The Night Owl

by A dude

10 Apr 2015 3265 readers Score 9.0 (59 votes) PDF Mobi ePub Txt


I was leaning against my black hulk of a van on the empty roof level of a parking garage, a usual perch, breathing in the open air and watching the sun set over the jagged skyline. An engine rumbled, and a green sports sedan pulled onto the lot from below. It parked not far from me, and the driver looked my way. I could tell the guy was nervous, hands clenching and unclenching on the wheel, deciding whether or not I was safe.

That's up for debate, though I admit I do look a little sketchy. I was wearing a tight black shirt, blue jeans, black shoes. Next to me was a huge, boxy van that had seen more than a few years of wear. I'm in my mid-thirties, lean, in shape, with a shaved head. I'm pale with heavy dark eyebrows, hazel eyes, a square jaw, and stubble for days - a scruffy man with a bit of the old pretty boy still poking through the seams. I knew I must have looked a little odd, standing there with my thumbs hooked in my pockets, not even smoking a cigarette, as if I'd been waiting for him.

He decided the risk was worth it and got out of his car. He walked toward me with an awkward wave, smiling easily, like a giant Labrador. This was a fine man. Late twenties, early thirties. Broad shoulders, muscled arms, sturdy waist, thick legs. He wore a buttoned up plaid shirt, loose jeans, and ridiculous leather moccasins with no socks. His face, though - a beauty. Square and masculine, light brown hair, a trimmed beard over a strong chin, bright blue eyes hidden behind thick glasses. He was a blessed crossbreeding of hipster and lumberjack. "Hey there! Sorry to bother you." A humming baritone.

I shrugged, smiled. "No bother at all." I've got a South Georgian accent, barely hidden. I glanced at his hand as he put it on his waist, noticed the golden band of a wedding ring. It seemed so out of place.

He went on. "I guess - well, I lost my phone today, and I've been backtracking all afternoon. Know how that is?" He laughed politely, and I caught his eyes on my midsection, where my shirt hugged my flat stomach. There was more than one reason he was nervous, it seemed. He made a rectangle with his hands, as if it would help. "About this big? It's got a blue case. Seen it? I was parked out here earlier."

"Ah," I breathed, holding up a hand. "Just a sec." I opened the passenger door of the van, leaned across, felt the evening air hit the small of my back as my shirt lifted. I fished his phone out of the side pocket, and as I rose I glanced in the rearview mirror. I could see him watching me, and not just because I might have his phone. He was looking at my backside, my exposed skin, staring blatantly, mouth slightly agape. That sealed it.

I unfolded myself and showed him the phone. He immediately grinned, hooted in relief, and I handed it to him. His fingers were soft and warm. "Thanks so much!" he gushed.

"Found it earlier, thought I'd wait for a while. See if anyone showed up to claim it." I smiled again. "Didn't know what to do with it otherwise."

He lifted his shirt a bit, pushed it into his pocket. I caught a glimpse of tanned skin. "Oh man, thanks. Thank you. Hey - can I get you anything? Pay you back?" His smiling face met mine, and something he found there cause a ripple of uncertainty. Understandable. I had been watching his big, meaty arms move under his shirt, thinking about how hairy is ass might be.

"Nah, I'm good." I locked eyes with him, and his brief elation began to falter. "Though, if you really do feel like paying me back, I wouldn't ask for much." I smiled warmly, cocked my head politely, leaning against the van with one hand, laying on the charm as thickly as I knew how - which is real, real thick. "Just let me give you a blow job."

This was met with a silent stare. He looked confused. Caught off guard. Which was fine. We stayed that way for a pregnant moment, each staring at the other, before he stammered out an answer. "I - uhm - hey, thanks for finding my phone, but..." He was blushing now, deep reddish pink, looking at the cement, the skyline, anything but me. That was good.

I raised my hands. "Hey, it's cool, no pressure. Just an offer. Thought you might enjoy it." I jerked a thumb at the van. "I've got a nice setup in there, if you're interested. Clean, cushioned, plenty of beer if you need some loosening up. No one ever comes up here. Anyway..." He was wringing his hands. "Tell you what. You go on and finish up whatever it is you're in the city to do. Whenever you're done, if you think you're up for it, come back here. I'll be here. Chilling."

"Whatever man, look...I've got to go. Ah...thanks again." He sauntered to his car, opened the door. I caught him giving me one last look, uncertain and completely off his guard, before he drove away a little too quickly. I shrugged to myself and turned back to the sunset, let the breeze from the ocean hit my face, sighed.


