Oliver Cloesoff is a 23-year-old recent college graduate who cannot find affordable housing or a steady relationship. And because of that, he moves back in with his parents in a quiet middle-class suburban neighbourhood filled with teachers, retirees, and young families. He is medium-built, down on his luck, and still jobless, despite his education.
He soon learns that a single mom in her mid-30s named Lisa Robins has moved into the house behind his parents’ with her 16-year-old daughter, Tori. Oliver has yet to see either of them in person.
One sunny afternoon, Oliver finishes mowing his parents’ yard and prepares to wheel the lawnmower into the garage. He paused near the wooden fence and spotted the new neighbour entering her backyard carrying a laundry basket. The fence is just high enough for him to peer over.
Lisa is of average height with an average build, long blonde hair, and a kind face. She wears a simple T-shirt and a short skirt. Even from this distance, Oliver can tell she is busty; the fabric of her shirt stretches across her chest. She looks young, but not too young—mature in a way that makes his pulse quicken.
Oliver cannot help himself. He keeps one hand on the lawnmower handle and stares as she strolls to the clothesline and sets the basket down. When she bends forward to retrieve the first item, her large breasts jiggle inside her shirt.
Is she wearing a bra? He wonders. She must be; her breasts would move a lot more if she wasn’t. But wow, they are spectacular.
Lisa reaches into the basket and pulls out a pretty white floral lace bra. She stands upright to hang it on the line, as Oliver feels his boxers tighten uncomfortably. Oliver feels himself breathe heavily. He has never had a girlfriend and harbours a secret fascination with bras—the way they look so pretty, how soft they seem, etc.
Just before she can clip the bra to the line, Lisa senses someone watching. She gasps, turns, and—with a friendly smile on her face and the white lace bra still clutched in her hand—walks closer to the fence. Her breasts bounced gently with each step.
“Oh, you startled me!” she chirped brightly. She smiles at Oliver. “Hi, I’m Lisa Robins. I just moved here with my daughter the other day. Who might you be?”
Oliver short-circuits. It is already surreal to have an attractive woman speak to him. But she does not seem to notice or care that she is still holding her own bra. He subtly looks at the lacy white garment in her fingers before looking back at Lisa.
“Hi, Lisa,” he managed, voice cracking. He took a deep breath. “I’m Oliver. Oliver… Cloesoff.”
His face reddens. He knows how ridiculous his name sounds. And hopes she has a high tolerance for terrible puns.
Lisa gives him a look of disbelief, then bursts out laughing. “Oh my god! That’s a good one.” She flashes a sly grin. “You must be a wiz with the ladies.”
Oliver offers a shy, apologetic grin. “Unfortunately, it’s the opposite. And I wish I was making up a name my parents clearly gave me while on drugs.”
Lisa’s expression flickers from a sly grin to one of empathy. She nods. “I see. How unfortunate.” A few seconds of awkward silence stretch between them before she glances down and gasps, suddenly realizing she is still holding her white lace bra. “Oh, I’m sorry!” Her cheeks flush scarlet. “I should get back to hanging these bras and undies up before Tori returns from high school. Good to meet you, Oliver.”
She turns, walks back to the clothesline, and resumes her task.
Later that day, Oliver sits in his bedroom replaying the encounter. He sees Lisa walking outside with the laundry basket, her large breasts moving enticingly beneath her shirt. He remembers her hanging up her bras. And he also recalls her mentioning a daughter in high school. She looks far too young for that. She must take good care of herself.
He sighs, slips off his pants, and prepares to masturbate to thoughts of his new neighbour. He places his hand over his boxers and massages himself. Eventually, he reaches orgasm with a triumphant “Oh god!” He feels his boxers become wet as he moans in satisfaction. He then smiles as he climbs into bed.
The next day, Oliver heads outside to the backyard, hoping to catch another glimpse of Lisa. She is nowhere in sight. Disappointed, he sits on the porch and scrolls through his phone.
A few minutes later, he hears a light tap on the fence. He looks over and sees Lisa’s smiling face. He waves and walks over. “Hi Lisa. How’s it going today?”
She is wearing a t-shirt and a miniskirt today. Oliver immediately feels himself grow tight in his boxers; her sizeable breasts look extra projected. He wonders what kind of bra she is wearing to make them stand out so much.
