Date: Wed, 6 Mar 2024 20:44:39 -0700 From: Skylar Williams Subject: Teenage Curiosities CHAPTER 5 (HighSchool) Disclaimer: The following story is a work of fiction; any resemblance to real persons living or dead is entirely coincidental. If you're not old enough to read this, go away. This story is fantasy. It didn't happen. Copyright Notice - Copyright February 2, 2024 by the author. This story is copyrighted by the author and the author retains all rights. This work may not be duplicated in any form, physical, electronic, audio, or otherwise without the author's expressed permission. All applicable copyright laws apply worldwide. Please donate anything possible to the Nifty Archive http://donate.nifty.org/donate.html. Chapter 5 Jeremy and I were spent. It was not only a long day, but our 69 session was intense and left us lying there in bed, not wanting to move. I could still taste not just his cum but his dick. As sweat dripped across my face, I lifted my head to see what Jeremy was doing. I could see his dick softening and the remnants of his load leaking onto his thigh. I looked down at my groin, and I was in the same state, soft and leaking. Jeremy sat up, wiping sweat from his brow. "Fuck, that was awesome." Looking around at the scene we created. "My throat is sore now, thanks." He laughed. "You were doing such a good job; I wanted to see how much you could take," I told him. "You were all the way down my throat when you busted. You don't have a small dick, bro." Jeremy laughed again as he lifted my soft dick wiping the leftover cum from my tip. "Let's get cleaned up." He rolled over my body, smacking his dick against my cheek. He stood up and stretched, showing off his naked physique. We walked into the restroom, looking at each other's bodies in the mirror. He turned on the sink and soaked a washcloth with warm water. "Let me get that for you," He gestured at my dick. He reached over and began to wipe down my cock. As good as it felt, I couldn't get hard again. He finished by rubbing my balls and groin, making sure he got all the cum, sweat, and saliva from my body. He ran the cloth back under the warm water and proceeded to wipe himself down; when he bent over the sink to wring out the rag, his gorgeous ass was in full view. Messing around with him, I stood right behind him; I grabbed both his hips, placing my cock between his cheeks. I gently pressed with back-and-forth thrusts. Jeremy jumped and turned around quickly. "Whoa, hold up!" he said, startled. I laughed, telling him, "I'm just messing, man. You did stick your tongue in my mouth, so I thought I could stick something in you." "That's an exit only besides you stuck your dick into my stomach," he laughed. I slapped his ass as I stood next to him at the sink. We brushed our teeth and went back into his room. He suggested we wear some underwear in case his parents entered the room in the morning. We both climbed into bed and fell asleep for the night. The next morning, we were awakened by a knock on the door, followed by Jack walking into the room. "Hey, Jeremy, Dad needs help picking up some lumber and asked if we could go with him," Jack stated. "Ugh, really? When is he leaving?" Jeremy asked annoyed "In about 20 minutes. Throw on some clothes, and let's head downstairs." Jack ordered. Chase walked in fully dressed, "My mom is picking me up in like 15 minutes. Guess I need to help fix a damn fence on my grandparent's farm." he complained. Looking over at me, he said, "I'll give you $20 bucks if you can help me. The other guys are working on the back acreage. I could use a hand, please?" I had planned to spend the day here with the twins, but since they were going to be busy with their dad, why not hang out with Chase? The guy needed my help, and I might get the chance to see him in his underwear again. "Yeah, that would be cool. It'd give me a chance to check out this farm you're always talking about." I replied. Chase's mom swung by and picked us up for the trip to his grandparent's farm. When we arrived, I noticed it was an expansive, beautiful land. The house and barn looked freshly painted and stood about 100 yards apart. We both jumped out next to the barn as his mom waved goodbye, leaving to address the fence. Chase led me to a row of ATVs they use around the farm. He grabbed some tools as we headed out to the other side of the farm. We spent a couple of hours fighting to get the fence repaired. By the time we had finished, Chase and I were covered from head to toe in dust, sweat, and dirt. This was far from the city life I was typically accustomed to, yet I'd found a liking for the dusty, sun-filled adventures as of late. As