Summary: Dean and Castiel are best friends in high school. Dean is a player with the girls and Castiel is a virgin. Castiel finally decided to come out of the closet to Dean, nervously. Dean wants to make sure.
Ring. Ring. Ring.
"Hello?" Dean answered his phone. He leaned back on his bed and relaxed, stretching his legs.
"Hey." Castiel responded, simply.
"What's up, Cas?"
"There's something I want to tell you. Can I come over?"
"Uh, sure Cas. My parents left to do some stuff. They'll be gone a few hours and Sammy's studying with some people. So, yeah, you're good."
"Okay. I'll see in a couple minutes, Dean." Castiel abruptly hung up the phone, grabbed his house keys and headed towards the door. His thoughts started to wonder about his upcoming confession. What will he think? Will he still be my friend? Will he abandon me? He's my best friend. He cares about me, right? Mr. Player and get all the girls. Hm. He finally decided to just wait and see. After a couple minutes of walking down the street, he arrived on Dean's doorstep. He knocked on the door.
Dean opened the door. "Hey man, come in. I got something to show you, up in my room. Let's go. So fucking awesome." Dean motioned to the stairs and Castiel followed his friend into his room for the hundredth time. Cas walked in and plopped down on a bean bag on the floor. "So, what's this thing?"
"Dean, cursing. You know I don't like you to curse around me." Cas reminded.
"Yeah. Sorry. Mr. Religion. So…uh, you first. What'd you want to tell me?" Dean grinned back.
"Um, I asked first, man. What's the secret?" Castiel flashed a mischievous grin to the teenager.
Dean grabbed something off his desk and turned around. He tossed a bag to the nerdy teen. As Castiel peeked inside the bag, Dean started to unzip his old, worn out jacket.
"Oh my- No way, Dean. How'd you get your hands on these?" Castiel's mouth hung agape as he stared at the shirt in adoration.
"Vintage Metallica classic tees from an actual concert. I guess this can be our birthday presents to each other for what I busted my ass getting them. Welcome, man. Be rockin' these, and maybe you can finally get a girl. I mean come on man, its senior year and you haven't gotten laid. We gotta issue here." Dean winked and teased the nerd.
Castiel laughed slowly. "Uh, right. Um, look Dean. That's sort of what I wanted to tell you. Since, you're my best friend and all; I really wanted to tell you first. Something I sort of discovered, I guess." Castiel looked up at a confused Dean.
"What, dude? You can tell me." Dean beamed, wondering what he could have kept from him.
Castiel swallowed and stared at the floor. He suddenly looked up and locked eyes with Dean. "Dean, I'm gay."
Dean just stood there for a minute, thinking. He finally said something. "Are you sure? I mean, like how do you know? Have you been with either?"
"No, but I mean- Um, this is awkward, but I find more pleasure when thinking of men when, you know-" Castiel tried to explain.
"I see. I support you completely if that's what you're looking for here, but man, to be honest; I think you should experiment to make sure. It's different. Trust me, thinking about someone and being with them, you're hands roaming their body, kissing, it's a different feeling." Dean smiled.
Castiel sighed. "I'm glad that you're not homophobic or anything."
"What? No, man, that's totally cool." Dean insured his friend.
"Okay. Um, one question though. How do you suggest I go on with this experimenting thing? I'm open to it and all, but I'm not exactly the girls image of Mr. Sexy or the guys' either."
"Dude, you are attractive. You just need to not look like a church boy. Let me help. First, don't comb your hair. Wild looks better. Messy is hot. Second, don't tuck your shirt in. And wear this jacket. Now, there. Look at yourself. Much better." Dean said as he fixed him up. "Hm…How to get a girl…" Dean pondered. He looked out the window. "Dude, that's it. Emily will help. Trust me. Let's go." Dean raced down the stairs, dragging Cas with him.
Dean called out into the street. "Hey, Emily! Do you have a minute?" She turned around and flashed a smile.
"What do you need?"
"Cas, uh, stay here for a minute." Dean walked over to her. "Look, you probably know Castiel, my friend. He's gay, well, he thinks he is. But, he wants to experiment to make sure, since he's never actually been with either. Would you be willing to, you know, show him the ropes and kiss him, maybe?" Dean asked, looking for some understanding.
