Lyle's Big Score

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I've got some disposable enema kits in that bathroom we showered in. If you want me to take you bare then I want you to go clean your chute out for me. I want you completely empty, so be thorough."

He sat silent for a minute.

"What is it?" I asked.

"I've never given myself an enema before. I'm afraid I won't know when I'm clean enough for you," he confided.

"I see. You're not the first bottom I've had who told me that," I calmly informed him, "I'll administer it for you."

"Thanks, Harvey," he said with a relieved smile, "You're an awfully nice daddy."

I helped him to his feet and drew him into an embrace, pecking his lips with a dry kiss.

"Thank you, son. Now, run along and I'll be there in a minute."

"Yes sir," he said and disappeared through the door.

I got an old sheet to use for a cum catcher and spread it out at the corner of the foot of the mattress that offered us the most room, tucking a bit of the sheet up under it. When I was done I went to attend to the task of cleaning him out.

Once we were done with that, we returned to the playroom. Pulling a bottle of Anal Ease from the top drawer of the bureau, I squeezed a healthy dollop in my left hand and began slathering my bare cock in it.

His breath quickened and his eyes were riveted to my display. Sensing his appetite for dominance, I puffed my barrel chest out till it was almost even with my belly and pointed at the corner of the mattress I'd prepared.

"Heel, boy!"

Lyle nervously giggled as he scrambled into position. His intuition was nearly perfect. He was angled in toward the center of the mattress with the corner sticking out from between his feet as they hugged its edge.

He was down on his forearms with his butt up nice and high, the cheeks parted wide and shamelessly flaunting his pristine looking, pink orifice. The only problem I foresaw was how widely he'd spread his knees.

"Lyle, from what you've told me about that boy who already fucked you, you need to understand that this is going to be a lot deeper - and it's probably going to last a lot longer."

"Okay," he nervously assented.

"Now, I'm probably thicker than he was, too."

"By a lot!" he freely admitted.

"So, you'd probably do yourself a big favor if you pull your knees together. It'll give your hole a lot more 'give' to stretch out on me."

"Yes sir," he obediently replied and did as I'd suggested, "Like this?"

"Yep, that should do," I confirmed.

I squeezed an equally generous amount of the gel onto my fingers to lube his hole with. I smeared it over its surface. He sighed and broke out in chills.

"That's cold," he observed with a chuckle.

"It'll warm up in a jiffy," I assured him, "Now, your hole still looks pretty well relaxed from that ass munching I gave you."

"Yes sir."

"So, I'm going to shortcut this process by just working it into you with my thumb. It's big enough to adequately prep you for what will follow, but without loosening you up more than I want you."

"Yes sir. I'm ready."

I slowly sank my thumb in as deep as I could manage. His hole offered me little resistance, but I heard a definite catch in his breath as it went in. I started gently pumping him on it.

"How does that feel?" I checked.

"Good. You've sure got big hands!" he confided.

I laughed.

"Yeah, I suppose I do."

Eventually I was able to pull my thumb completely out and re-penetrate him a number of times until I felt no resistance whatsoever. A satisfied moan floated up from him.

"I think you're good to go. Now let's try you on some daddy dick."

"Yes sir!" he excitedly agreed.

I spread my feet apart and stepped forward till I had his butt between my knees. Squatting down with my loins behind him, I pressed my left hand to the small of his back and took the base of my well lubed member in my right hand. My fingers cradled the base and I ran my thumb down the center of its top side to reinforce its tensile strength.

Perhaps two inches separated my bulky, glistening cock head from his tiny, shimmering pucker. Even at my age, and with my wealth of experience as a top, I couldn't help wondering how something so small and defenseless looking - barely the size of my cum spout - could possibly stretch enough to accept me. And yet, I knew it would.

I leaned in and pressed my meaty glans to it. A lusty, guttural groan escaped him and he ground his butt back on it.

"That's big! A lot bigger than Bruce's!" he announced, sounding a little unsure if he was equipped to handle me.

"Listen carefully, Lyle. If this becomes too painful, or even just uncomfortable, all you have to say is 'stop' and I'll pull out. Do you understand me?"

"Yes sir."

"My goal is to make you feel good...well, both of us actually," I honestly admitted.

He nervously laughed.

"All I want is to make you feel good, Harvey," he bravely asserted.

