East Side Prep

This story is entirely fictional, as are all the characters in it. To the best of my knowledge, there is not now nor has there ever been a school in New York called East Side Prep, and my depiction of it is not representative of any real school, past or present.
To my readers:
This story is set in the last days of the blissfully ignorant pre-AIDS era. That is the reason that no mention is made of condoms. It is certainly not my intention to encourage or condone such reckless behavior today.

Chapter I

In September of 1980, I was a freshman at East Side Prep, an upscale high school for boys on the corner of 86th Street and Madison Avenue in Manhattan. It had been a hard week. The first week of school is slightly traumatic for an incoming freshman in any high school, but at East Side, the seniors made sure it was pure hell.

In an effort toward freshman orientation, the school administration assigned every senior a “freshman buddy” whom he was supposed to befriend and show the ropes of the school. In practice, the seniors made their freshman buddies wait on them in the cafeteria, carry their books for them, and address them Mr. or Sir for the first week of school, which they called “Freshmen Initiation Week.” They abused us in any way they could think of.

I was lucky enough to get David Donovan as my senior buddy-abuser. He was the most popular guy in school. Aside from being incredibly handsome, he was the captain of the basketball team as well as the student body president. Although every time he passed me in the hallway he gave me a wedgie, and every time he saw me in the cafeteria, he made me wait on him and give him a shoulder massage while he ate, he was kinder than many of the other seniors were. At least he never hit me or reduced me to tears in front of everyone like some of the others did to their “buddies.” There was another advantage to having him as my buddy. The first time that I met him, he shook my hand, looked into my eyes, and I got a hard on. No guy ever had this effect on me before. After that, I noticed that I got a hard on any time he looked at me! I found it difficult to keep my eyes off him, and stared at his body whenever he wasn’t looking. Every day after school, I went home and jerked off imagining what he looked like naked.
Somehow, I made it through the first week of school. My last period on Friday afternoon was Phys Ed. The idea of getting naked in the showers with the other guys in my class made me nervous, so I took my time getting there, hoping that everyone else would be finished by the time that I did, and I could have some privacy. It worked. I looked in the mirror with some pride before I stepped into the shower. I was tall for my age, about six feet, with blond hair and blue eyes. If someone didn't know me, he would take me for at least a sophomore, I thought.

I was alone in the locker room toweling off, when David Donovan and some of his friends came in to change before they went to work out in the weight room. By the time I got my shorts on, the seniors began to undress. I had never seen an older guy naked before, and I couldn't believe how big their cocks were and how low their balls hung. I couldn't take my eyes off of David’s beautiful body in particular. He was about six feet two inches tall, with short brown hair, brown eyes, smooth skin with a little hair on his arms and chest, and a perfect suntan line. He was well muscled, and had the biggest cock of any of the guys. He reminded me of the Greek and Roman statues I had seen at the Metropolitan Museum. He looked even better than he had in my imagination. All of a sudden, I wasn't so happy with my own physique. Without realizing it, I started to stare at him.

I was shaken out of my trance when one of David's friends, said, “Hey, Dave this frosh is staring at your cock!”
I froze with fear. I just knew that they were going to kill me. David yelled, “Get your ass over here, Sheridan!”
Knowing that his friends were between the door and me, I went to him. He looked deeply into my eyes, angrily at first, and then his gaze softened and he smiled. He said to his friends, “Get the fuck out of here, guys! I'll take care of this by myself.”

After his friends left, he said “You know, Sheridan, I should kick your ass and report you to the headmaster for what you did.”
I broke out into a cold sweat. If David told the headmaster, he would notify my parents and expel me. Even if I denied it, there was no way the headmaster would take my word over the word of a senior and the Student Body President, no less. My life would be over!

He continued, “But I have a better idea. I'm going to make you an offer you can't refuse. You're going to be my personal slave for the rest of the year. Since you like my dick so much, you'll get to see a lot of it from now on! Any time I get horny, I'm going to take you in here, or the boy's bathroom, or an empty classroom, and make you suck me off. You'll sleep over my house any weekend I want, and I'll fuck you in my bed. Today, I'll teach you how to suck my cock. Eventually, you'll learn to take my cock up your ass. In return, I'll keep quiet about what happened and tell my friends to shut up too. Is it a deal?”
I looked at him in shock. Although I had been curious about what an older guy's body looked like, I had never even thought about doing any of the things he had mentioned. I said, “L-Let me think about it.”
“There's nothing to think about. Either be my fuck slave, or get expelled for being a faggot”, he said. I stared at him like a deer caught in a headlight.
“If... If I do what you want, n-nobody will ever find out?” I almost begged.

His face lit up in an evil, sexy grin. He knew he had me. “The only people I'll tell will be into this sort of thing too. You'll be my property. If I decide to loan you to one of my buddies, that's my business. I promise that the school and your parents will never know.”
After a long pause, I said, “Ok... I guess I don't have a choice.”
“Ok, what? I want to hear the words,” he said.
“Ok, I'll be your slave.”
“Take off your shorts and let me see my property, Sheridan!” he said.

