Chapter 23
OLIVER
This was meant to be a straightforward errand. Grab a pair of jeans for Drew, who somehow destroyed his last decent ones in what Jackson cryptically called an “acrobatic incident.” Quick stop, simple purchase, then back to campus.
But I’ve been dealing with underwear betrayal all week.
Elastic giving up the ghost mid-lecture, fabric bunching in places no fabric should bunch, bathroom trips that have nothing to do with bodily functions and everything to do with discreet adjustments.
And to get from the jeans to the exit, you have no choice but to navigate through the underwear section. Might as well stock up while I’m here.
I reach for the familiar blue package of boxer briefs—same brand I’ve worn since high school, same size that gets over the hockey butt without ripping. My fingers have barely closed around the plastic when something at the edge of my vision demands attention.
Three feet to my left, arranged in neat stacks by size and illuminated by a spotlight usually reserved for museum exhibits, is a tower of Fruit of the Loom briefs.
Tighty-whities.
My brain, that treacherous organ, immediately fires up a memory I’ve been trying to bury since the night it happened.
The skinny-dipping incident at the end of the semester.
Moonlight streaming through glass walls, turning water into liquid silver.
Clothes flying in every direction—board shorts, basketball shorts, boxers, boxer briefs.
And Ryan, standing at the edge of the pool in white briefs, while everyone else cannonballed and belly-flopped.
The white cotton clung to his narrow hips, the elastic band riding just below his navel.
Stop it, Jacoby. Stop these indecent thoughts right now.
But the display is right there, mocking me with its wholesome packaging and promise of “classic comfort.” The models on the package stare back at me with confident smiles, begging me to come over to the dark side.
I wonder what they feel like.
The thought arrives uninvited, kicks off its shoes, and makes itself comfortable in my frontal lobe. Boxer briefs have been my thing since puberty. There’s no reason to switch things up now…is there?
Three seconds pass. I snatch the package up, the plastic cool against my palm. My thumb traces the edge where the cardboard backing meets the clear front. Another five seconds. I put it back in its place on the shelf.
“You’re being insane,” I mutter to myself.
A woman with a shopping basket hooked over her forearm pauses mid-sock-selection, her head tilted in my direction. I squint at the package label, tracing the “XL” with my index finger, nodding thoughtfully.
Once she’s gone, I take a step toward the exit. Away from the display, away from the temptation, away from the absolutely unhinged idea that wearing white briefs will provide me with some kind of insight into Ryan Abrams’s inner world.
Flip, flap, flip, flap. My flip-flops announce my retreat across the store. The sound suddenly dies as I halt mid-stride, toes curling against the worn footbeds.
I look at the display again.
“They’re just underwear,” I mutter under my breath. “Material designed to support the male anatomy. There is nothing romantic or revelatory about a pair of white briefs.”
I find myself back at the display, my hand reaching for a pack before my brain can object. Size XL. Three pairs bundled together, because God forbid the underwear industry let you dip just one toe into these particular waters.
I flip the pack over and read the back—tagless comfort, and a contoured pouch for support. The model on the front is standing with his hands on his hips in a pose that says he has never once questioned his underwear choices. I envy him deeply.
I could try them on in the privacy of my own room, where no one will ever know. It’s not weird. People try new underwear all the time.
Fuck. I am absolutely losing my mind.
The internal debate that follows is worthy of a congressional hearing.
For: They might actually be comfortable. Ryan seems perfectly content in them, and he’s not the type to sacrifice comfort for aesthetics. Maybe there’s something to the classic brief design that modern underwear has lost in its quest for longer leg openings and trendier cuts.
Against: I am buying tighty-whities because I have a crush. This is not a valid consumer decision. This is emotional purchasing, the underwear equivalent of buying your ex’s cologne to smell it when you’re lonely.
For: They’re not overly expensive. The financial risk is negligible.
Against: The psychological risk is incalculable. If anyone finds out—Drew, Gerard, literally any guy on the team—I will never hear the end of it.
For: But what if they’re actually better? What if the entire boxer brief industry is a conspiracy to keep men from experiencing the superior comfort of a classic brief?
Against: What if I’m just horny and delusional?
Screw it.
I walk away with a package of tighty-whities and a pair of green boxer briefs, because if I don’t like them, well…I still need new underwear.
Drew’s jeans get yanked off a rack I pass without stopping. I grab a pack of socks from a nearby display and toss them into my basket. I do need them, but more importantly, they’ll hide the briefs between layers of normal, uncontroversial purchases.
The checkout line is four people deep. I slide in behind a woman buying bath towels and a man with an armful of dress shirts.
Soon enough, I’m next.
The cashier is a kid, maybe nineteen, with a wispy mustache. His name tag reads “Jason” in block letters, and he has the thousand-yard stare of someone who’s been ringing up strangers’ purchases too long to care about what they are.
“Find everything okay?” he asks, scanning Drew’s jeans.
“Yep.” My voice comes out approximately one octave higher than normal. I clear my throat. “Yeah. Good. Great.”
