Training Toby

By Robert Louis / Robert Halstead

Published on Oct 17, 2023

Gay

THREE

Toby was fortunate to end up with a nice roommate. Gordon College had an optional option on its information forms for a student to indicate sexual orientation. He left it blank, but when he found out who his roommate was supposed to be, he decided to come out right at the beginning so he could avoid any awkwardness later on. "I want you to know that I'm not sure about my sexuality but it seems that I'm mainly interested in guys. If this will make you uncomfortable, it's not too late to request a change. He got a quick reply from Derek, the potential roommate. "It's cool, whatever way you turn out, as long as we get along and can help each other out if needed. I'm pretty straight, but I haven't checked out the other option yet. So anyway, no worries, Toby, no worries. I'm looking forward to move-in day. I hope you are too."

And so that was a nice safe reply. Toby decided to show the emails to Nancy's Dad Ned, and he thought they were off to a good start. He told Toby he's also pleased to find out that Toby hasn't yet determined his orientation (although Ned was pretty clear that Toby was gay.)

Moving-in day came. Toby got there first and claimed his side of the room and by the time Derek arrived with his parents, Toby was already sitting at his desk and setting up his laptop to be compatible with the school's systems. As soon as Derek walked into the room the entire room felt brighter. And damn, Derek was beautiful! A little bigger than Toby but a similar build, dirty blond hair, green eyes and a kind face. "Studying already?" he asked.

"No. I just figured I'd get myself linked into the school email and Internet before I really needed to use it."

"See that, D?" Derek's Dad said. "Lucky you. You've got a roommate who knows his way around computers. I'm sure he'll help you hook up." "I know, Dad. What a relief. Toby, would you be willing to set me up too?"

"Not set you up, Derek, but I'll be happy to show you how to set it up and maybe even help you understand more about the way things work. That would be best."

"Smart man," says Derek's father, who was a larger version of Derek. When Toby stood up from the desk to shake the man's hands, he enfolded him in a warm hug that set Toby's heart blazing and Toby rested a bit in the man's hug for probably longer than he should have. But he'd seldom gotten anything but cursory hugs from his parents, who seemed to be getting colder and colder the more his father rose up in the ranks of his corporation. "Nice hug," said the man, who turned to Derek to say, "this kid is a good hugger, D. You'll do fine here." Then he explained to Toby that his family's love language was hugging, so he was glad to see that Toby wouldn't be freaked out by it. Derek blushed bright red and Toby couldn't get over how adorable he looked. Sure, he'd hug the big guy any time.

Once Derek was all unpacked and his mother made his bed for the last time, they wanted to take Derek out to lunch off campus to get away from all the traffic and they invited Toby to come along so they could get to know one another. He hesitated to accept but then Derek came over to him and put his arm around his neck and said, "You're coming with us, boy, even if I have to drag you there by the neck," and then lightly swatted his ass. Toby realized that he was in big trouble, especially when Derek called him `boy" and swatted him while having his arm around the smaller boy's neck. Toby interpreted what he did as a tiny act of aggressive domination. Damn, he was hooked!

They drove through the town and had no trouble finding several nice restaurants available. "Wow. Chinese even," noted Derek. "Let's go there." Derek's mother corrected him: "Don't you think it might be a good idea to ask Toby if he liked Chinese food?" Right away Toby jumped in. "I love Chinese food and seldom get it because my parents don't like it." "Well then, it's settled. Chinese," Derek announced and his parents chuckled.

As they were walking into the restaurant, Mack (Derek's Dad) held Toby back a bit to give him a piece of advice. "Son, never ever be afraid to speak up about what you like and what you don't care for. Never be afraid to ask D for anything at all. We're a fear-free family. I really respect how up front you were with D when you wrote him. Shows you're a man of integrity and courage. You'll always be safe with us."

Toby had to wonder just how safe it would be for him to confess that he already felt a bit bonded to this aggressive guy who would be his roommate for his first year in school. He decided to keep his own counsel for a while longer.