I gazed at Chase, his muscular form glistening in the sunlight, I took a moment to admire the way his tight jeans hugged his thighs, desperately clinging to his tighty-whitey underneath. "Hey, city-boy, ready to call it a day?" he joked, wiping the sweat from his forehead. "Sure thing," I replied, wiping the sweat from my brow. We tossed our tools onto the quads we rode out there. I followed Chase as he led me back to the barn. Once inside the barn, I glanced around at how organized and clean it all appeared. I thought barns were supposed to be old and dusty, but this barn was more modern. There looked to be an office in the back and a loft that ran the length of the structure. Chase led the way to the stairs by the office and motioned me up toward the loft. "What's up there?" I asked, intrigued. "My grandfather's office and stuff are down here, so he gave me the whole loft for myself. It's one of the perks of being an only grandchild," he laughed, making our way up the stairs. Entering the loft, I could see Chase's old desk and chair, which he had set up for himself in the back by the stairs. A couch and worn armchair were on a rug along one wall, along with some gym equipment, a hanging heavy bag, weights, and a wrestling mat. In the corner were some old boxes, a chest, and a couple of bins with linen. "Wow, this is your loft? This is huge!" I exclaimed, looking around the place. "It's like an office, gym, and lounge here." "Yep, when I stay here over the weekends, I have a place to do homework, work out, and relax, " he said, pointing to each section of the space. "Jeremy was saying that you were thinking of trying out for wrestling. Is that true?" he questioned "Yeah, my brother used to wrestle, so I thought about trying out," I said, still looking around the loft. "Well, I'm going to be on the squad this year, so if you want to practice before the season, I can help," he offered. "Man, that would be great; I need all the help I can get," sounding excited. "Cool. I have a couple of spare singlets you can borrow. They should fit. One of them is a practice one from last year." He mentioned looking around the room. He walked over to the boxes in the corner, pulling out some clothing. He pulled out a white Adidas singlet and tossed it to me. "Here, this should fit you, although the crotch may be too big," he laughed. "You want to start today? I'm a bit tired from fixing that fence." I said "Nah, we don't have to, I'm worn out too," he said, sounding bummed and holding his red high school singlet. I heard him chuckle and say, "Dude, check these out." He pulled a stack of books out from the bottom of the box. My eyes widened as I recognized the covers-- porn magazines from the 80s and some from the 90s. My heart raced as I glanced over at Chase, who was smiling ear to ear. "I found these here about a year ago," he stuttered, looking almost proud. "I thought you'd like to see them. Jeremy said you had some magazines of your own." Jeremy said what, I thought? Did Jeremy tell him other things, too? "This one is my favorite," he said, showing me a magazine spread open to a page showing a naked couple. The woman's breasts were exposed, and the man's hard cock was lying on top of them. I felt my cock start to grow in my pants, and I quickly glanced over at Chase to see if he noticed. Thankfully, he seemed too engrossed by the sight of the magazines to notice my growing arousal. Chase handed me a few, and we sat on the rug, leaning our backs against the couch, flipping through the pages. We didn't say a word, just passing them back and forth, mesmerized by the raw, unbridled sexuality on the pages in front of us. My cock was aching for release, and as if sensing this, Chase finally spoke up. "Screw it; these pants are too tight." Chase leaned back and reached down to unbutton his pants and unzip his fly. He pushed his pants down to his ankles, exposing his massive bulge in his tighty-whiteys. He kicked off his shoes and removed each leg from his jeans. He was sitting there in white socks and tight, discolored underwear. His cock was pressing hard against the fabric, revealing a clearly visible outline of his veiny shaft. The sight made my cock throb. Before last week, I'd never seen another guy's dick before, let alone one like Chase's. I was nervous yet excited, and with a newfound courage, I pulled off my pants and threw them aside. I felt exposed and vulnerable, sitting there in just my white boxer briefs. I could feel the fabric strain against the growing length of my cock as I watched Chase do the same, revealing the sheer size of his dick. "See something you like?" he joked, still smirking. He was