Gay stories 

The Liberation

February 22, 2014 / by gaystory

*All characters and situations in this story are entirely fictional. Any similarity it may share with a real event is purely coincidence. Also, I would like to thank AngelLove on editing this story, as it was a very exceptional job.*


It was getting to be unbearable. Gregory Kaplan checked his watch to make sure the room’s clock hadn’t been deceiving him. Yep, it was still only ten after nine, barely into second period and the school day. Like most seniors, Gregory, or Greg as he was called by his friends, could not stand sitting through the final pointless months of high school. However, unlike most of his peers, the thought of high school finally ending was not the cause of Greg’s immense impatience. If everything were to go as he had hoped, this day would be his final one as a virgin.

Greg was gay and had known this for several years now. He never took an interest to girls because he knew he would have to be the rock and the comforting one in relationships. Greg wanted to be the one cuddled and taken care of. Ever since his parents bought him his new laptop for his eighteenth birthday, Greg took advantage of it to find the steamiest and most arousing gay porn he could find. He particularly loved seeing gay teens, such as himself, being on the receiving end of anal sex. Greg was most of all enthralled by the faces of the young men his age taking their lovers’ cocks deep in their ass. Being the receiver of not only this wonderful act of lovemaking, but also the intimacy of their dominating partners was sometimes too much for Greg to handle.

Greg’s desires remained dormant throughout his high school years. He was raised by conservative Jewish parents, both of whom were well-respected in the community. Greg’s grandfather had even donated money to his prep school, and has a computer lab named after him. Needless to say, outing himself would be damaging on several levels. This conservativeness played to Greg’s advantage as well. None of his peers questioned his lack of interest in girls. They simply assumed it was a result of his strict faith and very studious nature. Greg also benefitted from not being a knockout either. His looks made him blend into the crowd, and aside from the other intellectuals, nobody really knew him until the school’s headmaster made a special point of announcing Greg’s acceptance into Princeton.

So for the past several months, Greg gained notice as the school’s Ivy Leaguer. Greg was rather pleased at this reputation due to the fact that everyone was completely unaware of Greg’s growing urges. These urges were culminating on this early May Tuesday. Greg sat there trying to be interested in his English teacher’s lecture on Dante, but it was futile. Greg gently rubbed the bulging cock in his pants as he replayed the chain of events in his head as to how this day came to be. How he conquered his fears? How he set things in motion? And of course, how he met him

Everything had started the past Thursday. Greg was at home on his laptop and had just finished an essay for his Philosophy class. Satisfied with his work, he decided to treat himself to some of his favorite sites. Greg soon wandered into a chatroom for gay men in his area. Since turning eighteen, Greg frequented the room often. Usually, he just read the sometimes hilarious chatter, but once in a while he’d engage in a private conversation with someone eager for a quick hookup. Of course, Greg would chicken out and not meet any guys from online in person.

“Knowing my luck, I’d end up meeting the rapist,” he would think to himself.

However, Greg was back at it. This time he was chatting with someone claiming to be named Lyle and twenty years old from a suburb a few miles away. Greg’s cock stiffened at the sight of Lyle’s nude picture. However, Lyle soon mentioned something about bondage, and Greg got frightened and almost immediately signed off.

“You’re a smart kid Greg. Fuck, you got into Princeton. You can arrange something with someone in school and not have anyone find out, can’t you?” he thought.

Greg just sat there thinking as he jacked off. How he wished for someone to give him this feeling for him.

“The Rainbow Star Support Group,” Greg softly muttered.

The Rainbow Star Support Group was considered to be the gay club at Oakberry Prep. However its members didn’t promote gay pride or rights at the school, but they served as peer mediators for students grappling with their feelings for people of the same sex.

“If only I didn’t have a high profile nowadays.”

Gossip was a major problem at Oakberry. The social circles were very complex and overlapped in quite unimaginable ways. Greg couldn’t take a chance of letting anyone find out about him, unless it was the guy he was making love to. He couldn’t go to a Rainbow Star meeting.

“However,” he started, “If I were to just sneak a peak in their room while walking past, then maybe I’ll be able to see a promising target.”

Greg grabbed his cell phone and dialed.

“Hello, Jodie”

“Greg, you know what time it is?” replied a tired-sounding girl.

“Jodie, what do you think about rescheduling the French Club meeting for tomorrow?”