Derek was pleased to see that this Szechwan Palace had sushi on the menu along with standard Chinese food. "Ever have sushi?" he asked Toby. "The only way I like sushi is if it's breaded and fried," he answered and the whole family cracked up. "Well, you can expect me to try to take away your sushi virginity," Derek said to Toby with a wink. "You can take away any of my virginity you want, dude," Toby thought to himself. Anyway, he ordered one of the typical combination plates as did Derek's parents. "Breaded and fried," chuckled Derek's Dad. "I'll have to use that one at work. Mind if I borrow it?" he asked Toby. "Sure. It's not mine. I heard it from a comedian one time."

It turns out that Mack was a chemist and his wife Cindy worked as a guidance counselor in a high school one town away from where they lived. "Derek would have hated it to be in the same high school where I know everybody's secrets," she explained to Toby, "so it worked out well." She thought it was admirable that Toby's father was wise enough to realize how important it was to live on campus and said she was looking forward to meeting him some day.

Toby wasn't looking forward to that at all. His father had begun to believe that money was a love language. Before Toby went away to school, he bought him a brand new Volvo (very safe), but his parents weren't around when he left for school, nor did they come up to campus with him. Toby packed his car himself and drove off by himself to start college. The fact that he really liked his roommate and his family offset any disappointment he felt about his parents' neglect at such an important time in his life.

Toby really felt at ease with them. He never felt as if they were interviewing him; they let him free to decide what he want to share about himself and his family. Toby was an English major and Derek a theater major, so there was a basis for some interesting conversations. Toby understood right away why Derek was so laid back about homosexuality; he probably had many gay friends and acquaintances. He was also planning to audition over the weekend for a part in a play called the "Laramie Project." Toby had never heard of it before, so the rest of the meal was taken up with explaining about what happened to Matthew Shepherd and a bit about the play itself. Derek said he had a monologue to prepare for the audition and Toby immediately volunteered to help him get ready. "First you'll have to read the play," says Derek. "Is it easy to get?" asks Toby. "You can read my copy. It was also made into a movie. Maybe we could watch that together tonight." "I'm up for it," says Toby. "Good boy," answers Derek.

"boy" again. Why did it send chills up and down Toby's back? The food was wonderful. Derek ate with chopsticks; Toby could not. At one point Derek asked Toby if he'd ever tasted ginger, and he put a slice on his chopsticks and put them to Toby's mouth. "Take this and eat it," he encouraged. Again Toby felt as if he were commanded to obey. He sucked it from the chopsticks. it was pretty good. "Like it?" "I do." "Good. So now you know you can trust me when I want to put something in your mouth," Derek says out of the side of his mouth so only Toby can hear him. Again Toby blushes. Derek reaches down and squeezes his thigh. "Yeah, you'll do fine, baby," he adds.

Could Toby feel any more fortunate? Not only was Derek hot as hell, but it seemed as if he kept throwing kinky hints and overtones to the guy he started calling `boy' and Toby loved it. Derek was very nice guy and they hit it off right from the beginning. Toby is surprised, to speak the truth. He's usually found that guys as athletic and good-looking as Derek would look down on him, but Derek is not only nice, he's a lot of fun to be with. They had a couple of intense late-night talks that helped them get to know—and respect—one another. Derek admitted to Toby that he had a habit of always wanting to be in charge of things and that Toby should call him out on it if it got too much out of hand. Toby in turn admitted to Derek that it would most likely be okay, that he felt safe with him and was naturally submissive. He told Derek about his former friend Mikey and what had happened with him.

"He doesn't really sound like a very nice guy," Derek judged. "You didn't go along with what he wanted but he kept pushing the idea and it made you increasingly uncomfortable. It's a good thing that you ended up having to move away. I think he probably would have forced himself on you if you had remained. Just because we're guys doesn't mean that we don't have the right to refuse anything. I'd never ask you to do something that you didn't want to do or that creeped you or frightened you. I suspect I will be asking you a lot, so get ready."

Toby changed the subject. "Besides, his cock was too damn big," Toby said and then wanted to pull the words back into his mouth while Derek meanwhile broke out into loud laughter. "It was ugly," Toby said. Derek laughed harder. "So what do you think is a good size?" he asked. "I never ever though of something being a good size. It was just that his was too big. Besides, he knew that I'm not all that big myself and it was just a way of him making a point and trying to humiliate me. I've been humiliated enough about my size, all through school, and the fact that I didn't start growing pubic hair until the end of 10th grade." "So you're a late bloomer. So what? I promise I'd never make fun of you because of anything like that. In fact, I have an idea if you're willing to go along with it. . . " Derek says with a kind of pouty look on his face like he's really hoping Toby would agree.