Night came, my favorite time. The buzz of evening traffic rose up from the street below, the occasional honking and the web of clacking shoes. A single light burned over the lot, and my van was parked just outside its direct glow. I opened the door. There were no seats in the back, just a couple layers of soft foam egg crates and various padding. I pushed my footlocker, which held most of my earthly belongings, against the seats in order to maximize the space. I spread out the thick blankets I kept there, straightened the tapestries that covered the tinted windows, pushed the pillows into a pile at the rear of the compartment, hid a bottle of lube under one of the egg crates. Just in case.

I turned and sat sideways in the passenger seat, door open and legs stretched, facing the shadowy entrance to the roof, where his car would or would not appear. I chewed on some mint gum, turned the radio on low while I waited. I thumbed through my phone, committing some of the newer content there to memory.

Some hours later, well after the racket below had begun to die down, I heard an engine again. There it was, a green sedan, creeping up from below. It made its way across the lot and parked a few spaces from me, well away from the streetlight. I spit out my gum. I wasn't surprised. Not really. Sometimes the married ones were far more predictable than the drifters.

He approached with his hands in his pockets, the wind pushing up his collar. Man, he was pretty. My cock was already getting hard, pushing against my jeans.

"Hey there. I'd almost given up on you."

He stopped a good four feet from me, looking me over. I could tell he still liked what he saw. It was as obvious as the fact that he didn't know why he liked it. "I don't know why I'm here," he said meekly, back straight as a board.

"Looks to me like you just need to have a little fun. Let your hair down. Maybe you're too stressed, hmm?" I produced a thick joint, lit up, and took a drag. I offered it to him and he took it, inhaled greedily, coughed.

"So what's with you just hanging out with the van?" he asked, not rude, just curious. "You live in it or something?"

"Most of the time, actually." I took the joint. "I have a few places I can get a bed if I need one, friends in all sorts of places. Other than that, I've got the road to myself." Inhaled. "I can't imagine having it any other way. What about you? You got a picket fence stashed away somewhere?"

He grumbled and changed the subject, obviously over the small talk. "So it's like you said, right? Just a blow job? I don't have to...do anything?"

I took the joint. "Not a thing. Not a damned thing."

"And - you're not gonna tell anyone?"

Smoke erupted from my mouth and nose as I laughed. "Who would I tell? The police? CNN? I don't know you, and you don't know me. You can get your jollies, get a new experience, and never think about it again. No strings attached." I handed it back to him.

He took another drag, clapped his hands together lightly. "Well...OK then." And that was that. I put out the joint.

I pulled the van's door open and half-bowed to him and gestured to the waiting blackness, as if he were a lady. He seemed to mull it over for a moment before hurrying inside, probably nervous that someone might see him out here, which I found funny. As he bent himself to enter his pants drooped and his shirt lifted, giving me a nice view of the small of his back, the crack of his ass. Only a little fuzz there, light brown and barely noticeable. I followed him in, skin buzzing with excitement, and shut the door behind me.

The windows of the van were draped in tapestries of vaguely Indian design, diffusing the street lights and casting everything in a redish-purple haze. It smelled of incense and a vague mustiness, not unpleasant at all. He was crouched at the back of the van, facing me, supple ass hovering above the pile of pillows. The riot of folded blankets lay beneath him, somewhat disheveled by his passage over them. He was silent, waiting, the muted light from the street glinting off his glasses, throwing his fine face into half-shadow. I positioned myself across from him and lowered myself onto all fours, leaning forward like some stalking predator. He shifted, nearly lost his balance. I grinned. "I'm real glad you showed up. Did I mention that already?"

He shrugged, obviously at a loss for words. Was he trembling?

I crawled across the tiny space between us and put my hand on his crotch. It was hard. Hard and warm. "Hey!" He fell back on his ass, legs half-closed, thighs squeezing my hand as I kneaded his cock through his jeans. "That was quick!"

I laughed. "This is what we're here for, right? Did you want to talk some more?"

He shrugged, and his thighs loosened. I gave his cock a nice, firm massage, and his legs fell open. I leaned back on my knees, looked him over. His shirt had lifted up a little, showing me that tantalizing bit of skin. "Why don't you take your glasses off? I'll put them in the front seat. Don't want those getting broken do we?" He complied automatically, agreeing with my logic. I deposited them on the leather of the driver's seat and went back to him, lowered my head between his legs. "This cool?" I asked, looking up his prone form.

