East Side Prep

About five minutes later, David pulled his ass away from me again.
“Ok Sheridan, now you’re going to suck my cock.”
He turned around and showed me his eight-inch hard on. He grabbed my hard, but two-inch smaller dick and measured it against his monster.
“This is what a man’s cock looks like, faggot!”
As he let go of my dick, I knelt down and opened my mouth, moving my face toward his mushroom-shaped head. As I did, he pulled his cock away and slapped me across the face with it.
“Not so fast, you little faggot! You have to work for it. Start by kissing my balls.”
I started planting hot, wet kisses all over his scrotum.
“Yeah, that's it! Lick my balls, Mike! Give them the best tongue bath that they've ever had!”

I started licking his huge balls. The smell and taste of his crotch was intoxicating! I started working my way up toward the base of his shaft.
“Oh Mike!” he moaned, “That's it! Work your way up to my head and swallow my dick!”
Within a few minutes, I had worked my way up to the head of his cock. There was a wad of pre-cum oozing from his slit. Before I could lick it off, he wet his finger with it and smeared it over my lips. I licked it off.
“You like the way that tastes, Sheridan? There's a lot more where that came from! Suck my dick!"

Before the words were out of his mouth, he shoved my head down on his huge, oozing dick. He gave me a minute to get used to it. It didn’t taste as bad as I thought it would. His cum tasted kind of sweet and salty at the same time, it reminded me of the sea. Although his cock was rock hard, its skin was silky soft. I realized to my horror that I liked sucking cock! I liked everything about David’s body, and I was starting to like the idea of being his slave.

I started to lick and suck his dick. I could tell by the way that his dick twitched in my mouth that he was enjoying it, and this knowledge made my dick even harder.
“Oh yeah, deep throat it!” he said as he grabbed the back of my head and shoved his cock down my throat.
My lips and nose were in his dark, soft bush of pubic hair, and I started to gag. He pulled me up just long enough to catch my breath and then shoved me down again. He repeated this a few times until I began to get the hang of it. Soon, I started going up and down on his cock by myself. I was enjoying the challenge of seeing how much of him I could swallow.
“Yeah, that's it!” he moaned. “You’re a natural cock sucker, Mike! Lick my head and play with my balls.”

I did what he told me and after a few minutes had passed, he pulled his dick away from me. I tried to put it back in my mouth, but he pushed me away.
“Mike, I’m going to give you a choice. If you want, you can finish sucking my cock and become my slave. If not, I’ll let you off the hook. I’ll forget that any of this ever happened, and I promise that nobody will ever know. I’ll give you exactly two minutes to think it over.”

I didn’t need two minutes to think, I knew what my answer was. David had awakened feelings in me that I had never known I had. I had known that I liked to check out other guys, but I never dreamed that I would actually have sex with one, and that it could be this good. Besides, David was the best-looking guy in the school, and a senior. To be honest, I was more than a little flattered that he would be interested in a lowly freshman like me.

I only hesitated a second before I said, “Please cum in my mouth. I want to belong to you, David. I’ll do anything you want; I like it.”
He took me in his arms and kissed me, softly and tenderly.
“Thank you, Mike,” he whispered in my ear. “You won’t be sorry.”
I thought to myself, “Maybe he’s not as tough as he seems.”
I started kissing his neck. Then I moved down to his chest, and kept moving down until I was in front of his dick again. I took it in my mouth, swallowed its whole length, and started sucking him off with even more passion than before.

He started moaning, and in a matter of minutes said, “I’m going to cum! You're going to swallow my whole load. If any leaks out, you’re going to lick it up, understand?”
I grunted a yes. He grabbed me by the ears and started pulling me up and down on his cock. I felt his cock starting to twitch in my mouth, and then it exploded. I felt blast after blast of his hot sperm shooting into my mouth.