"And, as your top for tonight, I appreciate that...probably more than you know. But, I don't want you to suffer anything you find more painful or unpleasant than you bargained for just because of that. Are we on the same page here?"

"Yes sir."

"Then say it for me once so I know what I'm listening for - and say it like you mean it, boy!"

I pressed my cock head to him firmly enough that he likely thought it was going on in.

"Stop!" he quickly blurted out.

"Very good. Here we go then."

"I'm ready!"

I sparingly pressed at his hole for entry, gradually increasing the pressure. Keeping a close eye on the point of contact, I could see that the harder I pressed the more the circumference of my bloated cock head expanded.

I suddenly began to wonder if he would be able to let me in. A minute or so later, I watched as his hole yielded at last and accepted the blunt tip of my glans. I increased the pressure enough to keep his straining muscle from spitting me out.

Giving Lyle a minute to adapt before proceeding, I then resumed and watched as my bulbous head started slowly disappearing inside him. He opened wider and wider as it slid through, only struggling for a moment with the top lip of my corona before he finally slipped over it and cinched tight. That moment provides one of the most intensely rewarding and thrilling visuals a top gets to enjoy during penetration.

"The head's in!" I informed him.

Lyle exhaled with a pained grunt.

"Ready for more?" I asked him.

He nodded in assent and I pushed in another couple of inches. At that point he was hosting about half of my full length.

"Is it all in?" he huffed.

"Do you feel my balls on your taint?"

"Uh-uh!" he grunted.

"Well that's how you'll know, boy," I informed him.

"Yes...sir" he struggled to respond.

Sensing that he needed me to finish the job quickly, I drew a deep breath and then slowly but steadily fed him the rest of my six-plus insertable inches. I tried to be gentle about it, but I swear it sounded like it nearly knocked the breath out of him as it slid in.

When my scrotum came to rest on him I rolled it around to emphasize my point. He sighed with relief.

"Your balls...it's in!"

"It sure is, boy," I said, softly stroking his well-padded back.

He moaned his satisfaction. I stayed put at maximum penetration and flexed my cock inside him a few times just to give him a thrill. A staccato laugh erupted from him.

"Wow! Do that again!"

I joined in his laughter and obliged his request.

"Big...so big!" he said as the shock to his system began to wear off.

"Stay with it, son. I promise to have you purring like a kitten before long."

I held still with my balls draped over his taint, waiting for his visible muscle tension to vanish. A few minutes later his head dropped onto his folded hands. His shoulders and sphincter almost simultaneously relaxed a bit.

Less than a minute later he was wriggling his butt on my cock and imitating the purr of a kitten. I burst out laughing, not yet giving him relief from the full depth of my penetration.

"It feels awesome!"

"Ready for more?""

He nodded. I patted his soft back a few times and then took hold of his ample hips. Backing a couple of inches out, I quickly shoved them back in. His arms went stiff and his back arched again.

"Don't fight it, boy. Give yourself over to it. Become one with my cock."

"Yes sir. I want to. I'm sorry. Try me again."

I did. He pressed his head down on his fists, but I could see the tension in his shoulders. However, he didn't buck like before.

"That's better...much better."

I waited a few seconds and then tried it again. He accepted me with ease. I did it another three or four times in succession just to be sure. He took it like a champ.

"Mu-u-uch better! Your chute's still tighter than a rubber though. Try practicing deep, slow breathing and just...relax...from the inside out. Can you do that for me?" I asked with my cock still buried in his ass to the hilt.

"I'll try," he responded, his breath still a little jerky.

"I can tell it's still painful for you. I'll stay right where I am till you get the hang of it. Okay?"

"Okay," he said, sounding desperate to comply with me, "Please don't give up on me."

"You feel my balls on you, right son?"

"Uh-huh."

"They're not going anywhere," I assured him.

I started massaging Lyle's back the way vets often do when they're giving an animal a shot. He soldiered on, trying to breathe just as I'd instructed him. I felt him forming to me.

"Good boy...you're getting there. Go-o-od boy!" I periodically encouraged him.

A few minutes later his inner tension magically fell completely away. His breathing was just what I was looking for. I tested him on a few more short strokes and found that he was able to sustain it.

"That's it, Lyle! You've got it now!" I bragged on him.

"Then fuck me!"

"Here we go."

