Over Again - A Milking Story




Sometimes when I wake up, I can't move. My body is fine, but I'm unable to make a muscle function. And when I think about it, I know exactly why. And now, nearly five years later, the events still haunt me...

I was 16 at the time, tall and lean, with sloppy dark blond hair and a cocky attitude. I was bursting with attitude and hormones, but mostly hormones. I was, like most 16 year olds, a walking erection. I jerked off four or five times a day, and looked forward to having sex with ... well, whoever.

I awoke when I tried to turn over and couldn't. I was obviously not at my cousin's house anymore. I usually slept flat on my back, but not like this.

My arms where at an unusual angle, out to my sides and up at a right angle, placing my hands just above my head. Something tight grasped my wrists. My eyes tried to adjust to the dim light, blinking away the dryness of a long sleep. But my mind was clouded by something -- something thick and restrictive.

Memories of early childhood fevers and delirium returned to me. But then I recalled the fight against a general anesthetic from having my appendix removed. That was it. I had been drugged.

As the room became more evident to me, so did my condition. I was nude, flat on my back, but lifted forward at a slight angle. I was shackled in some way -- firmly I must add -- at the wrists and ankles, a belt of some kind across my middle, pressing me against a padded tabletop. Each leg was lifted somewhat and spread slightly to each side, like an gynecologist exam table, opening my always-eager 16-year old crotch to whoever put me here.

There were things in the room around me, but the grey light was too dim to make them out. The only light came from windows set high above me on one wall. I seemed to be in a loft of some kind. I struggled to make out sounds or smells, but found myself grasping for sensations that weren't there. It was dusk outside, I thought. Or maybe early dawn. I didn't know. Not where I was, not what I was doing there.

I tried to move, to check the bindings, and noticed a steady pressure in my rectum. Blinking and looking down, I noticed a whitish tube that ran from a small bag hanging from stand beside the table to between my spread legs. The pressure in my ass was familiar but not really uncomfortable. Like when I put a finger in my ass in the shower. Warm and filling...

A warm current of something was dribbling into my ass, and I wondered why. The thoughts that came to mind worried and oddly thrilled me. I was getting very nervous, but before I could dwell on it, lights snapped on.

Blinded, I squinted down at a motion nearby, something beyond the rim of the lights set on me. Someone was there, moving toward me, slowly.

"Who is it?" I called. I struggled again against the shackles, but I was trapped. I feared for my life, but my muffled mind couldn't think clearly to react to it.

Nothing was the reply. Instead, they turned and moved a cart near me. I tried to see what was on it, but could only make out some kind of machine atop it. It resembled a small air compressor, I thought, or maybe a paint sprayer of some kind. I had no idea and my young mind was racing, grasping to make connections that explained why I was nude, exposed, and completely vulnerable.

The pressure was getting to my filling ass, and my cock was begin a slow crawl up my stomach, inching toward my face. The light played off my lightly colored pubic hair, while a nervous sweat was beginning to cover my smooth chest.

The lights in my eyes grew suddenly brighter, and while I squinted, the figure moved forward, down between my spread legs. I was suddenly acutely aware of my position and exposure, but as the figure bent and pulled the enema tube smoothly from my ass, sliding it out slowly, erotically, I watched horrified as my dick grew stiffer, arching up toward my face in small jerks, a thick-headed six inches sprouting from a boyish clump of pubic hair.

My legs strained against the binds as the slim tube was slipped from my clenching pucker, a few drops of lube following it out. As the warm fluid slid across my spread asscrack, my cock flexed, filled to bursting from the uncontrollable drives of a horny boy.

The figure placed the tube on its stand and wheeled the stand to the side. Then, moving again to a location between my legs, the figure lowered. I began to make out a few details. He was male, young, and very attractive --and oddly familiar. I'd seen him before, but where? His light hair was cut very short, and he wore only a loose t-shirt and running shorts.

Unconsciously, my eyes glanced at the high-cut shorts, looking for a glimpse of naked dick. Startled, I looked away. Again, I tried to place the face, but my mind was fumbling ...

