Even though Stan had asked Kyle to ride him after the events that had transpired during their last sleepover he'd changed his mind after learning that Kyle was a virgin, claiming that he wanted to make it special. So, instead they'd jerked and sucked each other off a few more times before passing out from exhaustion. Stan had even let Kyle come in his mouth saying that it was only fair. That part hadn't really mattered to Kyle. He was just happy that Stan had been willing to suck him off at all, but it had been pretty cool to watch Stan licking the remanence of cum off his lips.
After that night their weekly sleepovers were back on. After school on Fridays they'd go to Stan's house and head straight up to his bedroom and lock the door. They would strip down, crawl into bed, and fool around until they got hungry or fell asleep, but it had been a month since they'd started this and they still hadn't taken it any further. Kyle was getting worried and impatient.
"Why haven't we had sex?" Kyle blurted out one Friday as they were walking home from school.
"Uhh...you know..." Stan stammered to come up with an answer.
"No, I don't know. That's why I'm asking. We don't have to if you don't want to. I just want to know what's going on dude." Kyle was starting to feel self-conscious now that he'd voiced his concern.
"I do want to do it...it's just...can we talk about this when we get to my house?"
Stan looked around the quiet suburban neighborhood as if he was expecting someone to jump out and bust them, even though they weren't doing anything. Kyle just nodded in response. They continued the rest of the walk in silence. Kyle felt so stupid. He knew he'd eventually fuck this up, but he hadn't expected to do so this soon.
Instead of going up to Stan's room when they got to his house, Stan decided to take an interest in helping his dad try and fix the dishwasher. Kyle just sat at the table pretending to look over notes from his calculus class. After Stan and his dad failed at the dishwasher project Stan suggested he and Kyle eat dinner with the family instead of ordering takeout like they usually did. Even though he wasn't hungry Kyle didn't object, it wasn't like he could say "Sorry, Mr. and Mrs. Marsh, I don't have much of an appetite because my stomach is in knots over my sex life with your son."
"You wanna go to the arcade?" Stan asked after they finished washing and drying the dishes for his mom.
"Uhh...I was actually thinking I should go home." Kyle didn't want to stay there if Stan didn't want him there.
"What? No. Why?" Stan's voice was laced with panic.
Stan caught Kyle by the arm just as he bent down to pick up his backpack off the kitchen floor.
"Because you said we'd talk when we got here and you've barely said a word to me all night. Plus, you've done everything you possibly could to avoid being alone with me and now that we are alone you're trying to find another way out of the situation."
Kyle shrugged out of Stan's grip.
Stan sighed and ran his fingers through his short black hair, but the silky straight strands fell right back in place over his forehead. Cerulean eyes wouldn't meet Kyle's and it was so frustrating.
"So, yeah. I'm going to leave." Kyle didn't know what else to say. He and Stan had never had a problem talking to each other before.
"Don't, " Stan whispered just as Kyle reached the kitchen doorway.
"Why not?" Kyle didn't even turn around.
"Come upstairs...I wanna tell you something."
Stan was beside him and tugging on his arm a few moments later. When they got up to his bedroom Stan locked the door and plopped down onto his bed. Kyle sat down beside him.
"Stan, come on, man. You gotta tell me what's going on. I'm your best friend."
Stan finally looked at him. The intensity in his eyes made Kyle's cheeks flush the color of ripe strawberries.
"Kyle, I thought we were more than that. " Stan's eyes looked sad.
"Well, we are, but I'm always your best friend first. So talk to me."
Kyle could see the relief wash over Stan. Kyle waited as patiently as he could, but he needed Stan to say something before his head exploded. Just as he was about to threaten to leave again Stan cleared his throat.
"Uhh…Kyle, remember how I said I wanted to fuck you?"
"I thought that's why we were having this conversation."
"Yeah, well…remember how I said I wanted it to be special because it was your first time?"
"Stan, that doesn't matter to me. It'll be special because it'll be with you." Kyle threw his hand over his mouth but it was too late, the words were already out there.
Stan smiled at him for a brief second before returning back to his serious expression.
"Kyle, this will be my first time too…you know with a guy. Me and Wendy…you know…the summer before junior year."
Kyle didn't want to think about Stan having sex with Wendy; he was already jealous enough of her as is.
"Since, neither one of us have been with a guy like that before and I really do want to make it special for you, I did some research." Now Stan's cheeks were turning a little pink.
"Okay, so what's the problem?" Kyle wasn't getting whatever point Stan was trying to make and he felt like an idiot.
"Fuck…I don't know how to say this." Stan fell back on the bed and threw his arm over his face.