I did my best to swallow all of it, but there was just too much, and some of it leaked down my chin and on to his balls.
“You’re not done yet, Mike! You know the deal.” Smiling, he dipped his finger into the overflow and held it to my mouth. “Now lick it off, nice and slow.”
I started licking his sperm off his fingers as slowly as I could. He seemed to enjoy watching me do this, and I enjoyed the taste of his seed. When I finished, he took me in his arms, gave me a long hot kiss, and started jerking my rock hard dick. After only a few strokes, I shot my load all over his belly.
“Clean it up!” he said. I licked my cum off of him. It mingled with his in my mouth.
“Come on Mike, let’s shower, and get out of here. They’ll be closing the school soon. Do you think your parents will let you stay over my house for the weekend?”
I said that I thought they would.
“Good; nobody’s home at my place.”
“Are you going to fuck me tonight?” I nervously asked.
He looked into my eyes. “Do you want me to? Be honest.”
“Yes, Dave; I want to give you my virginity. I’m a little scared, but I want to be with you more than I’ve ever wanted anything in my life. I’ve wanted you since the first day we met.”
He kissed me. “Don’t be scared. I promise that I’ll be gentle with you. I want to make this the best night of your life.”
I trembled with fear and excitement.

Chapter II

After we left the locker room, David gave me a dime and sent me down the hall to use the phone while he went outside to smoke a cigarette. When I got outside, David was talking to his buddies, and to my surprise, two guys from my year.
“Hey Mike, you know my friends, don’t you?”
I knew who they were. They were the guys who had been in the locker room earlier. The seniors were Brian Callahan, Tom Warren, and Jason Corbett. The guys from my year were Jack Chivers, who was a nice guy and Steve Corbett, Jason’s brother, who was the biggest jerk in my class. For some reason he just seemed to hate me from the first day of school. He put me down or made fun of me every chance he got.
“Jack here belongs to Brian, and Steve belongs to his brother.”
I couldn’t believe it! I wasn’t the only freshman cocksucker!
“Hey how was he, Dave?” asked Tom.
“I picked the right freshman.” David said. “He’s a natural born cocksucker. He learned fast. Some of these kids get sick or freeze up, but not Mike. I’m going to fuck him in my bed tonight!”
“How big is his wee-wee?” Tom asked.
“It’s about six inches long; not bad for a freshman.”
I must have blushed ten shades of red.
“Look Dave, why don’t you let him give me a quick blow job. I don’t have a freshman of my own yet.” Tom said.
To my relief, David said no.
“Tomorrow afternoon you can all come over to my house and give him his initiation.”

Steve grabbed my ass and said, “I can’t wait to fuck your face, faggot!”
Before I could say anything David grabbed Steve by the collar and yelled “Who told you that you could touch my frosh? I’ve seen you treating him like shit all week. It stops now. He belongs to me now, and you’ll treat him with respect. Understand asshole!”
Steve managed to sputter, “Yes sir!”
“I’d like to apologize for my brother, Mike. He’s an immature little bastard.” Jason said.
“For your punishment asshole, Mike’s not going to suck your dick tomorrow; you’re going to suck his!”
“Fuck that! I won’t do it!” Steve shouted.
“Just for that, you’ll eat his ass too!” Jason said.

Steve opened his mouth to say something, but thought better of it. It was obvious that his brother wasn’t going to let him win.
“Well, I’ve got to get going now.” David said. “I’m taking Mike for some pizza, and then its home to pop some freshman cherry!”
All his friends laughed, and high-fived him; Jack winked at me and Steve scowled.
As we walked, David put his arm around me.
“What I said to Steve goes for everybody. If anybody gives you any shit, I want you to tell me, and I’ll put a stop to it damn fast. I won’t allow anybody to be mean to you. Since you’re willing to give yourself to me, I’ll take care of you. I owe you that much. When I promised you that you wouldn’t be sorry, I meant it.”
I knew now that underneath his tough façade, David was a nice guy.

