Warning: This story includes m/m stories of students around high school age, so don't read if this offends you.
These characters are of my own creation, and any similarities are coincidence. Any suggestions or critiques are welcome. I will try and get back to you if I can.
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::Side note:: I believe I may have skipped a step or two in the last entry, so, please bear with me. Keep the last part in your head, but we're going to put it aside for a few entries so I can catch everyone up. The gist is, Mr. D gave the boys this information for a price, but they didn't know that when he told them. So the boys have made a deal with Tony that they can let another person use him, should they so choose it. And now, on to the story.
Chapter 8
The weekend had passed, and today was Monday. That meant today after school I was going over to Matt's house. We had all talked it over with our parents, and they had agreed that I could help make sure their kids all passed classes, and my parents were overjoyed that I was trying to improve myself in PE. Which, as my friends had pointed out, was my weakest subject. I mean, When would I ever need to know how to avoid a dodgeball or do a push up, but I wasn't the one who made the rules at the school.
Things were truly normal. Matt and I were sitting beside each other, and our teacher was droning on and on about which elements corresponded with math, this will melt at what degree and with which element, blah blah blah. We were both smooth enough to wait until the teacher wasn't looking, and passed each other notes, and he had no idea. The first one included a fairly crude funny joke comparing him to a person who enjoyed lollipops in a more than unflattering way(and no the joke wasn't missed by me). But the note was written in a dead language that Matt and I had discovered, so even if he confiscated the note, he wouldn't be able to translate it. Hell, even I had a difficult time interpreting it sometimes.
The third or second note made my cheeks feel warm, and I was sure I was blushing coupled with a distinct lack of space in my slacks. He had written what his plans were with me during our `study session' after school. "Tony, perhaps you would like to come up and solve the equation on the board?" was all I heard, and I looked up to see our teacher staring so hard I felt like he was going to bore a hole in my head with a piece of chalk in his outstretched hand. Oh, how was I gonna get up there with a steadily growing erection in my pants? "The answer is seven, isn't it?" Matt said loudly enough to give the entire class a laugh. He was buying me time, and I focused as much as I could. I was definitely getting better at this since it was easier to get fucked if I didn't cum.
My boner had gotten down enough, so I stood up, and said sarcastically, "You forgot to carry the one." That got everyone laughing again, but I had already moved to the front of the class, grabbed the chalk out of the teacher's hand, and was in front of the chalkboard. I was trying to focus on the math problem in front of me, not the idea of Matt mounting me from behind while staring into a mirror. And here was my dick betraying me and raising up again. I finished quickly, and sprinted back to my seat.
"Don't worry, I'm the only one who saw." was all I heard Matt whisper to me. I gave him an evil sideways glance, and though he did smirk, he didn't say another word about it. And as usual, class dragged on, as did the rest of the day.
Matt and I had met up with Luke, Jason, and Todd as we usually did at our lunch spot. My normal lunch wasn't an option today because I had forgotten to grab my lunch money before I bolted out of the house trying to make sure I didn't miss the bus. However, Luke split his pizza with me. "Don't fill up too much. You're gonna have more to fill up on later." Todd joked. That did make me choke a bit on the pizza bite in my mouth, which made them all bust out laughing even more. It felt like we had only been there a few minutes, but we heard the bell ring, signifying that our lunch hour was over.
The day was over, and Matt and I met up after our classes and were walking towards the bus to take us to our house. I had my science book out, and was basically just reading verbatim the words on the page. But it did provide the illusion that I was starting our tutoring session. He would occasionally look around, and when he could tell no one was looking he'd swerve into me as a playful bump to get my attention as he grabbed his crotch and give it a nice tug, making sure I saw him wink at me. Oh, this was going to be so much fun.