holding up his magazine and gesturing to my hard cock. I blushed at the mere thought of my 5-inch penis compared to his monster. His dick just kept growing; it was stretching his underwear enough that they were pulling away from his thigh. Through the gap, I could make out the base of his thick dick. "I guess," I replied, looking back up from his package. He grinned and leaned back against the couch, then gripped his dick at the base, making the white fabric tighter on his mushroomed tip. Chase's cock was massive; I have never seen anything that impressive. "I'm so fucking hard right now," he asked again, looking back down at his massive tool. He slid his hands down the front of his underwear and took them off. His massive cock sprang up and slapped his stomach. The uncircumcised, 7-in meat was thick with swollen veins trailing down its length. My breath caught in my throat. "Shit, that's big," I murmured, involuntarily clutching my bulging underwear, where the 5-inch cock inside was aching to be freed. "Ever seen one up close?" he teased, making me blush. "Not that big, no," I replied. I reached down and gripped my 5-in cock through my underwear. There was a massive wet spot from my oozing precum. "Damn, looks like your rock hard too." Chase stated, "Can I see it?" He nodded towards my covered dick. I was nervous but couldn't deny showing him. I slid my boxer briefs off, revealing my 5-inch, hard, cut cock, covered in precum. He let out a low whistle. "Nice," he said. I watched as he reached out a hand, slowly wrapping his fingers around my shaft. My breath caught in my throat again as his hand started working up and down, my cock jumping in response to his touch. "Fuck, Chase," I groaned, letting my head fall back. "Knew you'd like that," he replied, his voice cracking with arousal. "Jack likes it when I do this to him, too." I almost didn't catch what Chase just said. He and Jack stroke each other, too? That makes sense; Jeremy has said they were close. They always hung out together without Jeremy. Chase's hand felt so good wrapped around my dick. I reached over and grabbed the base of his dick. It was warm and solid, and I felt like I was holding a club. His foreskin was soft like Jeremy's, and his girth increased from the base to the tip. Like Jeremy's dick, I rolled the skin back to see his thick pink head, releasing more precum to drip down the length. I moved my hand forward, applying more pressure and quicker strokes. Chase followed my lead, tightening his grip. Our bodies moved together as we found our rhythm, the loft filled with filthy, aroused groans. "Has anyone ever licked off your precum?" Chased asked nervously, breaking the trance we were both in. His eyes were glued to his hand, which was still furiously stroking my slick cock. I shook my head, gasping as Chase leaned in, running his tongue up the length of my cock. He paused, swirling his tongue around my head, collecting the sticky precum. "Mmm, you taste good," he murmured, sending a shiver down my spine. He bent in again and took more of my shaft into his mouth. Chase swirled his tongue around and around the sensitive tip, tracing the edges of my cock head with his tongue. Fuck, it felt incredible. I moaned and arched my back, pressing my dick deeper into his warm, wet mouth. With his free hand, he cradled my balls, gently massaging them as his head moved up and down. Fuck, this guy was going to make me cum in no time. Chase pulled away, panting. "Damn, your dick tastes sweet," Chase said, still gripping my dick in his hand. He moved his mouth back down, taking my entire shaft into his mouth. "Fuck, Chase!" I cried out as he hollowed his cheeks, working my dick in and out of his mouth. He was deep-throating me with apparent ease, his tongue tracing the underside of my cock. I could feel the ache in my balls grow as I neared the point of no return. "I'm going to cum," I warned him, knowing I couldn't hold back much longer. But Chase didn't stop. Instead, he worked my cock faster, deeper, his saliva coating my shaft until I couldn't hold back any longer. With a low, feral groan, I came, my whole sack unloading into Chase's eager mouth. My back arched, and my hips thrashed as he swallowed every last drop. I could tell he had done this before. As my body relaxed from the violent orgasm, I couldn't help but feel embarrassed at my body's response to him. "Damn, you cum a lot," Chase murmured, still gripping my slick shaft. Chase moved his mouth back down, lapping up the remaining drops of cum that escaped my tip. He moaned, and it sent a shiver down my spine. "You good?" he asked, his eyes searching my own. "Yeah, damn, you know how to