Chapter III

After we ate our pizza, we went to David’s apartment. It was in one of those old luxury apartment buildings on Fifth Avenue across from Central Park. He lived in the penthouse, which had its own roof garden and an incredible view of the park. The furniture was antique, and the colors looked as though an interior decorator had coordinated them. The painting over the fireplace was, as I would later learn, a genuine Cézanne. It was the kind of place that you only see in movies.

“Dave, this is the most beautiful apartment I’ve ever seen!” I said with wonder in my voice.
“Yeah, my mom and step father have money. They’re never here though. They live in England. I’m pretty much on my own.”
He looked at his watch. “It’s still early. Let’s hang out for a while and have a few drinks before I fuck you. The alcohol will relax you. Do you like beer?” I said yes, and he told me to sit down at the table on the roof garden. I went outside and looked over the railing at the postcard view of the park. As I admired the view, a horrible thought occurred to me for the first time. I was gay. Deep down, maybe I had suspected it. I knew that I liked to look at other guys, but somehow I had never equated those feelings with the drag queens and leather men who frequented the bars on Christopher Street in Greenwich Village. My eyes started to fill with tears. I didn’t want to be a freak! David came out, put the beers on the table, and saw that I was crying.

“What’s wrong, Mike?” He said with concern in his voice. I threw myself into his arms and sobbed. “I’m sorry I was so rough with you. I’m not such a bad guy, really. Don’t be scared; I would never hurt you.” He said.
“That’s not it,” I said. “I know that you’re a good guy. I just realized that I must be gay. It scares me! I don’t want to be a freak!” I sobbed.
David held me in his arms, and tenderly ran his fingers through my hair. “I know how you feel. It is scary. I was just as frightened as you are when I realized that I was gay.”
“You, Dave? But you don’t look queer, and you’re so popular!” I stammered.
David laughed. “I’ll take that as a compliment. Look Mike, not all gay guys prance around in drag. A lot of us look like the boy next door. You and I both do. I would never have guessed you were gay by the way you look or act. I only knew because of the way you stared at me when you thought I wasn’t looking. That’s something you’ll have to learn to control. It could get you into real trouble if you do it to the wrong guy.”

I breathed a sigh of relief. In my naiveté, I thought that it would show; that I had a scarlet letter on my chest that everyone but me could see.
“Thought you would get the urge to put on a dress and skip down the Yellow Brick Road, didn’t you?” He said. I laughed through my tears.
“This might sound conceited Mike, but today is your lucky day. Now you can talk to me. I didn’t have any gay friends when I was your age that I could ask for advice. I didn’t even have anybody to hold me when I cried. You’re the first person I’ve ever told that I was gay. An openly gay guy would be an outcast at our school.”
“Why did you trust me? I asked in disbelief.”
“It’s simple. You told me that you were gay first, and being a freshman, you have even more reason to keep quiet than I do. If they find out about me, I’ll only have a year in Hell. If they find out about you, you’ll have four. Since were fucking around, we’ll sink or swim together. Even without all that, somehow I just feel like I can trust you. I don’t know why.”
“If you knew that I was interested in you all along, you must have set me up in the locker room!” I said, surprised.

He smiled. “Guilty as charged. I saw you hanging around waiting for the rest of your class to finish so you could shower alone. From the looks you were giving me all week, I knew that you would stare at my cock if I undressed in front of you, so I got my friends to go in with me as witnesses and made you an offer you couldn’t refuse!”
“What if I had refused?” I asked.
“I knew you wouldn’t refuse, but if you had I wouldn’t really have turned you in or hurt you. I could never do that to you. You’re a nice guy, and I like you.”
“I like you too, Dave.” I smiled.
“What for, my body or as a person?” He joked.
“Both,” I said truthfully.
“I’m happy to hear that. I’d like you to be more than just my fuck buddy.”
“I’d like that too,” I said as I kissed him.
We sat together for a while and drank our beer. The more we talked, the more I liked him. Like me, he loved old movies and was interested in history and art. I found out that he wasn’t nearly as tough as he acted at school. He told me that he acted that way so people wouldn’t suspect that he was gay. He couldn’t even tell his friends, whom he fucked around with, that he was gay. They were supposedly straight and fucked around with guys when no girls were available.