As soon as we got to his home he opened the door, yelled, "Hi, I'm home.", grabbed my shirt collar and dragged me up the stairs to his bedroom. I found myself almost rushing past him to get there. "Hi bud, how was your day?" I heard his dad call after us. "It was great, just going up to study with Tony." Matt yelled down and I could tell Matt had been waiting for this all day. We got to his room, and he closed the door behind us. When he turned around, I could see his boner tenting out the front of his pants. Without waiting for instruction, I dropped to my knees, and he stepped forward until I could feel his denim covered crotch pressing against my face.
I tentatively reached up and began to unbutton and unzip his pants. I was soon greeted with a bulge in his boxer briefs that left nothing to the imagination. I could see the outline of the head of his cock clearly, but only for a second before his hand was on the back of my head, pulling my face into his crotch. He instructed, "Suck on it for me." I opened my mouth, and allowed the cloth covered head into my mouth. I heard him groan above me.
After a few moments, he ran his hands down his chest, and his thumb caught the band of his underwear and his cock popped right out, that monster lightly smacking my face. Without hesitation I opened my mouth and his head popped right into my mouth. I could already feel his precum coating my tongue, and it was a little bitter mixed with the sweet, but regardless of the bitterness, I loved it. His moaning was making me even hornier, and I began sinking more of his hardness into my throat. It was a stretch to open my mouth wide enough, but I was determined. I tried to remember my practices over the last few weeks, but try as I might I couldn't get more than half down with him just at the entrance of my throat. I still kept gagging, and he pet my head and said, "Don't worry, you'll get there eventually." I was glad he was gonna be patient with me.
"Why don't you go ahead, take your pants off, lube your ass up, and lie on the bed. I want you to keep your head down and don't look up until I tell you too. I'm gonna go grab the mirror." he told me. I was very excited, as I had been all day. Trying something new was gonna be really fun and I was aquiver of what was going to happen. He left the room to go find the mirror I could only assume. I took off my pants, found the lube he talked about on the table. I rubbed it on my hole, and I felt a tingling numbness. I lie down on his bed as he had instructed, took a quick glance around, but all I could really see from this angle was the wall a few feet away from me. I remembered his instructions, and I put my head face down on the bed cover and closed my eyes.
A few moments passed and I was starting to feel self conscious when I heard the door open, and steps came over to me. I heard pants hit the floor, and within a second I felt him poking at my hole. He pushed forward, and the head of his cock popped in. This time felt a little different, he seemed to be a little larger than I remembered. Perhaps I was just feeling differently this time because none of our other friends were around, and I hadn't been stretched this time. He was steadily pushing more and more into me. I could feel a gasp coming up, so I just bit into the mattress spread, and knew I had to just focus on holding on until he was all the way inside. Then he would give me a chance to relax and get used to him stretching me. It felt like forever, but soon I felt his balls hitting mine.
"WHAT the fuck!" was all I heard, and it was Matt's voice. My eyes shot to the entrance, and there Matt was standing with a mirror, and a look of shock on his face. Wait, if he was there, who was inside me?! I turned my head to gaze back at Matt's brothers' smirking face gazing back at me. "Andy, what the fuck are you doing?" Matt snapped at him. Without that waiting period, Andy started pulling in and out of me. "One of your best friends, by the looks of it." was Andy's only response as he continued fucking me with that huge seventeen year old cock. Matt didn't seem to know how to respond, or what to say. "I've already seen you fucking him, so why not give me a few minutes to enjoy it too." Andy pleaded. He wasn't talking to me, he was talking to Matt, and he had just referred to me as it.
Matt however looked at me, and said, "It's up to you. He doesn't realize that you're the one he should be asking, not me." Once again, Matt was making sure I knew this was my decision. I'm guessing Andy realized what he had done, and leaned down so he was leaning on me, still fucking, and whispered to me, "You don't mind, do you? I'm already in and going, I won't be more than a few minutes." My guess is he just realized I enjoyed it because I found myself pushing back, and he took that as a yes. "Why don't you make sure Dad doesn't come upstairs." Andy suggested to Matt.
