The day dawned as any other, and the morning began for him as any other weekday. The alarm sounded at six. I rose and turned it off; his ankle was chained to the post at the foot of the bed. I took my keys from the dresser, crouched down to the floor where he lay, and unlocked the shackle as he rubbed the sleep from his eyes. I smiled at the dry traces of my cum on his chin from the bedtime blow job he’d given me. I continued with the ruse of the ordinary routine: I dressed and ran, then enjoyed my breakfast of peanut butter toast and juice as he enjoyed his breakfast of my crotch sweat and cum. After my shower, I omitted the ordinary instructions about what he should lay out for me to wear to work. Instead, I shaved silently, insouciant.
I could tell from his reflection over my shoulder in the bathroom mirror that he was panicking. This had never happened before. We’d had a weekday morning routine for years. I always told him what to lay out for me. He couldn’t decide whether he should ask or remain silent. He shifted nervously from foot to foot, eyes wide, alternatively staring at the back of my head and down at the floor. I could barely contain my glee but somehow maintained an outwardly stoic façade. Finishing, I selected the spicy, citrus scented balm, the one that he loved most. My eyes met his in the mirror.
“What’s wrong?” I asked.
“I don’t know what you want to wear to work, Sir!” His fear was audible.
I turned and smiled. Not the cold, cruel smile that warns him I’m going to hurt him. Not the warm, loving smile that rewards him for good service. Not the lustful, dusky smile that drops him to his knees in an instant, begging to be fucked. I smiled the gentle, paternal smile, the one that says, “Stupid boy, I know what I’m doing.”
“I’m not going to work today,” I replied, but it did nothing to ease his anxiety, and I paused to lengthen the moment. “Do you know what today is?” I asked. His eyes were wild. I could almost see his mind churning, trying to attach some significance to the date. What had he forgotten? How was he going to be punished for his stupidity? He was slowly shaking his head, ever so lightly. No. No. His mouth opened. Nothing came out. I relished his misery, but all good things must end.
“It’s the 24th,” I said, stepping to him. I wrapped my arms around him, bending my face to his ear. “It’s been six months, and I’m going to let you cum today.” All that registered in his well-trained mind—from my tone, from my embrace—was that he wasn’t going to be punished. He didn’t even absorb the words. He sighed, half sobbed, in my arms as he raised his hands with trepidation to rest them on my back. I felt relief wash over him. He was too relieved thinking he was safe from harm, from pain, from punishment, to realize what I’d said. He was wrong, but I let him have the moment. Only in my mind did I add, “many, many times.”
When the words I’d spoken dawned on him, he jerked back with surprise. He looked at me with disbelief. “I’m going to cum?” he asked softly. I smiled broadly at his delicious, ignorant eagerness and nodded. “You mean for real? Not a milking?” he asked, referring the weekly, pleasureless extraction of semen I administered by massaging his prostate. I nodded again. It was better than any Christmas. He positively beamed. He tightened his grip around my torso and moved in, kissing my face, my neck, my chin, thanking me, praising me for my kindness, my goodness, my mercy. And as I indulged his outburst, I laughed to myself. Finally, I ordered him to bed.
He enthusiastically jumped in, still beaming, playfully spreading his hands and feet to the corners of the mattress. If only he knew. It reminded me of the early days in the dorm, when we’d played little bondage games, and he’d tease me into tying him down. I again took my keys from the dresser, this time unlocking his CB3000. He was already hard and drooling so I had to tug on the chastity device to slip his cock free. I ran the tip of my index finger along the tube on the underside of his throbbing cock. He closed his eyes and sighed. “How do you want to get off?” I asked.
His eyes half opened. His smile faded. Lust colored his face red. Lust and need. His gaze was plaintive. “Fuck me,” he answered. “Please fuck me.”
I smirked and nodded. I went to the closet and took his satchel from the shelf. The black bag, not unlike a doctor’s, that held his toys. The toys he liked. The toys we never used anymore. The toys I liked were in the basement, with the rest of the equipment. In his satchel he kept his vibrator, his plug, some leather straps, a novelty cat o’ nine tails—the flimsy, play kind, not the knotted leather one that hung from a beam downstairs—and lube. These were things he’d bought online, back when we were in the dorm, when bondage was fantasy and neither of us knew what we were doing. The satchel and its contents were among the very few things left to remind him of those days, and it was kept figuratively and literally just within his reach in the top of the closet, collecting dust.
He watched me, relaxed, perhaps wistful, as he saw me with it. I took out the straps and the lube. He smiled and raised his head to nuzzle my arm as I tied his wrists to the posts at the head of the bed. His arms secured, I knelt between his legs. “Do you remember the first time?” I asked him.
