Women's Underwear & Sibling Bond

A college man secretly wears women's underwear

The first time Leo pulled on a pair of women’s underwear, it was an accident born of curiosity and a late-night online shopping spree. A package had arrived for his roommate, Ben, a blur of mixed-up orders and shared Amazon passwords. Among Ben’s new video games and protein powder was a single, stray item: a pair of black cotton panties with a delicate lace waistband. Simple, soft, and utterly out of place.

Ben, upon discovering the error, had laughed, holding them up like a dead fish. “Well, these are going back. Unless you want ‘em, Leo? A little something for the weekend?” He’d tossed them onto Leo’s bed as a joke before heading out for the night.

Alone in the dorm room, Leo had stared at the discarded garment. It was so… small. So unlike the baggy, utilitarian boxer briefs that filled his own drawer. On a whim, a impulse he couldn’t quite articulate, he picked them up. The cotton was impossibly soft against his calloused fingers from hours of guitar practice. The lace was delicate, almost frivolous. He held them for a long moment, then, with a furtive glance at the locked door, he decided to try them on.

It wasn’t a sexual thing, not really. It was a sensory revelation. The fabric hugged his hips, a smooth, constant pressure that was somehow both secure and freeing. The soft cotton against his skin was a world away from the chafing, often sweat-dampened cotton of his boxers. He looked in the mirror, turning sideways. They were… cute. A secret aesthetic pleasure known only to him. A tiny, personal rebellion against the expected uniform of masculinity. A thrill, hot and sharp, shot through him. He wasn’t supposed to be wearing these. That was a large part of the appeal. It was his secret.

That was three months ago. Now, as he zipped his suitcase shut on the last day of fall semester exams, his entire underwear drawer had been quietly, completely revolutionized. The boxers were long gone, donated to a charity bin he’d driven to in the next town over. In their place was a collection of cotton bikinis, lacy thongs, and silky boyshorts in colors like lavender, mint green, and a daring cherry red. Each pair was a small victory, a private joy. He felt more like himself in them, a version of himself that was softer, more considered, and braver than the one who presented to the world.

But now, that world was about to collide with his secret. He was going home for three weeks.

The familiar dread of returning to his parents’ house—the questions about grades, future plans, his diet—was now eclipsed by a single, pulsing anxiety: What if someone finds them?

His mind conjured a hundred catastrophes. His mom, a whirlwind of efficiency, deciding to do a “helpful” load of laundry and pulling his delicate lace panties from his jeans pocket. His dad, looking for a spare phone charger and rooting through his suitcase. Worst of all, his little sister, Chloe.

Chloe. A high school senior, whip-smart, observant, and with a radar for bullshit that was almost supernatural. They were close, the kind of sibling closeness forged in the trenches of a happy but boring suburban childhood. They texted daily memes, debated the best order to watch Marvel movies, and complained about their parents. He told her about his roommate’s weird habits, about the cute girl in his Sociology class, about the stress of exams. But he had never, ever, typed a single word about the soft, secret cotton against his skin.

The drive home was a five-hour exercise in paranoia. Every time his dad called (“Just checking your ETA, son!”), Leo’s heart hammered, half-expecting him to add, “And by the way, your mother found a pink thong in your sock bin. Care to explain?”

He arrived home to the usual chaos. His mom engulfed him in a hug that smelled of cinnamon and laundry detergent. His dad clapped him on the back and immediately started talking about the gutters. Chloe launched herself at him from the stairs, a blur of messy bun and oversized sweatshirt. “Finally! The wifi’s been weird and I’m convinced it’s a sign of your absence.”

It was normal. Perfectly, blessedly normal.

The first week was a masterclass in covert operations. He did his own laundry, sneaking it down to the basement late at night. He kept his suitcase zipped and tucked under his bed, the secret compartment within a compartment. He changed in his bathroom, locking the door religiously, hastily stuffing the day’s chosen pair—today, a simple heather grey cotton hipster—into the pocket of the next day’s jeans. He was a spy in his own home, and the mission was maintaining a fabric-based integrity.

He began to relax. Maybe he could do this. Maybe he could get through the break without his world exploding.

The explosion happened on a Tuesday, a week after he’d returned home. Chloe was rampaging through the house looking for her favorite hair straightener, which had a habit of migrating. She burst into his room without knocking, a common practice he usually didn’t mind.

“Straightener emergency. Don’t mind me,” she declared, her eyes scanning his cluttered desk.

“Not in here,” Leo said, not looking up from his laptop. He was wearing a pair of light blue cotton panties with a small bow on the front, a fact that gave him a small, secret thrill even as he scrolled through mindless internet content.

Chloe, unsatisfied, dropped to her knees and peered under his bed. “You hog all the good outlets. Maybe it fell back here…” She tugged on his half-hidden suitcase.

A bolt of pure adrenaline shot through Leo. “Chloe, don’t—”

It was too late. She’d pulled the suitcase out and unzipped the main compartment, rifling through the sweaters and jeans on top. “Jeez, Leo, did you even unpack—oh.”

