Cries in the Dark
Jordan cried out loud as the thick, blunt cockhead forced its way into him. The first one was always the hardest, especially when it was a big one. Having penetrated the tight sphincter, the cock paused while the violated ring of muscle spasmed around it. Jordan’s breath caught, rendering him unable to inhale as the pain wracked his slender frame. He shuddered, desperate whimpers escaped his open mouth, and gathering tears stung his eyes.
The cock didn’t wait. It plunged deeper into his rectum, the well-lubed shaft sliding easily through the spasmodically-clutching orifice, the bulbous head plowing deep up inside his guts. Jordan’s mouth opened wide, but he had no breath with which to yell. By the time he felt naked hips pressing against his buttocks, the cock was so deep inside him it felt like it was pressing against his lungs. Another involuntary shudder shook his fully-impaled body, and still he couldn’t take a breath. His helpless bowels were stuffed so full of cock, it seemed like his whole body was ready to burst.
Finally, as the massive cock began to withdraw, Jordan was able to take a shallow, shuddering breath, audible as a shaky, whining gasp. He felt his insides being sucked outward as the giant cock pulled almost all the way out, then it suddenly plunged back in again, making him cry out nearly as loudly as the first time. It sunk all the way back in, filling him with its hefty mass, then back out again. In, then out, penetrating his guts, then sucking at them on the out-stroke, each thrust a harrowing epic of agonizing endurance. Tears rolled down Jordan’s cheeks, and he buried his face in the pillow, muffling the cries he couldn’t contain.
“Fuuuuuuck, that feels good,” said Aaron, the boy whose cock was devastating Jordan’s bowels. To him, this was a pleasure, an exciting and enjoyable pastime. He was loving the way Jordan’s ass was clenching around his cock, almost as though it were deliberately squeezing him to increase his enjoyment.
Aaron had come early, only a few minutes after lights-out, so he could be first. When he’d thrown back the blankets, he’d found Jordan ready, naked in his bunk except for the white stockings that encased his legs. The boy had looked up at him with frightened eyes, but as Aaron had begun tying him up, Jordan’s penis had stiffened to full, embarrassing erection.
He had tied him to the bunk with his ass in the air, his legs folded beneath him. He’d scooted him down to the foot of the bunk, so his butt stuck right out over the rail, his legs spread wide. This position spread his ass wide open, his buttocks taut, the crinkly bud of his anus fully visible and easy to fuck. By the time Aaron had finished rendering Jordan helpless in his bondage and begun lubricating his stiffening cock, another boy had already arrived.
Now, with Aaron’s cock thrusting in and out of Jordan’s helpless ass, the other boy, whose name Jordan didn’t know, stood watching, stroking his own tool into quivering hardness. This boy would be next to fuck Jordan, but he certainly wouldn’t be last. Last night he had been fucked by twelve boys in a row, and every night there were more than the previous night.
It had all started just two weeks ago. Jordan had been at the academy for almost two months. He had abstained from masturbating that whole time, not even once. The dorm was a crowded, bustling place, and privacy was hard to find. Jordan hadn’t felt secure enough to touch himself, terrified the other boys would see him and shower him with ridicule. It had happened to him in middle school, and he had endured the taunting and humiliating nicknames for over a year.
But after two months of not touching himself, Jordan had been desperate. He’d never abstained for so long, and his adolescent desire was raging for release. He had found that in the wee hours of the morning, between two o’clock and five, there was the least amount of activity in the dorm. The place was almost silent then, so that was the time he chose to finally relieve himself.
Jordan was not your average boy. He didn’t just rub one out under the blankets while no one was looking. When Jordan masturbated, he wore women’s stockings and panties, at the very least. Those were the only items he’d smuggled into the academy with him, so he put them on before he began. Just feeling the soft, silky lingerie against his skin made him hard as a rock. Under his blankets, at three o’clock in the morning, Jordan had begun to touch himself, while his roommate snored softly in the bunk above him.
After a few minutes, Jordan had needed the other necessary element for successful masturbation. With trembling fingers, he’d taken the tubular bottle of moisturizing lotion from his kit. The cap was rounded, the lubricating lotion right inside, so it was the perfect incognito tool for his purposes. He squirted a bit of lotion into his right hand, replaced the smooth round cap, and anointed the bottle with the lotion. Sliding his panties to the side, he gently worked the rounded end of the bottle into his bottom-hole. He sighed deeply when it was in, then lay there, panting, listening for danger, for a full minute.
