Thirty-Five Days
Summary: A month-long sex cleanse leaves Jimmy desperate, tortured, emotional, and completely obsessed with you.
Jon hought the cleanse was a joke at first.
Thirty days.
No sex.
No touching.
No “accidents.”
No “just the tip.”
No late-night grinding against your ass while pretending he was asleep.
He’d laughed when you showed him the article over breakfast, but the laugh died the second he realized you were dead serious.
“Thirty days, baby? You tryna kill me,” he groaned, but eventually agreed with that cocky smirk.
By day two the man was a mess. Morning wood so brutal he’d wake up humping the mattress before catching himself. Lunch wood while eating the sandwich you made him. Dinner wood. Random wood every time you walked by in those little lounge shorts. His thick dick stayed half-hard in his sweatpants like it had a personal vendetta against the cleanse.
You actually believed he was holding up his end… until the day you forgot your work badge.
The house was quiet when you slipped back in—until you heard the low, filthy groans coming from the bedroom.
You pushed the door open.
Jonathan was sprawled on the edge of the bed, sweatpants shoved down to his knees, one big hand furiously stroking his fat, veiny cock. The head was swollen and shiny with pre-cum, slick sounds filling the room as he twisted his wrist on every upstroke. His abs were tight, thighs flexing, mouth open in a silent curse.
“Jonathan.”
He froze mid-pump, eyes flying open, cock still throbbing hard in his fist. “Baby—fuck, wait—”
“You lying ass.”
“I can explain—”
“You’re cheating on the cleanse with your own hand?”
He looked genuinely pained. “I was dying. You don’t understand how bad it hurts.”
You stared at his leaking dick, then at his guilty face. “We’re fixing this. Tomorrow.”
The next evening you made him strip. Jonathan stood there naked, already rock hard, that thick Uso cock curving up toward his abs, veins pulsing. You sat on the bed and held up the thick black silicone cock ring.
“No way,” he muttered, but his dick twitched hard at the sight.
“Yes way. Since you can’t behave, you’re wearing this for the rest of the cleanse… plus five extra days.”
You lubed it up and slowly worked it down his shaft. Jonathan hissed through his teeth as you pushed it over his heavy balls and snapped it snug at the base. The ring squeezed tight, forcing his cock even harder. The head flushed dark red almost instantly, veins standing out obscenely. A fat bead of pre-cum oozed from the slit and dripped down the underside.
“Shit… it’s tight as fuck,” he groaned, hips jerking forward involuntarily. His cock bobbed, angry and trapped, the ring biting just enough to keep him aching and swollen without relief.
“Good,” you said sweetly, giving his balls a light squeeze. “That’s the point.”
The next three weeks were pure, delicious torture for him.
Jonathan walked around the house in a constant state of desperate, ringed hardness. The cock ring kept him throbbing 24/7. He’d pin you against the counter, grinding that hot, heavy dick against your ass while whimpering in your ear, “Please, baby… just let me put it in raw for five seconds. I’ll cum so fast you won’t even feel it.”
You’d reach back, stroke his trapped length, and feel how painfully swollen he was under the ring. He’d moan like he was dying, pre-cum smearing all over your fingers and your clothes.
Nights were the worst. He slept naked so you could watch him suffer. He’d wake up multiple times, cock purple and straining against the silicone, balls drawn tight. One night you woke up to him slowly humping the mattress, the cock ring still locked on, desperate little thrusts that got him nowhere.
“Jonathan,” you warned.
He whined into the pillow. “I hate you… but I love you. This ring is evil.”
By day twenty-five he was feral. You came home to find him in the shower, forehead pressed to the tile, water running down his muscular back while his ringed cock stood straight out, leaking steadily. He wasn’t even touching it anymore—just standing there throbbing, broken.
You took pity… sort of. You dropped to your knees in the shower and sucked just the swollen head into your mouth, swirling your tongue while he cursed and shook. The cock ring kept him from cumming no matter how hard you sucked. He was a babbling, desperate mess by the time you pulled off with a wet pop.
“Month’s almost over, baby.”
