This is an original work of fiction. Names, characters, places, events and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, is purely coincidental. If you are under 18 years of age, offended by stories which depict sex between consenting males, or live in a jurisdiction where reading/possessing such materials is illegal, please leave this site now.
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Chip and I got together on both Tuesday and Wednesday and each time was better than the last. Each day school seemed to take longer and longer until Chip and I could get to my house and have sex. We were getting closer to final exams and both of us were in study groups for different classes. My American History study group was being taught by the teacher and was in the north end of the cafeteria and probably had about 40 students. I hate this class, so many dates and names to remember. Chip wasn't in my study group but Tim was. We weren't sitting close to each other but we kept sneaking glances at each other. Just looking at Tim made me horny, so I knew that I was going to have Chip really pound my hole like Tim did in the basement. I had a hard time paying attention as my teacher went on and on. I caught Tim adjusting himself a few times and I was hard as a rock and had a hard time paying attention. I needed to pass this course with a high score on my exam to make honor roll, so I had to quit looking at him. Finally, we were done. I started getting my stuff together and was walking to my locker when Tim called my name. I stopped and turned around and waited for him to catch up. He asked if I wanted to get together and compare notes. I told him that I would love that. He asked if I wanted to get together today or tomorrow and I told him that I really couldn't today. I told him that I didn't have a study class and we could get together after school. He said that it was great and said he would see me tomorrow and left.
I didn't see Chip so I walked home alone. I had been home for about 15 minutes when the phone started ringing. I was in the bathroom getting my hole ready in case Chip had time before my parents got home. I ran and answered the phone. "hello!" "Hey Arch, it's Sr. I wanted to get together with you tonight. Meet me tonight after dinner." I said "I'm going to pass." "What? Why?" "you don't do anything to me and you just use me" "Arch, come on. I know you like it and you owe me" "I owe you, for what? Why would I owe you?" Sr said "I bought you all that stuff". "So you could use me" "come on Arch, how about this time I let you be on your back so you can watch me?" "how about, no thanks" "Arch, come on. How about we go to the Y? I can get off with you there. Maybe stick it in when I come? Or I could eat your ass and then when I am getting close I'll fuck you til I come? Please Arch" "I will say yes, if you agree to kiss me while we have sex." "Archie, I've told you that I don't like kissing" "well, it is making out while we have sex or we don't have sex" "FINE! Be ready after dinner!" and Sr hung up on me. Crap, I didn't want to have sex with him and I just agreed.
After dinner, I loaded the dishwasher and went upstairs to make sure that I was ready for when Sr called. He called about 8:30 and told me to meet him in ten minutes at the corner. I lubed up my hole and went to meet Sr. We had barely drove a block when Sr told me that he hoped I was ready for a good fuck because he needed to pound a hole. He drove to Sr's office, once we were in his office he told me to get down on my hands and knees. I told him that I wanted to kiss while we got off. He told me that he didn't want any talking and that we would get to the kissing and pushed me down to my knees. My ass was bare but he still had me keep my shirt on. He got behind me, pushed my chest to the floor and kept his hand on my back and then rammed his cock in my hole in one hard thrust. I was knocked forward and he flattened me to the floor and continued his assault of my hole. I felt like the wind had been knocked out of me and I was about to yell when Sr put his hand over my mouth. His face was next to my ear and he told me that I will never tell him no again. He kept pounding my ass and had moved his legs from being on the outside of my legs to where he was now pushing my legs further apart. His pounding never seemed to slow down. I could tell that I was going to have rugburn on my knees and my chin or cheek. He yanked my head back by my hair and said "you want that kiss fag? Here you go." and spit on my face. I was starting to get off on this rough sex but I didn't want him to know. I knew I was pushing it when I said " thought you were going to let me be on my back and you were going to kiss me". Sr said "fuck that shit" and pulled me by my hips so I was on my hands and knees again. I started squeezing my ass as tight as I could and was trying to make him cum. I could tell he was getting close and I started pushing back onto his cock. He stopped thrusting and told me to fuck myself on his cock and that he was getting close. So I kept clenching and releasing my ass trying to make him cum. He said "oh yeah Arch, fuck yourself on my cock. I'm so close. Oh yeah -- CLOSE -- SO CLOSE -- keep that up -- oooh fuuuccckkkk -- uuugh -- fuck oh fuck yeah! CUMMMMMIIIINNNNGGG!!!! WHAT THE FUCK ARE YOU DOING!!!" As soon as I felt the first pulse of his cock shoot into my hole, I pulled off of him. "What are you doing? Fuck Arch! What the hell! Look at my carpet! FUCK! What the fuck! God dammit Archie, look at what you did. Fuck! Go to the bathroom and get some towels and clean this up!" I stood up from my knees where I was facing him and walked across his office and turned on his light and walked to the bathroom in just my t-shirt. I got some paper towels and walked back to Sr's office. He was fully dressed and standing in the dark office, except now he had the flashlight from his phone pointed to the floor. I walked over to the cum and dropped the paper towels and started smearing them across the cum on the carpet. Sr said "what are you doing? Get down there and clean that up, I can't have a stain on my carpet." I wiped the floor a little bit and finally Sr said "I will come in early and make sure you can't tell in the daylight. Fuck Archie, I can't believe you did that." I got dressed and we left. Before he dropped me off he told me "I don't think it was funny and I will teach you a lesson. Now, get out." I got out of his car and walked home. I think he knew we wouldn't be getting together again.
