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Stiles had a new roommate named Derek, who, despite being straight, didn't seem to mind at all that Stiles was gay. In fact, Stiles got the feeling that Derek was kind of curious about it. Right from the beginning, it was clear that Derek was comfortable hanging out with Stiles and his group of gay friends, which was a refreshing change compared to many straight guys Stiles had met before.
Derek was a freshman who ended up being Stiles’s roommate after Stiles's previous roommate decided to drop out. This new living situation turned out to be a pretty interesting dynamic. Derek was still figuring things out, and as he spent more time with Stiles and his older friends, he seemed to be soaking up their vibes. Instead of feeling awkward or out of place, Derek blended in and engaged with the group, showing a level of openness that Stiles appreciated. It was nice to see someone who wasn’t just tolerant, but genuinely interested in being part of their world.
But then, something completely unexpected went down. One night, Stiles returned to their room later than usual and stumbled upon a scene that caught him off guard. There was Derek, lying in bed, and the moment Stiles walked in, he quickly yanked the sheets up to cover himself, his cheeks turning a deep shade of red. Stiles couldn't help but think he had just caught Derek in a rather private moment, likely in the middle of taking care of himself.
It wasn’t the first time Stiles had suspected this; after all, when you share a space with someone, you start to pick up on certain habits. You hear the subtle sounds that hint at late-night activities, and you can’t help but notice the crumpled tissues scattered around in the morning. It was almost a running joke between them, even if it was unspoken. Stiles often chuckled to himself about how Derek seemed to have a habit of indulging in these late-night sessions. It added a strange layer to their roommate dynamic, making it all the more interesting.
Derek didn’t say a word. He just lay there, completely frozen, still blushing like a tomato. Seeing this, Stiles decided to have a little fun, so he yanked the sheets away from Derek. What he saw was quite the sight: there was Derek, fully exposed, with his body on display and his erection standing tall. While the hard-on wasn’t shocking, what really caught Stiles off guard was the unexpected addition—a dildo was sticking out from Derek's backside!
"Well, looks like someone’s been exploring a little," Stiles teased, a smirk creeping onto his face.
Derek stuttered, trying to find his words, “I—uh—I just wanted to see what it felt like to have something—uh—back there.” He was blushing intensely, and despite the awkwardness of the moment, there was something endearing about how flustered he looked.
Stiles had always had a hunch about Derek, sensing that he was on the verge of coming out. Derek was undeniably good-looking, and it was clear that the girls on campus couldn’t help but drool over him. Yet, he hardly seemed interested in their attention, which left Stiles wondering what was really going on in Derek's mind.
Taking a seat on the edge of his bed, Stiles glanced down at Derek’s impressive erection. “Why don’t you turn around?” he suggested, sensing that Derek was willing to go along with whatever he proposed at this point.
Derek complied and turned over, exposing his muscular, well-defined backside, with the pink rubber dildo hanging provocatively between his massive hairy cheeks. Derek was a real catch—he played on the baseball team and had a body that could turn heads. Stiles couldn’t help but admire him for a moment before reaching out to grab the dildo, twisting it slowly and teasingly inside the jock.
Derek let out a low groan at the sensation, instinctively pushing back against Stiles's hand, clearly enjoying the moment. At that point, Stiles felt a rush of confidence in his instincts about Derek—his gaydar was definitely on point.
“Doesn’t that feel good? You wouldn’t be able to move it around in there like that all on your own, would you?” Stiles teased, grinning at the black-haired jock. He leaned closer, bringing his lips near Derek's ear, and added, “A rubber one’s nice, but how about we see what a real cock can really do for you?”
There was a time when a friend of Stiles had pushed Derek about his experiences, and Derek had insisted he was straight, claiming he’d never hooked up with another guy. It seemed likely that was true since, with Stiles and his crew, Derek had nothing to hide.
Suddenly, Derek turned to face Stiles, his big, soulful eyes wide with surprise.
“I—I would. I’d like that. I really would,” he whispered, his voice barely above a breath.
With that, Stiles carefully pulled the dildo out of Derek’s eager ass and set it aside. Then, feeling a rush of confidence, he started to strip off his clothes while Derek watched intently, his eyes lighting up with excitement at the sight. Derek had seen Stiles's cock plenty of times before, but never like this—never when it was fully erect. Now, it stood proudly, all nine thick inches of it. Stiles could have sworn he saw Derek’s jaw drop and his green eyes widen in disbelief, almost as if he were mesmerized. He’d noticed before, during gym showers, how Derek would sneak a glance at him, but this time it felt different—there was a hunger in Derek’s gaze.
“Wow, you’re really hung,” Derek managed to say, his voice filled with awe.
“Is it too big? Does it scare you?” Stiles asked, half-joking.
“Uh—no—it’s—it’s beautiful. I love it!” Derek exclaimed, his excitement palpable.