As I started on my third beer, I started to feel a little buzz. “I can’t believe this is happening.” I said. “This morning I was just an average kid getting ready for school, and now I’m in a Fifth Avenue penthouse about to go to bed with the best looking guy in school. It’s like a dream!”
“Do you really think I’m the best looking guy in school?” David asked, smiling.
“I think that you’re the best looking guy I’ve ever met. Nobody has ever had the effect on me that you do. I couldn’t take my eyes off you all week!” The beer was giving me courage.
“I couldn’t take my eyes off you either,” David admitted. “I almost came in my pants yesterday at lunch when I was making you give me that massage. After that, Tom said that he wanted to fuck you and I almost hit him!”

“I’m glad. He doesn’t make me feel the way you do; none of the other seniors do. You’re so much more handsome than any of them are.” I could swear he blushed.
I made use of my newfound courage, and put my hand on his crotch. He was hard. I unzipped his fly, brought his cock out into the night air, and started stroking it. He put his arms around me and found my lips with his. His kisses were long, hot, and passionate.
“Let’s go to my room.” He said.
“I’m ready.” I replied.

Chapter IV

David’s bedroom was as elegant as the rest of his apartment. It didn’t look like a typical teenager’s room. The furniture was antique, and there was a King size bed with a nice bedspread and satin sheets. As soon as we entered the room, we were all over each other. As we passionately kissed, we started undressing each other. When we were both naked, David guided me to the bed.
“Lay down on your stomach, I’m going to take you from behind,” he instructed
“Couldn’t we do it facing each other so we can kiss?” I asked.
“Not your first time. It would hurt too much,” he said. “I’m going to lube you up really well and I’ll take it very slowly. I would never hurt you, Mike. Do you trust me?”
I answered him with a kiss. “I hardly know you, but for some reason I’m sure that I could trust you with my life,” I said as I lay down on my stomach.

“I’m going to put my finger in your asshole with some baby oil to lube you up. I know you’re nervous, but try to relax your asshole as much as possible.” I felt the cold oil on my asshole, and then I felt his finger go in. It didn’t hurt, but felt strange. He held it there for a minute so I could get used to it, and then started pulling out and pushing in, deeper and deeper. It started to feel good. “Oh Dave, do it harder,” I moaned.
“I think you’re ready for the second finger,” he said.
I felt him put more oil in my hole, and then he put in two fingers. It hurt a little at first, but I soon got used to it and started moaning in pleasure again.
“One more finger and you’ll be ready for my cock!” He said.
Again, I felt the coldness of the oil and felt three fingers go in.
“Dave, it hurts!” I said this time.
“It’s ok, just relax your asshole. Pretend you’re taking a shit.”
I did what he said and soon the pain stopped, and I started to feel good again. After a few minutes he said, “I think you’re ready for my dick.”

He took his fingers out, lubed up his dick, and poured some more oil on my asshole. He got on top of me, and I felt the head of his hard cock press against my asshole.
“This is your last chance to back out. Are you sure that you want me to be your first? Is there anybody else who you would rather be with? You only get one first time, you know,” he said gently. “As much as I want you, I’ll let you go if you don’t really want me.”
“You’re the only one that I want. I’ve wanted you ever since the first day of school. Please fuck me!”
“I won’t fuck you,” he said. My heart sank. “You fuck somebody you don’t give a damn about. I’ll make love to you, if you want me to.”
“Yes, make love to me Dave. I want to feel you inside of me.”