suck a cock." I laughed. "Had some practice recently," he joked back. I put together who he was talking about. He and Jack were a lot closer than I realized. He leaned back; his dick was still solid and leaking more than ever. Grabbing the base, he held it and asked, "My turn?" he looked down with a smile. "Um yeah, I can try," Looking at his massive dick. There was no way I could deep-throat him like I had done to Jeremy. I did want to taste Chase, though. I got on my knees and leaned my face into his crotch. I could smell the sweat and musky scent of his man-sized cock. I grabbed the base of his dick and ran my tongue across his slit and head, cleaning any precum that had accumulated. He moaned as I began to suck his engorged head. His precum tasted just like mine and Jeremy's, but it felt slicker, making it linger in my mouth longer. I opened my mouth wider and took in his whole head and about an inch of his shaft. I started bobbing up and down on it while my hand still gripped the base tightly. Chase's body shuddered in pleasure as I sucked his dick, swirling my tongue around his head and shaft, applying pressure on the sensitive underside. With my other hand, I reached down to play with his balls, gently massaging them while continuing to let spit leak from my mouth down his impressive dick. Chase moaned loudly, his hand reaching for my head as he started thrusting into my mouth, controlling the pace. My mouth was stretched as far as it could go when I began to gag with him forcing more of his cock into my throat. I had to back off and gasp for air. "Sorry, too far?" He asked as he looked down at me. "Yeah, I don't think I could get any further," I said, feeling my jaw relax. "That felt good; that's the deepest anyone has taken me in their mouth," he grinned. "You have my precum on your lip. Can I get that?" He leaned in and kissed the bottom of my lip. I grabbed the back of his head and began to kiss him back. The wrestler in him seemed to take over because he started to muscle his way forward, pushing me to my back. Our kiss didn't break as he lay on top of me. I could feel the mass of his crotch rubbing against my hardening shaft. Chase raised both of my arms above my head and pinned them there as he kissed me deeper. His whole weight was on top of me, and he slid up my body from the sweat that we were both dripping. Chase had wedged his legs in between mine and, in one quick motion, spread my legs out wide. I was wrapped up in his tongue, exploring my mouth, when I realized what a vulnerable position he had me in. I felt his hips lower down my body as his heavy dick slid down my thigh. He was positioning it between my legs. His wet tip brushed past my scrotum as it glided under towards the entrance of my ass. "Whoa, what are you doing?" I asked, breaking our kiss. "Just fooling around. Why is this too much?" Chase asked back with a smile. "Careful where you put that thing." I joked back. "What? You don't like this? he laughingly joked before he gave his hips a slight thrust poking his slick tip up against my hole. "HEY!" I said while attempting to jump. He had one hand locked onto both of mine above my head while his body weight kept me in place. I was shocked that I couldn't move an inch; he was far stronger than me. "Chase, you can't just stick your dick up my ass," I said, trying to sound confident but failing. He chuckled at my statement, but instead of removing his dick, he wiggled it around my entrance. "Relax, Sky," he whispered in my ear. "I'm just playing around." But he didn't back his cock from my ass. He just kept rubbing it against my puckered hole. "This doesn't feel good?" He asked, still lightly poking his head against my hole. "A little, but I don't want anything inside of me, especially your giant dick," I replied with a nervous giggle. "I can go slow and take time for you to get used to it." He whispered in my ear, his poking continued. He wasn't going to let me up. I tried to find an excuse to get me out of this situation. I tried to reason with him. "Chase, I have never done anything like this before. MAYBE, if we had lube, but not without it. It seems like it would hurt too much." I heard Chase spit into his hand, which wasn't holding me down. He reached between our legs and felt him rubbing the head of his dick with his mouth lube. I couldn't help but feel a twinge of fear as I thought about what he was planning to do. I had never even considered anything like this with another guy before, but here I was, pinned under him, with his massive tool just inches away from my virgin ass. "Chase, please," I begged, my voice trembling with apprehension and excitement. "Let's