Training Toby

By Robert Louis / Robert Halstead

Published on Oct 18, 2023

Gay

FOUR

The following week, Derek has decided that he likes to have Toby walking the hallway naked and this becomes routine and Toby never objects or questions it. Even though some guys have given him scornful looks. Sometimes when they shower together Derek only brings one towel with him. Once he gets dried off, he tosses the damp towel to Toby and Toby has to do his best with Derek's used towel while Derek stands there watching him, then takes the towel from him and wraps it around his waist and heads back to the room, leaving Toby to follow naked and still pretty damp.

That Saturday, Derek takes a garbage bag and tells Toby to throw all his white boys' underpants in the bag to throw into the garbage. He's been giving Toby a fresh pair of boxer briefs to wear every three days but promises that he'll take him shopping for his own black pairs. They head to a discount big box store so he can have Toby get his own boxer briefs, which, although also solid black, are not nearly as nice as the ones Derek wears. They come in packages of five. "That's perfect," Derek tells him. "One pair every three days so you have a two week supply."

An older man overhears what he says to Toby and cant' help remarking how most guys put on a fresh pair of pants every day. "That's true, Derek answers, but Toby isn't like most guys. He needs me to help him realize that he's inferior to us. That's important to him." Toby blushes beet red and gets nervous because the man looks at him with a ravenous look in his eyes. "Tell me more about this inferior status," he asks Derek, but Derek, sensing Toby's unease, doesn't answer him. He throws his arm around Toby and walks him away.

"You okay?" he asks Toby.

"Now I am. Thanks for getting me away from that guy. He had a really hungry look on his face. I was afraid he was going to offer to buy me for a couple hours."

"What if he did and I agreed? Would you have let me give you to him for a couple hours?"

"The idea is hot as hell, but only as an idea. I'm not ready for anything that crazy. That would be taking too much advantage of my submissiveness."

"Noted," replies Derek. To change the subject he asks if Toby would take care of both their laundry from now on. By the middle of October, Toby's taking care of all their laundry and keeping the room clean because Derek's sports schedule takes up a lot of his time. One night, Derek lightly suggested that Toby be nude in the laundry room, but he can tell from the look on Toby's face that it's a bit much for now, so he changes his mind, and gives Toby one of his addictive warm hugs to reward him for being "such a good boy for me," as he puts it. Always, Derek has Toby's best interests at heart. He thinks the smaller boy is adorable and thoroughly enjoys making up new and creative ways to keep Toby turned on by the humiliation he seems to need more and more as they continue to "make progress" in their relationship. Derek sees it as a continuous process of taking charge of Toby because one night Toby admitted to him that he really likes feeling like Derek is in charge of so many things in his life. That earns him an hour of awesome hugs when they get back to the room, Toby naked while Derek is still dressed in jeans and a sweatshirt. His belt buckle makes marks in Toby's sensitive skin and when Derek realizes this has happened, he decides to remove his belt in the future. Nothing should ever mar the creamy complexion his little buddy was gifted with. They've talked about this late at night, usually with Toby naked in Derek's bed being held in his arms while Derek is wearing his underwear. "I like it when you're naked, Toby boy, especially when other guys in the dorm can look at your little dick and your baby-smooth skin whenever they see you." A few of the other freshmen in the dorm have begun calling him "naked boy," not in a mocking way, but rather simply as an affectionate nickname. One night, Toby takes a big step and reminds Derek how he had wanted him to do the laundry in the nude and simply says, "I'm ready to do that now if you still want me to."

Derek can't say enough about how happy this makes him and how proud he is that the boy is ready to take this step. "I know it will be good for you, baby," he says. "If I had my way, I'd have you going to class naked too, but I don't think the administration would be terribly happy about that." During these blissful times before sleep, Derek likes to get as much information as he can about Toby's reaction to the things that are happening between them, always making sure that he makes no "requests" that take Toby out of his submissive mind space by suggesting something that Toby isn't ready to handle. After all, they're both pretty new at this, so they have work together to makes sure Toby is always turned on by what they're doing and never fearful or uncomfortable. Toby confessed to Derek one night that he loves how protective Derek can be at times, especially when he's uneasy about something or when anyone at all gives him a hard time.

