Date: Mon, 1 Apr 2024 22:03:35 -0700 From: Skylar Williams Subject: Teenage Curiosities CHAPTER 6 (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 6 After leaving the farm and Chase behind, I thought about our afternoon in the loft and tried to block out the discomfort below my waist. I got home, slowly climbed my stairs, and jumped in the shower. I had plenty to shower off, the dirt and dust from work, the cum that had left the ass of my underwear soaked, and any thoughts about how I allowed Chase to take my virginity as he did. The warm water flowed across my head and down my back. Spreading my ass, I let the water wash away traces of Chase that he left in me. My hole was still quite sensitive, so I gently ran my fingers down my crack, feeling how much he had stretched me out. I cleaned myself as much as possible before drying off and heading to my room. Figuring there was still going to be some semen leaking out of me throughout the night, I threw on an old pair of tighty-whiteys and lay in bed. My mind kept racing. I had not ever intended to have another guy inside of me, but then again, I never thought I would enjoy sucking Jeremy and Chase. There have been a lot of new experiences, but today was different. I keep recalling Chase's weight on me, not allowing me to move. I didn't want it to happen, but once he was in me and the pain was manageable, I didn't fight it. I enjoyed it. I was so confused, and on top of that, I felt guilty that it had happened with Chase and NOT Jeremy. Why would that even matter unless I had some feelings for Jeremy? My mind wandered until I decided to fall asleep and overthink it in the morning. The following day, I woke to the smell of breakfast cooking downstairs. Sitting up in bed, I could feel all my body had been through the day before. Everything was sore. My thighs, back, arms, and chest from fixing the fence, and then there was my ass and jaw. Dropping my feet to the floor, I noticed a wet spot in my underwear, but not where it usually was. This time the cum in my underwear belonged to Chase, and it was coming from my ass. I pulled the tighty-whiteys down and saw the slick, clear-ish liquid in them. I balled them up and gently slid them against my hole to get any leftover juice before tossing them under my bed. I felt a bit gross and turned on. Willing myself to get dressed, I cleaned up and headed downstairs. Today was going to be just another day, and I didn't want to think about yesterday. After breakfast, I started my chores and quickly ran through them, ensuring I stayed out of the heat as much as possible. Saving the pool for last, I worked on brushing it down when I heard someone shout behind me. As I flinched, I lost balance and fell into the sparkling water. WHAT THE HELL WAS THAT! Breaking the water's surface, I saw Jeremy standing at the pool's edge. "Dude, sorry, didn't mean to scare you." he laughed. I swam to the edge and pulled myself out. "What the hell, man?" "I called your name a few times, bro. Didn't you hear me?" Jeremy spoke as I stood there, fully clothed and dripping wet. "Nah, I must have zoned out. Fuck, that sucked. Can you grab me a towel from inside?" I laughed back at him. Jeremy walked in to retrieve a towel as I kicked off my soaked shoes and socks. Peeling my dripping shirt off my body, Jeremy returned and tossed me a dry towel. "What's going on? I asked as I dried my chest and head. "Nothing, man. Just finished some stuff at home and wanted to see what you were up to." He said as he watched me dry myself. After drying off my legs and shorts, I wrapped the towel around my waist. "That's cool. Let's go upstairs. I need to change." I led Jeremy to my room; I contemplated whether I should tell him about my afternoon with Chase. I shut the door behind him and walked over to my closet when we got to my room. I pulled my towel off and unbuttoned my soggy shorts. Standing in front of him in just my dripping tighty-whiteys, I could feel his eyes staring at my package. The wet cotton fabric left very little to the imagination as I rifled through my underwear drawer, looking for a fresh pair to put on. "Sorry about yesterday, man. Hope you and Chase didn't work too hard," Jeremey said as he watched me. "WHAT? What do you mean? Did he say something?" I shot back. I was suddenly scared that Chase called the twins last night to brag about what we had done. Giving me an odd look, he replied, "Um, no. I was talking about being unable to hang out all day yesterday as planned. You know, having to go with my dad and leaving you to work on Chase's family farm." "Oh yeah, nah it's all good," I said as I pulled off my soaking underwear and grabbed the towel to finish drying my balls and groin. I noticed him smile a bit as my flaccid cock wiggled as I dried it, facing him. Forgetting about my sore hole, I winced a bit as my hands instinctually reached around my backside, continuing to dry off. Bending over, I placed