Is That My Underwear?!

AN: I'm so sorry this took so long to write! It's been 3 months, eek! I hope you enjoy it. I feel it's a little different than the other chapters, kinda adds a new layer of story and elevates it (however slightly) from being just a smutfest, haha. Hope you're not disappointed with how it all goes down. And now onto the story....


Troy could barely sleep. He kept having uncomfortably erotic dreams revolving around all the boys he'd been with lately. One minute he'd be drilling Ryan Evans into the piano, then suddenly he'd look down and see David Henrie on his back in the library. Before he could adjust to that, he then found Nick and Joe Jonas slurping on his painfully hard dick. The images would cycle through so fast, it soon felt like he was getting it on with all of them at once! He wasn't even sure how it was possible, but in his dreamland, Troy was literally fucking all four boys simultaneously.

Lost in his ecstasy, Troy barely noticed when a fifth boy came up behind him. Before he knew what was happening, he felt a painful intrusion from behind. Suddenly the rest of the boys were gone and Troy's upper body was pushed downward as the newcomer thrusted roughly into his ass. The pain soon turned to pleasure, Troy gritting his teeth to keep from screaming. Though who would hear him.

Troy had to steal a glance at his aggressor. Who was giving him such intense pleasure. He slowly craned his neck to look backward, catching a quick glimpse of the dark haired boy behind him...

And then he woke up, body trembling, an uncomfortable wet feeling seeping through his boxers. He lifted the blankets and glanced downward.

"Are you fucking kidding me?"


----------------------------


Troy walked around school that day feeling as though everyone was looking at him. He was embarrassed from that morning. He hadn't had a wet dream since before he discovered the joys of masturbation. Let alone after he became sexually active. You would think with all the play he'd gotten recently, he'd be a pretty dry well.

Yet something about that dream sent him over the edge. Was it just the thought of sex with all of those hot guys? Or was he really turned on by the idea of bottoming for a guy? Or more specifically, for the guy in the dream?

Lost in his thoughts, Troy ran right into his teammate Jason, sending their books scattering to the floor.

"Whoa Troy, where's your head at?" Jason wondered aloud.

"I'm so sorry, I'm just...tired I guess," Troy lied.

They kneeled down to gather their books. Both reaching for a math book, their hands grazed one another a little longer than necessary, before Troy snatched it away.

"You sure are jumpy today," Jason noticed. "Did you get fucked last night or something?"

"Excuse me?!" Troy gasped.

"I heard Sharpay had a party last night..." Jason said as if it was obvious. "You look like you may have partied a little too hard..."

"A party...drinking...right...right!" Troy stammered. "Yeah, I kinda got carried away I guess. You should have been there."

"Yeah...I tried to go...but I got kinda lost..."

Jason kinda drifted off, something that happened a lot with him. He didn't even seem to notice when Troy said "Catch ya later" and walked away.

Troy slipped into the bathroom to splash some cool water on his face. The misinterpretation of Jason's comment had brought his dream back to the forefront of his mind. It was all he could do not to get a hard on thinking about it.

Glancing down, he noticed his shoe was untied, probably from his run in with Jason. He bent straight down to fix it, only to catch a glimpse of himself in the floor length mirror. Bent over, ass exposed. It had to be his imagination, but "mirror-Troy" had a look of pure pleasure on his face and seemed to be bouncing back and forth.

Well that did it. Full hard on achieved. Great.

Knowing that class was starting shortly, Troy knew he couldn't wait for it to go away. And it was too painful and obvious to just try and hide it. So he had no choice but to go into one of the stalls and unzip his jeans.

The release of pressure was immediate and he was thankful for it. He slid his jeans and boxers down his thighs just enough for his solid erection to be released. Cool fingers wrapped around the hot flesh, providing familiar relief. There wasn't time to go slow, so he commenced a quick paced rhythm of stroking, using his other hand to fondle his somehow full testicles.

