “I thought something was up! I couldn’t put my finger on why you left for the bathroom soon after Oliver returned, but that makes sense.” She smirks before continuing. “I guess that’s as good of a place as any to go over how I got Oliver to wear my stuff, as well.”
After Tori finishes explaining, Lisa looks at Oliver. She giggles. “Honestly, I’m impressed. Not only because she left you a pair in your bathroom, but she convinced you to try on her underwear… and you could fit into a high school girl’s undies.”
Tori and Oliver laugh as well. It’s an absurd situation all around. And the realization that underwear connects all of their stories together is the icing on the cake.
But suddenly Tori’s phone beeps.
She pulls her phone out of her pocket and reads the text. Her face switches from joy to concern in an instant. “Oh shit! A friend of mine caught her boyfriend cheating on her with another classmate.” She gets up and starts heading towards the front door. “Sorry, I’d better go stop her before she polishes off her family’s ice cream.” She closes the door behind her.
And finally, Lisa and Oliver are alone.
Despite the sexual awkwardness of the last hour, Oliver hopes that Tori’s friend is going to be okay. Lisa, reading his mind, says to him, “Don’t worry, Tori’s a good friend. She will be just fine.”
Lisa then puts a hand on his shoulder. Oliver turns to Lisa and sees her with a shit-eating grin. “Now, what do you say to us finally continuing what we started the other day?” She giggles. “All our stories connecting because of underwear is getting me in the mood. And I can only imagine how tough it has been to be blocked not once, but twice.”
Oliver grins sheepishly.
Lisa stands up from the couch, her hand lingering on Oliver’s shoulder. She gives him that familiar, mischievous grin. “Come on,” she says, her voice low and teasing. “Let’s take this to my bedroom. More privacy… and way more comfortable.”
Oliver follows her without hesitation, his heart hammering as they climb the stairs. The house feels still and quiet now that Tori has rushed out. Lisa pushes open her bedroom door—the same one he peered into the night before.
She turns to face him, eyes gleaming with intent. Without a word, she peels off her t-shirt, revealing the pale pink t-shirt bra he has been obsessing over. Then she slides her jeans down her legs and steps free, leaving herself in nothing but the matching bra and panties. The tiny red heart detail sits right between her cleavage.
Oliver swallows hard and follows suit. He kicks off his shoes, pulls his shirt over his head, and drops his pants until he stands there in just his boxers. For a long moment, they simply look at each other. Lisa’s curves are soft and generous, and her skin is flushed.
Oliver gazes at the way the bra lifts and cradles her breasts, the way the panties hug her hips. She lets her eyes roam over his chest, down his stomach, and finally to the obvious bulge straining his boxers. A slow, approving smile curves her lips.
Lisa moves to the bed and pulls back the comforter and sheets in one smooth tug. Her breasts jiggle with the motion, straining against the pale pink cups, rising and falling with each breath she takes.
She turns around, and notices how hard he already is. Her smile turns wicked. Reaching behind her back, she unhooks the bra clasp with practiced ease. The straps loosen. Lisa then tantalizingly slides them off her shoulders one at a time, letting the bra fall away.
But just before it falls completely off her breasts, Lisa shoots a sly grin at Oliver. She playfully whines, “I’m hurt that Tori got to see you in her bra before I got to see you in mine.” And with that, she hands it to Oliver.
Oliver gulps. He takes Lisa’s bra and glances at the cups. It’s such a simple and cute bra. And not only that, Lisa actually wants him to wear it. His eyes then travel to the anatomy that this bra had been supporting only moments ago. Oliver’s breath catches. Her breasts are bare now—full, perky, nipples already stiff in the cool air. They are even more perfect than he imagined.
Lisa’s giggle breaks him out of his trance. “Well? You can either stare at my boobs all day, or you can try on my bra.” Oliver shoots her a sheepish grin before sliding his arms through the straps of Lisa’s bra.
Upon adjusting the bra onto his body, Oliver glances awkwardly at Lisa. Lisa smiles knowingly and nods. “Here, I’ll hook the back for you.” She goes around Oliver and connects the bra. He then pulls the straps onto his shoulders.
Lisa gives an approving nod and shoots him a sly grin. “How does my bra feel?”
Oliver looks down at Lisa’s cute bra, that is now covering his own body. He snaps one strap before glancing back at Lisa with a smile. “Like it’s giving me a warm hug.”
Lisa smirks and gestures toward the mattress with a playful tilt of her head. “Shall we? I bet you’ve been looking forward to this for a while.”
Oliver can only nod, throat too tight for words.
She flops onto the bed with deliberate drama, making her breasts bounce and sway enticingly. Oliver climbs on beside her, eyes locked on the rhythmic rise and fall of her chest as she breathes.
After a beat, he finds his voice. “Can I… touch them?”
Lisa’s grin. “Go for it. My breasts are yours to explore.”
He reaches out, cupping their warm, soft weight. For the next several minutes, he kneads and massages them gently. His thumbs brush over her nipples, as he marvels at how they respond. Lisa watches his face the whole time, clearly enjoying the look of pure awe on it.
Eventually, she gives a playful whine. “Don’t forget about the rest of me.”
Oliver grins sheepishly and lets his hands slide away from her chest.
Soon their bodies press together, grinding slowly through the thin fabric of their underwear. Oliver feels the damp spot spreading across the front of his boxers and mutters an embarrassed, “Sorry…”
Lisa winks. “No need to apologize. I’m soaking wet in my own undies.”
They keep sliding against each other for a few more heated seconds before Lisa captures his mouth in a deep kiss. When she pulls back, she whispers against his ear, “Go ahead, and pull off my underwear. We both know you want to.”
She sits up and lifts her hips to help. Oliver hooks his fingers into the waistband of her pale pink briefs, immediately feeling how slick and wet they are. He slides them down her legs, revealing her neatly trimmed mound. And sets them on the bed.
Lisa catches him staring and smirks. “If you were hoping for another Bush administration, I’m sorry to disappoint you.”
Oliver laughs, despite the heat in his face. The tension eases for a second. What a strange joke to make at a time like this.
Then she surprises him. “Want me to remove your underwear now?” He opens his mouth in shock but manages a quick nod.
Lisa’s smile is pure mischief as she tugs his boxers down, freeing his erection. She sets them beside her panties. Oliver gives a sheepish grin. “Sorry, but could I try on your panties? They look so comfy, plus… it’s getting drafty in here.”
She meets his gaze with a confused face before shooting him a sly grin. “But how are we going to have sex, then?”
Oliver gasps. “What?! Are you serious?”
She winks at him. “Of course. I already took my pill.” She giggles. “Why do you think I brought you into my room in the first place?”
Oliver’s eyes widened with anticipation. This is actually happening! He slowly lowers and positions himself inside Lisa’s waiting vagina. Or what his limited knowledge of female anatomy tells him is her vagina.
A few minutes later, they are grinding skin-to-skin. Their bodies move together in an urgent, perfect rhythm. Between ragged pants, Oliver manages, “I’m… going… to cum!”
Lisa’s voice growls back, just as breathless. “Do it!”
They moan in unison as release crashes over them, waves of pleasure coursing through both bodies until they finally settle.
After his breathing slowly returns to normal, Oliver lets out a long, satisfied sigh. “I’m glad you’re my neighbour.”
Lisa chuckles softly, rolling onto her side to face him. She drapes one arm lazily across his chest. “Me too, Oliver,” she murmurs, pressing a gentle kiss to his cheek. “Me too.”
