Training Toby

By Robert Louis / Robert Halstead

Published on Oct 21, 2023

Gay

EIGHT

Toby is crestfallen, especially since after being disciplined and humiliated, his usual reaction would be to jerk off, but he just can't now. He takes a pen and tries to stick it through the openings in his cage to caress his neglected little dick slumbering in its confined quarters, and this is even more humiliating. It really hits him hard right now that he no longer has the right to jerk off when he wants to.

Is he sure this should be his place? Can he really handle it? Can he truly trust Derek to know what is best, considering that Derek is also learning his way?

And at the same time, with all this lustful yearning, he realizes that he misses Derek so much and can't wait to feel one of his hugs even if he's going to be punished for doing something willful and irresponsible. And there it is, that idea: he is someone who gets punished by the guy he's falling in love with, and that's the way it's going to be.

He opens his computer and goes on to an communications app that has channels filled with clips of gay bdsm activity, strips naked, and starts to watch as much of it as he can stand. But damn, it's all so violent, and a lot of the Doms act like they despise their subs, and he realizes right then and there just how lucky he is that he doesn't have to take his chances in that sort of underground even though his head gets filled up with images and scenarios he never imagined possible. Would Derek bind him somehow when he's punished? Or will he be over Derek's knees?

Finally he turns off the computer. He sure does wish it were Sunday morning already so he can head home in his new car. "Home?" Where's that? With tears in his eyes he realizes that home is wherever Derek is. That's the only thing that makes sense.

He gets a text from August: "I gave Derek some ideas about how to punish you for leaving the party last night without asking permission or even without having the simply courtesy to let us know. Derek doesn't want to mark your body because he doesn't want the guys in the dorm to see you've been punished. I gave him some alternative ideas to try out. I hope he really hurts you badly so you never do anything like this again. Do not respond to this text. You no longer have permission to contact either one of us unless Derek orders you to."

Another blow to his pride, well deserved, he realizes. At the same time, however, he's greatly relieved that he most likely won't be subject to their treatment any longer.

He had trouble sleeping that night because he was so excited about getting to have Derek hold him again. Finally, at 3 am, he made himself some coffee and got on the road. He had arrived by 5 am since there was no traffic. He got to his room and was sound asleep by 5:30, remembering to strip naked in case he was still asleep when Derek got in. It felt so good to be back in that room again that he slept soundly and dreamed of Derek.

Before he knew it, Derek was not only in his dream but also in his room, bringing in his things and dropping them by his bed. His first item on the agenda was to go over to Toby, pull off the blanket and sheet, and snuggled up against him, slurping at his neck as Toby slowly woke up and started weeping. "What's wrong, baby?" "I'm just so happy you're here! It was so hard not sleeping in the same room as you, not getting hugs, not getting new rules to obey." Derek chuckled into the boy's neck.

"It feels so good having your jeans rubbing up against my bare skin. I missed that too."

"I missed spilling myself into your mouth, boy. But that's going to happen again very soon."

"How soon?"

"After I finish punishing you."

Toby's face falls, but inside he's actually excited if excited can include scared as well.

"So over the weekend I happened to meet a couple of men, friends of my older cousin, and they're both Masters, as in they have slaves. We had a good long chat and they gave me so many good ideas, including how to punish you without marking up your body. So anyway, boy, you're going to get two punishments. They helped me see why you deserve two."

"Why? What did I do?"

"Well, on a simply human level, two guys drove you to a party and expected to bring you back home, but you decided to leave early and never let them know. That's just rude, boy. You're 18, you should have better social skills than that. So that's punishment # 1. And then on a sub level, even though you were with two Doms, you decided to take off without getting any permission. Baby, you've simply got to get used to the fact that boys like you always need to be under someone's control. And if I'm not mistaken, you wish me to be the one that calls the shots in your life as your Dom."

"Yes, Sir, that's true. So are the punishments to be now?"

"Yes, I think that will be best. And then you can take a little break before you're able to show me how much you really do need to be under my control and my discipline."

Toby lets out a heavy sigh. "Wow." "Wow?" "Yes, just wow. So is this the time that I beg you to punish me?

"I guess you just did. But it's important for you to understand why this is now becoming part of your life."

"To help me improve my behavior?"

"Yes, and to help remind you if you're ever thinking of doing the same things again. Except for academic matters, boy, you no longer call the shots for what you do, where you go, etc. You must always make sure that I know where you are and that I approve of what you wish to be doing."

"I promise I won't do that again."

"I'm sure. And the punishment will help you reform your behavior, I'm sure."

"Will it hurt?"

"Of course. Punishment is useless if it doesn't hurt. But it won't damage you in any way, just give you pain. Humiliating pain. So let's get started. Stand in the center of the room."