"How could anyone refuse that face?" Toby asked himself. "What's your idea?" "We're talking about a lot of personal things, Toby. Maybe we should get physically personal as well."

"What do you mean?"

"Let's strip, both of us naked, and we can take a good look at each other and not have any secrets about that. My basketball coach made our whole team do that the first week of school. And it really helped. Showers was a lot less a problem because no one had to be afraid to look around wherever we wanted. So what do you say? I told you you could trust me. I promise I'd never make fun of you or say anything about you to anyone else."

Toby takes some time to think about it and realizes that he really would like to see Derek naked, so he agrees, trying not to sound too eager. So anyway, they make sure their door is locked and then stand at opposite sides of the room and Derek tells Toby to get barefoot as he strips off his own sneakers and socks. "Now shirts off," he says, and Toby obeys as Derek takes off his own. Derek holds his hands behind his head and says, "Come feel the hair in my pits and then I'll do yours." Toby gingerly steps towards him. "come on, don't be shy. See how bushy my pits are? Run your fingers through them." Toby begins. "Sniff them if you want. I'm not too stinky. I put on deodorant this morning and it hasn't completely worn off yet." Toby can't believe he's doing it, but he actually does step forward and put his face into Derek's pit and takes a sniff. "How's that?" asks Derek. Toby giggles as he gets more relaxed. "You're almost ready to turn stinky, but not yet."

"Ever sniff a stinky pit?" asks Derek. "No." "Some day you will, boy. Maybe even mine if I just skip using deodorant a day when I have practice and I'll save the smell for you to enjoy," he teased. Toby's face went bright read and to his dismay, he felt his dick getting hard. Derek keeps telling Toby what to do and Toby likes him more and more. "Okay, put your hands behind your head so I can get a look at your pits." Toby's pit hair is short and not plentiful. "Sweet," says Derek. It reminds me of my 14 year old brother's pits. He just started growing some hair there. Let me sniff." Derek goes to sniff but Toby puts his hands down and pulls back. "That's okay," says Derek. "I'm sorry I pushed too hard. It's always okay to say no to me, boy. don't forget. Stand here before me, please? Let me feel how nice and smooth your chest is, perfectly hairless. A lot of men shave their chests to get the look you have naturally." Derek runs his fingers up and down Toby's chest and then around his nipples. "Such nice little nubs you have there, Toby. Perky. Better than some girls. Can I squeeze them a little? I promise I won't hurt you."

By this point, Toby would agree to just about anything, so he nods and Derek holds one nipple between his fingers gently and then moves to the other. "So nice, boy. So nice. So go ahead, stroke my chest. Not too much hair, but there is a lot around my nipples. Kind of hides them." Toby blurts out something that really surprises himself. "Maybe you ought to shave them, just around them so they're not hidden."

"would you like to do that for me, boy?" "If you wanted me to, Derek, I'd try. But not tonight."

"Well then, it's time for pants to come off. What kind of underpants do you wear?" "The regular white ones my Mom always buys." "you mean little boy pants?" "I guess," says Toby. "never thought of it that way." "okay, drop the pants and let me see," says Derek, and as Toby complies Derek drops his as well revealing a nice pair of black boxer briefs and it's obvious that he is as hard as Toby is at the moment.

"What do you think of these?" asks Derek. "They look real nice. Much more manly." "Well then we'll have to go shopping soon and get you some. In the meantime you can wear some of mine since our waists are the same size." Derek goes to his dresser drawer and pulls out a pair. "here," he says, "just put them on your bed. You can try them on later and see if you like the feeling. But right now, we're obviously both hard. Time to get completely naked, boy. One, two, three, OFF!" Derek strips off his underpants and Toby, blushing again, follow suit. "Please don't laugh," he says plaintively.

"What's there to laugh at, baby? You've got a nice hard pecker there. And I like the way your tip is shaped. So what, that I'm bigger than you. Do you think that means anything? Does it make me better than you? Is that how you think about it, that the boys with smaller cocks should serve the boys with the bigger ones?"

