DISCLAIMER: This story contains graphic descriptions of homosexual activity between two males. If you aren't allowed to read such material, stop now. The author retains copyright. If you enjoy the story, I have a blog with more of my stories. E-mail me and I'll send you the link. Feedback and comments are always welcome. Midtown.expert@yahoo.com Thanks for reading.
Straight High School Cock--Caleb
It had been a hot month, even for August. There had been 30 days of three-digit temperature, and today was no exception. It was early Saturday afternoon, and I was taking Staci out to the lake to meet some of her girlfriends. About a mile outside of town, we saw somebody walking toward town, on the opposite side of the road. As we got closer, I could tell it looked like someone about our age. We got almost even with the person and Staci said, "Is that Caleb Moore?" "I don't know," I said, not really paying attention. I could tell the person was a guy and was walking at about a medium gait, with his head down. His shirt was soaked from the heat, and his hair was matted to his head. "Slow down," Staci said as we began to pass the guy. I did, and then as we passed him Staci turned around in the seat to get a better look. "Yeah," she said, "that's definitely Caleb." "I wonder what he's doing walking out here..." "I dunno," said to her, "maybe his car broke down." Sure enough, about a quarter mile up we saw a beat-up Plymouth off the side of the road. It was Caleb's car. "Yep," I said to Staci, "there's his car."
Caleb Moore was 14 when his parents were killed. His dad was an over-the-road truck driver, and was only going out for a week-end run. This was the first time Mrs. Moore had ever gone on a trip with her husband, and Caleb was going to spend the weekend with his grandmother. They had driven Caleb the 30 miles to drop him off at his grandmother's, and then were hit head-on by another semi 10 outside of town. Having no other relatives, Caleb came to live with his grandmother, who was well into her seventies at the time. Caleb was a shy quiet guy, and a loner. Although Caleb and I were both 17, I was a senior and he was a junior. He had been held back the same year his parents died, which only added to his loner status. Caleb never hung out with anybody, always keeping to himself. We all assumed Caleb stayed home with his grandmother, and probably locked himself away in his room.
I dropped Staci off at the pavilion, turned my truck around, and headed back to town. I drove past Caleb's car, and about a half-mile this side of town I saw him still walking. There was hardly any traffic on the lake road, so I wasn't surprised to see Caleb still walking. I slowed down, pulled up beside him, and rolled down the window on the passenger side. "Hey man," I said to him, "need a ride?" Caleb stopped, took off his glasses, and wiped his face on his shirt sleeve. He put his glasses back on, then kind of peered at me, like he recognized me but couldn't remember from where. "Oh, hi," Caleb finally said, looking down. "I see your car broke down back there," I said to him, "do you need a ride Caleb." Caleb stared at the ground again. Then he turned around and looked behind him, and looked ahead of him. He looked at me again, then looked back down. "Uhhhh," he said slowly, "yeah...sure..."
Caleb opened the passenger door and climbed in. He sat in the seat, his down, and his hands between his legs. I tried to make small talk, but Caleb just sat there silently. When I was talking to him, I kept glancing over at Caleb. I noticed he really wasn't a bad looking guy. He had dirty blonde hair that was kind of long in the back, and hung down in his eyes most of the time in the front. He was tall, taller than me, and thin. During all the small talk I was making, about the only thing Caleb did tell me was that he was doing "stuff for grandma" when his car "just quit." As we drove into town, I asked Caleb where he wanted me to drop his off at. He told me his grandmother's. With out town not being that big, and his grandmother living in the same town all my life, I knew where she lived. It was actually only about a half-mile from my house. Caleb's grandmother didn't have a driveway, so I dropped in off in front of the house. He got out of truck, shut the door, and began walking up the yard. After he was about half-way to the front door, Caleb stopped, and turned around. He walked back to the passenger side of my truck. He glanced through the open window at me, then looked at the ground. "Thanks," he said quietly, then walked back up to the front door.