On day thirty-five, the second the clock hit midnight, you pushed him onto his back and finally slid the cock ring off.
The relief made him growl like an animal. His cock sprang free—thicker, darker, and angrier than you’d ever seen it. Veins bulging, head glossy and leaking nonstop.
Jonathan didn’t even give you time to speak.
He flipped you onto all fours, yanked your hips up, and slammed into you in one brutal thrust. You cried out as he bottomed out, stretching you wide after a month of nothing.
“Fuck—finally,” he snarled, gripping your hips hard enough to bruise. He fucked you like a man possessed—deep, punishing strokes that made your eyes roll back. The wet slap of skin filled the room, his heavy balls smacking your clit with every thrust.
“You put a fucking ring on my dick for thirty-five days,” he growled, pounding you harder. “I’m gonna fill this pussy up until it’s dripping for days.”
He came the first time with a loud, broken moan, burying himself to the hilt and pumping you full of a month’s worth of saved-up cum. Thick ropes flooded you, so much it leaked out around his cock and ran down your thighs. But he didn’t pull out. He kept thrusting through it, fucking his own cum deeper into you, still rock hard.
He flipped you onto your back, threw your legs over his shoulders, and drove in again. Deeper. Harder. The overstimulation hit him fast after so long denied, but he couldn’t stop. His thrusts grew sloppy and frantic, eyes glassy as sweat dripped down his chest.
“Baby… I can’t—shit, it’s too sensitive,” he gasped, but his hips kept snapping forward.
You pushed him onto his back and climbed on top, sinking down onto his raw, oversensitive cock. You rode him slow and deep, grinding your clit against his pelvis while rhythmically squeezing around him. Jonathan’s hands flew to your waist, fingers digging in desperately as his head fell back against the pillows.
Tears immediately welled up in his eyes. His mouth fell open, breath hitching into broken sobs as you kept working your hips.
“F-fuck—baby, please,” he cried, voice cracking hard. Tears spilled down his temples, then his cheeks, faster and faster. “It’s too much… I can’t—oh shit, I’m losing it—” His big, muscular body started shaking uncontrollably beneath you, thighs quivering, abs clenching tight as another orgasm built against his will.
You didn’t slow down. You leaned forward, bracing your hands on his heaving chest, and rode him harder, milking his overstimulated cock with your tight, wet heat.
Jonathan broke completely.
Loud, wrecked sobs tore from his throat as tears streamed freely down his face. His eyes were squeezed shut, mouth open in a desperate, whimpering cry. “I’m cumming again—baby it hurts—hurts so fucking good but I can’t stop shaking—please—” His voice dissolved into raw, tear-soaked whimpers and gasps. Every roll of your hips forced another sob out of him, his cock pulsing violently inside you even as his body convulsed from the overwhelming sensitivity.
He came apart with a shattered, sobbing moan, hips jerking up weakly into you as dry, intense spasms ripped through him. Tears poured down his flushed face, chest heaving with harsh, broken cries while his whole frame trembled violently underneath you. The overstimulation had him crying hard—actual heavy tears, face wet, lips quivering, deep whimpers escaping with every aftershock.
When it finally subsided he was utterly destroyed: a boneless, sobbing, twitching mess beneath you. You gently lifted off his spent cock, cum gushing out as it slipped free. Jonathan just lay there panting harshly, tears still rolling down the sides of his face onto the pillow, body jerking with lingering aftershocks as soft, exhausted whimpers left him.
You brushed his soaked hair back, leaned down, and kissed the tears from his cheeks and temples, tasting the salt on your lips.
“Cleanse is over, baby.”
He let out a weak, watery, tear-choked laugh, voice completely hoarse. “Best… worst… month ever.” His hand shakily found yours, squeezing tight even as fresh tears slipped out from the intensity. “Never… never doing that shit again. Next time you even mention a cleanse, I’m tying you up instead.”
You smiled softly against his lips. “We’ll see, horn dog.”
Jon just pulled you down onto his chest, still sniffling and trembling from the overstimulation, already half-hard again against your thigh like the greedy man he was.