He nodded shakily, breathing heavily, obviously exhilarated. "It's what we're here for, right?" His voice pulsed with anxiety, sharp and unsteady.

I pushed up his shirt and undid his belt buckle. I pulled it free with two sharp yanks, making him grunt as his hips were jerked upward and around, like he was some doll. It was a nice sight. I tossed the belt behind me and went to work on the button of his jeans. He sucked his belly in as I did, shivering. I unzipped him and his jeans opened like a flower as his engorged cock all but fell out of his green plaid boxers. Even in this dim light I could see the big blotch of wetness at the head of it. I bet he'd been working himself up since our conversation outside, maybe even longer.

I pulled his jeans down to the middle of his thighs, glanced his way. He was lying down, back arched over the pile of pillows, looking up at the ceiling and taking measured breaths. "I'm gonna take these things off, cool? They'll just get in the way." He nodded, and I pulled them down around his ankles, tore off his moccasins, and marveled at his thick, slightly hairy thighs and calves, well-muscled with just enough cushioning to make them smooth and curvy in all the right places. My cock was raging in my pants. Even his feet turned me on, big and curved and slightly fuzzed on the top.

"Now these," I said, fingering the hem of his boxers. He only nodded, still looking up. I pulled the boxers off without teasing him too much, and his thick cock flopped out of them, sticky and hard, rising from a curly mound of light brown pubic hair. His pink balls drooped between his legs as he lifted them, fuzzy and large above a pair of fine, broad ass cheeks.

His legs dropped as I tossed the sticky boxers on top of his jeans and took in the view. He was gripping the blankets on either side of his hips, eyes closed, breathing through his mouth. The bottom button of his shirt had come undone, exposing the slight curve of his smooth belly, the rest of it taut over his well-muscled pecks, which were straining so much that the other buttons might pop off at any second. His cock was still hard, rising above his groin with a slight curve, a solid, thick eight-incher, uncut and leaking. He was a prisoner of his embarrassment, his excitement, his lack of experience. The whole situation was dripping with sex.

I ran my hands up his shins and pushed his knees down while spreading his legs, opening his bottom half like a butterfly, exposing him completely. His cock bobbed toward my lips as his back arched further, ready and waiting. "You ever gotten head from a man?" I asked, watching the tip of his cock glisten in the streetlight.

"Not once," he said quickly, as if he needed to make a point, as if that point wasn't moot the second he climbed into my van.

I put my hands on his warm inner thighs. They were great warm expanses of sensitive flesh, easy to push down and hold still. I put my tongue on the underside of his cock, ran it up to the tip, pushing into that swollen vein and letting my spit get the whole thing all wet and slippery. His thighs jerked and shuttered in my hands, and he sighed deeply. I looked up at him as my mouth closed around his juicy head, tasted the sweet slickness of his precum, pushed my tongue into is pisshole. His eyes were still closed, but his mouth was hanging open, and he moaned under his breath. I moved back down his cock and put one hand under his floppy balls, on his hot, fuzzy taint, where I lifted them to my mouth, took them in with practiced expertise, trapping them with my lips and massaging them with my tongue. He tasted like sweat, musk, salt. I let a muffled grunt of pleasure vibrate across them. Delicious.

He liked this, I could tell. His eyes opened, blue and crisp, and one hand moved to hover above my bald head, thought better of it, and rested on his hip, slithering toward his cock by never quite getting there. I put my fingers around his balls and his cock both, standing it straight up before putting my mouth around it again, taking it deeper, pushing my tongue against the underside and pushing it around the slick head while my lips slowly enveloped him. I pulled his foreskin back and lapped up the whole of it, hot and swollen. I ran my other hand over his pubes and invaded his shirt, felt him up. He didn't stop me, in fact moaned louder, said "yeah" once between exhalations. His stomach was heaving as I ate his cock. Both hands were on his hips now, his belly, touching himself while he watched me work. He wouldn't meet my eyes, though.

I kept his cock in my mouth, bent and throbbing, and unbuttoned his shirt a little, exposing his stomach. It was broad and stretched, with a trail of brown hair curving from the naval to the base of his pubes, hairless otherwise. He didn't protest. I undid the rest of it, pulled it around his barrel chest, exposed the entirety of his torso. His stomach may have been soft and smooth, but his pecs were banging. They were broad, flexed, built, graced with a sizable triangle of light fur between two pink nipples. I ran my fingers over them, found them hard as diamonds. He watched my hands, shivering under them, not knowing what to think of this. "You like that?" I asked, barely understandable with his thick cock in my mouth. He just nodded mutely.