My dick! my mind screamed. The man, with a firm hand, had reached out and grasped my rock-hard cock, squeezing firmly. I groaned, the sensation of another man's skin on my throbbing meat thrilling me, and I lifted my ass up to meet his slow caress. A single drop of pre-cum appeared at the tip of my purple dickhead. I gasped as his fingertip rolled it around the crown of my cock. My ass clenched and my thick dick twitched in his fingers.

Slowly, he began stroking my boner. Painfully slowly. Dry, short strokes that teased me. I moaned low. He looked up at me struggling on the padded table, and smiled a knowing smile.

He was doing something to me that I had dreamed about for years, since I had learned what cumming was like from an eager-to-teach cousin. He had showed me, late at night in the dim light of our uncle's pool, what it was like to jack his 14-year old and my 12-year old dick to cumming. Since then, I was hooked. In three years, I had read and seen plenty on the `Net about how to cum. I loved it all, especially with a large, condom-covered carrot shoved inside me. But that was always by myself. This was something new.

After a few minutes, I was about to go mad. The slow jacking of this menacing man was about to make me pop. I needed to get off, and my balls began to climb up in my sack, bracing themselves to blow their load.

Seeing this, he slowly stopped, placing my dick gently on my stomach. I moved, wriggling to get my dick closer to him, lifting my ass up as far as I could, offering my hard cock to him. "Please," I heard myself say.

That was exactly what he wanted. My lifted, exposed ass was quickly touched by his thick finger. Without warning, his tough, callused hands spread my ass further. Roughly, a single finger slid up inside me. I froze, but the lube was doing its job. Effortlessly, he shoved it in to the third knuckle. I moaned again, and a new string of pre-cum eased out of my stiff, twitching dick.

Finger after thick finger invaded me, rubbing, searching, exploring my insides. I groaned and wiggled around the table, wanting for the stranger to touch my dick again. But for several minutes, all I received was two or three fingers probing my rectum, shoving their way against my aching prostate.

"Do you want to cum?" he suddenly asked. The voice was matter-of-fact, almost playful.

"Yes," I said. "Please, yes."

"Are you sure?" he asked. His hand returned to trace a fingertip along the ridge of my cock. It flexed and added to the growing puddle of pre-cum on my stomach.

"Please, man," I managed. "I need to cum."

He smiled. "Okay," the deep voice spoke. "But you have to agree that I get all of it."

Not sure why he would want to swallow my spooge, I was in no condition to question. "Yes, take it all."

He half-laughed. "Oh, trust me," he said. "I will. All of it."

Moving toward me, his lips abruptly enclosed my dickhead, tongue dancing around the edges. I gasped and started in the restraints. Oh my God! I was NOT going to last at all. He slurped loudly at the pre-cum on the tip, teasing me more.

Sitting up, he looked at me and said, "You've never cum like you're going to tonight." I nodded, my cock close to bursting. His two fingers inside me prodded against my prostate and my cock lifted off my stomach, straining to the point of pain.

Lightly, he traced his tongue across the underside of my dick, base to tip. I couldn't deal with it anymore. Panting and crying out, my prostate battered by his fingertips buried inside me, my solitary dick lurched and twitched, untouched, as I cried out in the restraints.

"Oh fuck, man!" I shouted, my shrill voice echoing in the large room. "Fuck!! I'm about to cum. Oh God, it's too much, fuck! Touch my dick, dude, please! I'm going to cum!"

He only smiled.

"Uhhhh! Uhhhhhgg ... oh please!!" My dick was ready to burst. My balls were pulled tight against my cock. The only stimulation was his fingers deep in my hole. Bucking my hips, I ached for him to touch my cock, my asslips clenching his fingers.

Just as I was about to fire, the stranger's other hand smoothly slipped a wet, slick, clear tube over my cock. It was a bit longer than my dick, maybe seven inches long, and roughly the same diameter inside so it touched and slid all around my rigid cock. The interior was coated in a clear substance that was very, very slick and slightly cool. Attached to the end of the tube was a length of clear flexible tubing that ran to the machine I had seen earlier.