Although I was a year ahead of Caleb, we had one honors class together; first hour Geometry. On Monday morning he didn't show up until about half-way through class. He came in quietly, looked around for a seat, then walked over with his head down. After school I hung out with some of my buddies, and when I got home there was a white box on the kitchen counter with my name on it. I asked my mom where it came from. "A guy brought it over about 3:30 for you," she said. "A guy?," I asked her. "He was tall, blonde hair...really shy," she said. The only guy I knew that fit that description was Caleb. "Did he say who he was," I asked my mom. "No," she said, "he just said...'these are for Sam...'" I opened the box and there was a handwritten note sitting on top of two dozen freshly baked chocolate chip cookies. The note was written on lined notebook paper. I opened it up, and the handwriting was small and somewhat shaky. "Sam Miller," the note said, "thank you so much for helping Caleb out on Saturday. Please accept these for you kindness." The note was signed: Augusta Brookeover. Caleb's grandmother.
Caleb was late the next three days of school. Same as the first day, he came in about half-way through class. I tried to find Caleb the first day after school, to have him thank his grandmother for the cookies, but I couldn't find him. Finally, on my way home on the fourth day I saw him walking down the sidewalk a couple of blocks from school. I lived about two miles from school, and Caleb lived about another mile past me. Bus service was only available to kids who lived outside the city limits, so if Caleb was walking home, that meant his car wasn't fixed. I pulled up beside him, rolled down the passenger window, and told him to get in. As usual, Caleb's head was down as he slowly walked over to my truck. After he got in, I asked him about his car. "It's got a busted oil pan," Caleb said, "but it's still out on Lake Road..." "Why is it still out there?" I asked him. "I can't get it towed until after the first of the month, when Gram gets her check," he said. The first of the month was almost three weeks away. "Then," he continued, "I can't get it fixed for another month..." We sat in silence for a few minutes, then I had an idea. "Okay," I began, "what if we get John's dad to tow it to my place, and we fix it there...will that work?" John was a buddy of mine and his dad owned a towing company in town. Caleb was silent for a few more minutes. "Sam," he said, "I don't have the money to get it towed, or even get the parts to fix it...it'll just have to wait." "Dude," I told him, "John owes me some favors, so he can get it towed for free. We've got a big garage behind the house where my dad works on all our cars and trucks, so we can work on it there." "What about the parts," Caleb asked. "My dad's got lots of extra parts," I told him, "and I'm sure he'll have an oil pan to fit yours...and if not, we'll get one from the junk yard." "All it's gonna cost you," I added, "is your sweat." By this time we had pulled up in front of Caleb's house and stopped. Caleb sat there for what seemed like a long time, thinking over my proposition. Finally, for the first time since I'd given him a ride the week before, Caleb looked me in the eyes. "Okay, Sam Miller," he said looking at me, "I owe you one...and I promise I will pay you back." Then he added, "and I always make good on my debts." "Aight man," I told him, "you're gonna ride with me to and from school tomorrow, then we'll get this thing kicked out first thing Saturday morning...deal?" Caleb looked at me and stuck out his hand, and I stuck mine out in return. "Deal," he said as we both shook. Caleb opened the passenger door, then stopped about half-way out, and turned around. "Sam," he said, "why are you being so nice to me?" "Dude," I told him, "I don't have any reason not to be nice to you." "Now, shut up and I'll see you tomorrow morning at 7:30," I added laughing. For the first time since I'd be around him, Caleb smiled. Then he closed the door and walked up to his grandmother's house. It didn't even enter my mind at the time, but over the next few weeks I would think of at least one way Caleb would be able to pay me back.