She smiles back. “Can I ask you a question, Oliver? It’s been bothering me since we met yesterday.”
Oliver’s breath catches, eager to hear what she wants to know. He nods.
Lisa gives him a sly grin. “Was that your first time seeing women’s underwear? I ask because I noticed you were watching me bring out the laundry basket yesterday.”
Oliver gulps. Busted. But does she know the exact reason he was staring? He offers a sheepish grin. “Sorry about that. But yes, aside from knowing that women’s underwear exists and differs from guys’ underwear, I’ve never seen them in person.”
Lisa’s face softens into an empathetic smile. “Really? When we talked yesterday, I thought you just meant you don’t have a girl at the moment. But, you really have had little experience with women at all, have you?”
Oliver shakes his head sadly.
Lisa’s sly grin returns. “Let’s remedy that right now. I’ll be right back.”
She turns and disappears inside her house. A few minutes later, she returns with something clutched in her hand. Her breasts jiggle as she walks toward the fence. Oliver cannot see exactly what she holds, but it is obvious why she went inside.
Lisa grins and tells him, “Close your eyes and open your hand.”
He obeys. A moment later, something warm and soft but lacy lands in his palm. He opens his eyes and gasps. Lisa has given him a pair of her purple panties.
She giggles. “I just removed them, so please enjoy them.”
Oliver is stunned. What do you say to someone who just handed you the underwear they just removed? “Why though?” he finally manages.
Lisa shrugs casually. “You’re an adult, and a good-looking one at that. It’s a shame you’re unable to fully embrace your healthy libido during your prime. So please…” She nods toward the panties in his hand. “Think of me as your girlfriend and use them when you enjoy yourself.” She turns away, then pauses. “Doctor’s orders.” She winks playfully before heading back towards her house.
What the hell is going on?! Oliver wonders. He glances down at the panties—mostly purple cotton with lace along the edges, and soft. What he wouldn’t give to see Lisa wearing only her bra and these panties. Still, this is not something a normal neighbour would do.
And what does she mean by “doctor’s orders”? No doctor would ever prescribe using women’s panties to relieve tension. He sighs, deciding he will ask her next time he sees her.
Back in his bedroom, Oliver prepares to masturbate. He unzips his jeans, shoves his hand down his boxers, and rubs himself. He then closes his eyes and fantasizes what Lisa had done.
He imagines her stepping into her bathroom, watching herself in the mirror as she reaches up her miniskirt and drags the purple panties down her legs. He does not think she had enough time to masturbate in them before returning outside, even though they felt slightly damp when she placed them in his palm.
As the fantasy plays out, he lifts the panties to his nose and inhales. A sweet scent hits his nostrils, which triggers an immediate, powerful ejaculation. He moans through the satisfying orgasm, then collapses face-first onto his bed.
Later that afternoon, he glances out the window and sees Lisa tending her garden. She wears a tight-fitting top that emphasizes her huge breasts. Her bra is doing wonders; there is hardly any bounce despite their size. Oliver feels himself tenting again, as he pants. This is the perfect time to ask what has been on his mind—his parents are at work, and Tori is in class. Hopefully, he can calm down before he speaks to her.
A few minutes later, he steps outside and calls over the fence.
Lisa smiles and walks toward him. Oliver cannot help glancing at her chest; her breasts look especially appealing. While it’s clear she is wearing a bra, they still bounce slightly as she approaches. He scolds himself for reacting so strongly.
“Hi, Oliver! How are my undies treating you?” she asks with a sly grin.
His face reddens. “Uh… yeah, they’re treating me well. I had some fun with them after returning inside.” He panics when he sees her knowing smile. “But I didn’t, you know, release in them! I figured that you’d want them back.” He pulls the panties from his pocket—slightly drier now but clearly unused—and offers them to her.
Lisa giggles and waves her hand. “It’s all good! They’re my gift to you. Use them in any way you wish.” She pauses, glancing at the panties. “But, I’m surprised you did nothing more with them. That’s some restraint.”
He shoves them back into his pocket.
Oliver awkwardly clears his throat. “Anyway… Thanks for your gift. But why did you give me your underwear? Don’t you… need to wear them?”