He kissed my neck from behind, and then I felt his big dick head pushing into my asshole. He went in slowly, and I guess between all the lube he used and the fact that I really wanted him, it didn’t hurt very much at all. Before I knew it, I felt his pubic hair tickling me. “Are you ok?” He asked.
“Oh, yes! It doesn’t hurt like I thought it would!” He pulled part way out, and went back in. I felt a strange feeling, as though I was cumming on the inside. “What was that?” I asked.
“My dick pressed against your prostate. Did you like it?”
“Yes, can you do it again?”
“You bet!” He laughed. He started going in and out in a steady rhythm.
“Oh Dave, yes!” I shouted. It was the most incredible thing that I had ever felt. I had been jerking off for years, but had never felt anything even remotely like this.
“Oh Mike, you’re unbelievable! I’ve never been with a guy who made me feel like you do!”
“Go harder, Dave! Don’t hold back. I love this! I’ve never felt this good before.”
He started to go at it with all his might. I felt like I was in heaven. Everything seemed to be going in slow motion.
“You’re mine now, Mike. You’re a part of me. How does it feel to belong to another guy?” He panted.
“It feels GREAT! I want to belong to you FOREVER!”

The funny thing was that I really did feel like I was a part of him. It was more than just a physical feeling; I felt as if our souls were one as well as our bodies.
He started to go even harder and faster.
“I’m going to cum, Dave! I’m going to shoot all over your bedspread!”
“Fuck it, go ahead!”
A minute later, I started to shoot my load. The funny thing was that David started to cum at exactly the same time that I did! I felt his hot load shooting deep inside of me in rhythm with my own orgasm. It was wonderful.

After we had both cum, he lay on top of me for a minute to catch his breath. Slowly, he got up, pulled me to him, and gave me a long, hot kiss. I could still feel the warmth of his sperm deep inside of me.
“I never dreamed it could be this good, Dave.”
“Me neither. I’ve had sex lots of times, but I never felt anything like this before. It was as if we were one person. I mean it, Mike; I swear, it’s not just a line. Do you believe me?”
“Yes, I do. I felt it too. Oh, your bedspread!”
There was a huge puddle of cum on it. I had never shot so big a load in my life. David went over to it and to my surprise, licked it up, and swallowed it. I went to him and kissed him, sharing the taste of my passion.
“Dave, would you give me a hickey?” I asked.
He laughed. “Sure, but why do you want one?”
“This is going to sound silly, but I belong to you now. I want to wear your mark.”
“I don’t think it’s silly at all. I’m flattered.” He started kissing my neck, sucked hard, and put his purple mark on me.

Chapter V

We were lying in the bed in each other’s arms when David reached over to the nightstand for a cigarette. I asked if I could have one, too.
“I never saw you smoke before,” he said
“Well, I’ve only tried it a few times, but I’ve always heard that smoking after sex is supposed to be the best. I just have to try!”
David laughed, put two cigarettes in his mouth, lit them, and handed me one.
“I saw that in an old movie once. I’ve always wanted to do it.” He said.
“Now Voyager with Bette Davis and Paul Henreid,” I said with a smile. “It’s one of my favorite movies. I guess we have the same taste in everything.”

We just lay there for a while and smoked, giving each other an occasional smile. Underneath my calm exterior, my mind was spinning. Up until that afternoon, I hadn’t known that I was gay. Up until a few minutes ago, I didn’t know that one guy could fall in love with another. Nevertheless, I was in love with David. I knew it as surely as I knew the sun would rise in the morning. Should I tell him? Did he love me? Should I ask him? Would he laugh at me if I did? I wished I had some more of that courage the beer had given me earlier, but it had worn off long ago. I finally decided that I had to know.
“Dave, could I ask you a personal question?” I said
“Of course, you can ask me anything.” He smiled.
“Before you said that you liked me. How much do you like me?”
“Why do you want to know?
“I...never mind.”
“Please tell me, Mike. I want to tell you how I feel, but I’m too much of a coward to say it first. Nobody has ever said those words to me before, and I’ve never said them to anyone either.”
“Promise you won’t laugh or make fun of me? It would kill me if you did.”
“I swear I won’t. I would never hurt you like that.” He put his arm around me.