Is That My Underwear?!

Ryan was still on a high after his encounter with Troy in the music room. He had fantasized about the basketball captain for years, always secretly jealous that his twin sister had gotten there first. But now it didn't matter, because his dream had finally come true. He had been fucked hard by Troy Bolton. It was everything he thought it would be.

The problem was, it left Ryan hungry for more. As good as it had been with Troy, Ryan doubted the Wildcat would easily give it up again. So the blonde boy needed to find a suitable replacement. His choices were limited though. Ryan was the only openly gay boy at East High, and with the exception of Troy and Jimmie, he didn't think anyone else was quite as open to experimenting.

Wait a minute...there's a thought...Jimmie. Ryan had to admit, the freshman boy was pretty cute. He almost looked like a mini-Troy. And if this was the boy who could turn Troy Bolton gay, he must be a decent lay.

Ryan found Jimmie leaving one of his classes and heading to his locker. Like a panther stalking its prey, Ryan followed the younger boy. Once he saw which locker belonged to Jimmie, he disappeared into the crowd until he was sure Jimmie was out of the hallway. Removing a piece of paper and pen from his shoulder bag, Ryan jotted down a quick note: "Meet me in the theatre after school. Dressing Room 3. -T"

Ryan smirked at his genius before slinking over to Jimmie's locker and sliding the note into the grates. Now he only had to wait...

*********************************************************

Jimmie wandered into the theatre as soon as his last class let out. He was so excited to see Troy, and even more excited at the thought of sex with Troy again. He hadn't been able to think about anything else since the last time.

Coming up to the door labeled Dressing Room 3, Jimmie took a deep breath before reaching for the doorknob. When he opened the door he froze and dropped his backpack, not having expected the sight before him. A completely nude male standing with his back toward Jimmie.

Jimmie's eyes raked up the boy's nude form. His eyes paused once they reached the bubbliest butt he'd ever seen. The boy could have given J.Lo a run for her money. A slim yet strong torso led up to a blond head of hair that slowly turned to look at Jimmie.

"Don't you knock?"

"Ryan!" Jimmie exclaimed. "I'm so sorry! I thought...I didn't know...I..."

Jimmie's brain couldn't function enough to form words. His eyes kept being drawn to Ryan's delectable tush. Ryan smirked and turned his body to face Jimmie, which only caused the younger boy more problems. Now he was forced to stare at Ryan's ample manhood, hanging flaccidly between his toned legs. Jimmie's mouth watered slightly at the sight.

"It's okay Jimmie, I'm not very modest. Besides, we're both guys here. But perhaps you could close the door so that I don't end up giving someone like Ms. Darbus a show," Ryan laughed.

Jimmie shook himself from his stupor and began to step back out of the room.

"I said to shut the door, not to leave," Ryan called out.

Jimmie paused, a little confused. But in the end he shut the door staying inside the room, if for nothing else than to have a few more minutes staring at Ryan's beautiful naked body.

"Wh-what are you doing in here?" Jimmie asked, trying to make small talk.

"You were expecting someone else?" Ryan teased, plopping down on a couch, spreading his legs wide. "I have rehearsal later, and I needed to try out some costumes. The better question would be what are you doing here?"

A blush spread over Jimmie's cheeks, "I thought...I mean I was supposed to meet someo-"

"You thought Troy would be here," Ryan interrupted causing Jimmie's eyes to widen. "It's okay Jimmie. I know."

"Y-you know? Know wh-what?"

"I know all about you and Troy. That the two of you are together...in the biblical sense," Ryan grinned.

Jimmie shook his head intensely, "I don't know what you're talking about."

Ryan rolled his eyes, "Do you really want me to spell it out. I know that you and Troy have been fucking. And if I had to guess...I'd say you've been the one bent over while he plows your cute little ass."

Jimmie had to lean against the door for support. How did Ryan know all of this? Had he seen them...or had Troy said something?

"Look, Ryan...I don't know where you got this information from...and I'm not saying that it's true...but you can't tell anyone! It would destroy Troy."

"Awww, how cute. Little Jimmie is trying to protect his boyfriend," Ryan mocked. "Look, I don't care what you and Troy do behind closed doors. In fact, the idea of him giving it to you kinda turns me on."

Jimmie could tell, because Ryan's once flaccid member was slowly growing. And since Ryan was still sitting with his legs widely spread, Jimmie had a grand view of the rising erection.

"However," Ryan continued, "I understand that this is valuable information. In the wrong hands, it really could ruin Troy's life, and yours as well."

Jimmie stepped forward a little bit, resisting the urge to fall to his knees and beg, "Ryan, please, promise me you won't tell anyone. I'll do anything."

Ryan's eyebrow arched menacingly. "Anything?" he asked, slightly spreading his legs further.

Jimmie gulped, "Y-you want me to...what? Blow you?"

"Among other things."

"I don't know...What about Troy?" Jimmie asked worriedly.

"Hmm...Troy can join us," Ryan said.

"Troy can never know about this," Jimmie warned. "No one can ever know. Not about me and Troy. And not about me and you. You swear on it?"

Ryan made a show of crossing his heart, "You have my word."

As if it knew the deal was made, Ryan's cock reached it's full potential, laying up against his smooth, toned stomach. Jimmie eased his way forward and knelt before the blond stud. A tentative hand reached out to grasp the throbbing shaft before him. Ryan was about six and a half inches long, but the boy was incredibly thick. Jimmie's fingers didn't even meet. This was going to be a bit more of a challenge than blowing Troy's more slender dick. But what choice did Jimmie have?

The younger boy bent down and quickly engulfed the engorged head. It alone nearly filled his mouth. He began applying pressure to the most sensitive part of Ryan's body, sucking intensely has his hand glided up and down the thick shaft.

