His Father's Tough Love Ch. 05

That night, after his father had helped him to his bed and tuck him in for the first time in more than a decade, he stared at the dark ceiling, unable to fall asleep. He turned to his side to stare at the clock on his bedside table and watched the minutes tick by, turning into hours.

Even though his inflamed erection had been iced down to its flaccid state and locked away in the cage, it had only gotten rid of his erection temporarily but had done nothing to extinguish the burning need for release in his loins.

Soon after the cage had been locked and he had been tucked into bed, his shaft had returned to hardness, pressing against the bars of its captivity. His penis hardened as much as it could, trying to swell in girth and length only to find that the chastity cage was even smaller than his little 2 inch flaccid penis, not allowing it to grow into its 7 inches no matter how hard it pressed against the confinement.

Lifting the covers from his nude form, he turned on he bedside lamp to see what it looked like.

With a horrified gasp he shut his eyes. The sight that greeted him was just as bad as it felt. How his erection had been crammed into such a small nub of a cage he couldn't understand. It had already been tight and too short for even his flaccid penis, now he suffered with the reddened flesh that tried to climb out between the steel rings. His crown pressed hard against the end of the cage, keeping him in constant pain from the purple cockhead trying to break out.

He touched his testicles. Despite his fervent attempts at getting an erection, nothing could be done to achieve one so he could give himself an orgasm, to release the pressure as he did almost every morning.

It also didn't help that his genitals, especially his penis had been slapped and punished quite vigorously by his father several times that day as one of several punishments for being reckless and almost knocking a girl up.

Theo tried to see if he could, perhaps, masterbate even in his locked up state, after all, some parts of his dick peeked through the cage. Just as soon as he tried, he gave up. With the bars of the cage in the way, it just didn't feel good to run his hand up and down his cramped length. He also found that the stimulation was cancelled out by the pain of such a large organ being squeezed so tightly.

He turned his attention to his balls. He had heard some guys enjoyed playing with them but he had never really tried it. Despite his lack of a real erection, his testicles were forced close to his body, the cockring pulled his usually loose scrotum tight so his orbs were clearly defined.

His fingers traced along the skin, enjoying how smooth it felt. It was the first time he was without pubic hair and he had to admit it felt great compared to the bushy hair that used to obscure his private area.

He tried to pull on his testicles, but it was already pulled tight and hurt a little; after all, they had also been spanked for their part in the almost-fiasco of getting a girl in trouble.

Quickly finding there were no pleasure in pulling on his testicles, he was out of ideas. He had no idea how some guys liked to play with them.

His hand moved down to the newly smooth area between his balls and anus. He rubbed the soft skin, slightly wet from sweat. His finger arrived at his wrinkled anus. He remembered how large it had had to open for the plug he wore earlier, and was worried that it might still be gaping open.

He quickly jumped up to find a mirror, but the sudden movement made his penis hurt as it was still trying to harden in the cage and it was very uncomfortable for something that was so tightly packed to have to move.

He slowed down his movements and cupped his hurting sex in his one hand so it didn't shift with his movements as he walked to his bathroom for a mirror.

Under the bright light the difference between his sore, red sex bulging between the slats of the chastity, and his natural olive skintone everywhere else was striking. But there was nothing he could do about it, so he resumed his quest to see how his slightly sore anus looked after the ordeal of figging and plugging it had been through.

He bent over, his bottom facing the full length bathroom mirror. His hands pulled his bubble butt apart so he could see the little entrance between them.

In the mirror, between his olive buttcheeks, was a small, tightly wrinkled pucker that was only slightly red. He was relieved that it seemed to have contracted back to its original dimensions. Without thinking about it, his finger sought out the little pucker, tracing the tight ring. The gentle finger brought back the longing to have something embedded inside, made him miss how full he had been with the thick plug inside.

As soon as he realised what he was doing, touching such a forbidden place and on top of that wishing for it to be filled, his mother's words came back to him. This was an off limits area for him to touch.

Yet his father had touched it and it had felt so good, especially when he had removed it and it had grazed that special spot inside his rectum, he though dreamily.