I kept one hand on his stomach, fingered his naval, while the other held his thick cock still. I lowered my lips, opened my throat, and took him in completely. I could feel his precum sliding down my throat. He moaned, pumped his hips. I looked up at him and he met my eyes. He looked worried in his lust, brow furrowed, mouth whimpering with a slight frown, like someone was yelling at him for being bad. His hands were on my head, running over the shaved dome of it as I devoured his cock. His fingers worked their way down and felt my neck, my shoulders, ran over my firm biceps and forearms more than once. He was enjoying it.

I left it to bob freely in the open air and leaned back on my knees. I lifted my shirt over my head, stretched my lean torso as I did. I could feel his eyes on me as I tossed the shirt away, putting on a show. I keep myself in shape, as pale as I might be. Thin and athletic, sinewy pecs and narrow, muscular hips, with light trail of black hair from my collar bone down to my cock, the same hair that gathered lightly at my small red nipples.

He watched me intently as I lowered my face to his cock again, the hair of my chest brushing against his exposed ass. His hands were on me immediately, exploring my tight shoulders and back, spreading his legs even further and sitting up slightly to get more of my skin in his reach. His cock was a pulsing rod hitting the back of my throat, baptizing it with precum. He was loving this.

I tweaked his nipple with one hand, and he gasped. The other reached beneath his balls, below his taint, where his glorious slabs of firm ass hid something of great interest to me. I found it, hot and heaving and even a little loose - but it clenched, along with his entire body, as my finger poked at it.

I pulled the finger away immediately. "Sorry." I stroked him slowly, deeply.

"It's cool." His breathing quickened as I tweaked his other nibble. God, he was nice looking. "It's just...no thanks."

"Not a problem." He was still feeling my shoulders, my back. I grinned. I put the head of his cock in my mouth, reached behind me, and pulled my shorts down. I felt cold air hit my ass and thighs, and I kicked my shoes off, then the rest, until the only thing I still had on were my socks. All without letting his cock fall out of my mouth, keeping him hot for it, keeping him going. I arched my back and went to it with gusto, hands rolling over his thighs and the small of his back, giving him a fine view of my muscular ass as it perked in the air, the highest point of me. I may have been a little older than him, may have been slightly balding with a shaved head, but he watch my body move like I was some horny teenaged stripper.

"You can touch it if you want," I said between slurping sucks. "I'm real clean." He leaned over me, ran his hands up the curve of my back, cupped my ass cheeks awkwardly like some kid who'd just discovered masturbating. I flexed them and his hands clamped down hard, spreading them, brushing my exposed hole with his fingertips. My hanging cock was dripping stickiness onto the floor of the van, balls drooping low. He even pressed his hand into my taint, ran it up and down. This was good. Very good.

I pushed him away, leaned back on my knees, arms trailing over his luscious thighs. I pulled out the lube I had hidden earlier, squirted it into my hand, and pushed it up inside of me, flexing my torso for him as my arms stretched behind my back. He watched, panting, cock as hard as mine, each rubbing the underside of the other, mixing our wetness.

I didn't ask, and he didn't say no. I climbed over his thighs and straddled him. His hands were lifted on either side of him, as if he were afraid to touch me. His eyes were fascinated, eager, curious. I took his cock in one hand and my ass cheek in another, rubbed the head of his dick on my seeping hole. I've taken plenty of cocks in my time, and I lowered myself around it with relative ease, sucked it into me with the practiced muscles of my hole. Still, it had certainly been a while, and he was so damned thick. It stung quite a bit before I managed to relax enough. I hissed through my teeth, eyes closed, grunting as he filled me up. I felt his hand at my hip, running over my stretched stomach, tentative, exploratory. I groaned and pushed my ass into his lap, taking his entire cock. His pubes tickled my taint.

"Wow," he muttered, holding my hips, elbows at my knees. I began to fuck myself on his cock. "Wow, oh man, wow..."

I leaned forward and grabbed his pecs as I slowly, deliberately milked his dick. It felt amazing, I won't lie - and not just the delicious tightness of his manhood throbbing through my stretched bowels. I felt like a kid again, hitting up tricks for cash in that far off city, under a sooty skyline long lost to memory. I'd taken all sorts of cocks in those hungry days, begrudgingly at first, then loving it, figuring out what spots to hit, how to stay loose and limber. Figuring out that being wanted this deeply was something to be relished.

But this time it was different. This guy was younger than I was, and he was gorgeous, and he wasn't paying me a cent. I wasn't being held down in some old man's limo. His cock might have been throbbing inside of me, I was the one in control. I was fucking him.