When I walked in the house, I was surprised by how good I felt. I was in a great mood. I was proud of what I did with Sr. I told my parents that I was going to grab a water and go up to my room and play some video games. Mom stopped me and told me that I would be on my own for dinner tomorrow. She reminded me that both her and my dad were going straight from work to a work dinner with her boss. I admitted that I totally forgot with school and exams and said that I was going to study American History after school tomorrow. Mom said she would leave some cash for me to order pizza. I was thinking about being with Tim tomorrow during my entire conversation with mom. I was starting to worry that my dick was quickly rising in my shorts and since I didn't have underwear on, I had to get out of there. Thankfully, mom walked out of the kitchen.
Chip came up to me at my locker before school. He wanted to know if he could come over after school. I told him that I was studying American History with Tim after school. He wanted to hook up and said he wanted to try something but couldn't really talk about it at school. I told him that I would keep him posted if and let him know when we were done studying.
I saw Tim a couple of times during the day. My favorite was in the bathroom. I walked in while Tim was standing at the urinal. I was able to look down the row and could see Tim's big cock. He started talking to me while we were at the toilet, so I was able to look toward him without it looking weird. He said if we were still on for after school he had to run home first. He said it wouldn't take him long, he just needed to let the dog out and feed it. I told him that I would see him when he got there. I was excited, his delay meant that I could be sure that my hole was ready. I was glad that I didn't get hard while at urinal. I knew that I wanted to get Tim to fuck me. I thought about his cock when I was playing with my purple or Jeff dildos.
The final bell finally rang. I hit my locker and practically ran home. I didn't know exactly how much time I had to get my hole ready. I had a pair of white sweat shorts that were a little tight and a navy tank ready to throw on. I finished everything in the bathroom and went to my stretch my hole so I could take Tim's big cock with ease. I had worked from 3 fingers to purple and had purple going in and out of my hole. I had finally got Jeff out and had suctioned him to my bedroom door and got it in and kept hitting that spot in my ass that made me feel like I was going to shoot. I was working up a sweat when I heard the doorbell. I pulled off of Jeff and put both the dildos in my bag and slid it under my bed, pulled on my clothes and ran down the stairs to let Tim in.
Tim had changed and was in black basketball shorts and a Captain America t-shirt. He always looks like he just got off his surf board and knocked someone off their bike and stole it. He looked like he hadn't had a haircut since school started and we were done in about a week. I would say he had the rugged look. He had his bookbag with him. I asked where he wanted to study and our options were the kitchen table or my room. He said we should study in the kitchen so that we wouldn't be distracted and start playing a game or get on the computer. We went to the kitchen table and started going over our American History study class notes. I have to admit that I felt comparing our notes was a great idea and I told Tim that I was glad he suggested it. He said that he really thought I would say no because of what happened at the Martin's house. I told him that I wasn't mad or even upset about what happened. I told him that I was more surprised that it happened at all.
I asked Tim when he had to be home and he said that he didn't really have any special time to be home. I said that my parents were going out to dinner after work with some of the people from my mom's work and asked if he wanted to stay and have some pizza. He said "absolutely". I ordered and told Tim that we could go up to my room until the pizza arrived and play some video games. I bent over in front of time while trying to get the game started and pulling the games out for him to choose. I acted like it was harder than it was just so I was on my hands and knees in front of Tim. I knew he would be looking at my ass. We finally started a game that really wasn't my favorite. While we were playing Tim said "did I hurt you? You know that night." I said "when you first shoved it in my ass it hurt like mad. You have a really big cock, it is long and thick. It felt like you shoved a tree up my ass. When it was just a finger it wasn't that bad but your cock is SO much bigger than your finger. It was like going from a toothpick to a tree." "I'm sorry Arch. I am not going to lie to you and say that I never thought about fucking your ass before it happened because I did. I think everyone thinks you have an amazing ass. I shouldn't have done it like that" I said "I never thought it would happen like that either" I noticed Tim readjust his dick a few times so I did it too and was obvious. I then said "to be honest if you would have lasted a little longer, I probably would have cum. You kept hitting something inside me that was driving me crazy but I couldn't move. You had your big cock pounding my hole and Chip had his cock fucking my mouth, so I was stuck" "so you kinda liked it" "I guess so. I think about it sometimes when I jack off". Tim said "I think about it all the time". I asked Tim if he wanted to get naked until the pizza got here. Tim said "fuck yeah!" I turned off the game and turned around and took off my shirt and looked at Tim. He was hard and had a huge tent in his shorts. I turned around so that my back was to Tim and slid my shorts and underwear down at the same time. I looked over my shoulder at Tim and could see him staring at my ass. I said "hurry up and take your shorts off and take a squeeze". "What did you say?" I said "you heard me, it isn't going to squeeze itself". Tim yanked his basketball shorts down and then his underwear and out popped his huge dick. I knew I was going to get him back in my hole.