The painful twitching of his cupped cock snapped him out of it. Any thoughts of sexual pleasure had to go as it only worsened the pain and deepened his need for release.

He went back to bed, once again laying on his back or side. He usually fell asleep on his stomach, but it hurt too much to even think of laying on his imprisoned, bulging penis.

Then he gave up.

He would have to beg his father to allow him some release, to open the cage so he could feel better, so he could sleep. No matter how embarrassing, without it he would go mad.

With that decided, the next issue was whether to put on pants or not. It would be doubly embarrassing to flaunt into his sleeping father's bedroom to beg on his knees for his father to allow him release, to flaunt how weak his will was, to flaunt how pathetic his penis looked to be allowed to be stuffed so painfully into such a small device that completely emasculated him.

On the other hand, if he wore pants he would give himself a little bit of dignity, if there were any left after all he had been through that day, every part of him his father had already seen, his secret virginal hole fingered, his pubic hair shaved and his penis locked up. The down side was, his poor, obviously suffering cock would be out of view and his father might now believe him about how much pain he was in, how the small cage really compressed his natural generosity. He might not feel the pity he might otherwise feel if he did see the red, sad state of his once proud erection.

Theo thought it over and decided that his dignity had already been destroyed. No private place unseen, no natural reaction remained a secret from his father whom had even seen his cock in accidental orgasm that morning.

So, cupping his member in his hand to protect it from as much movement as he could, he walked shamefully to the master bedroom.

Knocking on the door softly to rouse his father, he felt like a toddler again, waking his parents after the time he had wet the bed.

A few knocks later a drowsy, "Come in," came from inside.

The bedside light turned on just as he walked in.

"Theo, what is wrong? Are you all right?"

"It... hurts, dad. I know we agreed to only remove it for the first time this Saturday, but it is so uncomfortable, it hurts so much I can't sleep," Theo finally removed his hand cupping his embarrassment.

His father was alarmed, seeing first the redness of his son's shamed face, then the state of the member that he had been so impressed by a few hours earlier. It was now like a red sausage squeezing out of its casing. Although he had managed to force the flaccid version into the cage with just a little effort, it was obvious that now that it was aroused, it must be in a lot of pain.

"Oh, Theodore..."

"Please Dad!" Theo begged.

Unbeknownst to Theo, his father had also been laying awake, worried that he had been too harsh on his son. After all, everyone makes mistakes from time to time, and seeing how his son suffered from something that he hadn't meant to make his son hurt, just control him, was too much to bear.

"I'm sorry... I didn't mean for it to hurt you so," he said sadly, his eyes still on the member trying to become erect, the balls so tight in their sac they had to hurt.

"That's okay dad, just please let me out!"

"I can't," his father said, leading him over to the safe. "This is a time locked safe. I had set the timer to only allow me to open it on Saturday."

Theo's stomached dropped as he stared at the digital display on the safe that read: Locked for 5 days, 10 hours and 11 minutes in crisp red letters.

"Can't you override it? There must be some code to make it open earlier!"

"No, I had bought this one specifically because it was perfect for making sure I kept my own schedule. There's no way to open it earlier. I'm so sorry."

Theo's mind stopped working, he was openly crying, begging incoherently. The pressure was so great that was all he could think of, all that mattered was orgasm.

Seeing his son break down like this broke his heart. Even when he was locking his son up he was worried that it was too extreme. Now he had to do something, anything to remedy it, to make Theo feel better.

"What can I do, Theo? How can I make this better?"

"I need to cum! Please, please, please!" Theo begged, no longer able to even try to save any dignity. All that mattered was an orgasm.

He was crying and mumbling plies for help, for release without any clear idea how his father might practically help him now that the key was more than 5 days out of reach.

He couldn't stand to see his son so broken, sobbing so sincerely. His mind worked quickly, remembering how his son had enjoyed the thick slide of the buttplug he had worked in and out of his anus a few hours ago.