Kyle had had enough of all of this. He climbed over and straddled Stan's hips and leaned down until their lips were just a breath apart.
"Stan, I don't know what you came across during your research that has you so scared, but I've done my own and I really don't think it'll be that bad. I've been keeping myself extra clean back there…you know just in case you decided you were ready and even practiced stretching myself."
Stan groaned and Kyle felt his cock stir beneath him. Kyle was so glad Stan wasn't looking at him because he was so embarrassed.
"I'm not scared. It's the opposite…Kyle, I'm so sorry."
"Sorry for what, Stan. Dammit, spit it out right now or I'm going to punch you in the face."
"Kyle, I want you to fuck me…okay. I got so turned on by the stuff I saw I started thinking that I wanted you to fuck me. I already blew my first time, so I know it's selfish to try and rob you of yours but it's all I can think about when I see you." Stan barked up at him.
Kyle gasped. Of all the things he had expected to hear that had not been one of them. The two just stared at he each other, Stan looking terrified and Kyle so confused he was sure his eyes would pop out of his skull.
"I knew you would think it was weird."
Stan turned his head away since with Kyle straddling him that was all he could do to get away from him.
Kyle forced the words in his head to come out of his mouth. "I don't think it's weird or selfish at all. It's hot…I just never thought you'd be into something like that."
"Why not?" Stan still wouldn't look at him.
"Because you always like to be the in charge. I just figured it applied to every aspect of your life."
Stan didn't say anything else, just stared across the room. Kyle reached down and softly turned Stan face to look up at him and then leaned down and placed a quick kiss on his lips.
"Stan, if you want me to fuck you all you had to do was say so," Kyle whispered the words into Stan's slightly parted lips.
They both shivered in response to Kyle's words. This wasn't usually like him, but if this was the only way he could have Stan completely then he'd have to push his shyness aside. Kyle climbed off of Stan and lay back on the bed, propped up on his elbows.
"Get up and strip for me," he tried to keep his voice as serious as possible, but on the inside he was so nervous.
Stan looked at him utterly confused at first.
"Do you want me to fuck you, Stan?"
Stan nodded.
"Then get up and strip for me, now," Kyle repeated.
Stan slowly got up from the bed and went to stand in front of Kyle. He reached for the hem of his shirt and began to pull it up his body.
"Go slow," Kyle instructed partly because he wanted to savor the moment and partly because he wanted to by time to come up with the right things to say.
Stan slowed his pace and inched the material of his t-shirt up his torso for Kyle's pleasure, before he tugged it over his head and tossed it onto the floor. Next Stan worked on his jeans. Kyle watched enraptured as Stan exposed more and more of his body to him. Stan's cock was already starting to peek out of the front of his boxers, seeing that made Kyle's cock thicken in his own underwear. Kyle quickly removed his t-shirt, but kept on his jeans and boxers, feeling more in control like that.
"Now, your underwear," he told Stan.
Stan slid his boxers down his legs and then kicked them into the corner with his jeans. He looked so fucking hot standing there completely naked, with his cock hard and twitching in front of him.
"Stroke you cock." Kyle licked his lips.
"Kyle," Stan moaned in protest.
"You've done it before. I'm telling you to do it again."
"It's different now," Stan whispered.
"How?"
"It was dark before, plus I didn't know you were watching back then."
"I want to see you clearly, so the light stays on, but you can just pretend I'm not watching if that makes you feel comfortable."
"How am I supposed to do that, Kyle?" Stan whined.
"I don't know and I honestly don't care. The longer you make me wait the longer you're going to have to wait for me to fuck you." Kyle was actually starting to like this whole being in charge thing.
Stan sighed with a pout, but then reached down and began to stroke his thick cock, stopping to twist at the head every so often. Watching this had Kyle rock hard in no time. Stan's eyes slid closed and he moaned as he fucked his own hand at steady pace.
"Stop," Kyle demanded when he started to suspect that Stan was getting close.
"Why?" Stan groaned.
"Because I want you to suck my cock. Get it ready for your tight little ass, Stan."
Dirty talk had always been something Kyle was self-conscious about, but when Stan moaned and immediately dropped to the floor in front of him he felt proud of himself for that little gem. Kyle watched as Stan gently reached out and undid his jeans and pulled out his cock. Once it was free Stan wasted no time before starting to bob his head in Kyle's lap, coating his shaft with spit from the head down to the base. Whatever Stan couldn't reach with his mouth he jerked off with a firm grip.
"Fuck, that's it. Take all of my dick, slut," Kyle whispered the same words Stan had said to him during that first infamous sleepover.