Her hand stilled. She’d pushed aside a folded hoodie and her fingers had brushed against something impossibly soft and… lacy. She pulled it out. It was a pair of black lace panties, one of his more daring acquisitions. They dangled from her finger, a tiny, damning flag of surrender.

Leo’s blood ran cold. He couldn’t breathe. This was it. The end.

Chloe’s face went through a rapid series of expressions. First, confusion. Then, dawning, horrified understanding. Then, a slow, impressed smirk. She looked from the lace to him, her eyebrows climbing into her hairline.

“Well, well, well,” she said, her voice a low, teasing drawl. “Look what we have here. Big brother. You dark horse.”

Leo’s mouth was desert-dry. “Chloe, I can explain—”

“No, no, no explanation needed,” she interrupted, a laugh bubbling in her throat. She carefully, almost reverently, placed the black lace back in the suitcase. “My big brother, the college man. Bringing girls home? Or… impressing them, I should say.” She waggled her eyebrows. “These are nice. A little racy, but nice. I’m… wow. I’m actually kind of proud of you. And a little disturbed. Mostly proud.”

She thought they were a girl’s. Of course she did. The relief was so potent it made him dizzy. He managed a weak, strangled laugh that sounded nothing like himself. “Yeah, well… you know. College.”

“Apparently I don’t!” Chloe grinned, getting to her feet. “My respect for you has increased, like, a thousand percent. Your secret’s safe with me.” She mimed zipping her lips and throwing away the key, then bounded out of the room, her straightener crisis seemingly forgotten.

Leo collapsed back in his chair, his heart pounding against his ribs like a trapped bird. He’d done it. He’d narrowly avoided disaster. He quickly re-zipped the suitcase and shoved it back under the bed, his hands trembling. He’d have to be more careful. So much more careful.

He thought that was the end of it.

But Chloe’s curiosity, once piqued, was a relentless force. The next day, driven by a nosy, sisterly instinct she couldn’t ignore, she went digging. While Leo was out getting a haircut with their dad, she slipped back into his room. This time, she didn’t stop at the first pair she found. She opened the suitcase properly. She moved the clothes aside. And she found them. Not one pair. Not two. But a whole collection. A rainbow of cotton and lace and silk. Dozens of them. All clearly his size. All clearly… his.

The initial theory of a forgotten girlfriend’s garment shattered. The evidence was overwhelming and bizarre. Her brother, her guitar-playing, sarcastic, slightly dorky brother, wore women’s underwear.

She stood there for a long time, just staring. The initial “ick” factor was there, a reflexive societal response. But it was quickly overshadowed by a wave of intense curiosity, and then, a slow-spreading, mischievous glee. This wasn’t just a secret; this was the mother of all secrets. This was blackmail material of the highest order. This was… hilarious.

A shit-eating grin spread across her face. She carefully rearranged everything exactly as she found it, her mind already whirring with possibilities. She left his room, closed the door, and practically floated downstairs. She needed to get out of the house. She needed to think. And maybe, she needed to go to the mall.

Leo noticed a change in Chloe over the next week. She’d look at him sometimes with a weird, knowing glint in her eye, and then burst out laughing at nothing. When he asked what was so funny, she’d just wave a hand and say, “Inside joke with myself.” He wrote it off as typical Chloe weirdness, his own panic from the “black lace incident” fading back into a low hum of background anxiety. The Christmas preparations provided a welcome distraction.

Finally, it was Christmas morning. The living room was a whirlwind of torn wrapping paper, the scent of pine from the tree mingling with the rich aroma of brewing coffee. Their dad got a new set of grilling tools and made appropriately appreciative manly grunts. Their mom loved the expensive scarf they’d all chipped in for. Leo got new headphones, a couple of video games, and a surprisingly nice sweater from Chloe.

The gift exchange was winding down, the comfortable clutter of a family holiday spreading through the room. Leo was basking in the normalcy of it all, feeling like he’d truly gotten away with it.

That’s when Chloe tapped him on the shoulder.

She leaned in, her voice a conspiratorial whisper in his ear. “Hey. I have something else for you. It’s in my room, on my bed.”

Leo turned to look at her. Her expression was a perfect mask of slightly embarrassed sincerity.

“It’s kinda personal,” she continued, her voice still low. “I’m embarrassed about you opening it in front of everyone, so would you mind? Just go grab it.”

A trickle of unease went down his spine, but it was drowned out by curiosity and sibling trust. “Uh, yeah. Sure. Thanks, Chloe.”

He excused himself, weaving through the discarded paper and boxes, and headed upstairs. Her room was exactly as he expected: clothes piled on a chair, posters of bands he’d never heard of on the wall, a faint smell of perfume and vanilla.

And there, in the center of her unmade bed, was a small, neatly wrapped gift. It was about the size of a book, wrapped in simple green foil paper with a silver bow. There was no tag.

This was it? This was the personal, embarrassing gift? It looked innocuous enough. Maybe it was a prank—a whoopee cushion or something. He picked it up. It was light. Soft.

