A Winning Smile

By Alex Madrigal

Copyright ©2025

I had imagined the stranger’s voice like velvet, but as I slid into the wooden booth across from him, I found it instead like flannel: warm and familiar and softly textured, something I could wrap myself up in. He kept his straw hat pulled down, but as I reached across to shake his hand the light fell across the lower half of his face. He smiled, the same winning smile I’d seen in his profile and which had made me message him.

Even on the app, I hadn’t seen his whole face. It wasn’t unusual, town like this. I didn’t begrudge the man his privacy.

“What’s this, a business meeting?” he joked as our hands clasped.

“Just a regular old business meeting between men, that’s all, sir,” I said, and his laughter, like his voice, was warm.

My gaze lingered on his hand as I withdrew to pick up my beer. His fingers came together to spin a coaster, a nervous motion that set the muscles rippling gently against the bones in the back of his hands. The coaster fell and he closed one palm over it firmly. A frission went down my spine as the vein connecting to his wrist tightened. I was already imagining those hands on my body.

“So what’s your — ” I began, but he cut me off.

“Let’s not spoil it with too much information,” he said, and once again he smiled. It was a cockeyed yet cocksure smile, lopsided beneath the fine, dark scruff of a beard two-days since shaving.

I leaned back, took a long draught of my beer. “That’s fine, that’s fine.” It wouldn’t have been the first time I’d met up with a man just for a quick suck in the bar’s single toilet.

But he surprised me. “You got a place nearby?”

I nodded, slowly.

“Can we go there?”

My stomach tightened at the promise of something longer and more satisfying. I crossed and then uncrossed my ankles, remembering the plug I’d so hopefully inserted before driving.

“Sure, sure, we can go there,” I said.

He thought I was hesitating. “Or, you know, there’s the motel down the way.”

“No, no,” I said. “I just thought — my place is fine.” I tried to smile at him.

He leaned forward. “You’re cute when you’re nervous, you know that?” he asked, and my cock brushed against the cotton of my boxers as it stiffened, just a little.

He rose unexpectedly. “I’ll get these,” he said, even though we’d both only drunk half our beers. I didn’t protest as he withdrew a worn leather wallet and pulled out a crisp, bank-fresh twenty.

“Saves me an ATM fee,” I joked, and he laughed even though it wasn’t funny.

We left our glasses sweating in the warmth of the dark bar and he followed me out to my pickup, his hat still low in the harsh parking lot lighting. His hands flexed against the denim of his jeans as the engine rumbled to life, and I tried not to wonder who he was. He knew the town, knew the bar was cash only, had come with money already withdrawn so the bar’s ATM wouldn’t show on his statement. It was too dark to see if he sported a ghost ring, white against the sun dark of his skin. Anyway, what did it matter if he was married?

The wheels grumbled as I turned off the two-lane highway and onto the dirt road leading to my property. The stranger rolled his window down and the scent of autumn rolled through the cab: drying hay, the corn almost ripe. The moisture of the cooling night kissed my cheeks and I slowed, letting the wind move over us. I turned again, onto my lane, and to our right my cornfield towered over us. The man whistled appreciatively. A moment later he said, “Say, maybe we don’t have to go all the way to your place. The night’s fine, isn’t it?”

I tightened my grip on the steering wheel. A narrow lane separated two fields of corn, and I cut the headlights to pull into it, illuminated only by the fog lights. When I killed the engine all was dark and quiet. Tall fronds of corn waved near the top of the truck like fingers, cradling us, and for a moment I allowed myself to feel like a sea creature nestled into the safety of a seabed, the sky an infinitely far surface above us. Then the heat of the stranger’s hand on my thigh brought me back to earth. He’d taken his hat off in the dark, and the light from the sky was just enough to illustrate the line of his jaw, his parted lips. I closed my eyes as I leaned toward him, and then his mouth was on mine, gentle and warm.

The floral note of hops on his tongue mingled with the vetiver scent of his cologne. He brought a hand up to cradle my cheek and I tried to kiss him with more insistence but he held back, keeping me wanting more.