Lisa shoots him an appreciative smile. “You’re sweet for caring. But you don’t need to worry, okay? I have plenty, thanks to my job.”
Oliver tilts his head. “What do you mean by that?”
Lisa giggles, leans close, and whispers in his ear. “I model lingerie for a living.” She leans back and speaks normally. “And the agency I work for lets me keep whatever piece I model.” She smiles. “So, believe me when I say, I have lots more where those undies came from.”
She returns to her garden.
Oliver stands in stunned silence. That explains her casual attitude about giving him underwear. Then he remembers another question. “Sorry, I’ve been meaning to ask. Could you tell me what you meant earlier when you said to think of you as my girlfriend when I enjoy myself? And why did you say doctor’s orders?”
Lisa thinks for a moment, then smiles empathetically. “I can tell how lonely you are. How deprived you are of a girl you can fool around with. And so, I gave you the next best thing: a pair of my panties.”
She smirks. “And as far as doctor’s orders, you think I haven’t noticed how you’ve been reacting to my body? Your breathing is erratic whenever you see me? And let’s not forget the first time we met, when you stared at me.” She looks directly in his eyes. “I can only imagine how pent-up you’ve been. And how much you need the feeling of something soft against you.”
Oliver opens and closes his mouth. Lisa is far more observant than he realized. She notices every time he stares, every time his breathing changes. He thinks back to their interactions. Despite his obvious reactions, she has never seemed to be offended by them. It dawns on him: she might have even wanted him to stare.
He clears his throat. “Ms. Robins, are you trying to seduce me?”
Lisa smiles and steps closer. “I don’t know. Am I?”
An awkward silence hangs between them. Oliver does not know what to say or do. Lisa is undeniably sexually attractive. Her breasts look better on her than on many of the college girls he knew—more substantial, more mature. Even with a daughter in high school, she has kept a youthful figure, no doubt thanks to her lingerie modelling career.
But does she feel the same way about him? He can’t believe anyone would find him attractive, especially when women his own age have shown little interest.
“So what happens now?” He wonders aloud.
Lisa pulls her phone from her pocket, glances at it, then looks at Oliver. “Right this minute? Nothing. Tori should be returning home soon. And I don’t think we need to risk her stumbling upon us, do you?”
She flashes a mischievous grin. “But how does 10:30 tomorrow work for you? My place? Tori’ll be in class, and I’m assuming your parents will be at work. Wherever it is they work. I have something I’ve been wanting to show you, and I think you’re going to enjoy it.”
Oliver nods and starts back toward his house. Just as he turns, Lisa calls after him.
“And remember what I said: use them when you enjoy yourself. They won’t give you the satisfaction of a girlfriend, but they will make you feel better.”
She winks, then returns to her garden.
Later, in his room, Oliver lies in bed trying to process the last couple of days. Lisa with her bras outside, pretending to be startled when she caught him staring, gifting him her underwear, and now this invitation. She has made it clear she sees more than she lets on. Does she know the exact reason he stares?
He shivers. It is one thing to be attracted to a woman; it is another to fixate on what she wears underneath. As a guy, he is not supposed to care about her bras and panties.
Then he remembers her words: “Use them when you enjoy yourself.” He reaches into his pocket and pulls out the purple panties. Then stares at them, admiring the pretty fabric—purple cotton with subtle lace along the edges. He runs his fingers over them, appreciating the softness. I can only imagine how comfortable she must be when she’s wearing these, he thinks to himself.
It suddenly clicks. A big smile spreads across his face as he gets off his bed. He pulls his jeans and boxers down and pulls Lisa’s panties up his legs. The cool cotton brushes his skin. He chuckles as he struggles to get them past his groin; women’s panties aren’t for his anatomy.
Finally, they are on. He immediately feels the difference from his boxers. Holy shit, these are soft! Aside from being tight in certain places, they feel like wearing nothing at all.
Returning to lie on his bed, Oliver closes his eyes and rubs himself through the fabric. He imagines Lisa lying in her own bed, absentmindedly massaging herself over them while watching something sexy on television. Eventually, she climaxes, her eyes fluttering as she moans through multiple powerful releases. And she’s not the only one climaxing, either. Oliver feels himself start to cum as well, with a strangled cry of “Holy shit!”