After school the next day, Mike himself went out and towed Caleb's car to my house. At 7:00 Saturday morning, my mom woke me to tell me I had a visitor downstairs. It was Caleb. I put on some shorts and a T, and went down to the kitchen where Caleb was waiting. He was wearing work overalls, and staring down at his hands when I came into the room. "Dude, you wanna eat something before we get started," I asked him. "No," he said, still looking down, "Gram fixed me something." I grabbed a couple of doughnuts and a bottle of orange juice, and we headed out to the big garage behind our house. Caleb and I spent the next three hours fixing up his car. We put the new oil pan on, changed all the fluid, and drained and refilled the radiator. I had helped my dad a lot when he was fixing our cars, and I thought I knew a lot. But Caleb knew way more than me. The conversations we had while we were working were pretty one-sided; me doing most of the talking. Every once in a while, Caleb would say "yeah," or "uh huh," and sometimes if I said something funny he would even look up and smile. But most of the time he kept quiet.
We finished up, Caleb turned the ignition, and his car fired up. He got a big grin on his face, and real loud said "YEESSSS!!!" Caleb backed his car out of the garage, and parked it. He got out of his car, stood up, and said "Remember Sam, I owe you one...and I always make good on my debts." "Forget it dude," I said, "I was glad to help you out." I was getting hungry, my doughnuts and orange juice having long wore off. "Hey," I said to Caleb, "you wanna go get something to eat?" Back to his shy self, Caleb looked down at the ground. "I can't," he said in a low voice, "I have do some stuff for Gram..." "That's cool," I said to him, "I'll see ya Monday at school." Caleb half-smiled, got into his car, and drove away. I was almost the back door of my house when I heard a car pull in the drive-way. I walked around the corner of the house, and saw it was Caleb. He got out of his car and began walking up the drive. I met him half-way. "What's up," I asked him. With his hands in the pockets of his overalls, Caleb was looking at the ground. "Do you ever work out, Sam?" he asked me. I was kind of surprised by the question. "You mean, like with weights and stuff," I answered back. "Yes," he said. "Yeah," I said back, "usually a couple times a week, at school...why?" "Uhhh," Caleb replied, his hands still in his pockets and still looking down, "I uhhh...I have some weights at my house, and uhhhh...if you ever want to work out together I uhhhh...I think it'd be fun..." "Man, I'd like that...," I said without even hesitating, "I've been wanting to get some equipment, but my dad said I have to but it myself...and something more important always comes along...yeah, I'd like that." "Good," Caleb said, finally looking up at me, "just let me know whenever you want to..." "How about tomorrow," I said, again without hesitation. "Ummm, yeah sure," Caleb said with a surprised look on his face, "I get home from church about 12:30, so how about around 2:00?" "That'll work," I said to him, "see you then..." Again, a smile came to Caleb's face. "Yeah," he said smiling, "see you then." I didn't accept Caleb's invitation because he didn't have any friends and I felt sorry for him. I accepted because there was something about him that I really liked, and I did want to spend more time with him. And the added bonus of getting to do some weight work was sweet!
I got to Caleb's house a little before 2:00. His grandmother answered the door, still in her "church" clothes. She asked me in, then pulled me into her and hugged me tight. "I can't thank you enough for all you've done for Caleb, Sam Miller," she said. "He doesn't have many friends," she went on, "and you have been just the sweetest thing to him..." Her voice was starting to choke up and she pulled away. "It's been my pleasure, Mrs. Brookeover," I said to her, remembering the manners I had been taught, "really." "Well, thank you," she said again, going into the kitchen. She came back into the living room, carrying a large white box. "This is just a little something to show my appreciation," she said, smiling, "I hope you like chocolate..." I opened the lid of the box and inside was a three layer chocolate cake. "Wow!" I said, genuinely excited, "it's really my favorite, Mrs. Brookeover...thank you." "No, Sam Miller," she said, still smiling, "thank you!" "Now I know you're not here to talk to an