Leo sat alone in his dorm room one quiet Thursday evening in early October, the campus outside buzzing faintly with the distant laughter of students heading to weekend parties. Ben, his roommate, was out at a study group that would inevitably turn into a beer pong tournament. The room was dimly lit by a single desk lamp, casting soft shadows over the cluttered space—textbooks piled on the floor, a half-eaten pizza box from lunch, and Leo's laptop humming idly on his bed. He had slipped into one of the sets Chloe had gifted him over the summer: a pair of soft pink boyshorts with delicate lace trim along the edges, paired with a matching push-up bra that she'd sworn was "universally flattering."
The boyshorts hugged his hips snugly, the cotton-spandex blend stretching just enough to feel secure without pinching. They provided full coverage over his crotch, the fabric smooth and breathable, molding to his form in a way that was both comforting and subtly teasing. The lace trim tickled lightly against his skin with every shift, a playful contrast to the practicality of the cut—boyish in style but undeniably feminine in execution. Up top, the bra was a revelation. He'd grown bolder since spring break, stuffing it with a pair of rolled-up socks to fill the cups, creating the illusion of modest breasts. The push-up design lifted what little he had, the underwire giving a gentle but firm support that made his chest feel... present. The straps were adjustable and thin, adorned with tiny rhinestone accents that caught the light like secret stars. He clasped it in the back with practiced ease, thanks to the full-length mirror propped against his closet door.
Standing there, Leo adjusted the straps, pulling them taut before stepping back to admire the full effect. He wasn't turned on by his own reflection—not in a narcissistic way. Leo had never been vain; his body was average, unremarkable in the gym-bro sense. No, what sent a warm thrill racing through him was the underwear itself. The bra was adorable in its sweetness: the soft pink hue like cotton candy, the rhinestones winking innocently yet provocatively, the way the cups curved with a playful bounce from the stuffing, evoking a girlish charm that was both cute and inviting. It looked like something a confident co-ed might wear under a sundress for a casual date—flirty, approachable, with just enough lift to make one feel empowered. The boyshorts matched perfectly, their lace edges framing the fabric in a scalloped pattern that screamed "cute overload," the little bow at the front centre adding a whimsical touch, like a gift waiting to be unwrapped. But beneath the cuteness was undeniable sexiness: the way the material clung to his growing arousal, outlining the subtle bulge without shame; the lace whispering against his inner thighs, heightening sensitivity; the overall set transforming ordinary cotton into something luxurious, sensual, designed to make the wearer feel desired. It was the contrast that got him—the innocent pink clashing with the intimate fit, the rhinestones sparkling like they were daring him to touch.
His breath hitched as he ran a hand over the bra's cup, feeling the sock-filling give slightly under his palm. The fabric was so soft, almost silky in its weave, and the push-up padding created a cleavage illusion that made his heart pound. Down below, the boyshorts cradled him perfectly, the seam at the front pressing just right against his hardening length. He shifted his weight, and the lace grazed his skin, sending sparks of pleasure upward. God, these were perfect—cute enough to make him smile at their playfulness, sexy enough to make his pulse race with forbidden heat. Chloe had nailed it when she picked these out; they weren't just clothes. They were an experience.
The arousal built quickly, a insistent throb that demanded attention. Leo glanced at the door—locked, thank goodness—and sank onto his bed, the mattress dipping under him. He closed his eyes, letting the sensations wash over him: the bra's straps digging lightly into his shoulders, a reminder of their delicate strength; the boyshorts' fabric stretching taut as he grew harder. His hand trembled slightly as he slid it down his stomach, fingers dipping beneath the waistband. The material was warm from his body, and he gasped softly as he wrapped his hand around himself, the lace trim brushing his wrist like a teasing caress. He started slow, strokes deliberate, imagining the set on Chloe—how the push-up would accentuate her curves, the rhinestones glittering under light. But no, this was about the lingerie itself, its cute-sexiness enveloping him, making him feel alive in a way jeans never could.
Minutes blurred—his breathing ragged, hips bucking subtly into his fist. He was close, so close, when his phone buzzed on the desk with Chloe's familiar ringtone, a upbeat pop song she'd set as her caller ID ages ago.
