Just to let you know, I've changed the names of the people in the story.
So it all started when I was 14. I went to a boarding school in a city which I wont say. Now I knew I wasn't Gay but I knew I wasn't straight. Not many guys caught my attention except for one. His name was Connor and he was a few months younger than me, and in a grade lower than me. I knew him because he was friends with my friend Steve's little brother. Since Steve's little brother liked to tag along with Steve a lot, Connor wasn't far behind. In my opinion he was utterly perfect. He had shoulder length brown hair (which was a turn-on of mine. Even after all these years, I have to admit it still is) and big, round green eyes. He was short and somewhat skinny but his face was round and cute. This made him look so innocent and pure. I was bound to change that if it killed me.
As for me, I was taller than Connor but not by any means a tall guy. I had jet black hair and hazel eyes that I thought kind of resembled Connor's. I was skinny and I had just got my braces off so my teeth were pretty perfect which I though made me look more attractive.
Alright so on with the story. I was in my room listening to my friends talk about whatever we talked about back then. I lived alone which most saw as a rare privilege but I was always lonely. Then one of the staff members opened my door and said to report to the principle; Mr. Barlow's office. My friends started ooh'ing saying I was in trouble so I kicked them out. Upon entering Mr. Barlow's office I noticed he was stressed out about something, which he always was when someone gets in trouble.
"What's the matter?" I asked, "Did I do something, sir?"
Mr. Barlow raised his head from his hands and said, "Alex, how would you like a new roommate?"
I liked the idea so I nodded and said, "Yeah sure, is it a new student?"
"No, it is Connor Graham," he said as my heart exploded into a million pieces, "I'm afraid something has come up and he has to switch roommates."
"Okay," I said, trying to keep calm, “but can I ask what came up?"
“I'm afraid I can't tell you," said Mr. Barlow. I really wanted to know what problem Connor had so I kept on trying to ask what happened.
"Come on, sir," I said, "I'm going to find out eventually and from kids that are gonna mess up the story so shouldn't I hear from a reliable source about who's gonna be living with me for the rest of the year?"
"Very well," said the principle, “sit down and I’ll tell you if you promise not to tell anyone."
"I promise," I said.
"Alright,” he said, “All I can tell you is that Connor and his roommate, Ben Hubbart(Steve‘s brother), got into and argument about a girl that turned physical. Connor has some bruises but I’m afraid Ben fell down some stairs and has a broken arm. So, since both of them were very well-behaved students before this, I decided to switch their roommate assignments to more responsible older boys.”
(SHIT!!!!) I thought, (Connor fights dirty!!! That’s so fucking hot!!!!) Connor was a very shy boy so it really surprised me that he would do this.
“I see,” I said, “So is that all?”
“Yes that’s all. Connor will move in on Monday so that will give you the weekend to prepare.”
“Thank you” I said. I was on top of the world as I left the office.
All weekend long I was trying to waste time to make Monday come faster by doing random crap. When Monday finally came, the room was spotless both beds in the room were made and all my books were neatly stacked because of my procrastination craze, so at least Connor would have a clean room to arrive to. I was listening to some Metallica when I heard a faint knock on the door. My heart skipped a beat or two and I opened up the door. He was standing there with his suitcases and he had a few small bruises on his face, which turned me on for some reason. Ignoring that, I told him to come in and he gave me a little smile and walked in. I helped him unpack and after a few minutes we were done. I really had to take a piss so I went to the bathroom down the hall. On my way back I ran into Steve and I told him about Connor moving in.
“Do you know why he had to move in, Alex?” He asked me.
“Yeah, Mr. Barlow told me that Ben and Connor got in a fight over a girl.” I said.
“Not exactly” said Steve, “Umm, how do I say this…Ben and Connor were…gay…for each other.”
My stomach dropped to my feet and all I could say was “WHAT?!?”
“Yeah,” he said. “Nothing serious; it was just making out and stuff they weren’t dating but Ben did start dating this girl and Connor got really jealous and they had a fight. That’s why he’s in your room right now.”
“Holy crap.” I said, “I guess I’ll go back now.”
“Alright, later” he said.
I walked to my door and I realized I didn’t remember where my key was, and since it was on a giant keychain I felt pretty pathetic. I reached under the plant vase on the floor right next to the door for my spare when I heard a noise from the room. It didn‘t take me long to realize Connor was crying. I was horny out of control now so I decided to wait for my boner to dissipate and I opened the door and walked inside. Connor was on his bed, his head on his knees and his hands on his head; crying. He immediately bolted his head up and his face turned red and he got up and wiped his face, obviously humiliated.
“What’s wrong, Connor?” I asked even though I already knew what was wrong.
“Nothing” He said.
“Are you sure because I know why you had to move out of your room.” I said
“Oh DO you?” He asked, getting a little pissed.
“Yeah. I know all about you and Ben.” I said, walking toward him, “Steve told me.”