old woman," she said to me, "Caleb's in the shed out back...he likes to call it his `work-out room'..." "You can go out the back door," she said, pointing to an outside door in the kitchen, "you boys have a good time..." I went out the back door, and walked the short distance to the shed. It was fairly good sized, probably 15-20 feet square. The shed sat along the back of the property line, perpendicular to the house. There was a door at one end, but I could see any windows. The closer I got to the shed however, I could hear the hum of a window air conditioner. I got to the door of the shed and saw it was slightly ajar. I knocked a couple of times, and this pushed the door about half-way open. Cool air rushed out, and it felt good hitting my body. I stuck my head in, looking around to find Caleb. About half-way down the right side wall I saw him sitting on a weight bench shirtless, his back to me, with weights and the bar lowered to his shoulders. Caleb's shoulders, arms, and back were a flow of ripples, leading to a very narrow waist. "Wow!!" I thought to myself, "I had no idea..." I waited until Caleb put the weights back in the holder before I made a noise. "Hey, man," I said loudly, just as he lowered the bar. Surprised, Caleb jumped up and turned around. If I thought his back was impressive, Caleb's front was amazing. He didn't have his glasses on, and Caleb's dirty blonde hair hung low into his eyes. Without his glasses, I could see Caleb's high cheekbones and I noticed his strong jaw line. His pecs looked hard and defined, and his nipples were erect. The muscles in Caleb's stomach started just below his pecs, and were a well sculpted eight-pack. Caleb's waist was narrow and sleek, with a perfect-formed "V." His baggy shorts hung low on his hips, and a dirty-blonde treasure trail started at his navel and disappeared into the waistband of his shorts. Instinctively, I noticed a bulge in Caleb's crotch area. "Dude, you are fuckin' ripped!!," I said, thinking it was to myself, but actually saying it out loud. Embarrassed by what I had just said, Caleb nervously began looking around for his shirt and glasses. He didn't say anything to my embarrassing compliment. Caleb fumbled around on a table beside the weight bench, and found his glasses. Hurriedly he put them on. Almost frantically, he looked around again for his shirt. Finally, he saw it on the opposite side of the shed, and hurriedly walked to get it. "Hey," he said, ignoring my earlier comment and pulling his T over his head, "I was getting a little head start...hope you don't mind..." "Not at all," I said, embarrassed myself by what had come out of my mouth this early in the game. I walked around the shed admiring all of his equipment, "You got some real nice stuff here, Caleb," I told him. "It was my dad's," Caleb said in a low voice, "it's all that I have left of him. Sensing he didn't want to talk about his parents, I didn't push him any further.
Caleb and I worked out for almost two hours. About a half-hour into the workout, I pulled my shirt off and threw it on the floor of the shed, hoping Caleb would follow suit. He didn`t. At the end of the workout, I grabbed my shirt from the floor and pulled it over my head. "That was awesome, man," I told him, "thanks for the invite." "Anytime you want to come over, just let me know," Caleb said, dividing his time between me and the floor. "You know I'll take you up on that, bro," I told him, smiling. I was headed for the door when I heard some movement behind me. I turned around and saw Caleb pulling his shirt off over his head.
Over the next few weeks, Caleb and I worked out a couple times a week. Between the time I was spending in the weight room at school and at Caleb's, my body was getting in great shape for the coming season. I was usually at Caleb's one day after school and on Sunday afternoon. On this particular week, I saw Caleb at school the day before our scheduled workout and told him I was going to be about an hour late the next day. I had to run some errands for my mom. As usual, Caleb avoided eye contact, and looked at the hall floor most of the time. During seventh hour the next day, I got a text from my mom. She said she had taken care of the errands and I could go to my workout as planned. I tried to find Caleb after school to tell him, but by the time I got to the parking lot his car was already gone. Getting into my car, I drove to the convenience store, grabbed a protein shake, and headed over to Caleb's.