“I dunno, it’ll be hard to tell all the members. They might have other plans.”

“We’ll just have them make an announcement saying it’s officers only. I mean all we’re gonna go over is the procedure for the election of next year’s officers at the end of the month.”

“Why does it have to be pushed up?”

“My aunt and uncle are having dinner with us on Monday, and you know Mondays, Thursdays, and Fridays are my only days I can do French Club.”

“Okay then, it’ll be brief. I have to work at five tomorrow. See ya tomorrow.”

“Bye, Jodie.”

“Bye, bye”

Greg hung up his phone and sat back in his chair.


Greg knew that the Rainbow Star Group met Fridays after school. All he would have to do is quietly take a glance inside to see whom he could pursue, as he left French Club. Aroused by this thought, Greg maddeningly stroked himself off and soon went to sleep. After breezing through another meaningless day at Oakberry, Greg proceeded from his last period class to French Club.

Greg served as vice-president of the club. The only real reason he bothered participating in it was because it looked nice on his transcripts. He would just sit there while Jodie, the club’s President, organized events and carried out the typical activities of an after school high school club. This meeting was no different. Greg couldn’t care less as to what Jodie babbled on about. He only was waiting for her to end things so he could sneak his long awaited peak at the Rainbow Star Group.

At around ten to four, Greg’s boredom was quelled as Jodie announced the meeting was over. Afterwards she walked up to him.

“You didn’t seem to be all too interested,” she remarked.

“I just wanted to be there to oversee things, is all.”

“Okay, well I gotta run. I’m cutting it close as it is.”


Once Jodie walked out of the room, Greg was alone. He peaked in the hall to make sure Jodie and the other officers had turned the corner and were headed to the parking lot. Greg gathered his books and walked past the turn and toward the room he had been told hosts the Rainbow Star meetings. Greg crept up and noticed a lit room with the door cracked open. Immediately he heard the flamboyant voice of Mitchell Rackers, one of the school’s most open homosexuals.

“This must be it,” he softly spoke.

Greg noticed that the people inside were positioned away from the door. He would now be able to make more than a quick peak. Greg stood a couple of feet from the door and peered inside and scanned the room. At first, Greg was chagrined. Most were known as openly gay and likely wouldn’t be interested in anyone closeted. Greg might have been paranoid, but he wanted to know for sure that whoever he would take a chance on, it would not come back to bite him. Soon, Greg heard a voice with a broken southern accent coming from the corner of the room. Greg couldn’t see who it was.

“Huh?” said a puzzled Greg. “How could he be?”

Living in an upper-class Long Island town, southern accents were few and far between. So when someone heard one, he could almost instantly throw a name and a face to the voice. This was the case for Greg. He knew in a matter of seconds that the voice belonged to Caleb Montgomery. Never in a lifetime would Greg have guessed Caleb of all people to be gay.

“If he is, then he is closeted. He has to be,” muttered Greg.

All Greg knew about Caleb was that his good lucks tended to attract some of the most attractive girls in the school. This alone should have been enough to rid from one’s mind the notion that Caleb Montgomery was gay, or even bisexual.

“No, this kid’s been said to have slept with Sophie O’Leary,” Greg said, “There’s no way he’s even closeted.”

However, the fact that Caleb was sitting in the support group for gay and lesbian students at Oakberry shattered all of Greg’s logic. Greg listened intently to hear Caleb speak, but the previous time he just spoke his name to introduce himself. Greg stood there for several more minutes, trying to get any information at all out of Caleb. He knew that Caleb might be a very real possibility for him. Greg could not stand it anymore. He had to know more. At the height of his frustrations, Greg gave out a sigh. It was loud enough where it might have been audible to the people in the room. Nervous over the fact someone heard. Greg fled the scene.

Pacing down the hall, Greg’s cock began to stiffen. Caleb Montgomery. Here was a guy who, sexual orientation aside, Greg would pick possibly first of any of the guys in his school to sleep with. His slow, southern accent was intoxicating. Greg would always envy how girls dreamily stared into his powerful, dominating eyes. He knew they would be lovingly protected by Caleb’s masculine embrace. But now it seemed Greg and not girls such as Sophie were better suited to receive Caleb’s embrace. These thoughts sent Greg swimming into a sea of arousal. He darted for a nearby restroom, entered a stall and began to jack off his swelling cock.