Nervously, I dropped my underpants.
“Not bad!” he said. He started to touch my chest. “Nice tits. Almost as good as a girl!” he said, laughing. He slowly moved his hands down toward my waist, and started to feel my ball sack and dick. He measured my soft dick against his hardening cock.
“Cute little wee-wee, not bad for a freshman. Don't worry; you'll be too busy making my cock feel good to pay much attention to your own little nub. Now, turn around and let me see your ass.”
I did what he said, and soon felt his hands caressing my cheeks.
“What an ass you have, Mike! I'll bet you have a nice virgin hole, too. Let's see. Spread your legs!”
I started to beg, “Please sir, please don't do this to me...”
“Spread your fucking legs, Sheridan, or I'm getting dressed and going to see the headmaster!”

With tears streaming down my face, I did what he told me to do. He reached over to his locker and pulled out a jar of Vaseline. He coated his finger and started to penetrate my asshole with it. I moaned in pain and humiliation.
“Yep, you're a virgin, all right. I'm going to enjoy popping your cherry!” I froze in terror.
He laughed, and ran his hand over my back soothingly.
“Don't worry, I told you I'm not going to fuck you right now; soon, but not yet. I have other plans for you first, and you can drop the ‘sir’. You have my permission to call me Dave like my friends do, since I’m going to be the most intimate friend you ever had in a few minutes.”
I breathed a sigh of relief as he pulled his finger out of my asshole.

“Turn around and face me!” he ordered. As I did, he pulled my body to his. I could feel his hard cock pressing against my smaller one. He pushed his mouth to mine and started kissing me. His breath was hot, and he pushed his tongue into my mouth. At first, I was tense and nervous, but soon started to relax. His embrace was warm and strong, and his body smelled of good cologne. I had never experienced a sensation like it before. Before I realized it, I was kissing him back, and my tongue was in his mouth. I was actually enjoying his kisses!
As we were kissing, he took my hands and started to move them around on his body.
“Feel me, Sheridan. Feel my body! I know that you’ve wanted to all week.”

I ran my hands over his smooth suntanned skin. I could feel the hard muscles in his arms and chest. I worked my way around and down to his ass. It felt smooth and tight, and the feel of his cheeks in my hands started to make my dick hard.
“You don't seem to mind this all that much, you little faggot! You’re as hard as a rock now!" he said between kisses.
I looked down in horror and realized that he was right. My dick was now at its full length of about six inches.
“On your knees, Sheridan!”

I braced myself for what I thought was coming next. I knelt down in front of him and found my face just inches from his huge cock and balls. Their musky aroma filled my senses. Just then, he turned around.
“You seem to enjoy feeling my ass, so I think I'll give you a treat. Kiss it!”
I hesitated. Kissing a guy and enjoying it was bad enough, but kissing ass? To my mind, that was the ultimate humiliation.
“Kiss it or I'm going to see the headmaster.”

With tears welling up in my eyes, I started kissing his cheeks. In spite of my self, my dick had never been harder.
After a few minutes of this, he said, “Now, spread my cheeks and French kiss my asshole, faggot! It's nice and sweaty, so you should really enjoy it,” he laughed.
“Dave, no... Please...”

Before I could finish the sentence, he spread his legs and bent over, shoving the open crack of his ass in my face. Knowing I had no choice, I buried my face in his crack and my lips found his asshole. I started kissing it the way I had kissed his lips a few minutes before. I stuck my tongue in his hole and started licking it.
I thought that the smell and taste of his ass would be revolting, but they weren’t. He was very clean, just a little sweaty. His ass had an almost pleasant manly smell, and it just tasted a little salty. My dick had never been so hard. “Oh yeah Sheridan, that's right! Give me some more tongue!” He moaned. I shoved my tongue in as far as I could. I was actually starting to like the taste of his ass, and the smell was making me horny beyond belief! I couldn't believe it! This guy was turning me into a faggot, and there was no way to stop him. Even if I could, I wasn't sure that I would want to. I wondered what he had in store for me next.

Suddenly, he pulled his ass away from me; so suddenly, that I was stunned and disappointed. He turned around and looked at my hard on, and said, “You know Mike, if you want some more of my ass, all you have to do is ask me nicely.” I knew what he was after. He wanted me to give up my last shred of pride by begging him to let me eat his ass. I didn't have the strength to fight him any longer. I didn't know if I wanted to. I seemed to enjoy letting him take control of me. I was confused. I looked back into his eyes.
“Please Dave, can I eat your ass some more?”
His face lit up in a big smile.
“So, you like eating my ass?”
“I-I don't know. I think I do,” I answered with surprise in my voice. He knew he had broken me.
“Tell me the truth; did you enjoy kissing me?”
“Yes, I did.” I said, as I blushed with shame.
“I'll let you munch for a few more minutes and then we'll move on.” He turned around, spread his legs, and gave me a few more minutes of paradise.