My phone vibrated in my pocket as I was walking down the street towards the subway. I had gotten a text-message.
"Hey, Dad!" I read. "Are you available now? What are your current rates for an hour together at my place?"
"Sure, boy," I typed in reply. "I'm available now." I quoted the rate posted on the ad that he must have seen.
"Can you cum over NOW, Dad?" came the next message, almost before I had confirmed the rate.
"Sure, boy," I typed back. "What's the address, boy?"
He sent an address that was an easy subway ride away. Now, about to descend into the subway, I checked the phone again and saw another text-message from the same number: "Dad, pls be sure to wear yr 501 jeans with the button fly." I read the message again, just to be sure I'd understood it right. Yep, that's what he wanted. I'd never gotten such a specific request for a certain outfit before. Jeans with a button fly. I had a pair of jeans like that, but was I wearing them? Of course not.
"Why couldn't he have said that sooner?" I muttered to myself, turning around to head back home to change pants real quick. "At least I got the message before I got in the subway," I realized as I climbed the stairs to my fourth floor walk-up. "It woulda been worse to get there and not have the right pants on."
I dashed into my apartment and rummaged through the closet, looking for the jeans with the button fly. There they were, hanging on the last hanger in the back - of course! I kicked my shoes off and wriggled out of the tight jeans I had been wearing. The 501 button-fly jeans were comfortable, but not tight. I figured that must be the look the client wanted. I felt the denim's scratchy slide over my ass-cheeks and folded my semi-erect cock and balls down behind the fly, slowly encasing them behind the buttons. I remembered that my cock had always gotten semi-erect when I was heading out to meet a client; a few more years of maturity had not made a dent in that, I saw. I glanced in the mirror. The slightly-too-tight t-shirt I had on had matched the tight jeans before but, now? It looked okay. Who was I kidding? I looked okay. Great even. But maybe the client was into another look. After all, he'd responded to my ad by calling me "Dad" and had asked for the 501 jeans; I realized I had to think about that now that my ad was appealing to the guys who wanted a "Daddy." I pulled the shirt off over my head and admired myself in the mirror, out of the corner of my eye. I reached into the closet and pulled out what I thought would go best with the new jeans: my red-and-black flannel shirt. I slipped my arms into the sleeves and realized that it was just a bit more snug than I recalled.
"I can make that work," I told my reflection. I buttoned up the shirt but left the top two buttons open so that the beginning of the cleavage between my pecs was clearly displayed beneath the straining flannel. Then I rolled up the sleeves to my elbows, exposing my forearms to view. I nodded to the guy in the mirror in appreciation. "Not bad. Not bad at all."
I knew the daddy-lumberjack I saw in the mirror would never have worn the shoes I had been wearing so I rummaged in the bottom of the closet and found the work boots that had been hiding there. I pulled them out and slipped my feet in, weaving the laces through the eyelets and tying them off in a single, easy to release knot. Ready to go now, I texted my client back: "On my way." Heading down the stairs back out onto the street and into the subway, the denim scratched my ass and crotch in a comfortable, familiar way as my cock still strained against the buttons holding it in for propriety's sake. The flannel also felt good, riding across my shoulders and chest and caressing my nipples. Was it my imagination that at least a handful of heads turned to watch me as I walked past them or as I took my seat on the subway? I don't think so. More people could appreciate a hot Daddy than I had anticipated.
I got to the address I'd been given and found a doorman standing vigil behind a desk in the lobby. The doorman looked barely older than high school. Blond fuzz, clearly the first attempt at a mustache, hung across his upper lip and he seemed to be swimming, lost in the heavy overcoat with the epaulets and gold braid on the shoulders. I gave him the apartment number and when he asked, "Your name, sir?" I had to stop myself from answering, "Dad." Instead, I grinned and told him "Michael" and he duly reported my presence through the phone to the apartment upstairs.
"Go on up, sir." He gestured towards the elevator.
"Thanks much." I gave a short, mock salute and made my way to the elevator. As I stood there waiting for the doors to slide open, I could feel the young doorman's eyes burning a hole through my flannel shirt. I smiled to myself and stepped into the elevator. As I turned to press the button for the right floor, I caught him quickly averting his eyes from me.