Toby takes the position. Derek comes over with his thick strap. "Hold out your hand, palm up." Toby does. Derek raises the strap in the air and brings it down striking the boy's hand with great force. Toby immediately curled up his fingers and pulls his hand back. "Now the other hand," Derek orders. Same thing again. Now Toby is shaking both hands in the air. "Put the first hand up again." Toby fearfully does so and of course the second blow is even more excruciating. Toby looks at Derek wanting to beg for mercy, but he isn't surprised that no mercy will be given.

"Now for the second punishment. Put your hands behind your back." Derek binds them with a tie, not too tightly, but Toby's hands aren't up to any significant action at this point. Derek gives the next order: "Kneel." The Derek gets one of the pillows of the bed and puts it on the floor. Bend down and lie your head in the pillow like you're groveling." Derek helps him bend down and get settled.

"So, faggot, spread your legs a bit more so I can see your balls better. Then don't move." Derek reaches into his case and takes out a tube of ointment (Ben Gay) and puts some on his fingers. "Ass up higher, slut!" With that Derek leans down and rubs the Ben Gay into the boy's balls then stands back. "don't move."

It doesn't take long before some serious pain sets in and Toby starts to moan with all he's got, saying over and over, "I'm sorry, I'm sorry, I promise to be a good boy." Derek sits on his bed and watches his boy enduring the punishment. "They told me it would keep getting more and more severe until it hits its peak, then it will gradually calm down. Ride the wave, baby."

Sure enough, that is what happened. Toby was so relieved when the burning on his scrotum started to abate bit by bit. He ended up with just a simple moan. His inner slave trembled as he realized that both cock and balls were now under the control of the Master. Inspired by this realization, Toby burst out "I belong to you, Derek. You own me."

Things have moved along much quicker than Derek had planned. He, too, has to adjust to the evolving nature of their relationship. Ownership? That's pretty intense. From what place inside Toby did that word emerge? Or was it part of the conditioning that August and Eric started imposing on the boy? Nonetheless, it didn't matter where the sentiment came from.

Ownership. If that be the case, then Derek has to carry an awesome responsibility on his shoulders. But for him, it was motivated more by the feeling of falling in love with his sub than be any kind of kinky Master/slave dynamic. Can a Master love his sub? Derek had failed to read anything about that in his explorations of the M/s scene. But he knew that deep in his heart, it was true. The more power Toby so willingly agreed to relinquish, the move tenderly Derek felt towards him—even if, as he now understood, he would need to punish the lad to keep him acting and thinking in a way proper to someone who realized he was so much less than a free man.

Meanwhile, for Toby, groveling before Derek, spanked hands bound behind his back and a faint trace of the terrible pain he had felt between his legs, what pushed his buttons more than anything else was the fact that in this new way of life he was embracing, he was a boy subject to punishment at the whim of the Master. Yes, indeed, punishment taught him so much. He recalled something he had heard in one of the stories Eric had read to him: "a true slave begins to cherish the lash." And gradually, as he was groveling before this man he loved so much, Toby got a quick flash of imagination about the day he would walk naked to the showers with the stripes of Derek's belt visible on his ass. For him these stripes would make him proud for they showed that there was a man who was teaching him how to become the submissive he was meant to be. The other guys in the dorm might laugh at what they saw written across his backside, but he wouldn't have been surprised if there weren't maybe one or two who really wished they could be cared for in the same way. Yes, indeed, punishment was a way of caring for a boy like him.

Finally, when Derek decided the boy had calmed down sufficiently, he helped him kneel up, than stand. He embraced his lover and Toby was so happy to be "home." "Home," that's in Derek's arms. Derek pulled the sub to his bed and laid him down gently before getting on top of him and wrapping him in arms of love. For the first time ever, Derek kissed him on the lips and Toby instinctively opened his mouth to him and let Derek explore him with his tongue. Both boys rejoiced in the kiss. Toby sucked Derek's mouth; Derek let his juices flow into the boy's mouth. For a moment he stopped. "You like that, huh?" "So much, Sir, so much," was Toby's reply and so Derek deliberately made more saliva to feed his boy.

"When I was at my parents' missing you so much, I tried to write a poem for you but I never completed it."

"Do you have it with you?"

"Yes, Sir."

"Go get it and read it to me while you're kneeling here."

"It's not very good, Derek."

"I don't care. I want to know what was coming from your mind when we were apart from one another. Go and get it and read it to me, boy. That's an order."

"Yes, Sir." Toby retrieves his notebook, brings it back to Derek, kneels down and reads it in a hesitant voice as if apologizing for how unrefined it was."

"You have conquered me; I crave you now

and all you want for me. You make me safe,

compliant,

hungry for the taste of you.

Apart from you these past few days, I found it hard to breathe,

my clothing constricts me,

naked is the only way I should be

for you;

my true home is at your feet,

bare naked and shaved.

The guys in the dorm call me

"naked boy"

not knowing I am naked

because you want me that way,

to walk the halls nude,

tasting shame, learning that all of them

are my betters.

Such love I have

for you, my Sir, Your eyes, oh damn! your eyes

pierce mine

and lay bare

my most hidden secret

shameful desires.