“Yes, Sir,” he answered seriously. He’d tacked on the Sir to remind us both of how much had changed since that first night I’d taken the Irish freshman exchange student into my senior dorm room three years earlier. I’d fucked him as I jerked his little dick. Now he was marked as my property, his cream-colored skin tattooed at the base of his neck and the sole of his left foot. We never celebrated that anniversary, though. Not when we met. Not our first time. There was only one anniversary that mattered now, and it was still months off.
Unlike that first night when he’d held his own legs aloft, his hands were bound now so I lifted his knees to my shoulders. I lubed two fingers and gently inserted them into his ass. I hadn’t taken his virginity that first night, but it had been a long time since he’d been fucked. Now, he’d had more than two years of experience as my slave, and he’d been fucked nearly every day. Sometimes more than once. I lubed my cock and positioned it just outside the opening of his cunt. He closed his eyes, and I leaned over and kissed him. He sighed again, deeply, no doubt lost in memory, smelling my aftershave balm. As I tasted the inside of his mouth, I slid slowly into him. He arched up to meet me. I reached for his little dick with my greasy hand. He moaned into my mouth.
“Seay?” I asked, pulling a few inches away.
“Yes, Sir?” he answered, his eyes opening and locking on mine.
“You have permission to cum. You have permission to cum all day long, until the sun sets. It’s not a trick. I won’t take it away. Do you understand?”
I thought his eyes glistened as he answered, “Yes, Sir” and closed his eyelids, sucking on his lower lip. I knew that he didn’t really understand what I meant, but it didn’t matter to him or me at that moment. He wanted to cum. It took less than a minute. His whole body trembled. His breath was ragged. I stroked his dick and fucked him, slowly. When I saw the signs, I buried myself in him, anticipating the sensation that I, too, hadn’t felt in six months: his ass constricting around my dick as he came.
The orgasm redefined the word electric. He whole body spasmed. His eyebrows shot up, his eyelids fluttered, exposing glimpses of white as the pupils rolled up into his skull. His mouth locked open, repeating “Oh!” over and over as his breath came and went in short, explosive bursts. His legs nearly crushed me, as he wrapped them around my waist, his toes curling and uncurling, wriggling. His fists clenched and unclenched. He turned his wrists in the leather straps, chaffing them, grabbing for the sheet. The feeling, from inside his ass, was inexplicable, and it lasted over three minutes. I don’t think I could have pulled my cock free if I’d tried, his sphincter was clamped so tightly. But I didn’t want to. I didn’t need to stroke in and out. The outward convulsions of his body were mirrored, if not amplified, inside him. I found myself fighting to keep my cum inside my balls as rings of viselike muscle rippled along my shaft and cock head. I even stopped fisting his slimy pole. Try though I might, I couldn’t fight my orgasm off for the duration his lasted. And mine finished before his, too.
When it was over, he was utterly spent. Despite six months of weekly milkings, we were both covered in his cum. He collapsed into the mattress, every muscle limp. And then the cramps hit him. His eyes flew open, his face contorting with pain, as the groin muscles which had atrophied over months of disuse knotted inside him. He’d been milked, of course, to keep his prostate and tubes healthy, but the long deprivation of orgasm had wasted the muscles that had jetted his cum up to his face and beyond. My cock could feel the ones lying beneath the thin skin of his perineum clenching in on themselves. “It hurts, it hurts, it hurts,” he chanted, frozen in pain. I smiled. I pulled my dick from his hole, and the internal counter-pressure it had contributed vanished. He shrieked as his innards readjusted themselves. As I wiped the cum and lube from my dick with a Kleenex, my just sated erection began to return, rejuvenated by his suffering.
He was completely oblivious as I took two more leather straps and pulled his ankles to the corners of the bed, securing them tightly. I waited patiently beside the bed, watching the lean muscle in his chest, his abs, his arms and legs, straining in pain, until the cramping began to subside. I scraped off with one hand the cum he spurted onto my abdomen, transferring it to the mop as I sat on the bed and brushed it gently. As the minutes passed, he again faded into the mattress. He was soaking wet, dripping with sweat and cum. “Ow,” he whimpered, his eyes still closed. I looked at the clock and smiled. 7:17. The day had just begun.
By lunch, he’d cum three more times. The once thick, white ropes of spunk had tapered off to spurts of cloudy precum. For his second orgasm, I blindfolded him then wrapped my fingers tightly around his shaft. With my thumb coated in his semen, I’d rubbed coarse circles around his knob, the sensitive glans usually protected behind his foreskin. It was tender under the best of circumstances, but having been touched so rarely for so long, and coupled with the powerful orgasm he’d felt just moments earlier, the sensations it afforded him were excruciating. And the suffering he displayed was delicious as he writhed uselessly in the tight leather straps that stretched his limbs to the corners of the bed.