"Um, sure thing." She glanced over at Castiel and sighed.
"What?" Dean asked to her sigh.
"Oh, it's just a shame a sexy guy like that's probably gay. Not feeling bad getting to tap that. Those piercing blue eyes and that sexy hair. Oof. Dean, he's a hot one." Dean smiled.
"Yeah, well he doesn't think so." Dean motioned with his hand for Cas to come over. Castiel made his way, over, smiling almost embarrassed at the situation. "Oh, don't be shy, man. She won't bite. Castiel, Emily has agreed to help you with your situation. I'll be over there," Dean said, motioning to the steps in front of his house.
"Hi, Cas." Emily glanced his body up and down. "You are one fine man."
Castiel blushed. "Why, thanks. So, um…how does this work. I've never really kissed anyone before."
Emily dragged the teenager behind some bushes. "Okay, so put your left hand on my hip." Castiel did as instructed. "Good. Now put your other hand on the side of my neck and gaze into my eyes. Lean in and let your lips meet mine. I'll start kissing you. Take your time."
Castiel gently grazed his fingers up her neck, settling on the side. He looked into her eyes, as instructed. Castiel found himself at a halt. "It's okay, Cas. Don't worry." Castiel nodded slowly and leaned in. Finally, his soft lips pressed against hers. She spread her lips apart, initiating the kiss. She gently sucked on his lip, making sure to move slowly. She leaned back as she sucked, to move back into him. Castiel reciprocated that action and glided his lips back and forth against hers. "Fuck, Cas. You're a natural." Emily breathed heavily as she broke the kiss. "Okay, now again, but this time let your hands roam my body. She wrapped her arms around his neck, pulling herself into him.
Castiel leaned back in, pressing his lips against hers with greater pressure. The kiss sped up, and Castiel let the hand resting on her neck fall and slide up and down her side softly. After a couple minutes both his hands roamed to her back and started gliding up and down her spine. He gently tugged on her lower lip parting their lips and his tongue grazed over her bottom lip. Emily whimpered before darting her tongue out to meet his. Their lips crashed together, Castiel's tongue invading her mouth. He experimented, swirling his tongue around hers and tasting her saliva. He finally pulled away, and breathed again. "Wow. Um, thanks." Castiel didn't really know what to say.
"Sure. Any time. So?" She asked.
"Um, I'm not sure yet. It felt good. I think I need to compare, but thank you for helping me. It means a lot."
"Sure. Good luck finding out." She waved as he walked towards Dean's house. Dean stood up and clapped him on the soldier.
"Come on, Cas. Let's go in and figure this out." Dean gestured towards the stairs once again. Once in Dean's room, Dean cast a smirk. "So, how was it? Bad? So, you're gay? Good? In the middle?"
"Um. I don't know. It felt good, but I think it could be better. I don't know. I haven't really, you know had experience with a guy, so I can't compare."
"Okay. Let's start with the basics on analyzing your kiss. Did you use tongue? Hands? Groping?"
"Yes, I started using tongue. That felt really good. I roamed my hands along her back, but there wasn't really any groping."
"Okay. So, you started using tongue. Interesting. Did you get any wood? Some startle in your pants?" Dean pondered.
"No. So, now what do I do?" Cas stared at Dean, looking for answers.
"Since, I am your friend, and I care about you, and want you to find yourself, I'll help you out a bit. I've been said to be a fantastic kisser."
"Dean. You're not gay. You don't have to-" Castiel protested.
"Cas, you're my best friend. It's okay." Dean assured him. "Come here." Dean patted the bed. Castiel sat down nervously. Castiel stared into Dean's green orbs and swallowed anxiously. He leaned forward, and pushed his lips against Dean's. Dean guided Cas' hand to rest on his hip. Castiel pulled at Dean's lip, nibbling. Dean parted his lips, letting Cas' tongue enter his mouth.
"Dean. Your mouth."
After a few minutes of making out, they were standing in the middle of Dean's bedroom, groping each other.
Dean's hands roamed, until they latched onto the waistband of Cas' jeans. Dean kneeled down on his knees and started taking Cas' jeans off.
"D-Dean. What are you doing?" Cas stammered, running his fingers through Dean's hair.
"Well, you're a virgin, so I assume you've never been stimulated by anyone besides yourself. There's a first for everything." Dean breathed, and continues undressing Castiel.