When he couldn’t wait any longer, he began shoving the bottle in and out of his bottom, while his right hand, slick with lotion, stroked his hard cock inside the panties. It felt heavenly. It had been so long… Jordan lost himself in a fantasy, thrusting the bottle in and out faster and faster, stroking, moaning softly in spite of himself. He reached a point where he needed to turn over and stick his ass in the air while he fucked himself, and he paid no attention when the blanket slid off of him. He was lost in his fantasy, and he was getting close, so close to cumming…
That was when the firewatch had burst in, shining his flashlight on Jordan. Jordan froze in panic, squinting at the light. The firewatch, an upperclassman named Dylan, grinned as he moved closer, taking in all the details of Jordan’s situation in the dazzling glare of his flashlight.
“Well look at you,” he said, barely able to suppress his delight. “When I heard you moaning, I thought you were just another pud-puller…”
Dylan was right beside his bunk, getting a close-up view of the bottle protruding from his upraised butt, before Jordan was able to break his paralysis. He dropped flat on the mattress and curled his body around his erection, trying to pull the blanket over himself to hide his shame, but it was far too late for that. Dylan put a knee on the bunk beside Jordan, leaning over him and yanking the blanket off the bed entirely. Jordan was left cowering, worse than naked in his feminine lingerie, trying to hide his erection with his hands.
“Hey, kid, relax,” said Dylan, his reassuring tone somewhat undermined by the grin he wore. He put his hand on Jordan’s bare hip. “I’m not gonna hurt you, I promise!”
Jordan was too horrified at being caught to even understand what Dylan was saying. It was like middle school all over again, only worse, because this time he was wearing his stockings and panties, and had his bottle in his butt. He wanted to die on the spot!
But Dylan kept talking to him in soothing tones, his hand still on his hip, and gradually Jordan’s panic began to subside. The older kid didn’t seem to be ridiculing him after all, despite his grin. When Jordan was finally able to listen, the firewatch was saying “…not gonna tell a soul, okay? I swear, it’s just our little secret. No one else needs to know.”
“R-really?” Jordan stammered.
“Yeah,” said Dylan. “This is a military academy, you know, and they really, really don’t like fags here. I wouldn’t want to get you expelled.”
Dylan’s hand on his hip began to exert pressure, trying to roll him all the way onto his stomach. Jordan was too frightened and confused to resist, but he kept both hands under him, cupping his swiftly-softening erection. When he lay fully face-down, Dylan’s hand left his hip and grasped the tube-shaped bottle still sticking out of his butt. Jordan tensed, his confusion and fear spiking. Slowly, Dylan began sliding the bottle deeper into him. When it was nearly all the way inside, he pulled it back out, then pushed it back in, out, in, out, in…
In Jordan’s harrowed state of mind, it took him a ridiculously long time to realize that Dylan was deliberately fucking him with the bottle. “Wh-what are you doing?”
Dylan just kept sliding the bottle in and out. Jordan didn’t understand what this meant, but it was less than reassuring. He reached behind him with one hand to stop the steady penetration, but Dylan dropped the flashlight into his lap and grabbed Jordan’s wrist. The bottle slid in and out, in and out.
“Hey,” said Jordan in a weak, uncertain voice, “don’t! Y-you can’t just…”
“Ssshhhhh,” Dylan shushed. “Just relax…”
Jordan was anything but relaxed. What was Dylan doing to him? Was he trying to humiliate him even more than he already was? But no. What Dylan was doing now wasn’t ridiculing or bullying. It was sexual. Dylan was fucking him with the bottle. He could only think of one reason Dylan would do that.
A strange new feeling settled over Jordan, even as his mind raced. He couldn’t stop Dylan from doing whatever he wanted. Dylan could get him expelled from the academy if he reported him. He could do nothing but submit. And deep down, Jordan realized then, he wanted to submit.
In, out. In, out. In, out. It was starting to trigger his libido. He could feel his penis hardening in his hand. He whimpered softly.
“Have you ever had a real cock in there?” Dylan whispered.
Jordan hesitated for a long moment. “No.”