I started with a slow, steady rhythm and gradually lengthened my strokes until I was withdrawing everything but the head. He moaned and groaned like the cock hungry boy nature had clearly designed him to be.

"You feel like a million bucks!" I paused to praise him.

Lyle sighed with contentment, so I resumed my measured pace and kept it up for a good long time. At one point, I sank in balls deep and succumbed to an earth shaking shiver that unexpectedly ran up my spine. He felt it and started giggling.

I rested briefly. To my surprise, Lyle started rocking on his knees to fuck himself on my stationary cock. I rolled one hand into a fist and rested it on my hip. The other I used to depress my pad to better enjoy the view.

Slowly but surely, the pace of his rocking picked up until he was loudly grunting each time his ass made contact with my hand. I was stunned by how naturally gifted he was as a bottom and dared not interrupt him. The pleasure he was bringing me was intense.

"Would you move your hand, please? I need to feel your balls on me."

I quickly complied, both arms akimbo at that point. He pressed his butt to my loins a few times and, on the last one, fervently ground his taint to my dangling scrotum. A deeply satisfied groan escaped him and he began milking my cock in his rectum.

"Daddy balls!" he blissfully cooed.

"You're hotter than a branding iron, boy...but you keep squeezing my dick like that and it's liable to blow."

"I want that, Harvey! PLEASE! Fill me with your cum!" he pleaded.

"I promise I will, but we're just getting started," I protested while planting my fists atop his ample haunches, "You've got a lot more in store."

Lyle regained his composure and relieved me of his reflexive clenching. I then collected myself to give him what he came for.

"Remember, if this gets painful you can stop me any time."

He immediately nodded. With his consent granted, I started reaming him with increased vigor.

The more he formed to me the greater my freedom of movement in him became. My hard-on reacted by stiffening until it was harder and, no doubt, thicker than I could remember it being in ages.

I finally reached a tempo that had my balls slapping his delightfully taut perineum like a bell clapper. I'll freely confess that, in the top role, I find that sensation intensely arousing myself.

Lyle responded by lowering his head to the mattress and reaching back with both hands to spread his buttocks as tightly as he could. It allowed me slightly deeper penetration, so I took advantage of it.

He started sounding out his ecstasy in a high pitched wail. Louder and louder he squealed, but still no utterance of the word 'stop'. I decided to push him a little harder.

His sphincter reacted by tightening its grip on my thrusting implement, but without all the spasmodic clenching. Having already come once, my cock was able to withstand that kind of constant pressure without risking orgasm.

Lyle responded to my persistent probing by pushing back into it. Seeing how pleasurable he found the steady slap of my balls, I increased the force and speed of my thrusts slightly.

His wailing morphed into a sustained flurry of staccato grunts and he let go of his butt cheeks to clutch at the bed linens. I was far short of the hardest fuck I'd ever thrown up a man's ass, but I could see that I was testing his tolerance. However, all signs were that he was still enjoying himself.

A minute or so later his staccato grunting transformed into a strange little squeaking sound that was oddly reminiscent of a lamb's bleat. Before I could ease up on him, though, he caught up to me and resumed his pleasure filled grunting. I chose to stay at him.

As he adapted to the heightened intensity of my charge, he let go of the linens and clasped his hands together, resting his head on them again. He soon settled back into his impassioned moans.

His tightness was so incredibly stimulating that I wanted more than anything to just let loose in him. However, in spite of his substantial build, I knew his inexperience required patience. So, I held back and contented myself with watching him indulge his mile wide submissive streak.

Eventually my scrotum began to tighten around my weighty testicles and I knew I was close. For all his moaning and wailing, Lyle seemed to be reveling in his bottom role, embracing the totality of his zealous commitment to it.

I pulled my cock all the way out of his ass and took a quick look at his hole. It was beginning to gape and the deep cleft that surrounded it formed a funnel that alleviated me of all effort to have to aim for it.

I plunged back in, maybe a bit too forcefully, and ground my balls to him. He yelped from the shock of it.

He'd said he wanted to get fucked hard, but I decided to err on the side of caution. Instead, I dug into him only as aggressively as I thought he could withstand and edged myself ever closer to my impending orgasm.

He responded by rising up on his arms with his back arched stiff as a board. But, still he hung in - bravely withholding the one word he knew I would respect.