I parked in front of Caleb's house as usual, and began walking around the house to the backyard. As I passed by the kitchen window, I saw Mrs. Brookeover standing at the sink. She saw me, smiled, and waved. I smiled and waved back. When I got to the shed, the door was closed as usual. I could hear the hum of the window air conditioner, working overtime on this hell hot afternoon. I reached for the door handle, turned it, but the door was locked. "Weird," I thought to myself, "it's never locked." I tried again, thinking maybe I hadn't turned the knob far enough. Nope, it was definitely locked. I knocked a couple of times on the door, but no answer. I figured that the noise of the air conditioner drowned out my knocks. Or, maybe Caleb wasn't in the shed. I walked around to the back of the shed, where the only window was located. Standing on my toes, I looked into the shed through the top half of the window. The bottom half was filled with the air conditioner unit. I stood to the left of the unit and looked inside. There were no lights on in the shed, but the window provided enough for me to see in. I didn't see anything. I moved around to the right side, and peered in. Inside the shed, the weight bench was located just to the right of the air conditioner, but slightly toward the center of the room. Caleb was sitting on the bench, an open magazine laid out before him on the opposite side. He was rubbing his crotch through his workout shorts.
I watched as Caleb turned the pages of the magazine with his left hand, while continuing to rub his crotch with his right. He would stop for a couple of minutes on certain pages and flat-palm rub his growing bulge. I saw Caleb glance down at the watch on his wrist, then turn back a few pages in quick succession. I looked at my watch too, and it was twenty-five minutes until I was supposed to arrive. I watched as Caleb found the page he was looking for, took off his glasses, laid them on the shed floor beside him, and leaned back against the bench bar. With his left hand, Caleb pulled up the left leg of his baggy workout shorts. His right hand reached in, and slowly pulled out his cock.
I had been standing on my toes for almost fifteen minutes, and my toes and the balls of my feet ached from the pressure. I wasn't about to let myself down and miss what was about to happen, so I alternated standing on one foot, while the other rested.
Regaining my stance, I concentrated on the scene before me. Caleb's cock was of average thickness, probably 5-5 ½", but it was a nice length. Although the first few base inches were hidden inside his shorts, what Caleb held in his hand was a good 6-6 ½. The head of his cock was slightly red, probably from all the rubbing he had been doing, and glistened with the wetness of pre-jizz. I watched as Caleb, with his cock in his hand, slapped it twice on the weight bench beneath him. Each time he slapped his cock against the bench, Caleb would close his eyes and tilt his head back slightly. With each slap, his cock seemed to grow in length. I could see pre-cum dripping from the head of Caleb's cock, and forming a small puddle on the bench. With his hand, Caleb pushed his cock down and slid it through the puddle. Slowly, he jacked his hard cock back and forth, concentrating on the pictures before him. Soon, Caleb's left hand went to the bottom of his T, lifted it up, and began rubbing his hard stomach. His hand disappeared higher up into his shirt, and its outline appeared around his hard pecs. Each time Caleb's dripping cock would form a puddle of pre-jizz, he would slide his cock through the jizz, then continue pumping.
I watched transfixed as Caleb began to slowly move his hips forward on the bench, fucking his hard cock into his hand. His shaft was rigid and shiny from the jizz lube, and seemed to grow each time he fucked forward. As if sensing it was almost time for my arrival, Caleb began to speed up his pumping. He brought his hand down from his chest and began rubbing the balls that were hidden inside his shorts. I watched as Caleb slowed his jacking, then hard pumped his cock four or five times. His mouth was open and his eyes were wide as he threw his head back, tossing his dirty blonde hair out of his face. Caleb stopped, and I saw his leg muscles tighten as his feet pushed hard against the floor of the shed. His hard stomach was moving in and out in hard, short breaths as his hand gripped his cock tight. Three short pumps, seconds apart, let lose the first shot of cum which flew easily past Caleb's head. A second, third, and fourth pump, each followed by blasts of jizz, flew in the same direction as the first. Caleb's head was still tilted back and his eyes closed, as he pumped out two more smaller shots. His stomach continued to make short, hard movements. A few minutes later, Caleb leaned fully back against the bench bar, his body now totally relaxed. His cock, now losing its hardness, continued to lay outside the left leg of his shorts. The weight bench was still shiny from the puddles of pre-jizz Caleb's cock had made.
