All characters engaged in sexual activity are 18 or older.
The underwear run at our university was the kind of legend that got whispered about in dorms long before anyone ever showed up to campus. It was ten years in the running, and every fraternity threw money and muscle behind it, raised thousands for the local shelter, and the photos that always ended up on somebody’s finsta. I’d heard the stories freshman orientation week, but I never thought I’d actually be standing at the starting line in nothing but sneakers and boxer briefs.
Mark was the one who brought it up. We were sprawled on the floor of our room, him scrolling on his phone, me pretending to study for chemistry. “Yo, Aidan,” he said, flashing that easy grin that made my stomach flip. “Underwear run’s next Saturday. Five bucks to sign up and the clothes get donated. You in?”
I remember swallowing hard, trying to sound casual. “Yeah. Sure. Sounds fun.” Inside I was screaming. Because here’s the thing, I’d been stupidly and hopelessly into Mark since the first day of pledge week. He’s funny without trying, kind in this quiet way that sneaks up on you, and he looks like he walked out of a Calvin Klein ad with wavy brown hair that's always perfectly parted, and cheekbones sharp enough to cut glass.
I, on the other hand, am a pale, skinny twink with messy blond hair and zero muscle definition. Extremely gay. Extremely still in the closet.
Saturday came fast. The quad was already buzzing when we got there with hundreds of people milling around in shorts and tees, music thumping from somebody’s portable speaker. One of the seniors, Jake, the Sigma president hopped up on a folding table with a megaphone. “Clothes off except shoes and underwear, people! Everything goes to the shelter!”
The stripping started slow, then all at once. Shirts flying, jeans dropping. I peeled mine off quick, trying not to make it weird, but when Mark pulled his T-shirt over his head I forgot how to breathe. He had a golden tan, lean muscle that flexed when he moved, and a perfect V disappearing into low-slung black boxer briefs that hugged him like they were custom-made. His chest and abs looked airbrushed. I stared way too long.
He caught me. Of course he did. A little smirk tugged at the corner of his mouth, eyes flicking down to my obvious blush and back up. He didn’t say anything, just raised an eyebrow like he was filing the moment away for later. My face burned hotter than the afternoon sun.
We tossed our clothes into the donation bins and jogged over to the starting line. Someone else with a megaphone explained the route: five-mile loop around campus, but you only had to finish the first 2.5 if you wanted. “At the halfway mark we’ll give you some extra info to help you decide if you wanna keep going.”
I frowned and leaned toward Mark. “You know what that’s about?”
He shrugged, biceps flexing. “No clue. Guess we’ll find out.”
The gun went off—really just some guy yelling “Go!”—and we were running. The first half was honestly fun. The sun on our skin, people laughing, music still bumping from the quad behind us. I kept pace with Mark easily, my runner’s legs were finally good for something. Every time the crowd shifted I had to force my eyes forward instead of letting them drift to the way his ass moved in those tight briefs or the flex of his thighs.
We hit the 2.5-mile mark in a shady grove near the tennis courts. Jake and the other presidents were waiting with folding tables and these smug little smiles. Everyone slowed, breathing hard, sweat cooling on our skin.
“Congrats on making it halfway,” Jake called. “Now for the twist.”
You could feel the energy shift.
“This year we’re upping the stakes. Anyone who wants to finish the full five miles has to do it naked. And,” he held up a black silicone prostate massager that gleamed under the sun, “one of these goes in your ass. Girls get the dildo version. They vibrate. We control the remotes. Make it to the end without cumming and you walk away with a $200 gift card to any store you want.”
There was dead silence for about three seconds, then chaos—gasps, laughter, and a couple people straight-up turning around and walking away.
My heart was hammering so hard I could feel it in my throat. I looked at Mark. His eyes were wide, lips parted, cheeks flushed from the run. But he looked… intrigued.
Another president yelled, “Five minutes to decide! Anyone heading back, party’s already starting at the quad where the houses are.”
Mark turned to me, voice low. “You wanna keep going?”
I laughed, but it came out shaky. “You’re serious?”
He lifted one shoulder. “Two hundred bucks is two hundred bucks. I’ll do it if you will.”
I swallowed. I thought about seeing him completely naked. Thought about him seeing me naked. Thought about that thing inside me, buzzing whenever they felt like it. My dick twitched in my briefs just at the idea. It was a bad idea, but I went for it anyways.
“Fuck it,” I said. “Let’s do it.”
His grin was instant, bright and sharp. He slapped my back, hard enough that I stumbled forward a step. “That’s my guy.”
Five minutes later only twenty of us were left. Fourteen guys and six girls. The rest were already halfway back to campus, probably texting their friends about the freaks who stayed.
They told us write our names on little tags, staple them to our underwear, and toss them into a bin. Mark and I locked eyes, took a breath, and slid them down together.
God, his cock was perfect. It was six inches soft, thick, cut, and hanging heavy over smooth shaved balls and a neat trim of dark hair at the base. It swayed when he moved. I couldn’t not stare. When I finally dragged my eyes up he was staring too—right at my half-hard dick—and we both went red at the same time.