Exiting the elevator, I walked along the hallway and peered at the numbers on all the doors. Coming to the correct one, I knocked. The door opened and I stepped into a lavish New York City penthouse.
I was standing in a large entryway, the walls covered in silk and filled with individually lit paintings and the hardwood parquet floor inlaid with elaborate geometric patterns. I saw a living room ahead containing leather chairs and a velvet sofa and which had a wall of windows looking out over the city. Off to one side from the entryway, between two paintings, was a dim hallway led into the depths of the penthouse.
Before me stood a man, roughly my own age, but more lithe and trim. He was clean shaven and wore glasses, his almost buzz-cut hair dark but not black. He was wearing a shirt and - surprise! - a pair of jeans. He was also holding a martini.
"Nice to meet you, Dad." He extended his hand to shake mine. "Would you care to join me in a drink? What can I get you?"
"Sure, boy," I answered, clasping his hand in mine for a moment. "How 'bout a beer?"
"I have several, Dad. Would you prefer a stout or an ale?"
"Stout, boy. That'd be just fine."
"Come with me, Dad. Right this way." He turned back into the living room and slipped his free hand into the back left pocket of my jeans, steering me into the living room beside him as he firmly grasped my ass beneath the denim and squeezed. Coming into the living room, he nodded to the elaborate bar that filled one wall and withdrew his hand from my back pocket. "I'll get you that stout, Dad." He walked over to the bar and opened the small refrigerator below it. Hearing bottles clink as he rummaged through what sounded like a large supply of beers and mixers, I stepped over to the window to admire the view.
Nearly all of Manhattan sprawled out before me. To one side I could see a large swath of Riverside Park as it hugged the banks of the Hudson and, across the river, I could see the buildings of New Jersey that lined the river as well. But mostly I could see Manhattan spreading out to the south and east, high-rise apartment and office buildings reaching toward the sky as the famous and not-so-famous buildings each vied the others for attention. Empire State and Chrysler, 500 Fifth and 30 Rock, the spires of St. Patrick's and the new Twin Towers rising from Ground Zero at the far south of the island. I could only imagine what this view would be like at night, all the lights of the city glittering in the dark as so many diamonds set against black velvet. Even as it was, in the daylight, it was magnificent.
"Here's your stout, Dad." He was back beside me, handing me the open bottle of thick, dark brew.
"Thank you, boy." We touched bottle to martini glass and then each sipped the liquor we held in our hands. Holding his martini in his left hand, he joined me in gazing out across the city and draped his right arm around my hips, tucking his thumb into the belt loop beneath my right elbow. I leaned my hip slightly into his and casually draped my left arm across his shoulders and let my thumb play with his ear lobe. I ran my thumb along the skin just above his shirt collar and he tilted his head briefly, catching my thumb between his cheek and shoulder. He sipped his martini again. I lifted the bottle and drank, noticing that his eyes were watching my Adam's apple rise and fall as the stout coursed down my throat.
Finally, I pulled the bottle away from my lips and his eyes rose to mine. "I was so glad when you walked in, Dad, that you had your 501s on. You don't know how many times I've asked someone to wear that style in particular and they said they would but then they arrived wearing zip-up jeans." He spoke in a nonchalant manner, as if we were discussing the weather and not a particular sex fetish. He sipped the martini again. "Of course, I paid them for their time and trouble in coming over but I was always so disappointed. But you didn't disappoint me, Dad. Not at all." His right hand, still tucked into my belt loop, pressed against my hip appreciatively and he turned to face me directly, pressing his crotch up against my left hip. I could see the denim of his jeans bloom as he began to slow grind against me.
"Yeah, boy?" I murmured, raising the bottle to my lips again. "They didn't wear the jeans you asked for? But you paid them anyway? You're too generous, boy."
"You think so, Dad? Maybe. Oh, but Dad, I can be so much more than generous," he promised me. "I can be so much more than generous with you." He set the martini down on an end table nearby and then knelt before me, where all the city, if it looked up, could have seen him.
