Taking Chances

By Angyl


“Come on Chris you have to believe me.”


“You honestly expect me to believe that Tyler is gay or bi…whatever.”


“Janie saw him and a guy making out last night.”


    I just could not fathom the idea of the guy I had been lusting after since 8th grade way gay or bi. I just did not seem real to me. Kristy was trying to convince me otherwise.


“Come on we both know how reliable he information is.”


“Dammit Chris, quit being so stubborn!”


“Look as much as I want it to be true I am not gonna chance getting my ass kicked over some rumor.”


    I knew Kristy was getting mad.


“Ugh why don’t you go up and ask him?”


“Now way Kristy, I am not as stupid as to do that.”


“Fuck you are pigheaded.”


    Kristy stormed off before I could even say anything. I watched her go. I knew she would be back later for round two. I got up and wandered to my locker. My head was swimming with thoughts of Tyler Jansen possibly being gay or bi. It was just too much.


    Tyler Jansen. God I have been in love with him since 8th grade. He kicked my ass in grade 9 when he learned I was gay. You would think I’d hate him for that, but I still loved him. When we entered high school he had really changed. He was a hottie, well always was. Now he had developed muscles, and a nice package. Yeah I had caught a glimpse of his 8 inches once in the shower. Thick and juicy is the best description, with those two nice jewels hanging right below. Almost got my ass kicked for staring, but luckily I jetted before it happened. He sprouted over the summer and now stands at 6’2. His skin was a dark tanned color. His hair was brown and shaggy. His green eyes made me melt even if it was from glaring at me. His cock was nestled in a nicely trimmed bush. He was uncut, unlike my cut cock.


    I am Chris Johnston. I am scrawny and kind of dorky. Well I think I am dorky. Everyone I know argues about that. I am not short 6’0 tall. I have short black hair and hazel eyes. I am not muscular like I said. My dick is about 7 inches and thick at the base, with two low hanging balls. I do not trim, because I have always preferred the natural look. I am also very pale, I hate sunlight.


    Let’s get back to Back to Tyler. I sat in front of my locker and watch as Tyler went to his. I used a book to shield the fact I was looking at him. I think he knew because he turned quickly and looked at me. He did not glare, just looked at me. Holy fuck what a difference that was. He took off and I sat there. Jesus maybe it was possible.


“Get a grip on yourself Chris.” I said to myself out loud.


    I gathered my books and took off to start the day. By lunch I had gotten a grip on myself. I wandered into the café and found Kristy in our usual corner. I prayed she would not make a big deal out of Tyler. I did not even have a chance to sit down and she was off on it.


“Are you going to admit that it is possible?”


“Fuck Kristy, do you every give up?”


    Having known Kristy for most of my life I knew the answer. She was the first one I told I was gay, and the first one to find out I was in love with Tyler. She found my journal open and his name written with hearts. I had to tell her or she would have nagged until I did tell her the truth.


“He is over there you should go ask him.” She said pointing to him.


    He was there, sitting all by himself. His usual troop nowhere to be seen. That was weird for him. I walked over and was gonna walk right by him at first.


“You can sit I am not gonna bite you or anything.” He said.


I turned to look at him, and he motioned me to sit. I was reluctant, but I sat across from him.


“Look Kristy told me about your liking me, not that I did not know about it.”


“Ugh she is so nosey.”


“It was my fault I got nosey.”


“As for the rumor about me and another guy it is totally true and hence why none of my friends are around.”




“I was such a jerk to you in the past and for that I am really sorry Chris.”


“I survived.”


“Yes but had I realized back then things I have now I may have done differently.”


“Is there a point to all this?”


“Chill man I am trying to make things right and hopefully more.”


    He looked around. The place was really busy. Even I noticed it.


“Come on let’s get out of here. We can drive over to my place, and before you think it this is not a set up I swear.”


“Yeah ok why not.”


    Tyler led the way to his car. I hoped in the passenger seat. He jumped in and we were off. I admit part of me was still leery about going with him, but another part was kinda excited. When we pulled up in front of his house I relaxed a bit. He led the way to his room and he flopped down on the bed.


“I was not too sure you would come with me.”


“I almost didn’t, but I guess I am into taking chances.”


“Yeah I guess taking chances are all part of life.”


“I’m still not too sure where you are going with any of this.”


“Look when I was with the guy everything seemed to fall into place.”


“What do you mean?”


“Well it felt right. I could not get it up with a chick, so I decided to try it with a guy to see what happened.”