My own cock was hard and aching, and I needed release. I couldn't take the chance of unloading in broad daylight behind the shed, so I quietly made my way the back door of Caleb's house. I knocked, and when Mrs. Brookeover answered the door I asked if I could use her bathroom. Three minutes later I shot my own load, hard and fast. Two minutes later, I closed the back door and headed out to the shed for my workout with Caleb.
Caleb had told me previously that he tried to work out every day, usually in the evening. He said that his grandmother was usually went to bed around 8:00, so he would finish what homework he had, then head out to the shed. Over the next week, I decided to see if Caleb was doing another type of workout. Around 8:30 each night, I would park my truck a few houses down from Caleb's, then walk down the alley behind his house, to his backyard. True to form, each time I got to the window of the shed, Caleb was either starting, or right in the middle of, his slamming session. Watching Caleb's hard, defined body, his dirty blonde hair falling into his eyes, then jerking his head to get it out of the way, and his hand gripping his rigid long cock, was the highlight of my day. It was while watching those sessions that I thought of a way Caleb could "make good" on his debt.
It was Sunday afternoon, a week and a half after I had first seen Caleb jacking in the shed. I purposefully told Caleb I was going to be about an hour late, hoping I would catch him in a session. To ensure the success of my plan, before I left my house I threw a Hustler magazine I had got my Skyler, my sister's boyfriend, into my bag. I headed over to Caleb's, parked my truck out front, and went to the shed in the backyard. I turned the knob on the shed door, and sure enough, it was locked. I walked around to the back and looked in the window. Caleb was sitting on the weight bench, a magazine laid out before him, and had just pulled out his cock. I waited for a few minutes and watched as his cock grew from the pulling. I saw as his cock head began to grow wet, as pre-jizz oozed out. As Caleb's right hand slowly jacked his cock, and his left hand went up under his shirt, I decided it was time.
I grabbed my bag and headed around to the shed door. I knocked four times, loud, waited a few seconds, then knocked loudly again. Over the hum of the air conditioner, I head movement inside the shed. I waited a couple of minutes, then knocked loudly again. I heard the lock turn on the door, then it opened about a foot. Caleb was looking out of the door, and his glasses were off. "Oh...hey Sam," Caleb said, his breathing a little hard, "I...ummm...I thought you were going to be late..." I pushed the door with my foot a little, and Caleb stepped out of the way. "Yeah," I said looking around the shed, "I got finished sooner than I thought." I walked into the shed, dropped my bag, and headed over to the weight bench. I looked down and saw a small puddle of pre-jizz Caleb had leaked out. Smiling, I looked at Caleb and said, "so...you ready?" "Ummm...yeah," Caleb said in his usual low voice, "let me get my glasses."
Caleb talked less than he had during our other workouts. He seemed distracted and having a hard time concentrating. I figured he was horny and frustrated because he hadn't been able to finish his jack-off session. Toward the end of our workout, I was sitting on the bench and Caleb was leaning against the table, having just spotted me. "So, Caleb," I said, putting my plan into motion, "can I talk to you about something?" "Ummm...yeah," he said in his low voice. "I've been thinking about what you said after I helped you get your car fixed," I began, "you remember...?" "I think so...," Caleb answered back. "...about how you owed me," I went on, "and how you always make good on your debts..." Caleb looked away from me and looked down at the shed floor. "Sam," he said, "I don't have any money yet, it'll be..." "I don't want money, Caleb," I said, cutting him off. "I have something else in mind..."