You own me now: all I need do is relax and obey."

Derek is silent for a bit of time, taking it all in. Finally, he says, "I would like to set up a file for your writing. Type this up and put it in that file. I suspect more writing will follow. More beautiful, heart-rending writing. Keep all of it. Don't restrict or censor anything that comes from your slave heart. This will please me so very very much, my love." He stands up and takes down his pants and Toby helps him get them off his feet.

"Show me your gratitude for being punished like a bad boy." Toby bends down low again and kisses Derek's feet with his eyes closed. "A good start, boy, but there is more for you to learn now in light of what you have written." He unbinds Toby's hands. "Stroke my dick and get it hard." then, "put the tip in your mouth the way I've taught you. Stroke it to milk me, boy, just the way they taught you." Toby is happy to show Derek what he has learned about pleasuring a mans cock, but for Derek it is no longer enough. "Take your hand away, baby. it's time for you to become my cocksucker. Do with your mouth what your hand had been doing. Jerk me off with your mouth, boy. Take it all the way in as far as you can go."

And so, just like that, Toby sucks a cock for the very first time, and he tries so hard to get all of it into his mouth that he gags several times. Derek takes the back of his head and pulls him up by his hair. "Open your mouth." Toby does so. "Your mouth is feeling dry. Let me lubricate it for you. Close your eyes and keep that mouth open." Four times Derek gets some saliva and spits it into Toby's mouth and Toby's dick fights to get hard in its cage but to no avail. "Thank you, Sir," he says. "Now back down, Toby, but don't gag. Slow and steady, up and down. Work my tip with your tongue when you can feel it in your mouth, then slide back down again. Watch the teeth but apply as much pressure as you can. Yes! That's it, cocksucker. Pretty good for your first time. Suck my dick, baby. Make love to me, you little faggot. Show me what faggots like you love to do."

Oh damn! That talk! At last he can do what he's been dreaming of for weeks. He gets to worship Derek's dick like the cock-hungry slut he is, and nothing could be better. He'd endure any punishment, any indignity, any insults in order to feel his Master's warm pulsating cock in his mouth so he can give is as much pleasure as he possibly can. Derek's moans and gasps fill him with joy. At last. Yes, at last, and he prays that he will be able to do this every day of his life. The fact that his own little dicky is locked up and restricted makes it even more wonderful because he can pour all of his attention on Derek's cock with no possibility of selfishly trying to take care of his own. Now, for the first time, he realizes why so many subs and slaves eagerly accept the cage as part of their regular routine. The dickless boy labors over the Master's dick, and yes, he realizes that he's beginning to think of Derek as `Master' and it's okay. Derek is everything to him. He belongs to Derek. And now, Derek is giving him free reign to slobber over his awesome cock, to tease it with his tongue, and there is nothing better. No better place to be than right here between the Master's legs. Derek is lost in his pleasure. Toby is lost in his servitude, right where he has always been meant to be.

Finally, Derek tenses and cries out as he spills his cum into his boy's mouth and now at last Toby is able to actually use his mouth to milk Derek of his seed, and he swallows eagerly. "Enough!" Derek orders. "Get down and suck my toes, boy. Get the flavor of my cum and my toes all mixed up in your mouth." Toby eagerly obeys. From time to time, Derek wipes a bit of remaining oozing cum from the tip of his dick and reaches down for the boy to lick it from his finger. "For how long can you serve me this way without tiring?" he asks the sub. "Let's find out. Keep working until I decide you've done enough. Pull my belt out of my pants and hand it to me, but don't stop working on my feet," he commands. Toby manages to get the belt free and hands it to Derek who slowly and lightly begins to land the end of the belt over the back of his slaveboy slobbering at his feet. The belt feels tender as Derek lays it across him and Toby finds himself wishing for the first time that Derek would hit him hard enough that he would really begin to feel it. "Between the toes, boy," says Derek and he does swing the belt harder, but not enough to mark the beautiful smooth skin of the boy's back.

Toby begins to realize that just because he wants something to happen doesn't mean that it will happen. it's not up to him to decide. He is completely under the control of the Master. He wants to beg "hit me harder," but doesn't dare do so; it's not his place to choose how things will progress; it is simply his choice to surrender to whatever may, or may not, happen to him. Submission to the most intense degree. Unexpectedly, his phone rang.

"You may go and get your phone," Derek told him. He picked up and looked at his phone. It was Uncle Harry. Toby panics a bit and show Derek the phone. Derek takes it and answers.

Thanks for all the emails. Some have asked me what they should call me. My name is rob and I think of myself as a slave without a Master. So call me whatever you enjoy. If you are a Dom or Master, please humiliate me. I deserve it and don't get enough of it irl.

Please keep writing me. Emails are my reward for writing.

subkodak25@gmail.com

Other Stories of Mine: The Alex Chronicles Sweet Subjugation Tommy Loves His Sub

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Next: Chapter 9


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