When he opens his eyes, he feels a large wet spot darkening the purple cotton. Sighing from the powerful orgasm, he closes his eyes again and immediately falls asleep.
The next morning, Oliver stands at Lisa’s front door. Why am I doing this? I want to do this, but this is crazy! What could she possibly have in mind? He sighs and rings the bell.
Lisa opens the door almost immediately, beaming. Oliver instinctively looks down and sees she is wearing jeans and a turtleneck sweater that emphasizes her huge breasts. He feels himself harden in his boxers, as he offers an apologetic grin. But her smile suggests she chose the top deliberately and is indifferent.
“Come in, Oliver. Welcome to my home!” She steps aside.
Once inside, with the door closed, she asks with a sly grin, “Well? Did you and my panties get better acquainted last night?”
Oliver’s face burns. He nods. “Yes… they’re so soft. I-I didn’t last long… and they became drenched afterwards.” There is no way he can admit she starred in his fantasies or that he wore them when he came. But knowing her, he probably does not need to say it.
Lisa giggles, as she leads him into her living room. “Good boy. I’m sure my undies felt incredible against your skin, as you brought yourself to the brink of ecstasy.” She grins slyly. “And I’m sure they’ll be needing a good wash, as well.”
He awkwardly clears his throat. “So, anyway… uh, what have you been wanting to show me?”
She turns to him and steps closer. “First, I know why you were staring at me the day we met. At first, I just figured like my chest. As all guys seem to. But then I remembered—you weren’t only looking at my chest when I was doing laundry.” She flashes a shit-eating grin. “You like my bras, don’t you?”
Oliver’s sheepish grin returns. He knew it! She knows he has a thing for bras. He might as well confess. He nods. “Yes, I do. That day I saw you carry the laundry basket to the clothesline. Even through your shirt, I could tell you had huge boobs. And… I got excited. I also figured you were wearing a bra, because they would’ve been moving a lot more.”
He gestures toward her chest. “And then, when you picked your bra out of the basket… oh my god! I had never seen a bra in person before. Such gorgeous white floral lacy cups! Such enormous cups, as well.”
Lisa laughs as she listens. “Look at you! For a guy, you have a surprising eye for boobs and bras. I’m impressed by your taste in lingerie.” She grins slyly. “Do you want to see what they look like?”
Oliver nods, both surprised and unsurprised by how well she reads him.
Lisa smiles, grasps the bottom of her turtleneck with both hands, and begins pulling it upward. She pauses halfway, her toned stomach exposed. “Are you ready?”
Oliver nods again.
Lisa pulls the sweater completely off and shakes out her long blonde hair. She stands before him in just her jeans and bra. She places her hands on her hips, grinning. “All-natural 32Fs! Just for you.” She slyly grins. “Tell me, Oliver, is this what you expected would happen when you woke up this morning?”
Oliver can only stare in amazement. Lisa’s soft, pillowy breasts fill the gorgeous white lace cups perfectly, heaving gently with each breath. The tiny red bow placed between the cups emphasizes the prettiness of the bra. He feels himself grow painfully hard in his boxers. No, he definitely did not expect this—not today, never.
As he admires her cleavage, Lisa giggles at his fascination with something so mundane to her. It is almost sweet how innocent he is about the female body. She grins slyly. “I’m also wearing matching undies, you know. Why don’t you unzip my jeans for me?”
Oliver does not need to be told twice. He has never been this far with a woman, and he is about to see this beautiful woman in only her underwear. Which is something he even prefers over nudity.
He bends down and unzips her jeans. And a glimpse of matching lacy white bikini briefs greets him. His eyes go to the tiny red bow just below Lisa’s waistband. The sight of something so cute, yet so sexy, is influencing him. He feels pre-cum leak into his boxers. Anticipating what’s about to happen next, he also starts exhaling with excitement.
Then he hears a low moan from above. He looks up.
Lisa’s eyes are closed, her face has the look of pure ecstasy. “Oh… god, Oliver! If you keep doing that, I’m going to have an accident in my underwear.” She moans.
Suddenly, without warning, the front door swings open.
A teenage girl’s voice calls out cheerfully.
“Hey, Mom! They cancelled afternoon classes, so I came home early!”