Since he had long suspected his son to be gay, he had done some basic research on gay sex and relationships to offer guidance if Theo had ever come out to him, which he never actually did. But that came in handy now, knowing about how some men could reach orgasm through stimulation of the anus and prostate.

Without further hesitation, he pulled the crying Theo onto his bed, letting him lay on his stomach. But Theo cried out in pain as his overstuffed organ was crushed under his weight in the unforgiving steel cage. He jumped over onto his back, hand rubbing the now extra sore flesh.

"Sorry," his father breathed, hand moving automatically to sooth the hurt. His hand rubbed the part of the exposed crown through the cage bars, kneaded the tight testicles until he received a pained moan from Theo both enjoying and hurting from his actions.

He grabbed the lube and guided Theo's thighs apart for the umpteenth time that day, but for the first time for Theo's pleasure. He spread them wide so he could sit right in front of the groin, bending the legs at the knees.

The position granted him an excellent view of the little pucker of his anus that his father now knew was still virginal. From his reactions earlier, he deduced that before that day, he had never even had a finger inside of that tight orifice. So far, the only things that had ever been inside his son's little flower had been his finger when he inserted the ice, and the ginger buttplug he had forced inside right after.

With a dollop of lube on his finger, he warmed the liquid between two fingers. With gentle pressure he massaged around the anus again, surprised that as soon as he applied any pressure, the little hole puckered open just a tiny bit. It seemed the muscle was still slack from the plug he had pulled out a few hours ago.

Taking the pucker as an invitation, he slid a slick finger inside to the first knuckle. The tightness contracted around him and Theo pushed against the invading finger with a moan so that the whole finger slid in.

"Oh... ahh..."

His father tried to twirl his finger around so he could stimulate the prostate, but instead, Theo's hips began riding the single digit, moans continually falling from his lips.

"More, please!"

With a little more lube, a second finger joined the first. He scissored them with the hope that one of them would touch Theo's prostate. Failing to locate the nub he had read about no matter how he twisted his fingers, hut noticing that Theo was loving the stimulation of just his anus.

"Oh, please, dad put in something bigger, please let me cum, it hurts so much to try to get hard in this cage!"

For the first time he wished that his ex wife had left some sex toys behind after she moved out, but he had never found any. He didn't have any of his own. While he was puzzling over that, Theo's hands reached out in blind pain and pleasure, and grabbed his own hard flash through his pyjama pants.

He couldn't help being hard. He had always been dominant, both in life, in the workplace and in the bedroom. It always fired him up to be in charge, to have someone at his mercy. And right now his cock didn't care that the one at his mercy, begging, was a man. Nor did it matter that he was his son. His cock loved the situation and had already started seeping precum, staining his pants. As he slept nude, and just pulled on some old pyjama pants when his son had knocked, his erect cock was very prominent, proudly pushing the material to a large tent with a wet patch at the very tip.

The hand blindly reaching to grab onto something drove his primal brain to the edge. His own lusty, thick cock wanted to fuck, wanted to drive into a wet, tight hole. His son wanted something larger than his fingers in his virginal tight hole. No more thought was needed.

He drizzled lube along his own hardness, rubbing it in to make his cock shine. He kneeled between the splayed thighs, his cock as hard as it had ever been ready to mount the slender boy that was so eagerly begging beneath him.

Angling his erection to point at the small, quivering entrance, he let his poke against, as if he was going to penetrate immediately, before letting the length slide down between his cosy cheeks.

The perky bubble butt hugged his length as he slid teasingly over the little hole and back down to the buttcrack so he could enjoy the please and groans that fell from his son's lips, encouraging him to take his son.

Finally he had enough of the teasing and from the looks of it, Theo was incoherent, desperate for the only thing that could bring him relief right now.

He tapped the cockhead against the pucker, a bit of his precum splashing on impact.

He looked at Theo's face, to make sure that he wasn't going against his wishes. Theo's eyes were bloodshot and red from crying, his body quivering and his poor member were trying to squeeze through all the small openings of the cage to try to obtain the erection, and thus orgasm, it so wanted.