“I think you’re gonna like it,” Dylan chuckled.
He abruptly popped the bottle out of Jordan’s bottom and stood up, began unbuckling his belt.
“No!” said Jordan in sudden panic, rolling away until his back was against the wall.
“Okay,” said Dylan, shrugging. “Wait here, I’ll be right back.”
“What?” said Jordan, but Dylan was already leaving the room.
Jordan was terrified. What was Dylan going to do? Report him to the company commander? Get some friends to hold him down? He had no idea. He fetched his blanket from the floor and wrapped it around himself, but he didn’t know what else to do. Above him, his roommate snored on, unaware of what was going on.
Finally, Dylan returned, closing the door behind him. After he set his flashlight on the nightstand, Jordan saw that he held a coil of rope. His eyes widened as Dylan cut two four-foot lengths from the coil with his pocket knife. When Dylan climbed onto the bed and began to forcefully move the boy into the center of it, he started to struggle weakly, but it was useless. Dylan was bigger and stronger that he was, and in moments he had Jordan pinned down, on his belly. He sat on Jordan’s back and tied his wrists to the railing at the head of the bed. He cut two more lengths of rope, and used them to tie his feet to the bottom corner posts of the bunk, spreading his legs wide.
“There,” Dylan whispered. “Now you don’t have to struggle.”
Dylan undressed himself leisurely, stripping down to his tee-shirt. His cock stuck out, waving in the air, already getting hard. It was twice the size of Jordan’s, and still hardening. He reached over and turned off the flashlight, plunging the tiny dorm room into darkness.
Jordan knew what was coming. His emotions were in turmoil, because there was a part of him that wanted it. He had fantasized for years about being forced to take a cock in his ass, and now it was about to happen! Dylan climbed onto the bunk and lay between Jordan’s spread legs. Jordan felt the thick shaft of Dylan’s cock settle between his panty-clad butt-cheeks. Slippery with lube, it slid up and down freely, soaking the filmy fabric and forcing his cheeks apart.
“Relax your butt,” Dylan whispered. “It’ll go in easier.”
The upperclassman drew back until just the fat head of his cock was sliding between Jordan’s cheeks, and pulled the thin panties to the side. Jordan held his breath as the fleshy bludgeon found the little dimple of his anus and began to push. He could feel it shoving its way inside, spreading the tight, nervous orifice wider and wider. Suddenly it was sliding through the tight ring, and the sharp pain made him cry out. Then the head of the thing was inside him, and he hissed as it slid deeper. It was much thicker than his little plastic bottle.
His roommate, Bobby, had stopped snoring, and there was a creak from the bunk as he moved. “Jordan?” he said sleepily. “You okay?”
Jordan, being impaled by a cock for the first time, responded only with a deep groan. Dylan’s enormous tool drove steadily into him, going so deep it took his breath away.
“Jordan?” said Bobby again, but Jordan still couldn’t answer.
Dylan lay on top of him, his massive cock buried to the hilt in his virgin ass. It throbbed inside him, a dominating, predatory monster demanding his entire attention. He could barely breathe. A thin whine escaped his lips, but he could manage no more than that.
Finally, Dylan began moving, and Jordan shuddered and gasped as the withdrawal sucked at his guts, then groaned loudly as the huge organ plunged back into the depths of his bowels. Every movement the thing made was devastating to him. It felt like a fist that had a fierce grip on his insides, and was sadistically pulling and pushing on them. Jordan couldn’t help groaning every time it pushed its way back into his tender depths. Tears rolled down his cheeks. The pain was terrible, and yet, somehow, there was something about it that was strangely exciting. In the midst of the agony, there was a twinge of excruciating pleasure. Though he had imagined it hundreds of times, the boy had never imagined it would feel like this.
“Jordan, what’s going on?” asked Bobby, fully awake now.
“Relax, kid, it’s okay,” said Dylan finally, his voice husky. “Your roommate’s got my cock in his ass. He’ll get back to you later.”
Bobby fell silent, while the fucking continued. Dylan took his pleasure in Jordan’s bottom-hole, and didn’t seem bothered by his agonized cries. He’d fuck him for several minutes, then stop and rest, his cock pulsing in the depths of the boy’s rectum. Then, when he was ready, he’d resume thrusting in and out.