As his hand jerked, Troy kept having visions of himself spread eagle, with someone pounding away at his tight virgin ass. It was no longer limited to doggie style, now Troy saw himself in all kinds of positions. On his back...bouncing on top...even in some kind of upside down pretzel.

Troy's cock was now leaking precum steadily. He was getting close, but not quickly enough.

What happened next was barely a voluntary action. As if it had a mind of its own, Troy's left hand found its way between his muscled ass cheeks, gingerly stroking his puckered hole. Even the brief contact sent a shock through his cock. Running his finger back and forth a bit, he then let the tip slide inside. It was super tight, he couldn't even imagine anything bigger going in. Yet even as that thought crossed his mind, the sphincter seemed to relax a bit around his finger, so he slid it a little farther in.

With his right hand still jacking away, Troy was now really close to shooting his load. Before that happened though, he wanted to keep going with his finger play. He pulled it out most of the way before plunging it back in, this time going even farther. It was a little uncomfortable, yet it didn't particularly hurt. He pulled back again and then began a quicker rhythm of short finger thrusts, ever now and then pushing it in all the way.

Whether it was the sensation of his finger in his ass itself, or just the thought of it being someone else's hot dick, Troy found himself reaching that glorious peak. His right hand sped up, his left hand gave a final deep thrust, and soon after the cum was flying. He had meant to aim for the toilet, but lost in his orgasm, that wasn't happening. It probably wouldn't have mattered anyway because his spunk was shooting off in a crazy arc, farther than he ever remembered it going.

Troy gasped for air, having to steady himself against the stall door. He was happy to see his dick deflating as the first bell sounded.


----------------------------


Troy thought is day would go more smoothly after the eventful morning. But during history class, when Zeke asked him if he wanted to bottom (in reference to bunk beds at an upcoming basketball camp) Troy had to excuse himself from class and make a return visit to the bathroom.

He was getting frustrated. Sure the earth shattering orgasms were great. But he couldn't keep running to the bathroom every hour, people would think he had a serious problem. Not to mention, his penis was getting sore from all this. Yet through it all, his horniness never seemed to wane.

By the end of the day, Troy had jacked off three times at school. He rushed home quickly to avoid anymore encounters with hot guys that he couldn't help imagine bending over for. Once he shut the door behind him, he let out a big sigh of relief. Maybe he could get through the rest of the day without molesting himself.

*Knock Knock Knock*

"Shit..." Troy groaned.

He contemplated ignoring the visitor. But realizing he had just entered the house, whoever was out there was sure to have seen him. So he inhaled deeply and whipped open the door, to find Jimmie standing on the porch.

"Hey Troy," the younger boy smiled uneasily.

"Jimmie...hey. What are you doing here?"

Jimmie paused before saying "I wanted to talk to you about something."

He seemed serious, so Troy invited him in and they went up to Troy's bedroom. Sitting on the large, neatly made bed, Troy devoted his full attention to a serious Jimmie.

"I don't really know how to say this...but I feel like I need to tell you the truth," Jimmie started, making Troy extremely nervous.

"Go ahead, you can tell me anything."

"I think I can. Okay...you and I have been...having fun together. And it's been really great. I mean I really enjoy it. Not just the sex part...but just being with you."

This was obviously difficult for Jimmie to say, as he could barely look Troy in the eyes. The older boy took his friends hand and gave it an encouraging squeeze.

"I like being with you too man."

This made Jimmie smile, but that smile quickly faded.

"Troy...I...I kind of...slept with someone. Someone else."

Troy had to admit, he was a little taken a back. More from surprise than anything. Jimmie didn't seem like the kind of person that got around.

But what also struck him was the look on Jimmie's face. Guilt. Like he had somehow betrayed Troy. Like he had stronger feelings for Troy than he let on.

This of course made Troy feel like crap. While Jimmie felt guilty for sleeping with one other person, Troy had in a short period of time fucked four other guys! And without really sparing a thought for his first.