He clasped my butt and leaned forward into my crotch, dragging his tongue along the edge of the denim concealing the metal buttons. He rubbed his cheeks back-and-forth, slowly and repeatedly, his eyes closed and quiet inarticulate murmurs rumbling in his throat. I took another swig from the bottle in my hand, resting the other atop his head. I thrust my hips forward and he groaned with even more delight, pressing his face against both the denim and my hard shaft within the fabric.
He pulled back slightly, arching up on his haunches, and worked the topmost corner of the denim fly between his teeth and tugged at it gently, back-and-forth until it popped free of the topmost button holding the fly shut. He closed his eyes again, pressed his nose into the fly and breathed deeply of the scent of denim and man-sex he found there. After a few moments, he grasped the denim in his teeth again and tugged gently again until it also popped free of the next button down. He inserted his tongue into the small space that he had opened and licked my flesh, tugging with his teeth on the wisps of pubes that he found poking up there. Then he returned to work on freeing the denim from the next two buttons going down the fly and my rod, rock hard and glistening, slowly slid into view. He touched his tongue to the glistening tip and pulled a strand of pre-cum with him as he pulled his face back to admire my Dad-hood. The strand of pre-cum hung there, thicker droplets spread out along its length, like dew drops hanging from a strand from a spider's web. His breath came in husky gasps as he was clearly trying to control himself before lunging forward and smearing the milky gossamer across his face.
He got his teeth around the denim surrounding the last button at the bottom of the row, tugging and worrying at it until it too finally came away from around the metal disk. He poked his nose into the open fly, into the thick rich underbrush that concealed the base of my massive man-oak quivering free now from the constraints of the jeans. He inhaled noisily several times, nuzzling the base of my cock, touching the tip of his tongue gently and repeatedly around the top of my sac, adding the taste to the scent that he found there.
Gradually he pulled his face back and licked the row of buttons itself a few times, his tongue sliding over denim and metal disks, leaving a slick trail along the open fly. He pulled his hands away from me and pulled his own shirt off, exposing his lithe torso, and then undid the top two buttons of his own jeans, letting his own stiff dick poke out.
"You gonna let out your own dick, boy?" I asked him gruffly.
"Can I, Dad? Can I please?" he whimpered. "It hurts. It hurts so good, it's so stiff, seeing you here and you letting your boy take good care of you. It needs to come out, Dad. Can it? Please?"
"Alright," I conceded. "It can come out. But don't touch it until I say so."
"No, Dad. I would never do that. I would never touch it unless you told me that I could," he promised eagerly. "That's what a good boy does. Right, Dad? Wait to touch it until Dad says it's okay?"
"That's right, boy. A good boy always waits until Dad says that it's okay." I pointed at my own dick and balls. "Now get back to work, boy," I instructed him.
"Yes, Dad. Right away, Dad." Finally, he grasped the bottom-most button in his teeth and gently tugged the jeans down until they were bunched around my knees, and then pressed his cheeks against my balls and his chest against my legs. From the sounds that came rumbling out of his chest, I thought this was the closest he'd ever gotten to Heaven. He grasped my now-naked ass and hugged, pulling my sac and legs even more firmly against his cheeks and chest.
After several minutes of increasingly passionate nuzzling of my cock and balls with his cheeks and tongue, the "boy" in front of me sighed contentedly and pulled back, looking up into my face again.
"Dad," he sighed. "I could worship this fat cock and these big balls o' yours all day." He nuzzled and kissed the place where they all came together once again. The stood and pressed his face against the topmost button keeping my flannel shirt stretched tight across my chest. He rubbed his cheeks across the flannel as he had the denim and then, one by one, used his teeth to unbutton the shirt as he had unbuttoned the fly of the jeans. Between each button he would insert his face against my skin and indulge himself there before moving on to undo the next button. I tousled his hair.
"Good boy!" I congratulated him. "You know how to make Dad feel appreciated!"
"Yes, Dad," he responded. "That's a good boy's job. I hope that I live up to your expectations, Dad. I so want to be a Good Boy!"
"You're making progress," I encouraged him. "You just might live up to Dad's expectations after all, boy."
