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.