Stan moaned in response. Kyle gripped a fistful of Stan's hair in both hands and began to fuck his mouth more forceful than he ever had before. Feeling the head of his cock hit the back of Stan's throat made his eyes roll back in his head. Kyle didn't stop until he started hearing Stan gag. That's when Kyle roughly pulled Stan off of his cock by his hair and stood up. He couldn't help but smile as he looked at the cock hungry look on his best friend's face as kneeled beneath him.
"Get on the bed."
This time Stan didn't hesitate or ask questions. Stan crawled up onto the bed and lay down in the center.
"Spread your legs for me," Kyle instructed as he removed his remaining clothes.
Once again there was not hesitation from Stan. Kyle climbed back onto the bed and settled between Stan's legs so that they were face to face. He descended on Stan's mouth with a need so desperate he thought he might consume the other boy. He used his tongue to fuck Stan's mouth the same way he'd used his cock to moments ago, but eventually they both had to come up for air. Kyle didn't let himself relax too long before he slid down Stan's body and began to suck on his nipples.
"God, yes. Kyle, that feels so fucking good," Stan moaned as he ground his cock up against Kyle.
Kyle reached between them and took both of their cocks into his hand as best as he could and began to stroke them together until both of them were panting and on the verge of coming.
"Kyle, I'm so close. Please fucking me," Stan begged beneath him.
"Not yeah," Kyle said as he slid down Stan's body even further.
Once he found a good position between Stan's spread legs he zeroed in on his target with his tongue. Stan slammed a pillow over his face and cried out the second Kyle's tongue started swirling around his puckered, virginal ring. God, Kyle wished that Stan's parents weren't home so he could hear him moan. Stan humped his hips up into the air as Kyle explored deeper inside his ass with his tongue. It wasn't exactly what Kyle imagined it would be or taste like, but that didn't matter because Stan was enjoying it.
Once Kyle had Stan's hole thoroughly coated he reached out and rubbed a finger over his entranced. Stan moaned from under the pillow again.
"I'm going to stretch you out, okay?" Kyle's controlled demeanor started to slip; he didn't want to hurt Stan and knew he needed to prep him first.
He heard what sounded like a muffled okay from Stan as he coated a finger with spit and moved it back to Stan's hole. He slowly pressed it in and watched as Stan's body tensed at the invasion. He stroked it in and out of him slowly until he could get it to move freely, then he pulled it out and coated another finger with spit to join the first, but stopped before putting them in.
"Dude, you have any lube? This would be better for you if I had lube."
Stan pulled the pillow from his face and nodded towards his nightstand. Kyle hopped up and reached over and rifled around the drawer, finding a half empty bottled of baby oil.
"Someone's been busy," he remarked with a smirk.
Stan tossed the pillow back over his face in embarrassment. Kyle went back to his previous position between Stan legs. This time he coated his fingers with the baby oil before pressing them against Stan's entrance. There was still some resistance, but not as much as he was sure there would've been if he hadn't used the oil. He stroked Stan's insides slowly just like before. He licked and sucked on Stan's balls to distract him when he started to wince after Kyle began the scissoring motion inside of him. He'd read about that online during his own research. Kyle's own cock was almost painfully hard and he knew he couldn't hold out for much longer so he hoped Stan was ready.
Kyle crawled back up Stan's body and settled between his hips with the head of his cock poking against Stan's well-prepped asshole.
"Kyle, put it in. I need you inside of me."
Kyle nodded and began to push forward. Stan bit down onto Kyle's shoulder as the head of his cock broke through Stan's barrier. Kyle winced from the pain of the bite, but kept pushing forward until he was halfway inside of Stan.
"God, I thought because you were smaller than me this would be easier," Stan confessed through heavy pants.
"Sorry, we can stop." Kyle offered even though that was the last thing he wanted to do.
"No, keep going I want this."
Kyle nodded and thrust his hips with a little more force, causing more of him to slip into Stan's body.
"Fuck," Stan hissed. "All of it, I want all of it."
Kyle could see that Stan's need to be in control was starting to creep back, so he pulled back until he was almost all the way out of him
"What are you– Ugh."
Before Stan could finish his question Kyle slammed back into him, forcing his entire length into Stan's ass.
"You son of a bitch," Stan growled up at Kyle.
"Well, you said you wanted all of it, now you have all of it."
Kyle began to pull back out of Stan again and just as he went to speak again he slammed his dick back into him. Kyle repeated this until Stan stopped trying to form sentences and just took what Kyle was giving him. Stan moaned and clawed at Kyle's back as Kyle fucked him relentlessly, driving them both closer to release with each thrust.
"God, you dick feels so fucking good. Don't…don't stop fucking me, Kyle." Stan groaned as Kyle slammed into him roughly.