The slick surface of the tube sliding across my rigid cock put my right over the edge, and my body locked into an arched position against the restraints.


Not caring where I came, my cock spat the first jet of semen far into the end of the tube. A thick, ropey jet that actually made a splattering noise against the plastic tubing.

At that moment, he turned the machine on.

The electric compressor-like noise startled me at first, but my next hands-free shot was already on the way out. My cock and whole body tensed again, and I grunted my way through another squirt of thick jism. Just then, the machine's suction pulled my first load clear of the tube and eagerly slurped up the second as it exited my pulsing dick.

The next shot was about to come out when the machine started a new maneuver. Jerkingly at first, the tube moved on my dick, sliding toward the end. As it did, it dragged the smooth jelly-like surface across my cumming dick. I stared in disbelief at this contraption as my third shot of cum exited my cockhole and was immediately sucked into the rubber hose.

At the far end of the hose, situated on the side of the machine, sat a jar about the size of a juice glass. With soft slurping noises, my cum dropped into the waiting container, quickly spilling across its bottom.

"Oh man! Oh fuck!!" I watched, fascinated, along with the stranger, as his probing fingers and the steadily stroking tube produced several more jets of cum, all slurped into the container. The machine worked me with painfully constant rhythm. It didn't react to my bucking, my thrashing and swearing. It didn't see the pleasure-laced agony it produced in me, didn't marvel at the enormous ropes of cum it pulled from my stiff young cock.

As my tender dick spewed jets, then trickles, of cum, the tube continued to work its way up and down my shaft. Unlike a hand or a mouth, the tube's interior surface covered and stimulated my whole cock equally, stimulating the entire length, base to tip; then as it moved toward the end, it focused all of its attention on my thickened, reddening dickhead. Then, it slid downward again, sending me into further fits of ecstasy.

I moaned and grunted my way through it all, the stranger's fingers wiggling within my slickened ass as my stretched pucker clenched down, flexed, and clenched again with each eruption. The stranger twisted his hand again and again within me. I'd never felt anything like this. My hips jerked forward involuntarily, feeding more of my spunk to the machine. It continued to ingest all I gave it, never tiring of my grunting spasms.

Slowly, my body began to relax from the orgasm, the cum slowing to twitching dribbles. A few sticky drops were all that remained, and they too were quickly devoured by the machine. I was finished.

I moaned, satisfied, as the strangers fingers slipped from my ass, bringing a small glob of cum to my dickslit. I had barely even seen or felt it leave me when the machine pulled it into the hose. The machine had covered the bottom of the jar with a shallow layer of the cum it pulled out of me, maybe a bit more than a tablespoon at best.

As my breathing started to slow, I noticed that the tube was getting warmer and that the speed of its pistoning on my cock was not slowing. I shuddered and shifted in my harnesses. "Uhh... dude..." I said, hoping the man was just distracted, maybe jerking himself after watching me writhe through the most powerful orgasm I'd ever had.


But he wasn't listening, he was focused at my ass, doing something I couldn't see. Slowly, a cool, metallic object -- an exceptionally fat, metal butt-plug of some kind -- slid deep inside me, stretching my ass wider than it ever had been before. I cried out and tried to stand in my harnesses, trying futilely to escape the cool mass as he worked it into me. And just then, my abused ass clamped down over the tapered base. It was obviously set inside me for a while. I dreaded the feeling it would make coming out. He looked up from between my legs, and smiled again.

"You said I could have it all," he said ominously. "I know you have more. So I'm taking it."

I didn't understand what he was talking about. And didn't care either. The stroking machine was still working my dick at a steady pace, dragging its slick interior over and over again on my hypersensitive cock.

"Hey, man, I'm done," I said. "Could you turn the machine off now?"

He shook his head. "No, don't think so. And you're far from done."

The sliding on my dick was driving my crazy. I tried to pull myself free of the continuous sucking, but there was no escaping its attentions. I was trapped. It sucked me more.