We scribbled our names fast, dropped the tagged briefs in the bin, and moved to the next table. There were boxes of toys and bottles of lube lined up like it was the most normal thing in the world.
Mark grabbed two matching prostate massagers—black, curved, and thick at the base. He handed me one and a bottle of lube. I squirted some on my fingers, reached back, and started working myself open. One finger, then two. The second I brushed my prostate I was fully hard, my cock bobbing against my stomach, pre-cum already beading at the tip.
Mark was struggling. He had lube on his fingers but kept hesitating, his face twisted like he was trying to solve a math problem with his asshole.
“I’ve, uh… never actually done this before,” he muttered, cheeks scarlet.
I blinked. “You’re insane. You sure you wanna—”
“If you can do it, I can do it,” he said, grinning through the nerves.
I laughed, shaky. “Dude, this is not my first rodeo.”
His eyebrow arched. “Yeah, I figured.”
Heat flooded my face again. I opened my mouth, closed it, opened it again, and then just focused on slicking up my toy.
When I turned back, Mark was still stuck , two lubed fingers hovering uncertainly behind him, face flushed with frustration.
He bit his lip, looked over his shoulder at me. “A little help, please?”
My brain short-circuited. “You serious?”
He nodded, eyes dark. “I trust you.”
My heart slammed against my ribs. “Yeah. Of course. Turn around, bend forward a little, hands on your knees.”
His ass was flawless—smooth, muscled, and completely hairless. His pink hole clenched when the air hit it, like it was nervous to be in the sunlight. My cock, already rock-hard, brushed the curve of one cheek and left a shiny streak of pre-cum on his skin. Neither of us mentioned it.
I squirted more lube into my palm and warmed it between my fingers. “I'm gonna start with just one, okay? Breathe in slow… good. Now let it out.”
I pressed the pad of my finger against his rim. He clenched instinctively.
“Easy,” I murmured, tracing little circles. “Push out a tiny bit, like you’re trying to keep me out but actually letting me in. There you go… fuck, you’re tight.”
The tip slipped inside and he gasped, back arching.
“You good?” I asked, voice low.
“Yeah,” he breathed, shaky. “Just… a lot.”
I eased deeper, slow and steady, until my knuckle pressed against him. Heat clamped around my finger like a fist. “That’s one. Feel weird?”
“It feels… full,” he said on a laugh that turned into a groan when I crooked my finger, searching. “Oh shit, Aidan—”
“Found it,” I whispered, brushing his prostate. His whole body jolted, cock jerking hard enough that a thick drop of pre-cum swung from the tip and splattered the grass.
“Jesus,” he panted. “Do that again.”
“Later,” I promised. “Gotta open you up first. Ready for two?”
He nodded fast, pushing back against my hand like he couldn’t help it. I slid out, added more lube, worked two fingers in together. He hissed, then moaned long and low as I scissored them, stretching him gently.
“Talk to me,” I said, watching his hole flutter around my fingers. “Too much?”
“No… keep going. Feels insane.”
I twisted, spread, curled until his thighs were trembling and his cock was leaking a steady stream. “One more,” I warned. I inserted three fingers now, slick and relentless. He took them beautifully, his breath hitching every time I nudged that spot.
“Fuck, Aidan,” he groaned, voice wrecked. “I’m so hard it hurts.”
“I know,” I said, throat dry. “Me too. You’re doing perfect. Think you’re ready for the real thing?”
He nodded, forehead pressed to his forearm. “Please.”
I pulled my fingers free slowly, watched his hole clench on nothing, begging. I grabbed the massager, coated it thick with lube until it gleamed.
“Okay, here it comes. Same trick, push out for me… good boy.”
The blunt head kissed his rim. I pressed forward steady, relentless. He opened up around it with a filthy wet sound, swallowing inch after inch.
“Halfway in,” I coached, one hand on the small of his back. “Breathe… there we go.”
I gave it one last push and the base seated flush between his cheeks. He let out this broken moan that shot straight to my balls, his cock kicking hard enough that another rope of pre-cum dripped from him.
I stepped back, hands shaking. He straightened slowly and turned to face me, flushed and gorgeous, seven inches of flushed, dripping cock bobbing between us.
“Still alive?” I managed.
“Barely,” he laughed, breathless. “Thanks. Couldn’t have done that without you.”
Anytime, I almost said. Instead I just swallowed and tried not to come on the spot.
Around us the other runners were moaning too, girls sliding dildos home, guys working toys in, everyone was hard or wet or both. The air smelled like lube and sweat and sex.
Jake’s voice cut through the haze. “Alright, pervs. You don’t have to run the second half. You can walk, crawl, whatever. Just keep the toy in and don’t cum. Line up.”
We shuffled into place, twenty naked bodies glistening under the sun, toys seated deep. My prostate was already throbbing around the silicone, every heartbeat reminding me it was there.
Jake lifted the megaphone again, grinning like the devil.
“On your mark… get set… go.”
If you enjoyed this story, consider supporting the author on Patreon.