Tim came over to where I was standing and started rubbing his hands up and down my ass cheeks. He had a hand on each cheek and was pulling and pushing on them. I think he was trying to catch a glimpse of my hole. He said "I love your ass!" I asked him "what was it like to fuck someone? Was it better than a pussy?" and Tim surprised me by admitting that he hadn't ever fucked a girl. I said to Tim "let's get on the bed" and we started to climb onto the bed when the doorbell rang. I told Tim to stay on the bed and that I would get the pizza and grab us a Pepsi or whatever and be right back. I grabbed my shorts without my underwear and ran downstairs. I grabbed the money off the counter and ran to the door. I opened the door and the delivery guy was kinda hot and I noticed that he was looking at my hardon. You could see it pretty clear since my shorts were tight and white. I dropped some of the cash on purpose and turned around so he could see my ass and bent over to pick up. I wanted the delivery guy to grab my ass but it didn't happen. I turned back around and he bent over to count the change to give me. I handed him a bigger tip than I normally ever do and thanked him and he said "no, thank you" and started walking away but he looked back and I just stood and watched him until he got into his car. I closed the door and ran to the fridge and grabbed to Pepsi's and went back to my room.
Tim was still laying on my bed naked and was still stroking his big dick. I said "want to get off first or eat first?" Tim said "let's get off". I was out of my shorts and on the bed in a flash. I sat at the foot of the bed so I was facing Tim. We were both leaning back and watching the other when I said "I have lube if you want some." "sure" he replied. I climbed across the bed so my ass was sticking up and got into my bedside drawer and got out the lube and handed it to Tim. He squirted some into his hand and started sliding it up and down his cock and handed me the bottle. I got back into place, squeezed some onto my cock and let it run down until I felt it running down my taint and then finally stopped. I rubbed my cock, then my balls and lifted my right leg a little and rubbed a finger across my hole. We were both watching each other. I was watching his face and eyes to see where he was looking. I started to really rub my hole more and more and I asked Tim if he wanted to rub it a little. He didn't even answer and moved until he was on his knees between my legs and reached forward and ran his finger up and down my crack. He kept looking up to my face looking for approval. I started lifting both of my legs out and wide, and then finally toward my chest. I told Tim to stick a finger in but to go slow. He asked if I was sure and I told him that I just told him to do it, so I am sure. He slid his finger in my hole and we both moaned. I said "put another one in" and he did. I started walking him through what to do. He had three fingers going in and out of my hole. I said "want to fuck me?" "Fuck yes dude!" I told him to lube up his cock and to go slow. He grabbed the lube and then lined his cock up to my hole and I told him to tease my hole a little and only stick a little in at a time. Tim started to push a little of his cock in and out and I told him to go deeper and he did. I said keep sliding in then back until your head is about to pop out but don't let it. Pretty soon he bottomed out in my hole. He leaned down and surprised me by kissing me. I didn't expect him to do that but I didn't want it to stop. He asked me if he was hurting me and I told him that he felt amazing. He said he didn't think he would be able to last much longer. I told him to really pound me and I would probably cum with him. He asked if he could come in me again and I told him he had to. Tim really started thrusting his cock in and out. He was bottoming out on every thrust. I reached down and started to jack my cock. We were both moaning and he started making grunts and groans so I knew he was getting close. I told Tim to kiss me and pound me hard because I was about to come. He leaned down and we were in a great French kiss with our tongues dueling and I felt it start. I was moaning into Tim's mouth and felt my cum start to shoot. My ass was flexing on Tim's cock and squeezing it. Tim yelled out "FUCK! FUCK! FUCK!" followed by crazy grunts as I felt his dick start to twitch and spasm as he unloaded in my hole. He leaned back down and started kissing me again and was holding my face. He suddenly froze and looked down at me and said "are you okay? Please say I didn't hurt you" "I am great! You fucked the cum out of me!"
I figured Tim would want to get up an off me and clean up but he didn't. Tim started giving me soft little kisses on my cheek and neck. He became real cuddly. He slid to my side and started rubbing my chest. He looked at me and said "Archie, that was so amazing. It felt like my dick exploded. Your ass is so tight and you are sexy. I'm sorry about what happened. I didn't care about you at all, I just wanted to get off. Sorry" and leaned up and kissed me.
I said "let's eat some pizza before it gets cold. I think we need to wash our hands first" and laughed. After we were done in the bathroom and were sitting on the floor eating pizza I said "since you are being honest, so will I. I never thought I would get fucked in the butt and never thought I would like it. I've thought about you fucking me every day since it happened. I'd let you fuck me everyday if it felt that.