Matt hadn't taken his eyes off of me, he was waiting for me to confirm a yes' or a no'. I was enjoying it, and couldn't wait until Matt was the one to fuck me. I gave him a quck nod, and said, "If it's okay with you, he is already in, and it doesn't seem like he's gonna last long." Mat gave a smile and said, "As long as you're okay with it, I am too. I can't wait to be inside you next." He turned and closed the door, but I could see his shadow beneath the crack in the door. Andy began pumping in and out more quickly. "I got him this lube, it numbs the area. That's why I was able to get in so quickly." Andy whispered into me.
He was still lying on top of me, his muscular weight was almost sort of pinning me down in place. I could feel his thrusts getting faster and faster. I heard him groaning more and more in my ear, and then I heard a grunt as he slammed balls deep into me, and I could feel something warm inside me, but that numbing cream had made it so I couldn't really feel his pulses. But I knew he had just finished inside me. He pulled out a little too quickly that made me gasp quickly. He grabbed his pants, opened the door without putting them on, and I head him say, "He's all yours. Better lock the door this time." I heard him walk away, the door closed, and locked.
Matt walked in front of me, and put the long mirror in front so I could see my body lying on the bed. My hair was a bit disheveled, and my skin was flush with a mixture of embarrassment and exertion. Suddenly, Matt was behind me, and I felt him pushing into me. Between the numbing cream and his brother already stretching me and leaving his load as lube, it didn't take much to have him slide in. He pushed until he was the one who was balls deep into me. He leaned on top of me, much like his brother had. But his eyes were locked on mine in the mirror. "This was what I had meant when I told you to lie down and don't look." he explained as he slowly pulled out of me.
It was so intense feeling him slowly sliding in and out of me while maintaining eye contact. He wrapped his arms under mine, grasping onto my shoulders, and this gave him a large degree of leverage to use my body pulling backwards to shove further into me. I gasped, and he just whispered, "Shhhhhh....we don't have someone to go into your mouth. So you're gonna have to be quiet. That may even be how Andy knew what we've been up to." Matt said as his thrusting picked up and he shoved in even more quickly. He had a point, I may have gotten to loud and alerted Andy as to the nature of our `study sessions'.
He was picking up even more speed, just as his brother had, and I knew he was getting close. He was holding onto me as he plowed me into the mattress. The numbing lube had mostly worn off, so now I could truly feel how much space his large cock was occuping inside me. His pounding picked up, and he lightly bit my neck as I felt his cock pulsing inside me, filling me up even more.
After a few seconds, he pulled off of me, but his hand firmly against my lower back kept me in place. I heard him rummaging for a second, and then I felt something cool but firm pushing into my ass. I gasped as something big pushed in, and suddenly it was inside me, but the bottom of it was much smaller. He moved his hand, and I rolled over. "What was that?" I asked him, still feeling it lodged into my sore bottom. "It's called a butt plug. It will make sure that you're loose all the time. Trust me, it will make getting fucked more frequently easier. Give it a few days, and you'll see. Now, let me explain how take care of it." Matt replied. And I listened to him tell me what was going on.
Earlier that day
Matt looked into the bag that Mr. D had handed him. He had explained the plan to Mr. D and asked for advice on how to continue. And now he had a bag that had been thrust into his hands. A bottle of lube and a strange rubber object that had an open and closing top and a smaller part under that and a flared base. "And what am I supposed to do with this?" Matt inquired. Mr. D rolled the top of the bag down so that no onlookers could see what was in it. "This is a numbing lube, and since you're gonna be the first one fucking him tonight, it will make loosening him up much easier. I've seen you in the locker room, I know what you're packing." Mr. D explained. Once you've fucked him, put this butt plug inside him. You need to convince him to keep it in at all times. It will make y'all using him a lot easier." was Mr D's instructions. "Keep me in the loop. And you owe me." was all Mr. D said as he sauntered away, a mischievous smile on his face that Matt couldn't see.