not do this right now; I don't know if I'm ready for this." But instead of backing off, he leaned in closer, his lips brushing against my ear. "What if I just stuck the tip in? I just want to see what it feels like," he implored me. I could feel the warmth of his breath on my neck as he spoke, and my heart raced. If I told him no, would he try anyway? He was as horny as I have ever seen any guy, Jeremy included. I had to get any control I could in this situation. "Okay, just the tip," I commanded, "if I tell you to pull out, then PULL OUT!" "Of course," he said in an eager voice. He pressed his hips with more force as his tip tried to break the lock my ass muscles had placed on my virgin hole. "Ouch! WAIT!" I yelped. "Dude, you need lube. That is hurting so much!" Chase released my hands and sat up on his knees between my legs. He spit on his hand again, this time making a larger pool of saliva coat his cock. He was stroking his dick and drooled a few more drops on his tip when he lifted my legs onto his shoulders. I was completely naked and vulnerable with my pink virgin hole exposed to him. He guided his slick tip to my entrance and looked me in the eyes, whispering, "I promise, just the tip." I could feel his large head begin to press against me, wanting to gain entrance inside me. I began to wince as he slowly applied more pressure. I was paralyzed with fear and a little excitement as his slick head just kept pressing against my entrance. It was just a small oval, no larger than a dime; my hole felt so small compared to his massive tool. I kept telling myself not to tense up. I knew that would hurt it more, but I couldn't help it. "Relax, Sky. You're so damn tight." Chase whispered into my ear, his hot breath making me shiver. He pressed the head of his dick against me again, harder this time. I sucked in a breath and felt a sharp pain as he broke through the tight ring of muscle that guarded my entrance. "Fuck, Sky!" Chase groaned, his eyes rolling back in his head as he sank just the tip of his dick into me. I bit my lip, fighting back a whimper of pain. It felt like he was tearing me open. He leaned back and lifted my legs higher so he could examine the area where our two bodies were connected. The pain was intense, and I felt any movement might make it worse, so I held perfectly still, watching him. "Bro, this feels awesome. Your ass looks like he is taking it like a champ. I can't believe how tight you are or were." He laughed, looking down at me. I was still wincing from the pain, but I couldn't deny that the feeling of his dick inside of me was also creating an intense sense of pleasure. "Please, can I keep going?" Chase begged his voice husky with arousal. I knew I should say no, that it was a bad idea, but the look in his eyes, the way his lips curved up at the corners, and the feeling of his dick buried inside of me made me say, "Okay, but slow." He started moving slowly at first, pushing in a little more, then stopping, letting me adjust to his girth. He was still watching his dick slide into me when he asked, "How's that feel? Should I keep going?" Closing my eyes and biting my lower lip, I nodded with approval. His tip was rubbing against something in my ass that was giving me so much pleasure. I wanted more. Chase pulled his shaft out an inch, spit some more of his saliva onto his shaft, and started to ease more of his pole into me. The deeper it slid into me, the more he lowered his body onto mine. Just as I could not take anymore, he whispered, "I'm all the way in." I could feel my balls rubbing against his pubes. The excruciating pain slowly became a pleasure. It felt so foreign, having something in my body. I felt the pressure of him in me, filling up my bowels. I could feel every inch of him inside of me. In a show of dominance, he whispered in my ear, "Can you feel this?" as he began to pump blood into his cock, making it twitch inside of me. He knew that he was in complete control as he tightened his embrace. "Yeah, I can feel it twitch," I whispered back as I submitted to him. "Good." Chase's strokes were short at first, but as he began to pick up the pace, I could feel every inch of him inside me. He was pounding my ass, his balls smacking against my flesh as he drove his cock in deep with each thrust. I moaned in pain and pleasure as he no longer worried about what he was doing to my hole. He had stretched me to the size he needed, my hole gripping his teenage cock as he fucked me harder. The veiny shaft massaged a spot in my ass that had me on the verge of cumming. With every push of his hips, I got closer to cumming until I couldn't take it anymore. "Fuuuuuuuccccckkkk!" I