When one concentrates that way on an uncut boy’s cock head, an orgasm is almost a survival instinct, as though the primal, subconscious parts of the brain calculate that only the expulsion of more slippery lubrication will ease the chaffing. At any rate, though the mechanism worked and the seed spurted out, sliming my thumb, its purpose was defeated. Nothing could save his dick today.
I did grant him a brief reprieve after that second orgasm, though. When I stopped rubbing with my thumb, the knob was red and all but glowing. It turned me on so much I had to interrupt my plans, straddle his chest, and fuck his face. Afterwards, I realized I had to pace myself better, because there was certainly no way I would put myself through what I’d planned for him.
Before the third orgasm, I clamped his nipples. He isn’t much for nipple pain because his are very sensitive. Not that I gave a rat’s ass. A hint of hoarseness had already crept into his voice, mostly from the begging for mercy he’d loudly—and futilely—offered on the way to the second orgasm. Thinking I’d save his voice, I plugged his mouth with a cock-shaped gag, strapping it in place around his head. Well, I admit that’s a lie: I knew he’d be screaming, I just wouldn’t be able to hear his words, and since the words weren’t going to do anything to save him there was no point in putting up with them.
With his nipples clamped, his mouth gagged, his eyes blindfolded, I untied his ankles from the posts at the foot of the bed and retied them to the headboard. Bent in half, his hairless ass was exposed and open, still a bit puffy from being fucked. I was gentle—truly—as I stroked around that hole with my fingers. Maybe too gentle. Maybe that’s why his abused little dick grew hard again, despite his every effort to will it flaccid. He’s just a butt boy. He loves to be fucked, to have things fill him and rub his prostate. It’s not his fault. But that didn’t stop me from using it against him. So I used the vibrating dildo from his satchel, his beloved little toy, the one that fit him so well and he’d chosen for himself so long ago.
I congratulate myself for my restraint, because I think I deserve it. I worked that hole with loving devotion, stroking slowly with that vibrator for over an hour as his dick quivered over his chest. I’d see him building up, getting close, his balls drawing up again and again, and I’d pull the latex phallus all the way out of him until he settled down. Each one was an opportunity to make him cum again, an opportunity to shoehorn one more climax in before the day ended and his marathon was complete. But I was merciful because I didn’t want him destroyed. Broken, yes. Babbling, yes. Willing to beg me never, ever to cum again, yes. But I didn’t want his servitude to become robotic, mindless, programmed. I wanted him to keep loving me, taking surprising initiative to please me, genuinely craving my smile and praise. And I wanted him physiologically sound, too, if only to be able to repeat this day in some new form months later.
So, I took him to the edge over and over again, for almost ninety minutes, almost until he actually wanted to cum again. It was when the battery began to fade—the vibrator hadn’t been used in ages and who knew how old the battery was—that I finally shoved him over the edge. And he came the third time, and his body was covered in sweat, the mop plastered to his forehead except the crunchy strands sticking up from when I’d stroked it with my semen-smeared fingers hours before. His chest and abs were a mottled mass of goo. Some had dried completely into hard crusty blotches; some was still congealing, resembling partially set gelatin; some was fresh.
I knew he was exhausted. I knew his throat was raw, raw from being fucked, raw from the cock gag, raw from his muted whining, whimpering, shrieking, and screaming. He looked adorable, his body balled up on the mattress, the vibrator shoved deep into his ass, the nipple clamps, the blindfold. One thing was missing, so I added it. I pulled out the vibrator and replaced the battery before ramming it back home and returning it to its highest setting. Then I took more leather straps and tied his balls. I wound the cord around his sack, stretching his orbs farther and farther down, alternating loops around so that each was separated from the other. They were so beautiful, red and shiny as they pulsed in their bondage. I then tied them tightly to the two bed posts, stretching them taut as the right cord balanced the left cord and vice versa.
I started softly as I beat them. Three soft slaps, very soft, barely palpable. One. Two. Three. Then a gentle squeeze. Then three more slaps, increasing in intensity by an almost imperceptible degree. And a squeeze, likewise slightly harder. I really don’t know which was worse for him, knowing that it would get worse and worse until he came or having to lie there impatiently waiting for me to get to the good stuff. I knew he liked ball pain. To a point, obviously. In that way, it was cruel, really, to take so long. But there were hours in the day. He was more than satisfied by the end though. After three orgasms, painfully extracted from his genitals and torturing the long-abandoned internal musculature, the fourth orgasm came very reluctantly and the slaps and squeezes were quite fierce by the time they produced the required result.
He was all but senseless when I left him quivering, panting, groaning, to have lunch.
It was the third orgasm after lunch, the seventh overall, that gave me what I wanted. It had taken ice cubes, Ben Gay, candle wax, urethral sounds, and clothespins to get there. It had taken a cock ring to keep his dick hard. It had taken stretching his nuts and paddling them. It had taken patience, and it had taken time. But at last, the precum tapered off to a trickle. At last, the seventh orgasm had been dry.