each foot into my dry white boxer briefs and pulled them up. Reaching into the front of my underwear, I adjusted my balls and dick so my soft bulge was front and center. "You should come over to my place. My mom is working late tonight, and my dad will be at the base all this week. Jack and I have the place to ourselves today." Jeremy offered, still not breaking his gaze from my groin. "That's cool," I said, grabbing a pair of basketball shorts and a t-shirt from my closet. When I turned around, Jeremy was standing right in front of me. I felt his hand cup my bulge gently. "I'll have plenty of time to show you what I was hoping to do yesterday," he said, smiling and giving my package a few squeezes. Damn, it felt good having his fingers drag across the fabric where my scrotum sat. Holding my clothes in one hand, I place the other on his shoulder, letting him rub me, his thumb and index finger sliding back and forth on my shaft, tugging my cock down every time he reached my tip. Almost milking the blood into my shaft, trying to get me hard. But before I could let him, I backed away. "Whoa, slow down. I can't say bye to my mom with a raging hard-on." I laughed. "Okay, get dressed; I'll meet you outside." I quickly put on my clothes and shoes and ran downstairs. I told my mom I was heading to the twins' house and would return later tonight. Racing out the door, I met Jeremy on the sidewalk, and we made our way to his house. As we walked up his driveway, we were met by his dad, loading the rest of his gear into his truck. This man was the picture of the modern American soldier. He looked like an older version of his sons, standing about 6'2", 215lbs, with short blonde hair, striking blue eyes, and a jawline that could cut stone. He wore a tight khaki shirt, army fatigue pants, and boots. His muscular physique stretched every bit of his clothing. "Hey, son, I'm heading out. Make sure to help your mom and stay out of trouble. " Mr. Collins called to Jeremy. "Also, when Jack gets out of the shower, have him change out his laundry. I don't want your mom doing it after work." "Yes, sir," Jeremy replied as he approached his dad and hugged him goodbye. "Be safe." "Later, Mr. Collins." I waved as I walked by. "See ya, Skylar. When your dad gets in town, let him know he owes me a rematch at pool." Mr Collins laughed, jumped in his truck, and left. As Jeremy and I made our way to his room, I saw Jack's door shut and could hear the shower going. Jeremy closed his door behind me and instantly said, "Dude, I got this new porn mag last night; check it out." He walked over to his nightstand, grabbed the magazine, and tossed it to me. Flipping through the pages, I saw that it was mundane stuff at first as I made my way to his bed. I was trying to sit on his bed as lightly as I could when I turned the page and saw two guys kissing as a woman watched. Flipping to the next page, one guy was bending over the bed with his head in between the woman's thighs, exposing his shaved ass to the second guy who was rubbing it. I quickly flipped the page to see how this scene progressed. The next page showed the woman grabbing the man's hair as he lifted his head from her crotch. He had an expression of pain and pleasure on his face while the second guy grabbed both hips and was directly behind him. I was getting hard; I wondered if that was the expression I made as Chase was pushing into me. "Pretty wild stuff," Jeremy said as he sat beside me. "That doesn't look like it feels good." He laughed. Recalling the searing pain from yesterday and the ongoing soreness of my hole, I gave Jeremy a crooked smile as I flipped to the next page. There was a photo of the man standing there looking down at his monster cock sliding into the other guy. Is this what Chase saw when he was lifting my legs and staring down at his cock, stretching me? "Yeah, that does look painful," I mumbled back. "You okay, Sky? You have been a bit quiet today," Jeremy said, now looking at me rather than the magazine. I should tell him about yesterday. If anyone was going to understand, I was hoping it was Jeremy. He and I were getting close. Not only have we messed around with each other, but we have also told each other everything. "Yeah, I think so. Some stuff happened at Chase's place yesterday, and I'm not..." I began to say but was interrupted by a knock on the door and Jack walking in. "Jerm, can you...SKY, what's up, man?" Jack greeted, wearing just his red briefs and still slightly wet from the shower. He made his way over to Jeremy's desk and sat in the chair. "Hey, Jack." I greeted back "Jeremy, are you showing him what we got last night? Some of the guys from Dad's unit came over, and one always brings some porn for us. I have a couple of new mags, too," Jack boasted. "So what happened at Chase's yesterday?" Jeremy jumped in. "Nah, nothing happened, just a long day on the farm." I downplayed. Jack looked confused at Jeremy and I. "What's