Caleb looked back at me when I said this. "Ummm...what?," he asked. "What I want, Caleb," I said slowly, "is your dick..." Caleb looked at me with a puzzled look on his face. "What?," he said, "I don't understand..." "I want to jack you off, Caleb," I said, looking at him, "I know you like jacking off, and I want to help you with it." Caleb looked at me stunned. "How do you know...," he said looking at me. "Bro, you're a healthy teenage dude," I told him smiling, "we all like it!" Caleb stood there, looking back down at the floor of the shed. "Sam," he finally said, "I can't do that...it's not right..." "Look, Caleb," I said, "I consider you my friend...we're friends, right?" "Yeah," Caleb said in his low voice. "And friends can talk about anything, right?" I asked him. "Yeah...I guess so," Caleb said back. "So let me ask you," I said, "you like jackin' off, right?" Caleb didn't answer. "And it feels good, right?" I went on. Again, no answer from Caleb. "So if we're friends, and you like jackin' off, and it feels good, why not let a friend help you feel good...?" Caleb still didn't answer, but he did raise his head to look at me. Although he was silent, from the look on his face I could tell he was thinking. I also noticed a bulge in his crotch that hadn't been there before. "And," I added, "you did say you owed me...and that you always make good on your debts..."
A few minutes passed as Caleb and I looked at each other in silence. He would look down at the shed floor, then back at me. Finally, Caleb pushed himself away from the table, and walked over to the shed door, and locked it. He walked back to the table and leaned against it. "Okay," he said in his low voice, "you can do it..." In the time Caleb had walked over to the shed door and back to the table, the bulge in his crotch had became noticeably bigger. Figuring I wouldn't need the Hustler magazine in my bag, I scooted off the bench, and got on my knees in front of him. It was evident Caleb was unsure what to do with his hands. First, he put them behind his back. Then he moved them and let his hands hang at his side. Finally, Caleb put his hands on the table behind him, on either side of his body. I looked up at Caleb as I reached for the front of his shorts. His eyes were closed.
As my hand touched the bulge in Caleb's shorts, his body flinched. "Relax, dude," I said to him, "just relax..." My palm moved over his bulge, and I felt Caleb's cock move and grow. I could hear him suck in his breath as my hand closed around the outline of his cock. With my left hand, I went to Caleb's right leg, and moved my hand under the leg of his shorts. Moving my hand up his leg, I felt something wet and sticky. Going up farther, my fingers soon touched the head of Caleb's cock, sticking out of the leg of his boxers. His body stiffened as my fingers rubbed his cock head and the exposed shaft. "Ahhhhh," Caleb breathed out in a low moan. With my first two fingers and my thumb, I rub over the slit in his head. Pre-jizz flowed out, coating my fingers. I could hear Caleb breathing hard above me. I removed my hand from the leg of his shorts, and brought both hands to the waistband of Caleb's shorts. I looked up at him, and Caleb's eyes were still closed. Grabbing both his shorts and his boxers by their bands, I slowly pulled down. Caleb's body at first relaxed, then stiffened again, as the top half of his long shaft met the cool air of the shed. It was all I could do to not bend forward and start licking the exposed shaft. I pulled his shorts down further, then out and over the head of Caleb's cock. Free from the constraints of his shorts and boxers, Caleb's cock bounced up to a 45 degree angle. A thin string of pre-cum, running from his cock slit to his leg, broke free in the process. Pushing Caleb's shorts and boxers to his ankles, he instinctively stepped out of one side, then moved his legs farther apart.
Caleb left his T-shirt on, and the dark blonde treasure trail that started at his navel disappeared under his T. His trail led to a full bush of dark blonde pubes, that wrapped around his shaft and continued to his balls. Looking full-on at Caleb's cock, I watched as it twitched in front of me. I reached my hand up to touch it, and felt a shudder go through Caleb's body. I looked up at him. Caleb was now looking down at me, his eyes fully open. Somewhere in the process, Caleb had removed his glasses, and he stared at me with greenish gray eyes. I wrapped my right hand around the shaft of Caleb's cock, and slowly began to jack. On the first forward jack, Caleb let out another low moan as a significant amount of pre-cum flowed out of the head. I caught the dropping ooze with my left hand, brought it to the head of Caleb's cock, and rubbed it around. I could feel his body stiffen more, and his hands press down harder on the table. It seemed like Caleb's cock grew harder and longer each time I jacked. A good 8", his cock seemed to grow the more I pumped. True to his personality, Caleb didn't talk while I jacked him, other than the occasional "ahhhh." However, his moans were almost ongoing and sometimes appeared to be whimpering.
