I Do so Want to Be Cool

"I know what you're thinking, but I promise, everyone's doing it." Tommy implored.

"I dunno, it just seems weird." Tommy was always the coolest person in school, and since he graduated, he had just gotten cooler. He had opened a jet ski rental business at The Lido, the coolest place to hang out all summer long. He had a fire red Mustang. All the girls swooned over him. And he was dating Jackson's sister, Kate; Former Prom Queen and National winning cheer captain. Usually, Jackson would follow Tommy's advice without question, but this piece of advice was something he hadn't expected.

"I was weirded out at first, too."

"Oh, so you've done this already?" Jackson said, buoyed that someone as cool as Tommy had already done it.

"Hell no... I mean, Hell, no reason why I wouldn't, but I'm cool already." Tommy rubbed his forehead, trying not to look suspicious. "It's my responsibility to share the cool with kids like you."

"I guess." Jackson slumped down in his chair, trying to decide. "Do you think people will consider me cool if I do it?"

"Totally," Jackson smirked to himself and rubbed his hands together, stepping closer to the sofa. "Besides, Kate wouldn't have suggested you if she didn't think it would help."

"Kate said it would help?" Jackson had always looked up to his big sister. She was only five years older, but she was the epitome of mature common sense; What Kate said, Jackson followed. "I'm still not sure."

"Look, Jackson, I didn't mean to spring this on you. You're eighteen; you're young; you can still develop coolness without my help. Maybe" Tommy edged towards the living room door. "Derek Taylor called, and I told him that if you said no, then he can be next, I know you won't' mind. If I remember, you two were always together in scho--"

"No way! Derek Taylor has bullied me my entire life. He's nothing but a mean jackass. He doesn't deserve to be cool." Jackson surprised himself by his outburst. His timid nature, the main reason why people bullied him all the time, didn't afford him too much confidence in confrontations. It was also why Jackson believed Tommy was offering him this opportunity. "There's no way I'll let you make Derek cool before me. I'll do it."

Tommy spun on his heels and smiled broadly. "Awesome. On your knees."

"Here?" Tommy didn't answer; he just pointed to the floor in front of him. "Good boy, right there." He added as Jackson slipped off the sofa and knelt in front of him.

"So, how do we...? You know?"

Tommy used both hands and gestured for Jackson to lift his arms. Jackson placed both of his hands in Tommy's, and Tommy put them both on this belt buckle. "You know how to undo one of these, right?" Jackson flushed red and nodded.

His first attempt to unbuckle Tommy's belt was unsuccessful. "Sorry. I'll get it."

"Calm down. We can go slow. I don't mind. I'm doing this all for you, remember that." Jackson didn't lookup. He was concentrating on the buckle intently, which made Tommy very glad. His grin had gotten far too broad, and it might have put Jackon off at the crucial moment.

"There!" Jackson said triumphantly. He pulled the leather from the metal loop and pulled each part out sideways, causing the top button to pop open. "Oh, one down."

Tommy smiled at Jackson as the eighteen-year-old smiled up at him from his knees. "Three more, and we can start making you cool."

Jackson, to his credit, didn't wait around. It had taken Tommy some serious time convincing Jackson that this was a good thing, but now he had. Jackson showed little in the way of apprehension. So-much-so, that when Tommy felt Jackson's hand cover his cock through his boxers, it surprised him.

"Wow. You're not wasting any time." Tommy said, smiling.

"Oh, sorry, was I supposed to wait?"

The naivety of the boy made Tommy's cock throb. "Cool guys, never wait. You take what you want."

Jackson stared at Tommy's crotch and plunged his hand back in through the fly he'd just opened. Jackson had never held another man's cock before. He'd seen plenty in the locker room, of course, but never dreamed of holding one in his hand, except his own. What he did know, however, Tommy had a huge cock.

Tommy pushed his jeans down over his hips and let them fall to his feet. Jackson was trying to manoeuvre the boxer's out of the way too, when Tommy jumped in to help, pulling them straight down from the bottom hem. Jackson's hand flew out, and he gasped loudly but never once let go of the warm, thick shaft of Tommy's big cock. "Fuck!"

"Yeah, it's not bad, is it?"

Jackson just shook his head without looking up. "It's huge."

Tommy put his hand on the back of Jackon's head. He had told Jackson he could go at his own pace, but this was a different time. "Remember those training videos I sent ya?" Jackson nodded and licked his lips as Tommy's cock got close to his mouth. "Just like you practised. Just think cool."

There was a split second when the tip of the cock nudged Jackson's lips, causing Tommy to think that Jackson was about to back out, but he needn't of worried. Jackon's mouth opened wide, and with Tommy pushing him down, the first few inches of cock disappeared quickly. Tommy moaned as Jackson closed his lips around the spongy head and sucked gently. He swirled his tongue over the ridge and hummed softly, causing Tommy to shiver slightly.