Leo froze, hand still buried in the boyshorts, a groan escaping him. It was their weekly call time—he'd completely lost track. Talking to Chloe was usually the best part of his week, her voice a bridge to home. But now? No way he could compose himself. His face flushed hot, arousal mixing with panic. He couldn't ignore her; she'd worry or tease him endlessly. Sighing, he withdrew his hand, adjusted the boyshorts as best he could to hide the evidence, and grabbed the phone. "Hey, Chloe," he answered, voice a touch too high.
"Leo! Perfect timing—wait, you sound weird. Everything okay?" Her tone was light, but he could hear the curiosity.
They dove into chatter: her latest shift drama at the coffee shop (a customer who'd demanded a "unicorn-free" latte), his midterm woes in sociology. Leo tried—God, he tried—to keep it steady, leaning against the headboard, the bra's rhinestones cool against his heated skin. But his voice wavered on every other word, breathy and strained.
Chloe paused mid-sentence about her friend's breakup. "Okay, spill. What were you doing before I called? You sound like you just ran a marathon."
Leo gulped, heart hammering. She knew him too well; lying was pointless. "Uh... wearing some of the stuff you gave me. The pink set with the rhinestones."
Silence for a beat. Then, a giggle—soft at first, building to full laughter. "Let me guess: You're getting turned on by a particularly exciting bra and panties. And I interrupted right before the big finish. Am I right?"
"Dammit, Chloe!" Leo groaned, but relief flooded him. "You're too smart for your own good. Wait... this doesn't gross you out?"
She laughed harder. "Nope, not even a little. You think I don't get turned on wearing sexy underwear? Dude, why do you think I own it? It's like... armour that makes you feel hot. I totally get it."
Leo sat there, stunned, processing. His sister—not just okay with it, but relating? Sharing this intimate thrill? Their sibling bond had always been close, but this twisted it into something deeper, more electric. He was silent for nearly a minute, the boyshorts still tented uncomfortably.
Finally, Chloe spoke, voice mischievous. "I have a wicked idea. Video call? I wanna see you in this magic set. Lol. Give me a minute... I wanna match." The call ended abruptly.
Leo's phone pinged a minute later: video invite on his laptop. He accepted, propping it on his desk, angling the camera carefully to show from chest up at first, though he knew she'd push for more.
There was Chloe, standing in her room, fairy lights twinkling behind her. She wore the exact same soft pink push-up bra and boyshorts—rhinestones sparkling, the push-up doing wonders for her full breasts, creating deep cleavage that made Leo's mouth dry. The boyshorts hugged her hips, lace trim framing her curves perfectly. She grinned, shit-eating and unapologetic. "Stunned silence means you like? Might make this my period set—pretty undies for when I feel like crap. Unless you object?"
Leo shook his head vigorously. "No objections. Wow, Chloe. That set on you... it's gorgeous. You gonna save it... just for that, or wear it sooner? In addition to now, I mean."
She twirled, the bra's cups bouncing slightly. "Tempting to wear it all the time. lol probably not a good idea though, right? Looks good on you too—show me the full thing!"
Emboldened, Leo stood, camera capturing him fully. The stuffed bra, the boyshorts stretched over his arousal. Chloe whistled. "Cute and sexy as hell. Those rhinestones? Killer."
Banter flowed—teasing about fits, fabrics, how the lace felt. But tension built, eyes locking through screens. Chloe bit her lip. "Can't hold back anymore. You?"
"No," Leo admitted, voice husky.
They didn't need words. Chloe sat on her bed, legs parted slightly, hand slipping into her boyshorts. "Watch me," she whispered, fingers moving in slow circles over the lace-trimmed front. Her breasts heaved in the push-up bra, rhinestones glinting as she arched. Leo mirrored her, hand delving back into his boyshorts, stroking firmly. The sight of her—the cute pink set on her body, so alive, the boyshorts darkening slightly with her arousal—pushed him higher.
"Feels so good," Chloe murmured, eyes half-lidded, free hand cupping her bra-covered breast, thumb circling a nipple through the fabric. "The lace... tickles just right. Tell me what you're doing."
