Is That My Underwear?!

Troy was having a great week. His team won the big game, due in large part to his great captain skills. He was one step closer to graduating high school and was being approached by several different colleges. And perhaps most importantly, he had experienced some of the best sex he'd ever had with none other than little Jimmie.

Though Gabriella was pretty much a prude and he'd only gotten to second base with her a couple times, Troy was well versed in the world of sex. After all, he was the most popular guy in school. Girls practically threw themselves at him, and boys too for that matter. And Troy was nothing if not an equal opportunist. He thoroughly enjoyed sex with both genders. But even still, there was nothing quite like having his thick cock engulfed by the tight anal sphincters of a good looking dude. Jimmie definitely fit the bill.

Opening up his locker, Troy noticed a slightly pink hat hanging off one of the hooks. He was quickly reminded, not only of his sexual adventure in the locker room, but of finding the hat left by someone fleeing the scene. And that someone had to be Ryan Evans. Troy needed to find out for sure what Ryan had seen.

Ryan was in the music room practicing a song for the spring musical. He barely noticed when Troy entered the room until the brunette boy dropped the pink hat on top of Ryan's sheet music.

"Lose something?" Troy quesitoned.

Ryan's lip ever so slightly turned upward. "My hat. I've been looking all over for it. Where did you find it?"

"No need to be coy Ryan. I found it in the lockerroom. I know you were in there yesterday."

"Come again?" Ryan asked.

Troy rolled his eyes at the pun, "Haha, you're a regular comedian. Look...whatever you saw, I'd appreciate it if you kept it to yourself. Or better yet just forgot about it."

"Troy, I'm gonna need you to stop beating around the bush and just say it out loud," Ryan pressed.

"Ryan please, this isn't just my reputation on the line, it's Jimmie's too. He's young, and he has years left to survive at this school. The last thing he needs is gay rumors spreading around."

Ryan's smile grew exponentially, "Let me get this straight, no pun intended...you, Troy Bolton, and Jimmie "Rocket Man" Zara are secretly hooking up, and you expect me to keep that a secret?"

"Ryan, I would hope you of all people would understand," Troy replied.

Ryan chuckled, "Oh I understand. But listen Troy...this is some valuable information. And it's stressful holding onto such a big secret. It would be so easy to just let something slip. Unless..."

Troy knew there would be a catch, "Unless what? You want hush money?"

"Please, money I've got. If you really want to keep me quiet, why not stuff your big dick down my throat?" Ryan suggested folding his arms matter of factly across his chest.

Troy's eyes widened in shock. Okay...that he had not expected.

"You want me to what? he asked incredulously.

"God Troy, are all your muscles depleting your brain?" Ryan teased. "I want you to give it to me the way I know you gave it to Jimmie. If I'm left satisfied...then your secret dies with me."

"You're blackmailing me to have sex with you," Troy said, still trying to wrap his head around the idea.

"Of course not," Ryan assured. "I'm blackmailing you to fuck my brains out."

Without him realizing it, Troy's penis had filled with blood and was pressing uncomfortably against the denim of his jeans. He'd be lying if he said he'd never thought about Ryan sexually. He was cute and had a nice, flexible body from years of dancing. And if there was ever any doubt that Ryan would be up for sex with another guy, that was out the window now.

Troy was shaken from his stupor when he noticed Ryan locking the classroom door and pulling down the shade.

"Ryan, what the hell? You wanna do it here?!" Troy exclaimed.

"Why not? You had no problem hooking up with Jimmie in the lockerrom. Obviously sex at school isn't taboo for you. Besides...I know about you and my sister in the theatre."

Troy blushed, "I can't believe she told you about that."

"We're twins, we tell each other everything. Everything," he emphasized.

Troy swallowed hard. He really had no choice here. With a few lingering feelings of hesitation, Troy reached down and unbuckled his belt. Making quick work of his button and zipper, the jeans fell to the floor leaving Troy in some majorly tented blue checkered boxer shorts.

"I guess this means you accept my offer," Ryan breathed, not able to tear his eyes away from the stretched fabric.

"Ryan..." Troy sighed. "Get over here and suck my dick."

Not needing to be told twice, Ryan rushed over to the waiting basketball captain and sunk to his knees. Normally, Ryan liked a little more lead up to the main course, but knowing this was a once in a lifetime opportunity, he didn't want to waste a second. Reaching to the waistband of Troy's boxers, Ryan yanked them down and his eyes locked on the source of many of his fantasies.

As expected, Troy's cock was perfect, like the rest of him. It was at least seven inches in length and close to six around. The thick shaft was smooth as velvet encasing a steel rod, with just the slightest of curves upward that was bound to drive girls and boys alike crazy. He kept his pubes well trimmed, and his larger than average balls hung just low enough to complete the portrait of perfection. A little drop of saliva ran out of the side of Ryan's mouth.