"Uh-uh-uh, pl-l-leasse, m-man..." I said, my body wracked by spasms of intense sensations traveling up my dick. It was maddening. From the time my orgasm began, the tube had slid up and down my cock, and it continued on and on still, relentlessly stimulating my spent cock. My mind was filled with sensations, and I couldn't decide what I my body needed to do -- cum, piss, cry out, laugh, scream. It felt like I needed to do them all, and yet, I could do nothing but whimper and shake on the table.

"No way, man. I can't cum again. Not yet." I was worried and getting uncomfortable. The machine didn't care and kept sucking me.

The young man had stood and walked to another machine nearby. The machine had a few large dials on it, and a meter of some kind. I noticed two wires running across the floor from the new machine. One went to the tube on my cock, the other ... went to the butt-plug buried inside me.

"I think you can," he said in a low voice.

"No," I said. I looked at my still hard cock inside the wickedly sliding tube. The inside of the tube was smeared with my cum, and my still-hard cock was becoming numb despite its attentions.

"In fact, you're about to cum harder than you've ever cum before," he said, reaching for a switch.

I didn't understand. Normally, I would need at least a short break before cumming again so quickly. And never had I been able to continue to jerk myself more than a few seconds past orgasm before the feeling became unbearable. But now my body couldn't escape the stroking, the nonstop sucking, of the machine attached to my teenage cock.

"No, man, please..." I begged. I just wanted the sucking to stop. I couldn't stand it anymore. "Please, just turn it off, I --"

He flicked a switch.

I screamed.

I came.

If you can call it cumming, that's what I did. Not from the stroking, not from the pistoning. But my body reacted like it was the cum of my life.

I can't begin to describe the sensation that coursed through my ass and into my cock. The butt-plug, pressed hard against my aching prostate, began to fire small but powerful half-second currents through me. They traveled inside me, through me, and out the sucking tube. The machine went into a high-suck mode, the tone growing higher like a vacuum cleaner sucking against your hand, as it pulled against my aching cock.


Hips bucking wildly in time with the currents, I came like nothing I've ever known. A huge gob of cum erupted from my cock. Felt it as it shot from the tip of my dick -- "poured" is more like it -- and heard the machine slurp it up eagerly.


Then I came again, another huge jet. Then another. And another. It was maddening pleasure, too intense to be enjoyable. It felt like my cum was a long piece of silken yarn, and with each twitch of my cock, the machine drew and yanked long strings of it from deep within me.


Each time my body wracked in jerking spasms that coincided with the pulses in my ass and cock. Each pulse of electricity clenched my ass on the tapered plug, driving it hard inside me, against my prostate, pushing my inner button over and over, making me jerk involuntarily. And with each jerk, my cock spewed more cum. I saw my volleys of cum filling the two empty inches at the end of the sucking tube. I could no longer speak. How long had I been cumming...?

"Guh-guh-UHHH! Guh-GUHHHH!!!!!"

I watched as much as possible, stunned and screaming, as my pulses of semen filled the end of the tube, outstripping the machine's ability to drain it all. Finally, after a solid ten seconds, the currents stopped -- and so did my cumming.

Panting, I collapsed against the table, my trembling body becoming wet with sweat. For several seconds, the machine sucked and slurped up my cum, finally emptying the tube again. And then the tube slid once again. And again. Just as before, it stroked and sucked my young cock.

"See," he said. "I knew you had it in you." He smiled smugly. "And now you don't."

"No more, please," I begged. "Please..." I wanted to cry, but there were no tears, just trembling, the shaking of my teenage body as the machine tried to drain me over and over again.

"Oh, you can stop at any time," he replied. "The machine can be stopped two ways."

"Okay ... what do you--" I gasped, writhing under the merciless stroking and sucking of the tube.

"Oh no," he explained. "It's not about me, It's the machine doing it. It wants your cum even more than I do. And once started, it won't stop until you meet one of two criteria."

I moaned and shifted again, trying to get this sucking tube off my tender young dick. It was killing me with torrents of post-cum stimulation, never slowing, bouncing over and over on my cock, suckling to get more cum out of me.