“God, Caleb!” He exclaimed, “Fuck!”

His strokes seemed to exponentially increase in speed as he reached quite the gratifying climax. Cleaning himself up, he was amazed at something. He still longed for deep intimacy even after he came. He still wanted for Caleb’s muscular chest to be pressed against his nude back as the lovingly snuggled. Usually after an orgasm, Greg’s mind would venture to non-sexual thoughts.

Leaning against the wall of the restroom, Greg was faced with a predicament, “How the hell can I approach him? Would he be pissed that I eavesdropped? Would he tell others I’m gay, too?”

A million more ‘would he’s’ crossed his mind as Greg played out scenario after scenario in his head on how he could screw this dream opportunity up. It is not every day that one’s most specific and greatest sexual fantasy had even a realistic chance of coming true. Greg knew he’d regret it if he were to drop the ball on this. Walking out of the school, Greg made a quick-minded decision.

“It has to be now.”

Greg exited the school and started to the library where he usually studied awaiting his mother who would pick him up on her way home from work. However, he paused at the bike rack pretending to unlock one of the bikes while he really kept his focus on the doors eagerly waiting Caleb. He needed to see him. He needed to talk to him. Greg figured that he could ask the right questions and not screw himself up. He realized that this was a delicate situation and that his reputation, Caleb’s, and that of both of their families could potentially be ruined.

An unseasonably cool breeze chilled every bone in the already nervous Greg’s body as he saw Caleb walk out alone. The bright virgin’s heart started pounding and his mouth went bone dry. Fortunately he did not have to get the conversation going.


Greg not trying to make direct eye contact swallowed hard. This he had not expected. He was tongue tied and could not think nor develop a cohesive thought.

“Anybody homes?” continued Caleb.

“Oh sorry. I was uh- just thinking about French Club,” replied a flabbergasted Greg.

“I guess the smart ones do get lost in thought a lot,” Caleb chuckled, “Which is why I wanted to talk to you.”

“Shoot.” Was all Greg could muster out.

“You look a little flush. You okay man?”

“I’m fine, just a bit too cold for shorts today I guess.”

“Yeah, you fool. I’m wearing a hoody and it’s almost not enough.”

“Yeah. So what’s your question?”

“You’re good at math right?”

“Sure,” said a humble Greg who scored nearly perfect on his SAT math.

“Good, because I’m kinda on the verge of fucking things up.”

“What do you mean?”

“See the math at my old school, I guess doesn’t count for credit here.”

“Not advanced enough?”

“I guess. So I had to double up this year and last to graduate. And it’s been a bitch. I don’t know how you do so good in calculus and statistics, and I can’t tell the difference between isosceles and salene trianges.”



“They’re called scalene triangles,” Greg corrected, nearly bursting into laughter.

“Well whatever. I need to pass the final to graduate. It’s so stupid. I’ll never need math again after this, and here it is fucking me up.”

“So you want me to tutor you?”

“Yeah, kinda. You want to at the library?”

“That’s where I was heading.”

“That’s a bit of a walk. I can drive you.”


Greg followed the unassuming Caleb in his car. The southern beauty explained to Greg how he had lied about getting good grades this quarter in math to his parents. They had been a nervous wreck that his poor performance in math would jeopardize Caleb’s athletic scholarship to Syracuse. Caleb explained that he had panicked and just lied to his parents to appease them.

“And if they find out, I’m fucked.”

“Well you needed help in geometry and what else?”

“Geometry 1 and 2.”

“That wasn’t too smart.”

“I got through Algebra 1 and 2 last year somehow.”

“The counselors are imbeciles at scheduling here. So what am I going to get out of all this?”

“Nobody’s gonna hear that you were snooping around the Rainbow Star meeting.”

Greg’s mind hit a wall. Should he feel duped because he’s being blackmailed? Or should he feel anger because someone he lusted for passionately was the one setting him up? His head went spinning.

“Stop the fucking car!” Greg exclaimed, “What are you doing! You saw me!”

Caleb parallel parked his car on the street.

“Yes I did.”

“And you think you’re gonna fucking blackmail me? What about you? If you out me, then you’re kind of in the same boat I’m in. Our reputations might be different, but they’re equally as damaging.”