He sat on the edge of her bed and started to carefully peel off the tape. The paper fell away to reveal a plain white cardboard box. He lifted the lid.

And his world stopped.

Nestled inside on a bed of white tissue paper were three pairs of women’s underwear.

One was white cotton with delicate black lace edging the legs and waistband. Simple, elegant. The next was a vibrant, solid green cotton, a boycut style. The third was sheer black lace, a daring and beautiful design.

They were beautiful. They were exactly his taste. And they were a message, delivered with the devastating precision of a cruise missile.

His blood turned to ice. His breath hitched in his throat. The room seemed to tilt on its axis. She knew. She knew everything. The black lace she’d found before hadn’t been a fluke; she’d gone searching. She’d discovered his entire collection. And this… this was her response. This was a Christmas gift wrapped in pure, unadulterated terror.

Panic, cold and absolute, seized him. His heart hammered against his ribs, a frantic drumbeat of doom. He scrambled to rewrap the box, his fingers clumsy and shaking. He had to get out of here. He had to hide this. He had to—

A soft laugh came from the doorway.

He froze, the half-wrapped package clutched in his hands like a live grenade. He slowly turned his head.

Chloe was leaning against the doorframe, arms crossed over her chest. The same shit-eating grin from a week ago was plastered on her face, wider and more triumphant than ever. Her eyes sparkled with utter delight at his palpable horror.

“Merry Christmas, big bro,” she said, her voice dripping with playful malice. “I hope you like those as much as your other undies I found last week. Maybe even more.”

The grenade detonated. All the air left his lungs in a whoosh. “Oh no!” The words tumbled out, desperate and pleading. “Chloe, I thought I was being careful! Please, you can’t tell mom and dad. Please. I only started wearing them the last few months, it’s not… it’s not a big thing, I just… please.”

He was babbling, on the verge of a full-blown panic attack. His secret, the core of his private self, was exposed, and the person holding it was his little sister. The humiliation was complete and crushing.

But then, something shifted. Chloe’s grin softened. The teasing glint in her eye faded, replaced by something warmer, something empathetic. She unfolded her arms and walked fully into the room, closing the door behind her with a soft click.

“Leo, relax,” she said, her voice now gentle. “Breathe. It’s okay. It’s nothing to feel ashamed about.” She sat down on the bed next to him. “But damn, it was shocking to find your panties, that’s for sure. I definitely had no build-up to that twist.” She nudged him with her shoulder, a familiar, comforting gesture.

Her words, her tone, began to slowly puncture the balloon of his panic. He took a ragged breath, then another. He looked at her, really looked at her. She wasn’t disgusted. She wasn’t angry. She was… Chloe. His sister.

“Thank you for understanding,” he whispered, his voice hoarse. “I know it’s a bit unusual to find your brother’s stash, but my reasons aren’t creepy or anything. They’re just… softer. And they feel… I don’t know. Nice. Cuter. It just makes me feel… better.” It was the first time he’d ever said the words out loud.

Chloe let out a warm, understanding giggle. “Leo, you could have told me you were into wearing full ballgowns and I’d still love you. Whatever your reasons are, you are still my brother.” She pointed at the box in his lap. “Now. Important question. Which pair are you going to try on first?”

He stared at her, bewildered. “What?”

“I’m serious!” she said, laughing. “I put thought into this! I made sure to buy you undies similar to my own. I figured if you’re going to do it, you should have the good stuff.” She leaned in, her voice dropping back to a theatrical whisper. “And I’m even wearing my own white cotton pair with black lace edges right now. So. Twinsies.”

The absurdity of it all—the terror, the revelation, the heartfelt acceptance, and now this offer of fraternal twin underwear—crashed over him. A laugh bubbled up in his chest, shaky and disbelieving at first, then growing stronger until he was laughing properly, the tension draining from his shoulders. She was insane. She was wonderful.

He looked down at the three pairs in the box. They were perfect. She had, somehow, nailed his preferences exactly.

“The green ones,” he said, a real smile finally touching his lips. “I think I’ll try the green ones first.”

Chloe clapped her hands together. “Excellent choice. Very festive.” She stood up. “I’ll give you some privacy. Mom’s making pancakes. Come down when you’re ready.” She headed for the door, then paused, looking back at him, her expression fond and just a little bit mischievous still. “And Leo? Welcome to the club. It’s much more comfortable over here.”

She slipped out, closing the door behind her.

Leo sat on the edge of his sister’s bed, holding the box of underwear. The fear was gone, replaced by a profound, overwhelming sense of relief and a love for his sister so fierce it almost hurt. He picked up the solid green cotton pair. They were unbelievably soft.

He changed right there, slipping off his old pair and pulling the new ones on. They fit perfectly. He looked in her full-length mirror. They were cute. They were his. And his secret was no longer a secret he had to keep alone. It was, somehow, miraculously, a new, strange, and utterly perfect thread in the fabric of his relationship with his sister.

He took a deep breath, smiled at his reflection, and went downstairs for pancakes.