"Either you can just wait the full hour the machine is set to run," he stated. My heart sank at the words. "Or fill the glass." I looked up. The jar was not even a quarter full. I couldn't do it.

I shook my head. "No, please, I can't... I can't cum anymore..."

He shook his head, disappointedly. "Again, I think you can."

And he turned the knob on the machine, and the currents started again.

My body locked and jerked. Screaming in agonizing orgasmic passion, I came again.

"N-n-no!! Stop! I can't -- UH-UH-UH!! AHHH-RRGG!! SHIT F-F-F-UCK SH-SHI-I-I-I-IT!!!!!!"

My balls were pulled tight against the base of my cock as another stream of jism coursed out of me. The machine pulled it up into the wiggling hose and dribbled it in the waiting jar. My ass clenched against the thick base of the enormous plug in my bowels, driving hard inside my guts as it ticked more and more electric current through my spasming cock. I didn't even feel the stroking anymore, just something coursing through my stiff dick. I couldn't tell what was actual cum and what we the effect of the electrical current. It didn't matter anyway. To the machine, it was the same. It pulled more of the silken yarn of cum from my rubbery red cock.

The twitching stopped, and I struggled to watch more of my cum, clearer than before and not nearly as much of it, disappear into the hose of the tube. The machine decreased its vacuuming, but the tube continued to slide again.

And again...

Whimpering, I panted in my restraints, the tube working my cock as though I never came at all. I felt light-headed and the muscles under my balls ached, feeling thick against the plug buried in me.

The stranger examined the collection jar and shook his head disapprovingly.

"You're going to have to try much harder," he said quietly. "I think you're holding back."

Emphatically, I shook my head, but it was difficult as my body thrashed in revolt against the insistent sucking. "N-n-no! I'm-m n-n-not! Pl-eas-s-se..."

"Maybe you need more time," he said.

"Y-y-yes!!" I cried out, shivering not from any cold, but in dread of the next orgasm, out of the sensations racing over my adolescent dick. "Yes-s-s, pl-p-please..."

"Very well," he said, moving toward the machine controlling the pulses. "You'll have plenty of time." He smiled wickedly. "A full thirty seconds ... of cumming."

My chest clenched tight. Thirty seconds? That was three times longer than the first two times, and now my --


The low-voltage currents lashed through my cock and took everything I had left in me with it. Thrashing in the shackles like an animal in a trap, my cock fed the last of my cum to the sucking tube.

But when the first shot seemed enormous to me and barely anything spewed from my battered cockhead, my heart sank. Again and again, my cock twitched, releasing dribbles of clear spooge into the tube. There was little left, and the machine was taking it all.

"Ugh... ugh... uhh..." My body was locked in a flailing I could not control, as my crank was subjected to the never-ending assault of the tube and the currents from deep in my ass.

Aching and throbbing, my red dick tried to offer more and more to the eager tube, but nothing was left in me. Pain shot through the base of my dick with each jerking spasm. But my body refused to offer any more cum.

I screamed over and over, begging the man to turn it off, to make it stop. But he only watched the tube, studying the tiny dribbles of semen that trickled from my puffed cock inside. Slowly, drops fell into the collection jar.

I'd lost track of how long I had cum, but it didn't matter. When I had finished cumming, the machine forced my body to keep cumming, on and on ... the full thirty seconds he had told me.

Then it stopped.

Barely able to move, I watched the tube slide across my dick again. And again. Only my right leg moved in protest to its onslaught, quivering in a futile effort of lift my penis away from the tube. The thought of cumming held no appeal to me. Only release, only to be free of the machine's sucking.

What felt like minutes passed. I thought maybe my dick would go limp, would slip from the tube, relieving my agony. But the sucking tube managed to keep it hard, to keep it ready to receive more stimulation. Even as it tried to shrink in discomfort, the vacuum in the tube pulled it full, and the lubed surface ran its sensations into my aching penis, leaving me to shake on the tabletop.