Damn, that gets Toby hot, that idea. Derek has already noticed that he wears his reactions on his face, so Derek is getting more and more information on what turns Toby on. He stares at Derek's dick and it's a perfect size and shape for him, maybe about six inches, nicely cut, a good size around. Toby finds himself wishing he could feel it in his hand. "So there," says Derek. "No secrets from one another. Now I gotta tell you, I'm kind of an exhibitionist. I like walking around in my boxer briefs or even naked some times. If it bothers you, just let me know. But don't be afraid to take as good a look as you ever want to. I'm cool about that. Back home, me and a few other guys had this kind of "club," and we'd hang around one of our houses and get naked together and all of us would hang out like that for the entire night. Always okay to look. A few times, we actually ended up having a circle jerk, but not too often. We used to call it the "no secrets club." "Really? Wow. Never heard of such a thing. Anything else happen at those naked times?"

"Usually we'd end up stroking off. A couple guys got into giving hand jobs to one another. Then it turned out that Sammy, one of the guys, wanted to try sucking cock and it turns out he really liked it. We never made a big thing over it."

"Did he ever suck your cock?"

"Yes, a few times. He got really good at it, too. He used to suck off most of us, but not all on one night. One night when I shot my load he kept his mouth on me and let me shoot it into his mouth and then he actually swallowed it down. Holy shit, did that turn me on! Him tasting my cum like that. Have you ever tasted it?"

"Yes. Whenever I jerk off I always eat my own. Then I had these two friends, August and Eric, and one night we all shot our loads and then tasted each other's. I felt so dirty. Swore I'd never do it again but . . . "

"You really eat your own cum? Every time?" "Yes." "Damn! No wonder you have such a creamy complexion!" Derek bursts out into laughter. "So I think I'd like you to have a taste of mine since it's something you've already done before. Come closer. Wipe the head of my dick with your finger then stick it into your mouth. Would you be a good boy and do that for me? Let me watch you put my precum into your mouth. Come on, baby. Make me happy by doing that."

Toby's blood began pumping faster as he reached out his finger and touched Derek's boner and took his precum into his mouth. "Good boy!" says Derek with a big smile on his face. "Come on. Take some more." Toby obeys. "Don't be afraid to admit you like it, boy. Nothing to be ashamed of. In fact, it makes you real special in my book, I promise." Toby is blushing like crazy, but feels safe with Derek. "I guess I should admit that it's true. I do like it. At first when I would eat my own, I made out in my head that it was something humiliating." "You dig that, being humiliated, Toby?" "Sometimes, but nothing too extreme. There were some bullies in my old school that really got too intense with me. I was relieved when we moved away from there."

"Why? What would happen?"

"Sometimes they'd get me somewhere and strip me naked then watch me jerk off and then lick my cum off my hand. But a couple of them started slapping me around and I got really scared around them."

"You didn't like getting slapped around?"

"It wasn't that as much as it was the way they'd make fun of me and call me names. I was afraid I was gonna get beat up. That wouldn't be any fun at all."

"Damn, Toby, this is all getting me so fucking hot. I need to shoot my load right away." Derek jumps down on his bed and furiously strokes his dick and then finally cums all up his abdomen and chest. Toby stands there watching, fascinated, while very slowly running his hands over his own dick. Once Derek's breathing settle down, he says in a sexy-sounding voice. "Okay to come over here, boy. Taste as much of me as you want. Just a little or maybe all of it. Whatever makes you happy. It's all here for you, Toby."

Toby slowly makes his way over to Derek's bed and bends over to scoop up some of it off his chest and then puts it in his mouth. "Holy fucking shit! Amazing, dude. Come on, take some more." And Toby does. "Baby, if you want, you can lick it all off me. I'd love that." But Toby has had enough. He backs off and starts stroking himself more intently and, when he finally does cum, he shows it to Derek and then begins to lick his hand clean, realizing that he hasn't done this in front of anyone since he left that school three years ago. Derek sits up, grabs his dirty t-shirt, and wipes himself down.

"Let's go shower, kid," he says to Toby. "I want you to walk naked down the hallway to the showers. Don't worry if anyone gives you a hard time. I'll take care of you. Go in and start showering. I'll come a little after you bringing a towel. I'd like other guys on this floor to get to see your cute little dick." Toby seems to find it impossible to refuse to do anything Derek asks him to do. He craves the humiliation, especially since Derek is so kind to him and makes him feel special. And safe.

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 4


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