moaned as I blasted my intense orgasm onto our bodies. My ass clenched down around his cock as each rope of cum shot from my dick. The clinching may have been too much for him as I felt his body tense up, and he squeezed my body tightly to his. "Im going to cum," he let out before impaling me with his full 7 inches. With each pulse, he grunted and moaned in pleasure. I could feel the warmth of his cum filling me up as he emptied himself inside of me. He gripped me even tighter, holding me down as he exploded in a rush of pleasure and release. Finally, he collapsed on top of me, our sweaty bodies sticky with a mix of my cum, and the musky scent of sex filled the barn. "Fuck, Sky," Chase panted in my ear, "That was incredible," his voice husky was spent. I couldn't help but agree. After a few moments of stillness, I felt him begin to soften inside me, his cock shrinking just enough for him to slip out with a wet popping sound. We lay there for a while, breathing heavily and limbs tangled together. The air in the barn was thick with the scent of sex and boy sweat. I could feel the stickiness of his cum leaking from my ass, dripping down my thigh and onto the rug on the floor. Chase sat up and lifted my leg, admiring the mess of what he had just made of my ass. "How does it feel getting bred for the first time?" Chase asked, smirking. I couldn't help but blush at his words, still reeling from the intense orgasm he had just given me. I was still lying on the floor of the barn, my legs splayed open and his cum leaking out of me. That sentence burned into my mind, knowing that my friend had just dumped all of deep inside me. He bred me. "Shut up," I replied, trying to sound annoyed but failing. I couldn't deny that the feeling of his cum filling me up, the warmth spreading through my ass, was incredibly hot. I felt like such a slut, Jeremy's cum in my mouth last night and now Chase's in my ass, but I couldn't help the satisfied smile that spread across my face. Chase grinned and leaned down to kiss me, his tongue slipping into my mouth and mingling with mine. "You liked that, huh?" he asked, his voice low and sultry. I nodded, biting my lip. "Yeah, I did. That was...intense." Still feeling embarrassed, I grabbed my underwear and threw them on, followed by the rest of my clothes. I looked over at Chase, naked, limp with cum and saliva dripping off his dick. Realizing that kid before me just took my virginity, I sat on his couch with my sore ass, not knowing what to say. "For my first time fucking someone, you weren't bad." He laughed, trying to break the tension. "Jack and I have never gone that far before. Maybe we should hang out more often." "Um, maybe we give it a few days. I don't think my ass could take that again." I tried to laugh, wincing as I shifted in my seat. Chase chuckled. "Aw, c'mon. You loved it." He winked, giving me a playful nudge. "I'm sure Jack would too." I raised an eyebrow. "Why you say that?" I asked in a low tone. "He mentioned something about your ass last night when we were in bed. Besides, your ass will be fine in a couple of days, believe me." He joked as he looked around for his underwear. "I doubt that. My underwear will still be soaking up your cum in two days. Anyways, how would you know?" I asked. Chase looked at me, "One of the ranchhands showed me how to do some of this stuff. Those are his magazines. I'll tell you about it another time, though." Chase has been fucked by one of the guys on this ranch? The thought raced through my head. I wanted details, but it didn't sound like he wanted to talk about it. "Yeah, I should get home," I said, not pressing him for more information. Chase got dressed and we walked downstairs so i could call my parents to pick me up. As we sat silently, he asked if I wanted to return tomorrow. I didn't know what to say; I knew I wanted to, but I wasn't sure if I was ready for another round. I could still feel the ache in my ass from the pounding he had given me. Something I didn't think would go away anytime soon. "I'm not sure if I'm ready for more right now. I need some time to process everything." I said, leaning up against the barn. Chase nodded, understanding. "I get it. It was a lot to take in. But let me know if you change your mind, okay? I had a lot of fun with you." He gave me a wink, and I couldn't help but smile. Despite the pain and the awkwardness, I had to admit that I enjoyed myself, too; it was a new experience I knew I would never forget. As my parents arrived, Chased thanked me for the help on the fence and said bye. It would be a couple of weeks before Chase and I hung out again, but we had much to catch up on when we did.