It was a slow and delightfully enjoyable project. I would occasionally moan and make my own other, appreciative noises to match his and even more occasionally lift the bottle of stout and drink as he occupied himself with the buttons until the bottle was finally empty and I set it on the window sill in front of me.
When he was finally able to undo the last button of the flannel shirt, he ran his hands up and down my chest before cupping my pecs in his palms and then slowly, delicately let his lips descend around my cock. I rested one hand atop his head and rubbed his cheek with the other.
"Good boy," I muttered. "Very good boy. Keepin' Dad feel good...." I gave a tentative thrust of my hips to test his gag reflex. His tongue guided it along and I felt my cock slide further into his wet, warm throat. "Good, boy," I repeated, my voice inadvertently huskier than usual.
"Mm, mmm," he answered. Was he agreeing with me that he was a good boy or was he expressing approval for the taste of the Dad-hood he had in his mouth? Hard to know. But he pulled his face back-and-forth a few times, slowly letting his tongue wrap itself around the Dad-hood trapped there. I pumped a few times to encourage him and grasped his ears to help him slide down over the last bit until his nose was tickled by the dark pubes there. He made squeals of delight and slurped happily away on the bone he had retrieved, like a puppy pleased to please its master.
"Good job, boy." I pumped a few more times, more forcefully, taking more control now that he had my whole Daddy-dick down his boy-throat. Rough and quick, then slow and gently, I fucked his face there in the window, overlooking Manhattan, displaying his good-boy skills to anyone able to look in through the window on the 29th floor.
He made more appreciate boy-noises and I, like a good Dad, encouraged and supported him in all his efforts with my own noises and increasingly rapid thrusts. The pre-sum and the spit filling his mouth around the Daddy-hood he struggled to keep contained made my slipping and sliding easy, going way deep and then nearly pulling completely out of his lips before plunging back again nearly to his tonsils.
"Yes, Dad," he choked and begged as he gagged on it. "Please, Dad. Give it to your boy. Give it all to your boy. Let me take it all for you, Dad."
I gripped his ears tight, helping move his head in time with my hips. Forward. Backward. Press his nose up into my pubes. Pull him back so that he could breathe again. His hands didn't know where to go. One stayed high above his head, clamped on my tit while the other slid down and around until it cupped my ass-cheek and grabbed it tight, pulling me forward.
"So, you think you can take it, boy?" I demanded. "You think you can take it all?"
He struggled to nod without losing hold of my cock. "Yes, Dad," he promised me, the words almost undecipherable as he tried to talk with that big Daddy-dick down his throat. "I can, Dad. I can."
"Yeah? I think you might, boy" I agreed, gasping and wheezing as the pressure mounted in my balls. "You just might."
He nodded again, slurping happily, his other hand now slipping down to grasp my other ass-cheek. My hips plunged forward, then back, then forward again. I could feel the jizz churning inside my testicles. The boy dragged his tongue along the length of my throbbing dick and I tried to pull back but he pushed my ass forward from behind, refusing to let me escape the prison of his mouth and - unable to resist - I exploded down his throat.
Again and again I shot and shot down his throat as he gurgled and gurgled, slurping it down as he kept nodding and muttering something that sounded like it might have been, "Yeah, Dad! Yes! Give it to your Good Boy!" His energetic swallowing urged ever more cum from my dick down his throat until I nearly collapsed over him, my hands dropping from his ears to his shoulders to support myself.
"Okay, boy," I gasped as I was finally able to catch my breath. "You can touch your boy-dick now." I gave him the permission he had been waiting for.
"Yes, Dad! Thank you, Dad!" He took one hand off my buttocks and spat a thick wad of cum and spit into it and then reached down to wrap his slick palm around his own dick and within a stroke or two he was writhing and groaning before me, his own load spewing out onto the floor between my feet.
"Oh, Dad," he gasped at last, hunched over there on his knees in front of me. "That was the best. No one's ever been so good to his boy before as you, Dad! No one!"
*** *** ***
When I got back to my apartment, I counted the bills in the envelope he had folded into my back pocket as I left. It was considerably more than the advertised rate. He had more than lived up to his promise of being more than generous. All for a good Dad who wore the right pair of jeans for his good boy.