As I began to jack his cock a little faster, Caleb moved his legs farther apart. He also began to move his hips forward, fucking his cock into my hand. With his balls continually producing pre-jizz, I alternated rubbing the ooze around Caleb's cock head and his balls. Each time my hand would touch his balls, Caleb would fuck my hand harder and more pre-jizz would flow out. Each time I would look up, Caleb would be looking at me. His long dirty-blonde hair would be hanging in his eyes. His jaw would be set and his nostrils flared.
My pumping had become faster, and Caleb eased off the hand fucking. His balls began to draw up in their sac, and I knew he was getting close. Caleb moved his legs even farther apart, and he began to push down hard on the table. More pre-cum was flowing out of his hard cock than before, and his moans were ongoing. Suddenly, Caleb's body tensed and his breathing became harder than ever. "Sam...Sam...," he panted, "you have to move...I'm gonna..." I had no intentions of moving, and pumped his steel hard cock faster. "SAM...," Caleb almost yelled as he was panting, "I can't stop it, Sam...I...CAN'T...STOP...!!!!"
Caleb's cock erupted in rocket shots that splashed against my forehead, cheeks, and chin. After the fourth shot, I pushed my mouth onto the head of Caleb's shooting rod, and jacked the remaining loads into my mouth and down my throat. Caleb's cock hardened more as soon as it touched my lips and passed into my mouth. As if it was revitalized, his cock pistoned out three more hard shots. This last move sent Caleb into orbit. "WWHHAATT?!?!," he yelled out, "AHHHH MAAANNNN!!!!!" I looked up at him, his cock in my mouth, and his eyes were half-closed and his mouth open. Caleb's hands never left the table, but his hips instinctively pushed forward, sending his cock down my throat. I felt more cum shoot out of Caleb's shaft, and slide down to my gut. His body remained tense, and his breathing short and hard, as Caleb's hips and my throat milked out the last remaining drops of his load.
Exhausted, Caleb slid down onto the floor of the shed as I pulled my mouth off his cock. His long dirty-blonde hair hung over his eyes, and his chiseled chest heaved in and out. I got up off the floor, and sat on the weight bench in front of Caleb. Finally, he looked up at me, pushing his hair out of his eyes. "Sam...," he started to say, then he stopped and looked down. I sat on the bench without saying anything. Finally, Caleb looked up at me again, with a grin on his face. "Wow," was all he said.
Caleb and I remained friends and continued working out a couple times a week. Although he "made good" on his original debt, Caleb kept insisting he still owed me, so I kept collecting. After graduation, I went to college and only saw Caleb a few times during his senior year. He had become more outgoing, smiling more, and had made quite a few friends. I saw Caleb once more before he left for college. I had come home for the weekend because Caleb's grandmother was throwing him a graduation party, and had specifically asked me to attend. Their small house was filled with people. Towards the end of the night, Caleb caught my eye and motioned for me to follow him. He went out the back door and headed for the shed. Once we got to the shed door, Caleb looked around to see if anyone was watching, then unlocked it. I followed him inside, and Caleb closed the door and locked it. I turned around and saw him standing with his back against the door, massaging his crotch. I walked over to him, got on my knees, unbuttoned his shorts, and pulled them down. As he felt his long hard cock slide into my mouth and hit the back of my throat, Caleb put his hands on my head. A long sigh escaped his lips, as Caleb slowly began to move his hips forward and slow-fuck my mouth. "Yeah," he moaned low, "this is what I'm gonna miss..." I felt his hands grab hard in my hair, and his body tense, as Caleb's cock pushed beyond the back of mouth and slid down my throat.