Obviously, no one knows that Toby by now often tastes Derek's cum like it's his duty. One night, after they'd smoked a joint earlier and Derek just finished cumming, Toby went over, bent down, and licked the tip of Derek's dick and clean his piss slit. Then he licked up the rest of Derek's cum off his body. Derek promises him that he'll never give away that secret because it would embarrass him as well if anyone knew. "But you know what would make me very happy?" he asks Toby one night. "On the nights when I have play practice I'd love to find out that you find someone else to play with, someone else's cum to taste. I don't want you sucking anyone's cock yet until after you get used to sucking mine, but maybe we can find a way to get the message out there that you're a cum slut. We'll have to figure out something about that." In the meantime, they both jerk off every night before going to sleep, and eventually Derek decided he wanted Toby to cum first and eat it off his hand before he has to clean up Derek's cum. He watches Toby shoot his load, and then only after that does he shoot his own and have Toby lick it all up off his spluge from his body. Toby was a bit confused about this change in plans until at last Derek explained that by making the boy "service him" after cumming himself, he's sure that Toby is doing it as an act of humble submission to his superior roommate.

One night when Derek was in a particularly frisky mood after smoking a joint, he ordered Toby to kneel at his feet and when it was time for him to shoot his load, he was to cum on Derek's feet. Then he wanted Toby to lick up his cum off Derek's bare feet. Toby resisted at first, so Derek was going to let him off the hook, but first he appealed to the boy's growing submissive nature. "I want you to show me how much you worship and adore me, Toby. I want to see you submit to me this way. If you're a good boy and do it for me this once, I won't ask you to do it again unless I feel you need to be punished for being too uppity with me. Understand, boy? So make me happy. Show me how much you want to please me, how much you want to humble yourself before me." Toby shed a few tears, but finally bowed down to the floor and did what Derek wanted him to do, and once he thought he was all finished with the humiliating task, Derek raised each of his feet in the air and made him lick him clean between his toes as well. Toby obeyed, but it turned out that he was licking up tears as much as cum that night. Once it was over, Derek treated him like he was the most precious little boy he had even had the joy of taking care of and how proud he was of him. Funny sort of contradiction. By humiliating himself more than he ever had done before, it made Derek proud of him. Go figure.

When at last, Derek sent Toby back to his own bed for the evening, before he fell asleep, Toby realized that Derek had purposely introduced a new concept into their relationship. The possibility, or rather, the reality of the fact that there were going to be times when Derek felt it necessary to punish his little cum-licking buddy as an attitude adjustment. This both turned Toby on and frightened him, and he made it point to raise the issue during their next nightly chat, wanting to know if Derek was really thinking that he should be punished at times. "I don't see any reason to punish you to correct your behavior or your attitude now at all," explained Derek, "but let's face up to the fact that the time will come when I decide it must happen." "Yes, Sir," answered Toby, indicating that the message came through loud and clear and that Toby realized that he was truly becoming a sort of submissive slave to his awesome roommate. The "yes, Sir"'s were coming from his mouth more and more frequently lately.

The night before they were going to leave for Thanksgiving vacation, Derek told Toby that he's really like to shoot his cum directly into the boy's mouth that night so he could have it to remember while they were apart from one another. Toby's eyes grew wide but then Derek ran his hands over the boy's eyes, forcing him to lower them in a submissive gesture and he replied, "yes, Sir, but how do you want to make that happen?" "I've got it all figured out, boy. I want you to put your mouth around the crown of my cock and hold it there while I jerk my shaft until I shoot my cum into your mouth," he replied. "come here and kneel down before me and once I get hard, put me in your mouth and think about how hot it's going to be when I shoot down your throat, baby." Toby was trembling inside with excitement and humiliation as Derek stood over him, got hard and ordered, "Okay, boy, put my dick in your mouth the way I told you I want you to." Toby obeyed and it didn't take long for Derek to shoot his load, so turned on by this new act of degradation he had come up with to give Toby something to think about over the vacation. So turned on by this did Derek become, that after Toby had swallowed his load, he ordered the boy to kiss his feet as a sign of his submission. After all that, Toby got a very special hug before he was sent off to bed and this time, for the very first time, Derek actually kissed him on the cheek, praising him for all the progress he was making as Derek's personal cum slave. That was the first time Derek had ever kissed him and also the first time he had ever used the word "slave." Toby trembled over that throughout the vacation.

The next day, before they both left to go to their respective homes, Derek asked Toby to give him August's phone number so he could call August and explain this new way he was getting Toby to take his cum and suggesting that August think of using him the same way while he was back home. Toby's first reaction was to resist, but Derek gave him such a stern look that Toby didn't dare refuse. This was the very first time that Derek didn't back off when Toby hesitated or resisted. Another notch in Derek's belt, Toby realized. He thought about this a lot over the vacation, especially when August invited him over the day after Thanksgiving.

"Derek called me, you know. We had nice long, hot chat about how he was taking care of you. He gave me some ideas for things to do this weekend, and I gave him some ideas about things he might want to consider for your future." Toby wallowed in the humiliation, but also was anxious about the fact that Derek and August seem to be sharing him and teaching him new things. Anxious and turned on at the same time.

Please let me know what you think. 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 5


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