In the few years I had been sexually functional, let alone active, I had never had more than two orgasms in a half hour period. My young body had never been subjected to anything like this. A week of cumming, an eternity of sucking, all packed into a span of 16 minutes. I didn't know what more was left inside me, but my mind was screaming in my head, but my body, wracked with spasms of cumming and of over-stimulation, could not react to any thoughts -- only the raw sensations on my pathetic cock.

The sucking machine took me through another two orgasms, each ejaculation smaller than the next, until only a few drops trickled out -- even though the sensations grew more furious and my screaming more intense.

The stranger examined the growing collection of my young spunk. It was milky on the bottom, but the top layers where growing clearer with each dribbling ejaculation.

"Not bad," he said, almost comforting. "But we're still not there yet."

I tried to speak, but managed only a guttural moan. My eyes pleaded for him to stop, to make me stop cumming. But he only looked back at me, a strange curiosity in his eyes. His arm moved; it was about to begin again.

Over the almost soothing din of the machine, milliseconds before the currents began. I heard the relays click. I watched as my hips lifted again against the restraints. The sliding tube increasing its suction on my cock. The ticking of electrical current took assault on my prostate once again, making the muscles far at the base of my dick, deep under my aching balls, begin to twitch and contract.

The sounds I made were not human. My cock strained and jerked within the clear tube, the head flaring with each spasm, slit gaping, seeming almost to cry out silently at its orgasmic agony.

The pressure built quickly within me, and moved toward my cock, past my tightened balls. It was a wad of cum, massive, enormous. I felt it moving up my dick, and despite the torture of the past sessions, I ached for release, to feel the cum pass through my hard penis and watch it slurp into the bouncing hose, dribbling into the cum-collecting glass.

My hips thrust in mid-air, driving my cock toward the tube, searching for release, aching to feed more of my forced cum to the suckling machine.

"Uhh-uh... Uhhmmmm... guh...ming...UGGHHHH!!!!!"

It was almost out of me now, the tube waiting, impatiently rubbing my dick over and over, sucking to pull the wad clear of my pitifully spent balls.

My cock grew enormous and hard in the tube, lifting the hose a bit as the tube traveled the short length of my violated cock. I was going to cum again. Again...


I tried to watch the huge wad jet out of me and into the tube. It felt as though it was three times bigger than any of the others. My body screamed and beat itself against the table, my hard teen dick waving lewdly, and the tube still firmly attached and sucking away.


My cock lurched in the tube.



My dick lurched again and again in the tube, my hips thrusting uncontrollably toward the ceiling, but nothing came out. Only more of my screams.

The stranger turned a dial then on the machine.

Without a pause between, the new pulses ticked through my adolescent crotch.

Stronger. Much stronger.

Every muscle in my young body flexed with the pulsing in my ass. Legs flexed against the ankle straps, my arms tight in the restraints, back arched, hips bucking.


Second after second ticked by, my body wrenching, squeezing whatever it could to offer the machine. It nursed on my tender dick as I screamed again and again in torment.

Then I heard the slurping began. I watched a pitiful dollop of cum leak from my dick. And the machine took it from me, into the hose, into the glass. Over and over, the machine stroked my cock, tried to make me cum. It sucked cruelly me as I dry-came into the tube.

"Uh... d-don't-t... ah-ah-mm...k-k-kuh...Guh!!...Guh!!!!"

It sucked me past what any cum could be, past what any 16-year old -- or any male -- should ever endure. My eyes lost all focus and I looked down, amazed that my dick remained hard within the sliding tube.

The pleasure of cumming was gone, gone like all of my semen down the hose of the sucking tube. My young body -- "young, dumb, and full of cum" --had offered all the cum it had; and the machine wanted more.

I jerked and tugged, thrashing my pathetic dribbles into the vacuuming tube. I couldn't take it anymore. The sensations were too much, too intense. As the ticking kept my body in the throws of the longest, driest, most agonizing orgasm I could imagine, my mind faded out. My vision grew dim, swallowed into unconsciousness as the machine swallowed my brutally coerced semen. Mercifully, I passed out.

And even then, the cumming continued...