"You like that don't you, Stan? You love having me shove my cock up your tight little ass," Kyle whispered into Stan's ear as gripped onto his hips for dear life.
All Stan did was moan, "yes" over and over again in response.
"No, say it Stan. Say you love having me shove my cock up your ass." Kyle was back to feeling brave.
"I love it, Kyle. I love having you shove you hard cock inside of me. I want you to come…I want you to come inside of me."
Kyle couldn't believe his ears, but before he could say anything in response his dick took it upon itself to do just that. Kyle whimpered and shook as he sprayed Stan insides with load after load of cum. He didn't even know it was possible for him to have that much inside of him. After awhile his legs gave out and he collapsed on top of Stan.
"That was so fucking hot," Stan said as he stroked Kyle's back.
Kyle just nodded.
"But, Kyle…I didn't come."
Shit! Kyle had been caught off guard and hadn't made sure to get Stan off before he shot his load. He carefully pulled out of Stan, who winced in pain. Kyle felt a little guilty for getting so rough with him his first time, but Stan had practically begged for it. He sluggishly made his way back down Stan's body and took his impressively hard cock into his hand.
"Kyle," Stan called out softly.
"Yeah."
"Can I fuck you now?"
Kyle's ears and cock perked up at the thought of that; Kyle was nodding and turning around to present his ass to Stan within seconds. Kyle had love being on top, but since he'd first watched Stan jerk off he'd imagined what it would be like to have Stan fuck him.
"I should only need some lube and a little stretching." Kyle's entire body began to blush as he said the words over his shoulder.
Stan nodded and grabbed the bottle of baby oil. He popped open the cap and poured some directly onto Kyle's ass and began massaging his eager hole.
"That's it, moan for me, baby."
Kyle hadn't even realized he had been doing that, but wasn't surprised. Stan slowly slipped one finger inside of Kyle, which Kyle immediately began to rock back against.
"More, I can take more." Kyle groaned, as he moved himself back even faster on Stan's finger.
Stan promptly replaced one finger with two and began to finger Kyle faster and harder. Kyle buried his face in the blankets to muffle his screams.
"Stan, fuck me before I come again. I want you inside of me when I come this time," Kyle begged from the foot of the bed.
Stan pulled his fingers from Kyle's ass and immediately began to press his fat cockhead into Kyle's opening. Stan was bigger than Kyle so even with the prep it still took some time for him to bottom out. Once all the way inside Stan leaned forward and planted soft kisses on Kyle's neck, shoulder, and back until Kyle gave the go ahead for him to move. Once Stan had permission he started pumping into Kyle like a madman and Kyle loved every second of it.
"Your cum is dripping out my ass while I fuck you, Kyle. Does that turn you on?" Stan asked as he slammed into Kyle harder than before and just ground himself inside of Kyle.
"Yes," Kyle cried out as Stan churned his cock inside of him. That was literally the sexiest thing Kyle had heard in his entire life.
"Do you want to taste your cum?"
Kyle quickly nodded then felt one of Stan's hands shove him further down into the mattress before he began to shuffle around behind him.
"Here you go."
Stan held up a single finger with a thick glob of cum on it. Kyle stuck his tongue out and let Stan smear his own cum onto his tongue. Even after his cum was gone Kyle licked and sucked on Stan's finger.
"You really are such a slut, Kyle, eating your own cum after it's been up my ass, while I fuck you. Only a slut would do that."
Kyle knew it was true and the thought only made him harder and he started to stroke his rejuvenated erection in time with Stan's rough pounding in his ass.
"But, you know what Kyle?"
Kyle shook his head.
"I like that you're a slut, because you're my slut. Isn't that right?"
Kyle pulled his lips off of Stan's fingers, knowing he'd want verbal confirmation.
"Yes, Stan, I'm your slut." Kyle moaned just at hearing himself say those words.
"Good boy, but just so you don't ever forget I'm going to shoot my load in your ass as a reminder every time we fuck, so you know who you belong to."
"Yes…yes." Kyle fisted his cock even faster and slammed back onto Stan's dick harder. "Fuck, I'm going come again." Kyle cried out only seconds before erupting all over his hand and Stan's blankets.
"God, you're even tighter around me when you come," Stan growled before he started to spasm and explode inside of Kyle's well-used ass.
They both let out another slew or curses as they continued to fuck at each other until their bodies were so sensitive it hurt and they had no choice but to separate.
"So, how was your first time?" Stan asked after awhile.
"Incredible," Kyle replied.
"Ditto," Stan said in return as he scooted over and spooned up against Kyle's backside.