going on? Did I interrupt something?" "Sky was telling me about yesterday at Chase's farm," Jeremy said. "Oh, Sky, what's up"? Jack asked. "You know, nothing really. I don't know," I continued to mumble. Why was I worried? Chase had told me that he and Jack messed around. Jeremy and I messed around. I don't think the news of Chase and me doing the same would come as a huge surprise. I guess? "Well, after we fixed a stretch of fencing, we went back and hung out in his loft," I mentioned, staring at Jack the whole time. I wanted to gauge his reaction, knowing that he and Chase would hang out there looking at magazines and playing with each other. Jack sat up straight, and his eyes widened. I could see the gears turning in his head, possibly wondering what Chase had told me about when he hung out in the loft. "What did you guys do up there?" Jack asked cautiously. "He showed me around, and we talked about wrestling. He was interested in me trying out for the squad this year," I responded. "Did he have you try on one of his singlets and run through some drills? He's super hyped about wrestling and does that whenever I hang out." Jack mentioned with a smirk. "Nah, he showed me his collection of singlets, but I was too tired after the fence to roll around. He did show me his collection of magazines. We looked through a few of those for a bit." I admitted. This information had the twins both leaning into what I was telling them. Their curiosity was noticeable as Jeremy scooted to the edge of the bed next to me, and Jack shifted his weight in the chair. "Well, Chase being Chase, didn't miss the chance to pull his dick out," I said as I turned to look at Jeremy. "Was he hard? 'Cause that thing can be intimidating when he's hard." Jack laughed. "If stuff like that bothers you, you should say something to him. He's cool but immature, so he doesn't understand that not everyone wants to see that thing. I can say something to him if you want. He probably thought that you wouldn't care since you saw us naked in my bathroom Friday." "Nah, that didn't bother me at all. I was curious to see what he looked like hard. In fact, he let me feel it, and we messed around a bit." I told them. "Really?? What did you guys do?" Both of them asked simultaneously. "Well, we were both jacking off together when he leaned in and licked a drop of precum off my tip." Jack's eyes got big, but Jeremy didn't react. "He sucked me until I came," I said bluntly. "Did you do it back to him?" Jeremy asked. "I tried." I laughed, rubbing my jaw, "but his dick is huge. I couldn't go more than a few inches." "Duuuuude, you both sucked each other????" Jack asked. "Did you guys do anything else?" Jeremy asked while giving Jack a scowled look. Jack sat back in his chair, and I could see that his bulge was more prominent than when he had walked in. His semi was noticeable. Ignoring Jack's question, "Yeah, we did. I wasn't able to make him cum like he did me. So he started kissing me, he fell on top of me, and things kinda went from there." I stated in a low tone. "What do you mean things went from there?" Jeremy quizzed. "Well, you know, he was on top of me, and he kinda stuck it in me." "WHAT THE FUCK IS GOING ON?" Jack exclaimed, standing up. "He fucked you? In the loft? You're gay?" Both he and Jeremy had shocked looks on their faces. Although, Jack seemed more curious. "That's one way of putting it," I stated. "It wasn't planned. I didn't even want to, but I was pinned down and didn't know what to do. After a few minutes, I just went with it. AND NO, I'M NOT GAY. It all just kinda happened. ARE YOU GAY? You wanted to feel my dick on Friday while Chase was in the shower." I exclaimed, glaring at Jack. "No, I didn't mean it like that. Sorry man. That came out wrong. I was just curious and a bit shocked." Jack said apologetically. "Look, I think we're both shocked about you and Chase. Didn't think you guys were cool like that," Jeremy chimed in. "Dude, we're not. It just happened. I'm not proud of it, but you asked what was bothering me," I said, calming down. "Can I be the asshole in the room and ask...was it fun?" Jack quipped with a smile. I thought Jeremy would tell him to shut up or roll his eyes, but he was also interested in my response. I laughed. "Kinda. It hurt more at first, but then it was fun. It felt really weird. My ass still hurts." "Damn, I bet. Chase has one of the biggest dicks I've seen. It's like getting fucked by a horse." Jack chuckled. "Too soon to ask for details?" "Yeah, maybe later," I said. "Would you do it again though?" Jeremy asked with a smile. "I don't know. I mean, definitely not with Chase. That was too much," I joked. "We can keep this between us, right?" "Yeah, of course, man. Chase is the one with the big mouth," Jack said. "For sure; besides, I think we all have enough on each other that blabbing would suck for all of us." Jeremy agreed. Jack started to say, "Besides, now that I know