“Then hold it. Take it in your hand,” Stiles encouraged.
Derek’s hands shook slightly as he wrapped his fingers around Stiles’s rigid shaft for the first time. Even though he might not have touched another guy before, he was no stranger to his own body, so he knew exactly what to do. As he began to stroke Stiles’s stiff member, he looked up, his eyes filled with longing. Stiles recognized that look all too well; it was the unmistakable gaze of someone who was eager to please and receive cock, the look of a bottom. And that suited Stiles just fine because he had always preferred to take the lead in these situations and be the top. He liked being in control, guiding things in the direction he wanted them to go and Derek’s big ass deserved to be topped and get the best experience.
“Take it in your mouth!” Stiles urged Derek, waving his cock in front of him while he reached around to pull Derek's head closer. Without hesitation, Derek opened his lips wide and hungrily wrapped them around Stiles’s shaft, all the while looking up at him. Stiles couldn’t help but admire how handsome Derek looked in that moment; his lips stretched around Stiles's thick cock made him look especially cute.
It was one thing for Derek to handle Stiles’s dick with skill, especially since he claimed this was the first cock he had ever touched aside from his own—and Stiles believed him. But now, as Derek licked and sucked, he seemed like a natural, as if he had been doing this for ages. Maybe he had practiced with that dildo of his, or perhaps he just had a knack for it. Some guys have that instinct from the very first time they take a cock in their mouths. Stiles remembered his first partner telling him that he was one of those lucky ones.
“Can I see your ass?” Derek asked, his tone playful.
“Is that all you want?” Stiles replied, a hint of playfulness creeping into his voice.
“Uh—no—” Derek stammered, his cheeks flushing again, which only made him look more appealing.
“What else do you want?” Stiles pressed, eager to hear Derek admit it.
“I—I want to lick it!” Derek blurted out.
Stiles recalled how, back at the gym, he’d caught Derek not just sneaking glances at his cock but also checking out his ass with that same curious gaze. So now, Stiles turned around, presenting his smooth, rounded backside to Derek, making it clear what he wanted. He even reached back to spread his big cheeks apart, giving Derek an unobstructed view of his pink and tight asshole.
“Lick my ass! Eat my fucking hole!” Stiles commanded, his voice low and demanding.
Derek didn’t hesitate. He dove right in, his tongue exploring Stiles’s crack with enthusiasm, as if he had been craving the taste of a guy’s ass for ages. Stiles let him savor the moment, enjoying the attention as Derek feasted on him before turning back around.
“You’ve never done this before? Eaten out a guy?” Stiles asked, genuinely curious.
“No, never, I swear!” Derek replied, looking both excited and nervous.
“Well, you sure seem to have a taste for it,” Stiles teased.
“And for this,” Derek said, taking Stiles’s gargantuan cock back into his mouth, sucking eagerly.
Derek was really getting into it, his enthusiasm clear as he took Stiles’s shaft deep. But Stiles’s cock was eager to fill another part of Derek now. That’s how all of this had started—when Stiles caught Derek with a dildo up his own ass. Now that Derek's backside was empty, Stiles was more than ready to fill it. With his nine thick inches, he was prepared to give Derek an experience he wouldn’t forget.
“Turn over and get on your elbows and knees,” Stiles instructed, and Derek quickly complied, presenting his bubble butt for Stiles. Stiles held Derek’s hefty cheeks apart, noticing that he was still slick from the lube he had used earlier. But Stiles was thicker and longer than that dildo, and despite all the play, Derek was still a virgin. Stiles wanted to make sure Derek enjoyed his first time, so he knew he needed to ensure that Derek's ass was well-prepared. He reached for his tube of lubricant sitting on the dresser, squeezing a generous amount onto his fingers to get ready.
“Let’s get you all set,” Stiles said, giving Derek’s ample derriere a light slap as he applied the slick lubricant into Derek’s crack, working it in thoroughly. Since Derek had already played with his dildo earlier that night, Stiles wasted no time in slipping three of his fingers into Derek’s eager hole. The black-haired jock gasped, instinctively pushing back against Stiles’s fingers while looking over his shoulder, his eyes now filled with desire, clearly ready to devour Stiles’s cock.
“You’re about to get fucked for the first time, Derek,” Stiles stated, emphasizing the moment. “You’re going to take a cock up your ass. And not just any cock—my nine thick inches. What do you think about that?”
“I say fuck me, bury it deep inside me, and really go to town on my tight fat ass!” Derek groaned, his urgency palpable as he craved the sensation of Stiles’s massive cock.
With that, Stiles withdrew his fingers and took a moment to admire Derek. There he was, completely exposed and vulnerable, his well-lubricated hole staring back at Stiles like a target. Stiles took hold of his own cock, rubbing the smooth head against Derek’s slick opening, smirking as he watched Derek start to thrust back, eager to feel Stiles’s dick.