"Mmmmmm...I can see why Troy likes you. Try to take more," Ryan urged.

Jimmie, eager to please, widened his mouth and eased more and more of Ryan into it. It didn't take long before he was filled to the max, gagging a bit and having to pull off.

"Sorry, it's too big," Jimmie apologized, still stroking the now saliva drenched rod which throbbed in his hand at those words.

"Don't worry, there are other things we can do," Ryan said, standing up and pulling Jimmie up with him.

Jimmie's eyes widened, "Ryan...I don't think I can handle you...ya know, in my ass. I've only been with Troy."

"Relax kid," Ryan laughed. "I'm gonna be the one handling you."

With that, Ryan grabbed onto the bulge in Jimmie's pants.

"Oh yeah, this feels like it'll work just fine," Ryan complimented before making quick work of Jimmie's pants.

Jimmie's knees quivered and his breath hitched when Ryan's hand made first contact with his throbbing erection. In the few days since being with Troy, he had almost forgotten how good it felt to be held by another person.

Ryan, realizing Jimmie's inexperience, didn't want the boy to blow his load before the real fun started. So he stopped his stroking and reached for a condom he had left on the table. Ripping open the foil package, he positioned the condom between his teeth before bending down to ease the rubber onto Jimmie's cock. Once situated, he pulled off, gently grazing his teeth along the shaft, causing Jimmie to buck forward a bit.

"Easy there cowboy. Save the thrusting for what's coming next."

"Ryan...I've never...topped before," Jimmie informed.

Ryan couldn't get over how cute and innocent this boy was. At least until he'd been corrupted by Troy Bolton's big cock.

"Don't worry, it'll be much easier than bottoming."

Ryan got on the couch, laying on his back. He hitched his legs up and beckoned Jimmie to get into place. Jimmie nervously got onto the couch as well, situating himself between Ryan's legs. His stiff dick was like an arrow pointing straight toward Ryan's puckered hole.

"Here," Ryan said, wiping his fingers along his own cockhead collecting a generous amount of precum. He proceeded to massage the clear liquid along his hole, letting two of his fingers slip inside. After a brief moment, Ryan removed his fingers and nodded at Jimmie.

The brunette eased himself forward until his head was pressed right up against Ryan's anus. He pushed forward slowly and was amazed as his head completely disappeared inside of Ryan. It was tight, but not uncomfortably so. Ryan was obviously no stranger to anal sex.

"You can go all the way," Ryan assured. "I'm fine."

Jimmie didn't need to be told twice. He grasped onto Ryan's thighs and plunged his full six inches completely into Ryan. Even though he was prepared, Ryan couldn't help but gasp at the sudden intrusion.

Jimmie was in another world. His dick was completely surrounded by this tight warmth...similar to oral sex, yet different at the same time. It was like five mouths being on him at once, sucking him from all sides. As he pulled out so that only the first inch or so of himself remained buried, the sensation was so intense he almost thought he would lose it right there.

"Ryyyyannnn."

"Just take it slow Rocket Man. We're just getting started," Ryan breathed.

Jimmie gave himself a second to relax. In the meantime, he wrapped his hand around Ryan's still hard manhood, giving it some slow strokes. After a few moments had passed, Jimmie pushed back in, and then started a steady rhythm.

"Yessss, just like that," Ryan moaned.

This was very different from Ryan's tryst with Troy. That time had been fast and rough (and uber hot). Jimmie was much slower and thoughtful with his movements. Ryan could feel every inch as it slid in all the way, tapped against his prostate, then retreated back out again.

"Am I doing okay?" Jimmie asked, shaking Ryan from his thoughts.

"You're doing great. I was just thinking how different you are from Troy."

Jimmie froze in mid-thrust. Ryan realized what he had just said. Probably not the best time for that revelation.

"You mean...you and Troy...you've been together?"

Ryan noticed the hurt in Jimmie's eyes. He could lie and try to spare the boy's feelings. But really it was too late for that. The truth was out.

"We hooked up the other day," Ryan admitted.

Jimmie sat in silence, still lodged in Ryan's ass, as he digested this information.

"I didn't know you two were together at the time," Ryan lied, trying to save himself.

Jimmie's mind was racing. He was hurt, angry, still aroused, confused. He didn't know what to say, what to do. It was almost without his knowing that he began moving in and out of Ryan again. Ryan was as shocked as Jimmie, especially when the younger boy started going faster and faster.

Before either of them knew what was happening, Jimmie was going on four cylinders, pounding into Ryan's tight ass, his cum-filled balls slapping against Ryan with every thrust. Ryan couldn't help but start jacking himself off, taken over by the intense pleasure Jimmie was administering.

Almost simultaneously, both boys shuddered and gasped as their orgasms overtook them. Ryan shot his thick load onto his stomach and chest while Jimmie came still buried inside Ryan.

There was an awkward silence as the two boys cleaned themselves up and redressed. Ryan finally broke it.

"Hey, are you okay? I know it must hurt knowing that Troy went behind your back like that."

Jimmie shrugged with a frown, "I guess we never said we were exclusive."

"I don't want you to feel bad about what we just did..."

Jimmie raised his head and said flatly, "I don't. If Troy can fuck other people, then so can I."

Jimmie grabbed his backpack from the floor and headed to the door without looking back.

"And that's just what I intend to do."


AN: Sorry it took so long for this chapter! I went through a big move in August and it's taken awhile to get settled. And sorry for those of you who were looking for more Troy action, I felt like I needed to do something a little different this time and had another layer to the story...keep things fresh. But fear not, Troy will be back in the next chapter in the AV room...there may be a Jonas brother involved...or two...that's all I'm saying, haha.