When he reaches for the Fruit of the Loom pack, heat floods my cheeks, my ears, and my neck until I’m basically a tomato with a credit card.
He scans the briefs without even glancing at them. The price appears on the screen, and he drops them into the bag.
That’s it. No raised eyebrow. No knowing smirk. No intercom announcement: “Price check on tighty-whities for the emotionally compromised hockey captain at register four.”
Jason tells me my total. I swipe my card through the reader with fingers that are definitely not trembling, grab my bag, and walk out of Macy’s at a pace that falls somewhere between “casual stroll” and “fleeing a crime scene.”
The drive home is fifteen minutes of me glancing at the Macy’s bag in my passenger seat as though it contains a live explosive. Every red light feels like the universe giving me an opportunity to turn around and return them. Every green light feels like the universe daring me to keep going.
I keep going.
The Hockey House is quiet when I arrive. It’s that dead zone of mid-afternoon where most of the guys are either at the gym, at the beach, or napping. I take the stairs two at a time, bag clutched to my chest, and close my bedroom door behind me with a soft click.
With the lock engaged and the blinds drawn, my privacy is now secured. I pull out Drew’s jeans and toss them on the bed—I’ll bring those to him later. The socks go in the sock drawer. The boxer briefs go in the underwear drawer.
All that’s left is the pack of white briefs.
I tear open the packaging with more care than I’ve ever put into extracting underwear. The briefs unfold in my hands, bright white and impossibly clean, the cotton soft against my fingertips. They’re lighter than I expected.
I fold them neatly. Then I reopen my underwear drawer and survey the landscape: boxer briefs in various colors, stacked on the left; jockstraps for game days, on the right; a couple of compression shorts wedged in the back.
The white briefs go underneath everything, hidden beneath layers of perfectly acceptable, socially uncomplicated underwear.
If anyone ever goes through my dresser—which, living in the Hockey House, is not outside the realm of possibility—they’ll have their work cut out for them, finding the contraband.
I close the drawer and step back, wiping my palms on my shorts. One day, I’ll try them on and see what the fuss is about. But today is not that day. Today, I am a man who purchased tighty-whities and put them away like a rational adult, and that’s where this story ends.
I go downstairs and eat a sandwich. I spend twenty minutes watching a documentary about deep-sea creatures that someone left paused on the living room TV.
I bring Drew his jeans, and he grunts a “Thank you” without looking up from whatever he’s reading on his phone.
I head back to my room and sit on my bed.
I check my emails and respond to a text from Mom about whether I’m eating enough vegetables.
My eyes drift to the dresser.
No.
I refuse to acknowledge the dresser’s presence, even as it looms in my peripheral vision, a wooden monument to my indecision.
I open Instagram, scrolling mindlessly through my friends’ posts. A picture of Mason wearing new sunglasses. Alex’s latte art, taken by Kyle, of course. A video of Jackson failing spectacularly at a backflip.
The dresser continues to exist.
“This is stupid,” I announce to my empty room before crossing the floor in three steps, yanking open the drawer, and digging past the boxer briefs and jockstraps like a man searching for buried treasure.
My shorts slide down my legs. The boxer briefs follow, landing in a heap at my ankles.
Cool air kisses my bare skin as I balance on one foot, then the other, stepping into the leg holes of the white briefs.
The cotton glides up my calves, over my knees, and as I pull them into place with a gentle snap of elastic against my hipbones, my breath catches in my throat.
“Oh,” I breathe, eyebrows shooting into my hairline.
The first thing I register after years of boxer briefs hugging my thighs is the sudden freedom.
The waistband sits higher than I’m used to, right at my natural waist, and the elastic is snug without digging in.
The pouch cups my junk with a gentle firmness that feels less like containment and more like…
support. The kind that says I’ve got you, go about your day instead of the boxer brief equivalent of a loose suggestion.
The mirror on the back of my door doesn’t lie. I look fucking damn good.
I turn sideways. The mirror reveals a perfect half-moon curve where the white cotton hugs every inch without a single wrinkle or fold. No bunched fabric between the cheeks, no extra material sagging at the thighs.
“Huh.”
I’m at my desk in four strides. The laptop screen flickers to life, illuminating my face in the dim room.
My fingers tap-dance across the keyboard: men’s white briefs.
The search results load—there they are. Hanes.
Fruit of the Loom. Calvin Klein. I click the first option, scroll past the reviews (4.
5 stars, 3,782 ratings), and hover over the dropdown menu.
Small? Medium? Large? XL? XXL? My finger trembles slightly before selecting my size.
The “Add to Cart” button turns orange beneath my cursor.
This is no longer an experiment. This is a conversion, and I feel absolutely zero regret.
Delivery estimate: two days. I’ll need to intercept the package before anyone else sees it, because the last thing I need is Drew examining my mail and discovering my underwear evolution.
I sit down in my desk chair and stare at the order confirmation on my screen.
Nobody will ever know…except maybe Ryan.