Troy, who was now just anxious to have his aching erection touched, weaved his fingers into Ryan's blond hair and brought the boy toward his body. Ryan, who loved being taken control of, put up no resistance and opened his mouth as wide as he could to allow the entrance of Troy's dick.

It was clear this wasn't Ryan's first time, as right out of the gate he slid down almost three-fourth's of Troy's shaft, without so much as a gag. Keeping the cock lodged in his throat, Ryan began to hum sending wicked vibrations along the Troy's head. Ryan slowly slid his lips back up the shaft, almost to the very end before plunging back down. This time, his nose buried into the curly hairs around Troy's base. Troy had never been deep-throated so completely before. It was amazing!

"Oh my God...so good..." Troy moaned.

Ryan pulled off a little bit and focused on the head, while his hand began to stroke the now spit-soaked shaft. Ryan sucked hard on the flared head, tasting Troy's precum as it oozed out liberally. Then he reached around and grasped onto Troy's incredibly firm ass cheeks with both hands, forcing the boy back down his throat again. The pattern continued of alternating deepthroating with attention to the head and firm stroking. Troy's balls were churning and he knew he wouldn't last much longer. But he didn't want to cum yet. Not like this.

His fingers still latched in Ryan's hair, Troy forcefully yanked the boy upward til he was standing.

"What the Hell?!" Ryan whined.

Troy quickly whipped Ryan around and pushed his upper body forward onto the piano, so that the blonde was laying face down along the upper half of the keys.

"Troy!" Ryan squealed, though he was actually getting turned on by Troy's aggressiveness.

The brunette reached around Ryan and undid his pants, quickly pulling them just barely over his ass, along with his black briefs. Two beautiful globes appeared, silky smooth and bubbly.

"What are you doing?" Ryan continued playing the victim. His own leaking erection was pressed almost painfully against the cold piano.

"I'm gonna fuck your brains out," Troy said matter of factly. "Just like you wanted."

Troy reached down to the jeans still wrapped around his ankles. He luckily had a condom in the pocket, expecting to see Jimmie after school. Tearing open the foil, he wrapped the latex around his throbbing cock. The condom was lubricated, but to help Ryan out, Troy reached around and ran his fingers over Ryan's sensitive cockhead. There was ample precum for Troy to collect, proceeding to massage the cum covered fingers along Ryan's anus, letting two fingers slip in. He began the stretching process, but Ryan slammed his hand on the piano keys jolting Troy by the cacophony.

"Just do it already!" Ryan pleaded.

Troy needed no further commands. He removed his fingers and positioned his dick, letting it slowly slide in all the way to the hilt. Ryan clearly wasn't a virgin, but his muscles still encased Troy's penis almost as tight as Jimmie's had. Troy pulled back out til only his head remained inside Ryan, before slamming back in. He repeated this action, each time subtley changing the angle and increasing his speed.

Ryan cried in pleasure. His body lurched forward with each of Troy's pistoning thrusts, each time pushing his chest against the piano keys. The room filled with the sweet music of the boys fucking.

Troy had already been close after Ryan's stellar blowjob, so he knew he wouldn't last much longer. But to his suprise, before he reached the edge, Ryan began screaming and moaning as his seed spurted out onto the side of the piano. He hadn't even been touching himself, and yet he just had on of the most intense orgasms of his life. Ryan collapsed on the piano, giving off one last string of notes.

Before he could even catch his breath though, Troy pulled out of him and pushed the boy back down on his knees before him. Having removed his condom, Troy rapidly stroked himself, grunting as his orgasm built. While his right hand was busy, Troy used his left hand to pull Ryan by the hair so that his cockhead rested on Ryan's lips. No sooner had he done that, than his body started quivering and shot after shot of hot cum hit Ryan on the mouth. The blond opened up and accepted a healthy dose of Troy's spunk, proceeding to slide Troy's still twitching cock back into his mouth cleaning it off as best he could.

With a slight pop, Ryan released Troy who fell back into a chair panting heavily.

"Was that...enough...to keep you quiet?" Troy asked.

Ryan wiped his mouth and nodded emphatically, "After that...I'll do or say whatever you want. But Troy...I should tell you something."

"What? Ryan, please don't tell me you already told someone."

"No, no, I haven't said a word. But you should know that I'm not the one who left that hat in the lockerroom. I didn't know anything about you and Jimmie til you just told me."

Troy's breathing stopped. Ryan hadn't known, and he had told him!

"But...but...how..."

"You should also know that the other day I let someone borrow that hat," Ryan continued.

Troy gasped, "Who?!"

To be continued...

Who borrowed Ryan's hat? You guys can help decide. It could be an obvious choice like Chad, Zeke, or Jason...a kinky choice like Coach Bolton...or an off the wall choice like one of the Jonas Brothers or David Henrie (playing the role of a random high school student). Let me know what you think and I'll try not to take so long getting the next chapter out!