After his body settled down from the sensation—the pain had long ago overtaken the pleasure—I unbound him and removed the accoutrements of his torture. I’d had to replace the leather straps on his wrists fairly early on because he’d rubbed the skin raw and I hadn’t wanted him to draw blood. I’d wrapped them in gauze and substituted proper leather cuffs. I’d replaced the tit clamps with clothespins, to match the ones I’d used on his foreskin, inner thighs, scrotum, earlobes, and armpits. I’d interchanged his vibrator with dildos, so many dildos. Long ones, thick ones, ribbed ones, as I’d fucked his ass, battering his prostate from the inside even while taxing it repeatedly with the incessant demand that it yield up cum.
His body was covered in sweat and spunk, some dry, some gelatinous, and punctuated with red welts where the pins had been and droplets of black candle wax. I untied his legs, still bent over his chest, and he whimpered as the muscles were at last able to relax and straighten. I untied his nuts, now stretched inches from his groin and throbbing, purple and swollen. I pulled the cock gag from his mouth, listening to the raspy sighs and gasps, noting the new bite marks he’d left on in.
“Please, Master, please, I don’t want to cum anymore. Please don’t make me cum anymore, please, please, put it back on me, Master,” he moaned hoarsely, referring to the CB3000. His voice sounded alien, dry and dull. He’d shouted and shrieked and screamed and sobbed over the past ten hours, all muted by the gag. Only the wrist cuffs and blindfold remained as I lay beside him and stroked his face, which was wet with tears, sweat, and cum. The mop was plastered to his head.
“You were a good boy, Seay,” I murmured in his ear, “you were a very good boy.”
He was too limp to move. Too much strength and effort had been wasted as he’d fought his bonds, fought not to cum. Now he was drained, on every conceivable level. He was almost done, but I had to take him one layer deeper inside himself, one Dantean ring lower into the pit. I rolled off the bed. I returned with a bowl of hot water and a wash cloth. I washed him gently, caressing his abused body, lovingly scrubbing away the sperm and the wax. Soothing away the pain a bit. His dick was lifeless as I cleaned it, unable to stir even as I peeled back the foreskin to wipe away the last of the Ben Gay.
He was beautiful as he lay there, utterly spent, his pale, hairless body almost radiating, bedecked in the red splotches that told the tale of the journey he’d taken. I massaged him after he dried, using warm lotion. I went to the kitchen and made chicken soup, then came up and spoon fed him. He was so small, so helpless, so unsuspecting as he finally relaxed, arms outstretched and eyes covered. I lay beside him, on my side, nuzzling his neck. He had made me proud. But I was still unsatisfied.
“Give me one more, Seay. Just one more. I know you can,” I whispered as I licked his neck.
Instantly, his breathing accelerated. “No, no, no,” he began chanting softly, turning his head from side to side on the mattress. I reached down and cupped his package with my hand, massaging it gently. “Please, please, no, please,” he continued. I kissed my way down his chest.
“Sshh,” I replied. For the first time in more than two years, for the first time since he’d sworn to be my slave and I to be his master, I licked his cock. I recognize that sucking a slave, second only to be fucked by one, is ordinarily the lowest form of submission, and that for a master to do so would permanently damage his authority. But this was no ordinary circumstance. This was the final step in forever severing the mental association between orgasm and pleasure, substituting joy and anticipation with fear and dread.
As I sucked him, I fucked
him with two
fingers and kneaded his sack with the other hand. Even
after all he’d been through, even
despite having willed himself not to, he grew hard.
He was trembling, but not with pleasure. He
couldn’t even raise his legs to fight me
off. As I fellated him, he kept begging
me to stop. It took a long time to bring
him to the edge. As he felt himself
nearing the inevitable, he stopped begging.
He was crying. At first I thought
he was whispering gibberish, but then I remembered the phone call so
the one when he’d called his parents to say he wasn’t going home, that
fallen in love, that he was staying in
“ . . . guigh orainn na peacaigh, anois agus ar uair ár mbáis,” he whispered. Seay was praying. He’d been a good Irish Catholic once, a former altar boy, and I’d stripped him down to prayer in his native tongue. I’d won.
His eighth and final climax was marked by nothing more than a spasm of his little cock in my mouth, and a muted, guttural grunt. That’s all he had left. He didn’t move as I released his arms. His eyes didn’t open after I untied the blindfold. I turned out the light and climbed in beside him. I wrapped my arms around him and told him how good he was, how pleased I was, how much I loved him. He curled up against me, weeping, begging me to never make him cum again, swearing he’d always be a good boy. And before I left him to fall asleep, I watched him lock the CB3000 around his dick, both of us knowing how superfluous it would be now.