He moaned, a desperate sound, raw lust. His hands had moved to my ass, gripping it tight, spreading it while I fucked him. I held his knees as his hips started pumping into me, let him take control of the rhythm for a while. He grunted and moaned, eyes rolling over my body and back in his head, loving every thrust he took. His hands ran up my flanks and cupped my pecs, grabbed them like they were tits, thumbing my nipples. I was impressed, and appreciative. I groaned happily, kept myself as tight as I dared, and I could feel his dick loving it.

I leaned back, pushed his gyrating hips into the blankets, made them still. I began to fuck him again with my hands planted behind me, my entire body burning and flexing with effort. My hard cock bobbed and weaved between his hands, which were firmly planted on either side of my dark pubic hair. My cock wasn't as thick as his, but it was certainly longer - a sight to behold, if I do say so. His eyes watched it bounce around between my legs. He grunted, licked his lips. I milked him steadily with my ass, kept his cock hitting my sweet spot, moaning unabashedly as I used him like a toy.

Surprisingly, his hands closed around my slick cock. He was jerking me off in time with my fucking, considerate and clumsy, but effective nonetheless. Before long I spurted despite myself, groaning stormily and showering my body with streams of hot cum that reached all the way to my chest. I kept pumping him, and he stayed hard and vocal with my spent cock in his hand - but he wasn't close to spurting himself. I could tell. Probably too coy to unleash with a stranger. More likely he was thinking too much about cumming in the company of another man.

I kept him locked inside me and grabbed his neck, pulling him up and forward. I let him slide out as I turned around and got on all fours, bent myself across the footlocker with my knees knees apart. It gave him a nice view of my arched back and my sweaty, open ass. I knew it looked good, a thin strip of wet dark hair around a gaping pink hole. "Put it in," I ordered. "Fuck me."

I felt it nudge at the edge of my chute, unsure. I reached behind me, took up two handfulls of his wide, firm ass, and pulled is hard cock into me, eating him alive. He grunted and grabbed my hips, and pulled me to him, rammed it in to the hilt with a satisfying wet sound. It felt so nice to be filled again. "Good boy." He began to pump into me, slowly, still too considerate. I glared at him over my shoulder, pumped my ass back at him. "Fuck me, you bitch. Fuck me like your wife."

That did it. His breathing became harder, grasp firmer. He slammed into me once, twice, and then he was going hard, some real and true rutting. I grabbed the seats in front of me, biting my lip, grunting, then crying out low in my throat like some bitch in heat. I hadn't been fucked like this since I was sixteen. He was really using me. My cock was hard again, slapping my stomach with each crazed stab he gave me. Even the van was groaning, shaking on its axles each time his cock grazed my prostate.

He slapped my ass, more confident than he'd been all night. "You like that?" he barked, lost in his lust. I just moaned louder, low and rumbling, and he fucked harder, faster, until his grunts became a long, throaty wail, almost feminine. I felt his dick swell, and my ass was abruptly filled with a monster load of hot cum. It seeped out of me, spilled over my thighs.

He stayed in me for a moment, sighing, hands resting on the small of my back. Then he pulled out. I could feel his load dripping onto my balls. I looked back at him. He was already putting on his shirt. He wasn't looking at me when I handed him his boxers and jeans, not that I minded. It was understandable. Common, even.

"Can I...have my glasses?" he asked, barely meeting my eyes.

"Sure." He put them on, looking at me with eyes in full focus. I leaned against the back of the driver's seat, feeling glorious, one leg up with the other outstretched, hard cock resting on my thigh. He glanced at it. "Oh, don't worry about that. I'll take care of it. You've done more than enough for one evening." I smirked at him, and he mumbled something about needing to get home. I put on my shirt and boxers and opened the door for him. He jumped out and walked briskly to his car, not saying a word. A bit rude, but again, a common reaction. I'd seen it before, and I wasn't taking it personally. Besides, I knew this wouldn't be the last time I saw him, whatever he might think.

I took a picture of his license plate with my phone as his car pulled away. It went into a folder full of other bits of his life that I'd sent to myself with his phone earlier in the day, while I'd waited for him to show up. Phone numbers, including his. Emails, most of them boring. Pictures of his pretty blonde wife at a Christmas party, pictures of his erect cock all all different angles, pictures of some black-haired chick named Tammy flashing her shaved snatch, entire text conversations between he and Tammy, dirty and explicit and secret.

Got you.