“Yeah, I’m definitely going to fuck you hard,” Stiles said, still teasing as he pressed the tip of his cock against Derek’s lubed hole. Derek pushed back eagerly, clearly wanting to take it in. Stiles began to push inside, slowly working the tip in. He loved the visual aspect of sex, and his gaze was glued to the spot where his cock was beginning to greet Derek’s greased entrance. As Stiles slid in bit by bit, Derek gasped and groaned, feeling every inch as Stiles filled him up, stretching him wide. This was a significant moment for Derek—his first time—and it was one that would stick with both of them. Stiles reveled in the sensation of being the first to claim Derek, who was clearly ready for this experience.
“Everything okay?” Stiles asked, checking in, though the way Derek was moaning and pushing back told him everything was just fine.
“Oh yeah, I love this!” Derek panted, a look of sheer satisfaction on his face.
Stiles could see the joy in Derek’s green eyes, and he was determined to make this a memorable experience.
Stiles had only had a couple of encounters with virgins before, and those times were nothing like this. The guys he had been with previously could barely handle him for more than a minute, often backing out because he was too much for them. But Derek was different; he had prepared himself well, and now he felt incredibly tight around Stiles’s cock. Stiles loved the sight of his dick disappearing into Derek’s inviting hole, a sight that ignited his inner exhibitionist.
Feeling incredibly aroused, Stiles began to thrust into Derek, who was taking it like a champ. He had started the night as a virgin, but now he seemed to know exactly what to do. This only fueled Stiles’s desire to keep going, his thick shaft sliding in and out of Derek’s eager asshole.
“Are you having a good time?” Stiles asked.
“Oh, yeah!” Derek grunted, breathless. “Fuck my ass, just like that!”
Stiles appreciated Derek’s enthusiasm as he pushed back against his thrusts, wanting every inch and needing it hard. But Stiles decided to tease him a bit, slowing down the pace, pushing inside Derek slowly, inch by thick inch, before pulling out just as slowly. He made sure to work every inch until all nine were buried deep inside Derek, his balls slapping against Derek’s plump and jiggling cheeks as he pumped away. Finally, Stiles left his cock buried inside, twisting his hips in a circular motion.
“Oh God! Oh fuck! I can’t believe how amazing this feels! I’ve wanted this for so long, especially from you!” Derek confessed, his excitement clear.
“Glad to be of service,” Stiles replied gruffly, leaning closer. “I’m going to make you my little fuck boy; your ass is going to know my dick really well.”
While Stiles wasn’t strictly a top and enjoyed sucking and being penetrated himself, he knew that with Derek, he would primarily be taking the lead and be the top. He also wanted to make sure to get a taste of Derek’s impressive cock someday, but for now, it was all about the rough action.
He pushed Derek down from his knees onto his stomach and began to really pound into him, pinning him to the bed. Derek gasped and groaned, gripping the sheets as Stiles continued to thrust into him, the bed springs creaking with each powerful movement. Derek was clearly eager to submit, squirming as Stiles jackhammered into him.
Eventually, Stiles shifted to lie on his side, bringing Derek down with him. This position allowed him to reach around and grasp Derek’s cock while he continued to thrust. Stiles enjoyed this position, especially as they neared the end, having Derek’s hard dick as a handle while he kept pumping away.
“I’m going to make you cum, and then I’m going to cum inside you,” he whispered in Derek’s ear.
“Wait a little longer, okay? I want more, I really need it!” Derek begged, his desire evident.
Stiles could tell that Derek was a greedy one, a true glutton for pleasure. He was the perfect match for Stiles’s stamina, a true powerbottom is what the jock was. Pulling out, Stiles climbed back on top, facing Derek, watching his handsome face contort with pleasure as he continued to hammer into him. As he thrust, he reached down to stroke Derek’s cock.
“Shoot it for me, Derek,” Stiles urged, twisting his hand around Derek’s shaft. “Let me see you blow a nice, big load.”
Suddenly, Derek gasped, his body arching as he released, a powerful wave of pleasure washing over him as he sprayed himself. At that moment, Stiles let go as well, filling Derek’s hot, newly-fucked ass with his own release, leaning down to kiss him, their cum mixing between their lips.
Once they had both caught their breath, Stiles pulled out and lay beside Derek, who had a look of pure contentment on his face. With a satisfied smile lighting up his features, Derek leaned down and gave Stiles’s cock one last devoted kiss. Stiles knew that from that moment on, Derek was now a willing devotee to his thick, pleasure-giving shaft.
“I feel like a new man,” Derek said, looking up at Stiles, his expression blissful.
“You should,” Stiles replied, “because you’ve just been fucked!”
“And not just any fuck, but by you and your beautiful cock,” Derek whispered, continuing to kiss Stiles’s still swollen shaft, Stiles smiled as it was pretty obvious what the power bottom jock was doing by bringing Stiles’s big cock to life again, eager to get more cum up his greedy asshole.