Slowly he pushed through the tight ring. At first it was easy enough to begin his slide inward as the plug had slightly loosened him up earlier. But then the inner muscles of Theo's virginal channel tired and clamped tightly against the intruder.

With difficulty, his father paused so the previously innocent flower of Theo's anus could clench as tightly as it needed to, before it blossomed open so he could slide the rest of his length inside.

Despite how much his pained, cramped member had made him want this, need this release that only his father's thick rod could provide, he suddenly didn't know if he could bear the pain of having his little opening stretch so much. But his father was gentle with him, pausing when he was balls deep inside so Theo could get used to opening to the sensation while his father gently brushed the damp hair from his forehead.

A little while of being soothed by encouraging words from his father, the pain receded and he was ready for more.

The wide girth in his delicate rectum began to recede, pulling the entire cock from Theo's hole with a pop. He looked on in wonder as his father dripped more lube onto the twitching manhood that curves slightly towards his father's stomach.

The the head quickly nudged at this loosened slit, immediately pushing in with a single push until the full, rounded testicles slapped against his bottom, still red from the spanking earlier.

Sparks flew behind Theo's eyes as the thick helmet of his father's cockhead slipped past that magical spot the buttplug had so briefly teased earlier.

His head fell against the pillows and his open mouth couldn't form coherent words. Fortunately his father immediately understood and began to rock back and forth against the spot until Theo's spread legs wound themselves around his father's waist, afraid that the magnificent erection might go away.

An unfortunate effect of the incredible pleasure of having the cock nudge his prostate was that it seemed to encourage what was left of his formerly proud organ to rebel against the poor, locked up little dicklet it had been forced to become.

His pecker hardened against the bars but was smaller than it used to be while soft. His cockhead couldn't even emerge from its leathery turtleneck of a foreskin to weep its tears of desire, making a wet mess inside his foreskin before dripping over the steel rings of his chastity cage.

His father began making full strokes, pulling out so only his head was inside the shuddering channel before slamming back so his balls could bounce against his ass and his entire cock could once again enjoy the tight, hot channel that seemed to be milking the thick cock while it thrusted in and out so it could massage the jewel of pleasure hidden in Theo's rectum.

Losing any sense of space or time, all that mattered to Theo now was the erection inside his tight heat, weeping its own liquid love, mingling with the ample lube his father had used to make sure is pucker wasn't permanently damaged from accepting a ramrod this thick to take his first fucking.

The better it felt, the more and harder his father stoked against his prostate, the worse the head of his penis hurt. It couldn't understand why it couldn't swell and take on its manly form, couldn't understand why, despite the pleasure, it was still small and soft and hidden in its own foreskin.

The pain grew too great and his cock seemed to give up on its erection, his flaccid cock still too big for the tiny cage, but was no longer actively hurting itself by straining against the unmoving bars. Suddenly, he could feel only pleasure, could really enjoy not only how great it felt to have his prostate worked but also the finer pleasure of having his sheath fucked by something that was obviously just too large to fit inside such a small place. He finally felt the pleasure his mother had made him ashamed to feel, the joy of his sphincter gasping open to hug and clench around a thrusting manhood.

The lube made each thrust squeak, his channel clenched and unclenched to bring them both more pleasure.

When the pain from his cock faded away, Theo could focus on other things and finally noticed that his father, always so in control, seemed for once to also be trying and failing from suppressing faint moaning from the tight channel locked around his cock.

Theo's heart thudded quicker, knowing that he was the one bringing his father to the edge of his control.

Despite the fact that he no longer even had a chubby, his soft, small, compressed cock still signalled its enjoyment by leaking trails of silvery precum all over his cage and crotch.

Finally he couldn't take it anymore as his father's rock hard manhood ground against the sweet spot again. His hips jerked upwards, his balls tightened even more in their already tight sack, and his soft cock jumped within he cage as it spewed his cum all over himself and his father's stomach.

The orgasm felt different, the pleasure originating from a different place than his usual masterbatory sessions, or even the few times he had managed to orgasm while on viagra when having sex with Carmen.