"Troy?" Jimmie asked timidly, snapping the older boy from his reverie.

"Oh, sorry. I just...I'm surprised is all."

"I know. I feel horrible. I know you and I aren't even remotely together like that...but I couldn't stop thinking about you when it happened. And then afterwards I felt so bad about the whole thing. I guess I just wanted to be honest with you, in case..."

"In case what?" Troy asked, though he already knew the answer.

Jimmie blushed, not able to say anymore, "I should probably go. I'm sorry again."

"Jimmie wait!" Troy yelled, grabbing the other boy by the shoulders. "I'm not mad at you. I could never be mad at you. You're a great friend and we do have a lot of fun together. And I don't want that to change. But I should tell you-"

Troy never got a chance to finish. Halfway through his sentence, Jimmie pounced forward and captured Troy's lips with his own. Troy barely knew what was happening as he was pushed backwards, the back of his knees hitting the bed sending both boys crashing to its surface.

There was something in the way Jimmie kissed him that made Troy forget everything else. Whatever he was going to say. Whatever he had done that day. Even all the other guys were pushed out of his mind for the time being. Right now, there was just him and Jimmie. And the two raging hard-ons between them.

Jimmie, still on top of Troy, lifted the basketball star to a sitting position, with the rookie straddling his lap. He broke their kiss only long enough to lift Troy's shirt over his shaggy head. Pushing Troy back to a laying position, Jimmie kissed his way down the tanned torso, paying special attention to Troy's pebbled nipples and placing a kiss on each ab. He made quick work of Troy's jeans, lifting his friend's hips to ease the material down his thighs.

Jimmie massaged Troy's steel rod through the flimsy boxer shorts he still had on. But soon they were gone as well, and Jimmie wrapped his sweet lips around the swollen head of Troy's cock.

This didn't even compare to Troy's solo sessions at school. Jimmie's mouth was in a league of its own. Jimmie, who had been good at this even during their first encounter, had somehow gotten even better. Troy's fingers ran through Jimmie's smooth locks of hair, guiding the bobbing head deeper and faster. At one point his entire cock was completely enveloped, Jimmie's throat constricting around the top half. As he slid back up the shaft, Troy's pulsing head reappeared with a pop.

Jimmie took this time to stand up. Troy propped himself up on his elbows to watch Jimmie drop his pants and boxers. His beautiful, slender dick bounced into view, hard as a rock and leaking at the tip. Troy wanted nothing more than to lean forward and engulf the thing, but to his surprise, Jimmie turned around and bent over, exposing his tight, puckered hole.

"Fuck me Troy," Jimmie cooed.

Troy stood up, his manhood nudging up against Jimmie's smooth cheeks. He was definitely ready to go, and Jimmie obviously wanted it. But something didn't feel right. He couldn't do this.

"Jimmie, wait, stand up."

The younger boy rose and turned to Troy, causing their cocks to knock against one another like swords. He looked a bit concerned.

"What's wrong? You don't want to?"

"No! I do!" Troy assured. "But I need to tell you something. You were completely honest with me earlier, and I need to do the same."

"Okay..."

"Well..." Troy took a deep breath. "I slept with someone too. Actually...more than one someone."

Jimmie's eyes went dark, like a light had been turned off inside him. From their closeness, Troy could even feel a slight deflating of the boy's erection.

"H-how many someones? No...wait...I don't wanna know."

"Jimmie, I'm really sorry. Like you said, you and I are friends. I didn't think there was anything more to it."

"You're right," Jimmie sniffed. "I guess I can't be mad at you for something I did myself. And there's no reason we can't be with other people. We're just having fun after all..."

"But it's more than that!" Troy exclaimed. "I see that now. When I'm with you...everything else...it all just slips away. And at the end of the day...you're the one I dream about."

Jimmie could barely breathe. "Really?"

"Yes. And look...the only reason I slept with the other people was because someone found out about you and me. I was just trying to find out who it was and put an end to it. I wanted to protect us. But everytime...things just got out of control."