“You got it up no problem?”


“Yeah but I did not realize anyone would see me, but there was something missing still.”


“What’s that?”


“You; all I could think of was you.”


“Me? Why?”


“I don’t really know how to explain it, but I guess deep in my mind I am attracted to you.”




“You are not making this easy on me.”


“Why should I? You made my life hell.”


“Look I am truly sorry for that. If you do not want to be here then go I won’t stop you.”


    Life is about taking chances and I was about to make the biggest gamble of my life. I got up and walked over to Tyler. I pushed him down on his bed and got on top. I kissed him like I had never kissed a guy before. Both our dicks reacted in the same way. We got hard almost instantly upon contact. My hand roamed down and began massaging his through his shorts. He broke the kiss and looked at me.




“You wanna get naked now?”


I never said a word, I got off him and he helped my get undressed, and then I did the same for him. He was on his knees before I could say anything and taking my cock in his mouth. He was really good as he made me moan.


“Shit you are really good at this.”


    He moved me to the bed and got beside me. His cock was right in my face. He went back to sucking me off. I took his cock in my mouth and began giving him the same thing. Our heads bobbed up and down in tandem. I reached around and started playing with his hole. He was tight, but I was able to work one finger in. Tyler let his ass muscles relax as we sucked each other off. I admit that 69 has always been one of my favorite positions. I was more excited by the fact that I was 69’ing with the guy I lusted after for so long. He was pretty good for only having done it once before. He kept hitting all the right spots on my cock or something, because before long I was ready to blow my load.


“Dude pull off I am about to blow!”


    Tyler made no move to pull off; he just kept bobbing on my cock. I could not keep it in and soon I filled his mouth with my jizz. Almost simultaneously he shot his load into my waiting mouth. He let out a couple grunts as he did.  He moved up next to me and smiled.


“Yes that was definitely what I had been missing.” He said.


    I was content to just lie there with Tyler. Which we did for a bit but the he rolled over and looked at me.




“You know there is something I would like to try, that I haven’t yet.”


“What’s that?”


“I wanna get fucked.”


    Now normally I am the one who gets fucked, but this was a dream come to reality. I looked at him and smiled. He rolled over and grabbed some lube, and a condom, but then he threw the condom back in the draw. I was already hard in anticipation of taking his virgin ass.


“You know it is gonna hurt.” I warned him.


“I figured as much, but as long as it is you I am ok.” He replied.


    Tyler laid on his back and offered his hole to me. I squeezed a generous amount of lube in his crack and worked a finger into him. Slowly working it around and loosening him up. When I was satisfied I slowly worked in a second and then a third finger. He grunted when I worked the third one in.


“You ok?”


    He nodded.


“Ok here I go.”


    Removing my fingers, I quickly lined my cock up. I began to push in. The head of my cock slipped in past the sphincter. I held it there to allow him time to get used to it, and then slowly I pushed my whole cock inside him.


“Oh my god!”




“That feels so good!”


“It gets better.”


    I began to slowly pull my cock out stopping before I was completely out, and then pushing back in slowly. Tyler relaxed as I worked my cock in and out of him. I began to slowly pump faster.


“Fuck yeah never knew it felt so good!” He moaned.


    I reached down and was about to play with his cock, but just touching it caused him to shoot. I grabbed his legs and really started to pound his ass. I wanted to fill him with my hot cum. I got faster and harder as I felt myself getting close.


“Uhh…oh yeah…here it comes!”


    With one final hard thrust in I emptied my cock inside him. I kept going until I felt my cock go soft and slip out. I looked down and saw my juices leaking out of his hole. I leaned in and kissed him on the lips. He wrapped his arms around me, and pulled me close.


“I definitely think this is what was missing.” He said.


   I spent the night with Tyler. We fucked a few more times, and he even fucked me. We were both tired as fuck the next morning as we got ready for school. Before we headed out he took me in his arms again.


“You know I really don’t care what people think.”


“Think about you?”


“Well you and me to be more precise.”


“Does that mean you are asking me out?”


“I thought that was clear last night?”


“I know was just making sure.”


“Well yes.”


    So there it was, taking chances had been a gamble that for me had paid off. When Kristy saw the two of us walk in the school hand in hand she grinned from ear to ear. Her boyfriend Jason was also grinning. We were getting congrats from fellow students. Not at all what I thought would happen. Even a few of Tylers friends came over and congratulated us. It was as if it had been meant to be.