I whimpered as he broke away, the silence cracked open by his door opening. I didn’t hesitate, I followed him out and gestured to the bed of the pickup. It was still strewn with loose strands of hay, but he didn’t complain as I lowered the tailgate, then turned back to him, took his face in my hands to kiss him as I wanted. He was shorter than me, and as I moved my hands against his back I felt him harden. I cupped my hands against the denim-clad surface of his clenched buttocks and then, surprising him, lifted him onto the lowered gate.

“Hey,” he said, laughing, and I shushed him, pushed him down. His cock sprang free when I undid his fly, already pearling with pre-cum. He moaned as I leaned down to taste it, swirled my tongue around the swell of his head. He was recently showered, his skin clean with the lingering scent of Ivory, and as I laced my fingers to tuft up his pubic hair his cock hardened further, eagerly seeking out the warmth of my lips.

I teased him a little longer, bringing my other hand to cradle his shaft before letting myself envelop him, bringing him deep into my mouth to fill me up. He tried to thrust but I kept him steady, easing into a rhythm I liked before letting him join into it, my tongue gliding over his fullness.

“Fuck,” he moaned. “Let me fuck you before I come.”

With one last deep pull I withdrew, and he sat up on his elbows to look at me. For a moment I thought I recognized him before I swiftly looked away, pulling the condom out of my back pocket before I could let my mind seek out a hypothesis.

He put a hand on my chest as he rose. “You don’t mind, right?” he asked, referring to our brief text exchange before we agreed to meet.

“I do either,” I reiterated, and he nodded, pleased.

He laid his flannel down on the truck bed before bending me over, and my cock throbbed in anticipation as his hands moved over my exposed back. He made an appreciative “mm,” as he spread me open, rubbing his thumb along the edge of the plug. I closed my eyes at the teasing sensation of the plug turning inside of me, then gasped when he tugged it, not hard, just enough to test me. My muscles flexed against it, keeping it firmly in place as he rubbed his cock against the flesh of my thighs, teasing me until I moaned.

Finally, with one deft motion, he put his fingers under the rim of the plug and pulled it free. I whimpered softly as my cock formed a bead of wetness, hoping — begging — for the release that was soon to come. “I like a man who comes prepared,” he said, his words muffled slightly as he used his teeth to rip open the plastic casing of the rubber.

“A boy scout’s always prepared,” I replied, and he laughed, giving my ass an appreciative slap.

When he entered me a merciless little prayer escaped my lips, a breathless hallelujah, that god so loved the world he gave us cocks as fine as this, and holes to receive them with.

When he had come the stranger leaned into me, remained inside me as he wrapped his arm around me to find my shaft. I was so close it only took three strokes. I expelled into the dirt below my truck bed, and the stranger moaned as my muscles tightened involuntarily around his cock.

We were quiet as I backed the truck to the road and then returned to the highway. I glanced over at him as we passed beneath a streetlamp, noticing he’d donned his straw hat again, and all I could see was the strong line of his jaw, the lips I’d kissed and might never kiss again.

“Stop here,” he said before I turned into the bar lot, and I pulled over 20 yards away from where another car was parked on the side of the road.

“It was nice to meet you, stranger,” I said, and he paused with his hand on the handle.

“I know who you are,” he said.

I said nothing. My face and first name were clear on my profile. It was he who had something to hide, not me.

“You’re Pastor Willard’s boy,” he finished. “God rest his soul.”

I nodded. “I am.”

“You still go to service?”

“Do you?”

He laughed. Slowly, he reached up and removed his hat, let the faint light outline his features.

But I didn’t know him. Maybe I’d seen him at the feed store, or back in the day, somewhere in the pews while my father preached.

I whistled. “I didn’t know this ugly town made boys as gorgeous as you.”

He put the hat back on his head, cracked open the door. The last I saw of him was that winning smile, sideways and shining.

About Alex Madrigal.:

Alex lives and writes in New York City.