that you are willing to..." "Don't even finish that sentence. You're probably still wanting to feel my dick." I joked back. As Jack stood up to leave, we all noticed he was still semi-hard. His uncut meat was filling out those red briefs, and a precum spot was clearly visible. He looked down at his bulge, "I could use a hand if you're not tired from Chase," Jack joked. "Dude, get out. You're a dick," Jeremy shot back. Jack, smiled and cupped his bulge, "You're loss, Sky!" I noticed Jack's ass covered by those red briefs. It looked like a ripe apple as he walked out and shut the door behind him. Jeremy looked at me, "You really okay, man? It didn't sound like you wanted Chase to do that to you." "I'm cool. Talking about it made me feel better. My biggest concern was what you and Jack would think. I know if I didn't say something, Chase would brag to Jack, and you'd both find out anyway." I said. "Sooooo....you're good, right?" Jeremy asked again. Chuckling at his concern, "Yeah, bro. I'm cool." "Cool, 'cause I got hard there for a second." Jeremy laughed. "Did you?" I asked. Jeremy stood up, unzipped his shorts, and lifted his shirt, exposing his round mound of meat. He, too, had a wet spot of precum. I would have thought I was looking at Jack again if Jeremy wasn't wearing white briefs. Shit, he was getting me hard. "Fuck, okay," I said with a slight laugh. I have no idea what had gotten into me, but I wanted to see his dick and lick the precum off. It felt like my 14-year-old hormones were in control. "Can I help you with that?" I asked. "Hell yeah, if you want," Jeremy said. "Yeah, sit on the bed and lean back," I instructed. Jeremy sat back on his bed and leaned on his elbows. I spread his legs and kneeled in front of him. His shorts were still unzipped, so I slid them to his ankles. He lifted his shirt higher to get a better view. He looked so hot laying there in his white briefs, his balls tucked under his semi-hard shaft. I leaned forward and licked the spot on his cotton underwear, tasting his familiar sweet precum. I began to play with his package as his breathing sped up. I could smell his teenage scent, musky and sweet like a freshly used cumrag. I opened his fly and reached down into them, pulling out both his balls and shaft so they were fully exposed through briefs. I stared for a second, admiring the uncut cock. Wanting to feel it grow in my mouth, I leaned in, using my tongue and lower lip, scooped his dick into my mouth, making sure I swallowed it to the base. Jeremy let out a low moan as his light pubes tickled my nose. He placed his hand on the back of my head as his dick became engorged in my mouth. It filled up all the space as it grew and inched down my throat. Making sure to get more precum, I moved my tongue back and forth against the underside of his shaft. A few seconds later, six and a half inches of rock-hard boy meat had taken over my mouth and throat. He pulled the back of my head into his groin, making sure he was as deep as he could go, before letting go and allowing me to come up for air. Pulling his shaft from my mouth, I noticed how much saliva was dripping off his dick. I grabbed the base and used it to stroke. My mouth wanted more, so I licked his hooded tip and went back down, matching my strokes. His moaning was getting louder, and our eyes met as I looked up at him. He was staring down at me, watching as I worked his cock up and down. He mouthed "fuck" to me, signaling that he was enjoying every minute of this. I guess that is why neither of us heard the door open behind me. "Um....should I come back later?" Jack asked as he walked into the room. Pulling Jeremy from my mouth, I yelled, "SHIT!" I quickly stood up and wiped my mouth. Jeremy scrambled to tuck his dick into his underwear but couldn't get it back in the fly now that he was hard. "Calm down, damn. It's not like I didn't already put it together earlier. You two mess around like Chase and I." Jack admitted. "You're not going to say anything, right?" I exclaimed. "Dude, who the fuck am I going to tell?" Jack stated, sounding annoyed. Still in his red briefs, he shut the door behind him, walked over to Jeremy's bed, and sat down. I looked to Jeremy to gauge his reaction. It was his brother. Was he comfortable doing this in front of his twin? Shooting a glance at Jack and his bulge, Jeremy looked over at me, lifted his shirt, and leaned back onto his elbows. Hell, this could be fun, I thought to myself. I spread Jeremy's legs again. His flaccid dick was still dripping with my saliva. I looked at Jack and then put my focus back on Jeremy. Lifting his soft penis, I stretched his foreskin as he showed me and stuck my tongue into the void under his tip. I let his foreskin wrap under the tip of my tongue and began to lick side to side. As Jeremy moaned, I could feel his foreskin tighten around my tongue as it started to retreat from the blood swelling his cock. I pulled my tongue back