"I understand Troy. Really I do. In fact, I was trying to protect our secret as well."

"So we're both on the same page," Troy discerned.

"...and what page is that exactly? I mean, what are we?"

Troy sighed, not sure he even knew. He liked Jimmie, really he did. He actually cared a lot about the little guy. But he wasn't ready to be tied down to one person. His escapades lately had just opened the door to wanting to try more and more new things. Could he have both? Jimmie and everyone else?

Then he had an idea.

"Jimmie...look, I like you. I want to be with you. But I'm not ready to be exclusive."

"So what..." Jimmie asked, "...you wanna date me but be able to fuck other people on the side?"

"No! Well...yes. But there's more to it than that. I think we should both be allowed to go out and experience new things. We're young. And there's a surprising number of gay boys in this town. To quote Sharpay and Ryan, I want it all. But I also want to know that no matter what, I have you in my corner. My friend, my lover, my confidant. And I wanna be the same for you."

Jimmie seemed hesitant, "That sounds good on paper, but Troy...we're dealing with strong emotions here. How do I know that you're not just using me. Having your cake and eating it to or whatever."

Troy smiled, leaned forward and kissed Jimmie tenderly.

"I want to show you how much I care about you. And only you."

"How are you gonna-"

Silenced by another kiss, Jimmie jumped a bit when Troy's hand found his softened cock. It didn't take much for it to be firm again in Troy's soft hand.

Then Troy stopped kissing Jimmie and leaned into his ear and whispered, "There's a condom and some lube in the nightstand."

Jimmie without thinking, turned and retrieved the items. Upon turning around, he nearly dropped them. For there was Troy Bolton, bent over his bed, naked ass spread and ready for the taking.

"Troy...what are you doing?"

"What does it look like I'm doing?" Troy smirked over his shoulder. "I'm about to get fucked by my sexy boyfriend. The only boy in the world that's allowed to fuck me."

A smile crept along Jimmie's face. This was it. The proof that what he and Troy had was more than just sex. There was a mutual caring and trust between them that wasn't to be shared with anyone else. It didn't matter how many boys Troy screwed. At the end of the day, his ass belonged to Jimmie.

The Rocket Man readied his throbbing erection with the condom and lube, also applying some of the grease to his fingers.

"Relax," he instructed, grazing his fingertips between Troy's cheeks, stroking the opening.

Very gently, he eased his pinky in. Better to start slow he figured. Little did he know, Troy had already done a pretty good job of stretching himself throughout the day.

"You can do more," Troy assured. "I'm good."

Not needing further encouragement, Jimmie added another finger, and another. He would pull them out so that only the tips remained, before plunging them back in as deep as he could. Once inside, he used a scissor technique to stretch the muscle further.

"Are you sure you're ready for this?" Jimmie asked one final time.

"Way past. Please Jimmie, fuck me now."

Placing himself at Troy's entrance, Jimmie eased his head in slowly. Troy's hands immediately gripped the covers, his teeth clenched. It felt like a fire had erupted in his ass. But the pain was kinda far off, almost like when you have Novacain at the dentist. You knew it should hurt, and it did a little, but it should be so much worse.

"Troy, you have to relax. I won't hurt you."

They both exhaled and Jimmie pushed in a little further. He made an effort to stroke Troy's back in hopes of calming him a bit. It must have worked, because Troy was no longer clenching, allowing Jimmie to slip in a little further.

"Alright, we're about a third of a way there," Jimmie said.

"Jesus Jim, do you have an anaconda back there?!" Troy exclaimed.

The younger boy laughed and grabbed at Troy's dick, "Hey, if I could handle this beast, you can't complain mister!"

Troy chuckled too. His laughter combined with the attention now on his cock, allowed Jimmie to add another two inches easily enough. Pulling out most of the way, he paused briefly before plunging almost all the way in.

"Oooooh godddd," Troy moaned loudly.