"Yeah, I suppose. But, it didn't really work too well when I did it. I think I was doing something wrong." He sighed as his pants were removed.
"What? Oh, well. I'll have to teach you a little later." Dean smirked. He let his thumb swipe across the hipbone, just above Castiel's boxers. He pulled the undergarment down swiftly, and left it on the floor. "Ready?" Dean paused, before continuing.
"Yeah. Please." Castiel huffed as his erection continued to jut out into the air.
Dean gripped the base of Castiel's erection firmly. "Holy fuck!" Castiel exclaimed, as his erection throbbed at full capacity, his knees starting to buckle.
Dean chuckled. "Who's cursing now, Mr. Religion?" he laughed to himself again. "Okay. Uh, you look like you'll need some support standing. Uh, I've got an idea. Hold on." Dean locked his elbows behind Cas' knees and using his strength, lifted him up and headed towards the wall. When Castiel's back met the wall, Dean released him and got back on his knees. Dean grabbed the base of Cas' cock again, while the thumb of the other hand massaged the head. Castiel's breathing became more rushed.
Dean smiled and remarked, "I'm going to give you one fantastic orgasm for your first." Castiel grunted at the thought. Dean's hand by the head slid down the shaft and began twisting sharply. Castiel threw his head back in pleasure and it banged loudly against the wall. Dean continued to pump him a few more times. Dean strengthened his grip on the base since it was Castiel's first time and he didn't want him to climax too soon.
"This is the good part." Dean said, before going down, Castiel's cock filling his mouth. Dean licked the precome off of his head. Dean swirled his tongue around him before backing off to plunge back on him.
"Fuck!" Cas yelled suddenly. Dean immediately applied more pressure to the base, his release still being too soon. "Dean, I need to-" Castiel begged, biting his lip.
"I know. Not quite yet. Soon. When I let go, you can." Dean continued going up and down on Castiel's cock, the head hitting the back of Dean's throat, making his gag reflex kick in. The hotness and the tightness of Dean's mouth from the gag reflex nearly sent Cas over the edge.
"Dean, I can't hold much longer." Castiel panted, his erection aching.
"Okay. Hold on." Dean hollowed his cheeks as much as he could, stopped moving on Castiel's cock and sucked on his dick as hard as he could and released the grip on the base. Cas moaned loudly and spilled his load into Dean's mouth. Dean began swallowing it around the cock. The come continued to spurt out at the sensation of Dean sucking on the semen surrounding his cock. After a minute, Dean finished and came off of the cock with a pop.
Dean stood up, pushed Castiel against the wall roughly and kissed him, his tongue intruding Castiel's mouth. Castiel pushed Dean right back, still kissing him, towards the bed. "Cas, what are you doing?"
"You said you'd teach me how to masturbate."
"Yeah, but you're not-uh, ready." Dean was confused.
"But you are." Castiel gestured towards the bulge in Dean's boxers. Castiel pulled Dean's boxers down and tossed them across the room. They sat together at the edge of the bed. Castiel placed his hand over Dean's and guided it to Dean's erection. "Teach me."
"Eye, eye, captain." Dean gasped. "Follow my lead." Dean began pumping his dick, thrusting up to meet each movement. Castiel's hand lay on top of Dean's, gliding up and down with Dean's. Castiel moved Dean's hand away and began pumping him. "Fuck Cas, you're so good. Now try twisting your hand a little."
Castiel tried that among other tactics, including massaging both the head and base. In no time, Dean climaxed, spilling on himself and Cas's hands. Castiel licked the seed off and they lay together, cuddling on Dean's bed.
"Cas, I have a confession. I think I'm bisexual." Dean said with a smirk.
"Oh, you don't say? I sort of noticed. Yep, I'm definitely gay." Cas laughed. "So, do I need to head home now?"
"Well, actually, I have three more hours before my parents get home. I was thinking, you really shouldn't be a virgin at your age…" Dean trailed off.
"Oh, well. That's unacceptable, isn't it?" Cas smirked back.
"Yeah." Dean mindless mumbled, as he climbed on top of Castiel, tore his shirt off, and began making out.
THE END.
A/N: Hey, thanks for reading, guys. Hope you enjoyed the porn. Please review with appraise or criticism. Thanks!