"Stroking slow," Leo breathed, pace matching hers. "The boyshorts hug me tight... your set looks amazing on you. Those cups... pushing you up like that."
She moaned softly, fingers dipping deeper, the boyshorts' waistband pulling down slightly to reveal smooth skin. "Imagine the rhinestones sparkling while I... yeah. Faster now?"
They synced, breaths syncing—hers light and gasp, his deeper groans. Chloe leaned back, propping the laptop for a better view, hand working visibly under the pink fabric, hips rolling. Leo's stuffed bra bounced with his movements, the illusion adding to the eroticism. "Close," he warned.
"Me too," she panted, eyes on him. "Come with me, Leo. In our cute, sexy set."
Release hit them together—Chloe's cry muffled as she shuddered, boyshorts soaked; Leo spilling into his hand, the fabric containing the mess warmly. They rode the waves, smiling breathlessly.
"Best call ever," Chloe said after, adjusting her bra.
"Agreed," Leo laughed, spent and closer to her than ever.
A few weeks later, mid-November brought rainy afternoons perfect for holing up. Chloe and Mia were in Chloe's room, textbooks open but ignored, rain pattering against the window. They'd been cramming for biology and history tests, brains fried. Mia stretched, grabbing Chloe's laptop. "Break time. Let's see what your bro's up to. Need a laugh—maybe he has some college stories?" Without waiting, she initiated a video call to Leo.
Chloe's stomach dropped. Oh shit. What if he was mid-session again? Their mutual masturbation had become a semi-regular thing—late nights, shared sets—but Mia knew nothing. Privacy mattered. "Mia, wait—"
Too late. Leo answered, looking casual in jeans and a sweater, dorm behind him. "Hey, ladies. What's up?"
Relief washed over Chloe... until Mia squinted. On Leo's bed, peeking from under a pillow: a flash of teal lace, unmistakably panties like Chloe's boyshorts.
Mia grinned wickedly. "Leo, studying hard? Or just Human Anatomy 101? Whose pretty panties are those? Girlfriend?"
Leo glanced over, face paling. He laughed it off. "Ha, yeah, anatomy's my best subject. Just... laundry mix-up." Casually, he reached over, nudging them out of sight.
Chloe changed the subject fast—tests, rain, anything. But Mia's eyes lingered thoughtfully.
Two weeks of close calls followed: Mia dropping by unannounced, nearly spotting a bra strap under Leo's shirt during another group call; Chloe intercepting a package. Tension built.
Then, alone in her room one evening, Chloe's phone buzzed. Text from Mia: I know, and I want in.
Chloe stared, heart racing. Know what? The underwear? Leo's secret? Their shared sessions? She typed back: Know what?
Mia's reply: Everything. Saw the panties. Overheard you on a call once—pink set, rhinestones? Hot. Leo's into it too? Tell me. I want to join the fun. No judgment. Promise.
Chloe's mind whirled. Mia—bubbly, impulsive Mia—intrigued, not repulsed. This could explode their world, but in a good way? She called Leo immediately.
"Bro, emergency. Mia knows. About the underwear. And... us. She wants in."
Leo's voice cracked. "In? Like...?"
"Yeah. Think about it. Could be our trio now."
The rain outside Chloe's window intensified, mirroring the storm of possibilities brewing. Leo, back in his dorm, slipped into the pink set again that night, arousal tinged with nerves. Chloe did the same at home. Their next video call included a third invite—Mia, grinning in her own lace set, ready to explore.
What started as a sibling secret was evolving, boundaries blurring into something bolder, braver. Leo stuffed his bra, Chloe adjusted her push-up, and Mia revealed her curves in black lace. "Show me how it's done," Mia said, voice eager.
They did—hands moving in unison, cute fabrics straining, sexy moans filling screens. Leo found the sets even hotter shared with two, the rhinestones and lace a symphony of sensation. Chloe laughed through gasps, Mia's enthusiasm infectious.
By the end of winter break, the three were inseparable in secret—care packages now for all, video sessions steamy and supportive. Leo's confidence soared; he wasn't just wearing underwear. He was owning it, with sisters in spirit beside him.
The game had levelled up, and none of them wanted to stop.