A few inches further and Jackson gagged, and Tommy let him pull off a little before he pushed forward again. "I hope you did train. Cool kids don't gag." There was a cough, followed by a second, but no gagging. Tommy could feel Jackon's tongue and throat convulsing, but not in a gag. They were swallowing. Jackson's nostrils flared as he sucked in a deep breath through his nose, and Tommy felt a vast cavern open up, and Jackson's head slid forward. It was hard to hear who was louder. Jackson's frantic nose-breathing, or the roar from deep within Tommy's chest, but all at once, an assault of sexual noises filled the house, and it didn't stop.

Tommy allowed Jackson to pull back and gasp around his shaft before he plunged Jackson's head forward once more, causing more spasms and roars to echo around the room. Slurping and saliva-sloshing sounds could be heard as Jackson's throat artistically massaged the thick shaft causing Tommy to shout, "Best head ever!"

Jackson was surprised, but he was proud to hear those words and relaxed into the motion. The whole event had never really been in Tommy's control. He needed leadership, Tommy knew that, and he was happy that a man he could trust, his sister's boyfriend and the coolest guy in town, would be the one to help him through this.

Jackson closed his eyes and squeezed Tommy's muscular thighs, marvelling in the sensation of feeling a huge cock pound his throat. His jaw ached, and his throat felt numb, but he just kept repeating a single word in his head. "Cool"

Jackson had started to lean back throughout the face pounding, and Tommy was following until Jackson felt his back against the soft sofa cushions. He flicked his feet out from under him and sat on the floor as Tommy continued to grind his crotch into Jackson's face. With each thrust, Tommy moved forward, and Jackson slipped down until his neck was on the edge of the sofa and Tommy crouched over him. Tommy let go of Jackson's head and gripped the top of the couch. From that position, Tommy was perfect placed to begin slamming into Jackson's gullet with full force. Tommy's arms fell to his sides and just purred his enjoyment, as surprising as that might have been to Jackson.

It didn't take long for Tommy to reach his zenith. The suction of Jackson's lips and his spasming tongue lapping against Tommy's wide shaft would have been enough, but the soft, watery glove of Jackon's throat put Tommy over the edge and hard. He ground his crotch into Jackson and whaled. His cock throbbed and expanded, causing a moment of panic for Jackson, who envisioned the bulbous knob of Tommy's cock getting stuck in his throat. He didn't have to worry.

Tommy's cock expanded and contracted quickly at first as it emptied the contents of a full ballsack deep in Jackson's throat. Jackson could feel the load slipping its way down to his belly, and it made him shiver with delight, another surprise for the afternoon. As Tommy's contractions subsided, he pulled back a little, spraying Jackon's tongue with more thick cum. Jackson had followed Tommy's instructions to the letter. He'd watched the training videos. He knew he had to swallow, and as any dutiful apprentice would, Jackson did as instructed and gulped it down.

Tommy was spent and exhausted. The whole event had taken less than ten minutes, but it felt to Jackon like an hour. He stayed there, with his head on the sofa cushion, smiling at the ceiling.

"Wow, you're something else, kid," Tommy said, pushing the tab of his belt through the loop of his jeans.

"Thanks," Jackson said, not looking up. "So, this is what it feels like to be cool?"

"Err, I guess," Tommy said, looking around for his jacket.

Jackson sat up and licked his lips, and laughed. "I never knew being cool would taste so good."

Tommy pulled his jacket on and straightened up. "Dude, are you serious? I can't make you cool. I just thought you were gay."

"Why would you think that?"

"Kate has said she thought you were for years."

"So, this whole time, you thought I was gay? Why the bullshit about making me cool?" Jackson began to cry.

"Dude, you said it yourself last year at your parent's Christmas party. 'I'd do anything to be cool, absolutely anything.' You said that straight at me and winked." Tommy let out a short chuckle.

"I was fucking drunk, you bastard!" Jackson snivelled. "Wait until Kate hears that you conned me and cheated on her."

"What? I don't think so. I'd hate for this to get out." Tommy held up his phone and tapped play.

The noises were all too familiar for Jackson. He didn't need to look, but he was mesmerised by what he saw and began biting his lip when he did. "When did you take that?" He asked without looking away from the screen, then he swallowed in unison with his digital self, remembering the sensation of Tommy's load a moment earlier.

"Don't be sour. Sure, it's a surprise for you. I get it. But Kate's in college, and I needed to get blown. Would you prefer it was one of the new high school cheerleaders?" Jackson didn't respond. "No, I didn't think so. Besides, we've both learned something new today."

"Yeah, I learned that you couldn't be fucking trusted."

Tommy smiled as he reached the door. "Maybe, but more importantly, we both learned that you're a fantastic cocksucker." He pulled the door open and stepped outside. "Call me when you're ready for another taste. But don't make me wait too long, or I might have to share your new little secret."

The door closed, and Jackson thought for a second. He licked his lips and smiled.