It sounded like a good 'oh god', so Jimmie pulled out and pushed in again. And again. Troy's moans only increased, Jimmie now driving six inches of meat into Troy's tight ass. Each thrust sent Troy deeper into the mattress, the bed springs squeaking under the pressure. All he could think was thank goodness his parents were at work.

Jimmie slowed, then stopped before saying, "Flip over."

He wanted to look Troy in the eyes. So the older boy turned onto his back, Jimmie lifting his legs up so they rested on his shoulders. He was quickly sheathed again in Troy's warm heat. After about five thrusts, Troy's head snapped back and he let loose a scream. In this new position, Jimmie had managed to find Troy's sweet spot.

"Oh my god!!!! FUCK!!!! YES!!!!"

Hearing this only made Jimmie thrust faster and deeper. The scene before him was so hot. Troy Bolton, naked, on his back. Legs in the air, impossibly hard dick bouncing against his six pack abs. Sweat glistening on his tanned pecs, shaggy hair flying everywhere, eyes rolling back, with a look of 100% pure pleasure etched on his face. He couldn't take it anymore.

Jimmie pulled out and snapped off the condom. He didn't even get his hand around his dick before it started blasting warm cum all over Troy's body.

"Oh god...oh yes..." he breathed heavily.

Troy stroked himself as he watched his lover and was subsequently covered in his boyjuice. He could almost still feel Jimmie pounding away at his prostate, like an echo inside him.

"Shit, I'm cumming too!"

As white cum shot all the way up to Troy's neck and chin, Jimmie leaned down and covered the spurting head, wanting to taste Troy. He was rewarded with a mouthful of spunk, which he instinctively swallowed while Troy spasmed on the bed.

When all was said and done, the two boys laid side by side on the bed, both a mess, but too spent to move.

"Jimmie...I can't even put into words," Troy said.

"I know. Right there with ya."

Troy couldn't believe it. He had just been fucked in the ass. It crossed a line he never thought he would allow himself to cross. But he liked it. Actually, he loved it. All of his fantasies, even his dream the night before of Jimmie giving it to him didn't compare to the real thing.

"I'm really glad I got to share this with you Rocket Man. And like I said, this is something reserved for you and you alone."

"Thank you Troy. That means a lot. And just so you know, it goes both ways. I won't bottom for anyone but you. Never have, never will," Jimmie promised.

Troy's curiosity got the best of him, "So...are you ever gonna tell me who you had sex with?"

Jimmie looked ashamed, "I guess it can't hurt...it was...Ryan Evans."

Troy bolted upright. "You too?!"

"Wait!" Jimmie said sitting up. "You and Ryan..."

"Yes! It was all because I found his hat in the locker room that day we had sex in there. Whoever left it had seen us. I obviously assumed it was him, so I confronted him. Apparently he had given the hat to someone else, but he still ended up blackmailing me into fucking him," Troy explained.

"So that's how he found out about us," Jimmie deduced. "He threatened to tell people if I didn't have sex with him too."

Troy became very angry. Who did Ryan think he was? He couldn't just go around manipulating people into having sex with him. It was one thing to target Troy, but to go after little Jimmie too. No. He went too far.

"Troy, what are you thinking?"

"I'm thinking...it's time we issue a little payback...this time together."


AN: Well I hope that was decent enough to make up for the long absence. I can't apologize enough for taking so long to update. Everyone has given me such positive feedback, I wish I could churn out a new chapter every day! I will try to get better.
Some people might be disappointed that Troy gave it up to Jimmie. May not have been the "hottest" choice, but for me it's the only thing that made sense (as much sense as this kind of story can make, haha). It's not for sure that this "only bottom for each other" thing will last forever, so fear not if you want to see him taking it from other people eventually. Obviously the next chapter will deal with Troy and Jimmie teaming up against Ryan. After that, I plan to get back to the "who had the hat" storyline. Thanks for sticking with me!