“My family knows and they’re proud of me still and know I’m mature enough to gradually handle coming out to others. I’m not a self-loathing closet case.”

“Fuck you. Fuck you. You think I like being closeted? No I fucking don’t. But I don’t hate myself for what I am.”

“Go to a meeting then. Surround yourself with people like you.”

“Yeah and let Rackers blab his ass off. My parents will find out and freak. I guess they’re not as tolerant as yours.”

Greg’s eyes had begun to water. He might not have been self-loathing, but he was ever fearful of the repercussions that would arise if anyone ever figured out his little secret.

“People like me just can’t be gay. Or live openly as one.”

Greg hit his head back against the passenger seat’s headrest in dismay. He was choking up, holding back the flood of tears.

“And people like you aren’t afraid to fuck up someone’s life because you’re too stupid to save your own.”

“If it’ll make you feel better, I’m the only one who saw you. You only have to worry about me.”

“Gee, wonderful only one person is blackmailing me.”

“For Christ’s sake, it’s only tutoring. I don’t want fucking money or anything.”

“It’s the point Caleb. It’s the point! This isn’t…..”

Greg’s words broke off into an uncontrollable weeping. Caleb immediately became ashamed with himself and moved to console him, but then put his arms down, not knowing what to do.

“This isn’t what?” Caleb quietly muttered, “Greg?”

“I was waiting for you outside.”


“I looked in the goddamn room to see if there were any guys whom I could go out with secretly.”

“And you saw me?”

“Heard you. I was gonna talk to you and play it cool. Fuck Caleb, you’re amazing. I wanted you before I knew anything about all this.”

Caleb sat there simply frozen in his seat. He felt like punching himself right in the gut. What could he possibly say that could fix any of this? Right beside him sat an inconsolable Greg. He gazed out his window fixating himself on the light drizzle that had just started to fall.

“I think I’m gonna get going,” started Greg.


Caleb squeezed Greg’s thigh and moved in for a deep kiss. Greg was stunned by the sheer shock. This was his first kiss with anyone. He sat back allowing for an anger-ridden Caleb to maddeningly thrust his tongue into Greg’s mouth as tears began flowing out of Caleb’s green eyes. Soon Greg’s own tongue responded and their loving mouths moved in harmony as Caleb reached for the handle to move his seat back. He moved Greg on top of him as he remained pressed against his car’s vinyl lining. No words were spoken as the two frustrated young men, crying in both anger and newfound jubilance. Finally, after what seemed to be months locked in their mindless trance of passion, Greg broke through.

“Oh God, Caleb. I love…”

“No you don’t. You love this. Now, shut up.”

The two resumed their passionate kiss as Greg soon began to paw at Caleb’s bulging groin.

“Not here, Greg.”


“You’re a virgin right? Totally?”


“You’re not losing it like this. My house is going to be free Tuesday. Meet me in the lobby after school. Tell your parents you’re going to study.”

Greg could not believe these words. These blissful, magical words. It had all been spelled out for him right here, even an excuse to penetrate the parent problem. It was almost too sublime for Greg to consciously believe. He only nodded as Caleb’s soft lips warmly breathed his sexual desires into Greg’s tingling ear.

“Tuesday?” Greg finally said.

“Yeah, Greg. Tuesday.”

As the passion was reaching its crescendo, Greg was snapped out of his daydream by the sound of his teacher.

“Do you have an answer Greg?” the teacher inquired.

“Um…The Divine Comedy,” responded Greg, who uttered the first thing he could think of related to the subject he thought they were discussing.

Subsequently, the other students burst into laughter.

“It appears our Princeton Tiger is taking a break from his scholarly pursuits in favor of a comedic one,” said the teacher chucking.

The bell rang a moment or two later and Greg was spared any more awkwardness. Throughout the seemingly endless school day, Greg searched the halls in hopes of catching a glimpse of his soon to be lover. He was only kidding himself as they never crossed paths in the hall. He himself had even sworn off contact with Caleb in hopes of having a perfect continuation of the raw sexual energy he had shared with Caleb in his car. At last, the school day’s culminating two-thirty bell sounded. Greg darted toward his locker and discarded his books. A great swell of blood had rushed to his cock, and Greg simply ignored concealing it. He had grown too thrilled to care about anything other than Caleb. However, he couldn’t become giddy with glee at the sight. He was still closeted and Caleb just about.

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