A pleasing mixture of his heated moans and pained whimpers filled my ears. I knew I had my dick well up into virgin territory. However, he seemed to find whatever pain he was experiencing as a result both rewarding and empowering.

He steadfastly refused to utter the magic word. I threw a little more of my substantial weight at him and thrilled to his impassioned wails of submissive bliss.

Before long, I was so consumed in my sensory overload that my strokes inadvertently lengthened until my cock was completely withdrawing before lunging back in through his open orifice.

Suddenly I felt his ring start wildly clutching at my thrusting member and knew he was coming. I lost all sense of propriety in the heat of that glorious moment and persisted in reaming him throughout his intense orgasm.

"Daddy! Daddy! Oh-h-h-h-h-h! DA-A-ADDY!" he finally cried out while I speared him.

Fearing I might've finally exceeded his tolerance for pain, I quickly pulled out and firmly pinched my base to fend off coming. When I inspected his condition, I was both shocked and delighted to discover his hole helplessly yawning open so obscenely large as to exactly match the girth of my punishingly engorged tool.

The determined looking thing that jutted from my loins was fiercely bloated, every vein it sported standing out in stark relief against its gleaming, butt-slicked surface. I contentedly pressed my frenum down in the cradle at the bottom of his utterly stunned sphincter and released my pinch.

I proudly bore witness as the gaping slit in the center of my crimson cock head jettisoned two thick, copious streamers of my pearl white discharge into the mouth-sized opening of his cum hungry chute.

Before it could launch a third, I hurriedly powered the throbbing cum cannon back down into the comforting warmth of his well-churned bowels and did as he'd asked. I counted seven more gushing eruptions, each one coating his tenderized love tunnel with yet another generous helping of my soothingly viscous gift.

At the conclusion of my otherworldly orgasm I withdrew my dick, my eyes still riveted to Lyle's paralyzed orifice. It remained open for a few seconds longer, leaking a beautiful trail of my semen down onto his barely perceptible scrotum before snapping shut in three herky-jerky stages.

He lowered his head back onto the mattress and remained perfectly still. I grabbed my dick in my right hand and stroked out a few more pearly globs onto the roughly inch long trough formed by the purple-hued, pouting lips that had formerly been his tiny, pristine looking pucker.

I then stood up, getting a little worried when he still hadn't moved after a couple of minutes. At last, he let fly with a deeply satisfied groan and reached a hand back to smear the puddle from my finishing move around on his vanquished anus.

Lyle used what little energy he still had to push himself up erect on his knees. He slowly turned on them and crawled down off the mattress to kneel at my feet.

His puppy dog eyes appeared to be on the verge of tears as he stared up at me with an unreadable expression. I began to fear that I'd misread his body language and inadvertently crushed his youthful vitality.

Suddenly he threw his arms around my waist and pressed his cheek to my keg-like paunch. He then looked up at me and began peppering it with boyish kisses.

"Thank you, Harv!" he paused to say.

"You're welcome," I softly acknowledged, sinking my fingers down in the mop of dirty blond curls that covered his round head while he resumed his show of gratitude.

He rested his haunches back on his heels and dreamily marveled at my cum drooling hard-on. Tentatively reaching up, he wrapped his pudgy hand around it and lovingly stroked it a few times.

When he finished that, he lowered his fingers to his nose and sniffed them. A curious expression overtook him as their odor registered with him. He then touched them to his tongue and made the cutest face at the tart flavor that permeated it.

Lyle suddenly realized what he'd done and quickly looked up to gauge my reaction. I smiled down on him. The room seemed to brighten with the smile he beamed back up at me.

He looked back at my cock and then up at me again. His expression signaled that he suddenly felt conflicted about something, maybe even a little shamed by whatever it was that had crossed his mind.

With obvious uncertainty, he touched his lips to my leaking my cum spout. He gave it a tender kiss and then self-consciously licked my ejaculate from them.

"Go ahead, boy. It's nothing I haven't seen before," I assured him, sensing what he wanted to do.

With that said, Lyle proved me right. He wrapped his hand around the base of my ass-slimed cock once again and stuffed his mouth on the top half of it.

As if my words had freed him of all his guilt-ridden inhibitions, he happily indulged himself the ultimate act of submission. His tongue eagerly played over the vein-ribbed surface of my swollen cock while he feasted on our fuck juice.