After a while, Jordan realized that what had been only a twinge of pleasure at first was now more than a twinge. It had come to match the pain, and seemingly to surpass it, though it was hard to be sure. He still couldn’t contain his cries, but their timbre had changed.
At last, after what seemed an eternity, Dylan reached his breaking point. He suddenly began to pump Jordan’s ass hard and fast, and now he, too, was groaning. Jordan’s cries hit a crescendo when Dylan was hammering into him as hard as he could, and moments later Dylan’s groans, too, hit climax as he flooded the boy’s rectum with spurt after spurt of hot, thick semen.
Jordan was sobbing softly as Dylan pulled his softening penis out of the boy’s anus. He untied him then, and put his uniform back on. The lengths of rope he’d used were folded together into a bundle. Before he left, Dylan whispered to Jordan.
“I’ve got firewatch again on Thursday. Be ready for me about eleven o’clock. Wear those stockings, they’re kinda sexy.”
With that, he was gone. Jordan wasn’t sure how he felt about the whole thing. He was too tired, and too traumatized, to finish masturbating, so he lay there for more than an hour with an ass-full of semen, thinking about it. Bobby quietly asked him how he was doing, and he said he didn’t know.
Jordan couldn’t stop thinking about it the next day, and the day after that. Part of him felt like he had been raped, but there was another part that found the incident strangely exciting, and was looking forward to doing it again. Weird new emotions had been awakened in him, and try as he might, he couldn’t analyze them. When Thursday rolled around, he still hadn’t decided if being raped by Dylan was a good thing or a bad thing, but he found himself getting ready for Dylan’s visit.
At eleven o’clock Dylan found him naked under his blanket except for his stockings, his bottom-hole enemized and pre-lubed with lotion. He tied him down as he had before, and fucked him long and hard, with Bobby watching over the edge of his upper bunk.
After that, Dylan came every night, and every night Jordan was waiting for him. He had come to crave these nocturnal visits, and he found that they left him fulfilled in a way that masturbation couldn’t. He didn’t even mind that he didn’t have an orgasm himself, it was somehow more satisfying when Dylan came inside him.
On the ninth visit, Dylan arrived in Jordan’s room slightly drunk. He was a bit more careless, more reckless than usual, and he deliberately left the door open while he fucked Jordan. He was especially rough with him, and it took him a long time to cum. Jordan’s cries had been audible all the way to the end of the long hallway, and by the time Dylan was done with him there were five other boys standing in the doorway, watching. Dylan, feeling magnanimous, offered them a round with Jordan’s ass, and they eagerly took him up on it.
Jordan was at once mortified and excited by this development, but since he was still tied down, there was nothing he could do but take it. It turned out to be the most frightening and exhilarating experience of his young life, and at the end of the night he had six loads of hot semen in his bottom.
The next night Dylan deliberately left the door open again, and this time there were eight boys lined up at the door when he was done. Dylan just left Jordan tied down and went to bed. Jordan lost count of how many times he was fucked that night.
Now, two weeks after that first night with Dylan, Jordan was being fucked by Aaron, and the other boys were already lining up. Tying Jordan down and fucking him had become a nightly ritual for more than a dozen eager boys, and every night there were more of them. Even his roommate Bobby had joined the queue.
Aaron finally pumped his load into Jordan’s bottom-hole and stepped away, to be replaced immediately by the next boy. Jordan groaned as the second cock of the evening forced its way into his hole. As number two slipped into the familiar rhythm, Jordan heard two boys talking by the door, a conversation he had heard a dozen times now.
“Is he okay with this?”
“Oh fuck yeah, he loves it.”
“Are you sure? It sounds like he’s in pain.”
“I know, but he likes it when it hurts. Here, look… See how hard his dick is?”
“Yeah, it’s totally hard.”
“That’s how you can tell he likes it. You wanna go next?”
Jordan’s face flushed in humiliation, like it always did when he heard the boys pointing out how much he loved this. Still, he knew he wouldn’t give it up for anything. He didn’t know how many boys would find him tonight, or how many more would be added tomorrow night, or the night after that. There were already boys coming down from the upper floors. How many were there in this dorm? A hundred? Best not to think about it, he decided, giving himself up to the moment. Best not to think at all…
The irony of it all was that his father had sent him away to the military academy to learn how to be a man.