into my mouth, trying to slide his whole shaft back down my throat. "Oh my god!" Jeremy moaned as I used all the spit in my mouth to coat his dick before I pulled it from my lips. Gripping the base of his cock again, I used both my hand and mouth to stroke him. Not wanting to leave Jack out of the fun, I placed my left hand on the inside of this thigh. I was slowly rubbing up and down across all the fine hairs, leaving my hand to linger when I reached the space between his scrotum and thigh. Jack leaned back onto his elbows, mirroring his brother. "Slow down, I'm getting close," Jeremy whispered. I felt a hand on my head pulling me towards Jack. Getting the hint from Jack, I shifted to between his legs. Inches from my face were a stretched pair of red briefs with a growing wet spot. Like his twin, Jack leaked precum like a busted faucet. I grabbed the base of his dick, pumping more precum into the cotton. Wanting to make him moan, I squeezed his cock while dragging the tip of my tongue up his thigh until my nose was buried in the pocket of his crotch. Letting out a quick lick from my tongue against the taught skin of his spread legs, Jack let out, "OH. MY. GOD. DUDE." Jack smelled just like Jeremy. A mixture of cum and sweat. After taking a deep inhale, I released my grip on Jacks's cock. I reached into his fly and pulled out his dick and balls so he sat there just like his brother. Seeing Jack's groin exposed for the first time, I realized it was identical to Jeremy's. I took a glance at Jeremy's hard rod, watching him pump it as I tended to his brother. Their cocks were the same; the feeling of my precum soaking the fabric around my dick reminded me about how much I wanted to bust. Jack's dick was pulsing in anticipation of what was coming next. Leaning in, I licked the precum, tasting his sweet juice. I pulled the foreskin back and wrapped my lips around his tip, sucking more liquid out. Hearing his moans, I slid his shaft into my throat until I could feel his pubes on my face. Mimicking the job I was performing on Jeremy, I grabbed the base of Jack's cock and used the lube from my saliva to stroke him in and out of my throat. After a few strokes, I pushed Jeremy's hand away from his dick, gripped his shaft, and moved my mouth down his pole. Making sure I kept massaging Jack's pole, I looked up to see the brothers with their heads back, grunting lowly. Making sure I used my mouth to jack them off equally, I would keep sliding each dick down my throat until the breathing increased pace, then would switch. After about 3 minutes, Jeremy stated that he was getting close, followed by a loud moan. I quickly switched from Jack back over to Jeremy just in time to have him buck his hips and blast rope after thick rope into my mouth. To prevent any from spilling out, I took two big gulps of semen and felt it slide into my stomach. Noticing how sensitive he was getting, I lifted my head and tugged on his dick two more times, milking the last drops of cum. I pointed the tip of Jeremy's cock toward Jack, looking Jack in the eye; I licked the last drops of his brother's cum. "Fuck bro, can I cum in your mouth??" Jack said excitedly. I jumped back to Jack's cock, increasing the pace of the stroke, knowing he was going to bust soon. He placed his hand on the back of my head, making sure my mouth hit the base of his shaft with every stroke. Thirty seconds of this, Jack's dick started twitching in my mouth. He reached down, grabbed my chin, pulling my mouth off his dick. "Open your mouth," he commanded as he kept me about an inch from his tip. Opening my mouth wide, I gave his dick two more pulls when he exclaimed, "I'm cumming". Looking up to see his face; he was staring down, watching the first couple of blasts shoot into the back of my throat. His moans got louder as I continued to pull each string of his cum into my open mouth. A few seconds later, he released my chin, allowing me to swallow his deposit. The last couple of ropes landed on my chin and hand, both of which I licked up as he was coming down from his orgasm. Continuing to wipe Jack's mess from my face and hand, I stood up, followed by Jeremy. He was tucking his dick back into his underwear when he motioned down to my dick. "You need help with that?" Jeremy asked. Reaching into my shorts, I shifted my dick up so it wasn't straining too hard. Jack lifted his head back up to look at my bulged shorts. "Give me 5 minutes to catch my breath, and I'll give you a hand," he chuckled. "I'll help, too," Jeremy responded. "You should call your mom and see if you can sleep here tonight." Feel free to communicate at stories.genx@gmail.com On Wed, Mar 6, 2024, 8:44 PM Skylar Williams wrote: ‐----‐--------‐-------------------------------------------------------------- -------------------------------------------------------------------------------- -------------------------------------- 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.