He turned beet red again and then he burst into tears again and sat on the bed. Something changed in me as I watched him fall back on the bed, tears running down his fair skin, which was now red with the embarrassment of his biggest secret having been found out. I felt guilty and sad for having made him cry but I knew then that I truly did love him. I decided to take a chance and I lay down next to him and I gently called his name. Right as he looked up I moved my lips towards his and kissed him slowly at first but when I found out he liked it by the way he grabbed my back and moaned softly I grew more passionate and I began to French kiss the boy who had just moved in an hour ago. I broke the kiss and began to slowly kiss his neck with my lips. This was obviously tickling him and he began to giggle a little bit. I slowly removed his shirt and I moved down from his neck to his nipples. I began licking and caressing his nipple with my tongue and he began to relax on the bed and moan even more so. I moved back up his body and started kissing him again. As I made out with him I began to move my hands behind his head and gently pull and tug at his hair. His soft and lush hair and the smell of his beautiful body was enough to keep me content for the day but then he did what I never expected him to do. In one swift move he undid and removed his shorts and followed suit with his underwear. I broke the second kiss of my life to raise from the bed and admire my crush of months now naked in front of me and begging for my love.
“What are you waiting for? Do me.” He uttered. I guess when I changed, I changed to a more sadistic and wicked version of myself because I wanted to make him my bitch but at the same time I wanted him to be my prince. I wanted to make him scream but I didn’t want to hurt him. I took my clothes off as well and I resumed my position on top of him. I kissed his cheek softly and then I slowly lowered my head down his body, all the while licking his skin, stopping every once in one spot to torture him a little bit. When I finally reached his cock, I went straight to his balls and dragged my tongue across his delicate skin. When I reached his dick I took a moment to admire it. It was uncut and about 5 ½ inches long and had a modest tuft of hair at the base. I gently kissed his head before engulfing a good three quarters of it. The feeling of finally having his dick being eaten was great for him and he exploded with pleasure. I moved his dick in and out of my mouth all the while moaning deeply to softly give off a vibration onto him. As I was sucking him off, though, I figured out how to fulfill my sadistic side. I listened closely to the sounds he was making and when he started to breath in deeply I knew he was about to cum and I stopped abruptly and took my mouth off him. He was obviously very close to cumming because he whimpered and he grabbed the sheets of the bed.
“AAAAHH!!!! WHAT THE HECK?!” he yelled, “WHY DID YOU DO THAT?! I WAS ABOUT TO CUM!!!!! YOU’RE SUCH A… A…BIG JERK!!!!” I had to laugh a little about his word choice. Connor was still pretty innocent inside no matter what act he put on. He couldn’t bare to cuss at me and he knew it.
“Don’t worry, baby,” I said calmly, “I’ll finish the job.”
And with that I took his cock in my mouth again and worked it in and out once more. I let him cum this time, which he didn’t do that much but it was enough to fill a modest portion of my mouth. Instead of swallowing it, though, I slid my way up his body until I reached his head. I grabbed his head and kissed him passionately and letting his semen flow into his mouth. The moment he tasted his cum in his mouth his eyes opened wide and he tried to pull away but I kept his head in a vice grip and continued to usher the cum into his mouth. Once he swallowed I broke the kiss and smiled at him. He giggled and blushed a little bit.
“That actually tasted pretty good.” He said.
“Yup. Now it’s my turn.” I said.
“Umm, ok. Let me just get up and you can lie down. I wanna taste more cum.” He said.
“What? Oh, I don’t want a blowjob.” I said.
“What? What do you want then?” He asked but as soon as he asked his face flushed a little and he said, “Oh, Alex, I don’t know, I’ve never done that before.”
“I though you wanted me to do you.”
“Well, yeah, but I didn’t mean… well… is it gonna hurt?”
“I don’t know. I’ve never done it before, but I’ll be gentle.”
“Do you promise?”
“Just tell me if it’s too much for you and I’ll stop.” I was half lying. I didn’t want to stop but I had been so mean to him already. I went into the bathroom and I found some lotion to use as lubrication. I went back the bedroom and I relaxed on my back on the bed and after I rubbed the lotion on my cock Connor sat on my stomach facing me. He looked nervous, which only made me twice as hard watching him. My cock was about 6 inches and uncut. I saw how scared he was but I was confident Connor would last. He scooted back and placed his ass over my cock. I sat up and looked in his scared virgin eyes. I couldn’t believe I would be the one to take his virginity.
“Ready?” I asked.
“Yeah.” He said, shakily.
“Hey Connor.” I said
“What?” He asked
“I love you” I said.
He blushed and he giggled and said,
“I love you too.”
I moved my hands up to his face and embraced it for a moment. I moved my hands to his shoulders and grabbed them. I firmly pushed his body down as I thrust my cock upward. As soon as it penetrated him he screamed so loud I though someone was going to come in and check that I wasn’t murdering him. I remembered then that I forgot to lock the door but I didn’t care one bit. He hugged himself to my chest and held me tight. He was hurting a lot but he didn’t tell me to take my dick out of him. After a while let go and I lay back down on the bed.
“O.K… Go.” He said.
I started pumping my hips slowly and my cock started to work it’s way to an orgasm. After I knew he was fine a started pumping faster and soon enough I started bringing my cock farther out of his asshole until only my head was inside him and thrusting it back inside. I watched Connor’s face and he was enjoying every second of it. His eyes were closed and every time I thrust back into him he took a sharp intake of breath and a slight smile crept across his small face. Finally I started to cum and I yelled,
“Connor I’m about to cum! Oh shit, you’re such a good fuck! Oh shit!”
As soon as I shot my load into him he grabbed my hips and threw his head back. He screamed as his insides were filled with my cum. It was at that moment I heard the doorknob turn and the door open.