Date: Thu, 12 Feb 2009 23:48:49 -0500 From: The Dip Subject: Challenged 2 Thanks for the accolades from those who emailed me. I'm glad you enjoyed it as much as I did writing it. It is a fictional story of boys experiencing and experimenting with their newfound sexual awakening and the bonds and friendships that can grow as they face their various challenges together. A lesson we can all learn from. For those who are interested, I am working on more chapters as the story unfolds... P.S. for those who might be interested in something a little different, check out in Transgender- Teens my story "Choirboys" Enjoy! Challenged 2 I woke up suddenly when I heard the front door slam and quickly rolled away from Mikey and dangled my arm down the side of the bed. I thanked god we had fallen asleep with our shorts on as my mom stuck her head in my open door and I raised my head groggily as she quietly asked what we had been up to. "We went down and had a sub and then came back and Floyd came over and we got in the hot tub and fooled around. Floyd was quite helpful in helping Mikey get up and was impressed by how big his muscle... muscles were and had him shoot to see how far he could" I could feel the bed jiggling as Mikey was trying to stifle a laugh as my mother replied "well that Floyd is quite the little shooter too when he does it with you. I'm glad he had somebody else to fool around with, I know he likes to play with you. Well have a good night boys, I'll see you in the morning when you get up" She closed the door and Mikey almost choked as he laughed softly and lifted his head and looked at me, "I can't believe you said that! Fooling around? I think it was more like a fondling around! And seeing how far I can shoot? Man!" We both had a good laugh and he snuggled up behind me and pressed his bulge against the crack of my ass. He nibbled on my shoulder as he rocked his hips against mine and played with a nipple then ran his hand down and slid it inside my shorts as I sucked my stomach in. "MMMmmmm... Guess what? "he whispered in my ear. "let me guess" I said and knelt up beside him and he undid my shorts and worked them down, then I stood up and took them off and fired them on the floor. I looked down at my hangar that starting to swell "I'm not ready yet " and Mikey grinned as he waved me back down beside him and pulled my skin back and forth and played with my balls. I went hard as he worked on my joint and I said, "That's better. Now I'll see if you're ready", and pulled his shorts off as he lifted his hips. His semi flopped over on his hip, "looks like you're not quite ready yet either". I straddled his hips and squatted down, my balls resting on his and lifted his semi so the underside of our cocks were together and grabbed them both, which was a bit difficult because he was so big, and started stroking till he was hard too. We switched and he slowly jerked our twin peaks. I laid down on top of him so our cocks touched side-by-side and started to move my hips, scraping my cock on his pubes as his thick shaft rubbed on mine. I lowered my face till it was only a few inches from him and gave him a warm smile as I pumped my hips, my balls rolling along his thin leg, and he smiled back and I laid my head down beside his and breathed into his ear. His warm breath felt good on mine and he put his hand tenderly on the back of my head and I darted the tip of my tongue into his ear and swirled it around as I continued to gyrate my hips on his. I lifted my head and gave him another smile and a kiss which he eagerly responded to and I slid my tongue into his mouth and he sucked on it. I could feel him starting to squirm, so I dropped my head beside his again and pressed my hips down harder and started to pump my hips faster. He responded by putting his hips in the opposite rhythm and started to groan in my ear. "uh... uh... uhh....oh.. oh... ohhh... ughh UGGHHH!!!!". He raised his hips and tensed up as I felt his wetness spread between our sweaty stomachs. My load poured out as I gasped in his ear and his cock pulsed, continuing to spew warm boycum and mixing with mine. I pumped my hips a couple of more times to empty my balls and our stomachs made a couple of sucking sounds from the juice between them and I collapsed on him and dropped by head beside his and we laid still, breathing hard in each others' ears. I rose up on my hands and looked at him and gave him a big smile and a quick kiss, then raised my stomach and made the sucking sound. He giggled and I raised it up and down again quickly, squishah, squishah, squishah... , and we both broke out in laughter and I slid back and licked some of the blended cum off his stomach. "Look ma, no hands! That's quite a cum cocktail!" I said laughing and fell back down beside him and he leaned over and licked some of mine. He moved up and gave me a quick kiss on lips, "that was great, Chad, you're the best! I'm going to wear this tonight to remind me of you ". We pulled the covers up and he rolled on his side and I spooned him and fell asleep. I woke up once in the night and we were both lying on our backs but the next time I woke up he was spooning me with his big hard cock in the crack of my ass and his fist wrapped around my hardon! Man he couldn't get enough, well as a matter of fact neither could I! I slowly started to move my cock back and forth in his clenched fist and he responded by sliding his cock up and down my crack. He moved his hand and hardon in rhythm and I could feel his warm breath on my neck as he continued breathing heavily. He pressed his hips hard against mine and stiffened as his warm boycum spilled onto my back and my load shot out onto the sheets as he squeezed hard. We were lucky that we both took the about same amount of time to cum and he bumped his hips till he was dry and my cock pulsed till it was empty. His load ran down my back and onto the sheets as mine dibbled out of my tender knob and on to them too. He relaxed and left his arm over my hip and whispered behind me "that was great again, Chad. Do you think I'm doing it too much? Am I unusual?" "No" I whispered back, "you're not unusual. I've done it seven or eight times in a day!". He let out a sigh of relief and we fell back asleep. We woke up in the morning and he was lying on his back with his hard cock sticking straight up. He giggled and said, "I wake up every morning with a hardon, and I never knew what to do with it. But now I do, thanks to you!" and stroked himself. A . I swung around and propped myself up on my elbow and started to jerk him off. He did the same to me as I watched his balls jingling between his legs and his thick shaft throbbing in my hand. A shot flew out of his angry knob and landed on his stomach and he fired a couple more as I released my load and it puddle on my pubes and stomach mixing with the flakes of dried cum from last night's session. "Well we're ready for the day! Guess we better have a bath and maybe put some clothes on for a change!" I said and got him up and walked him into the bath. I started filling the Jacuzzi and slid him into it. I spread his legs and sat down between them and we soaped each other up and had a lot of fun splashing each other. When we were pretty waterlogged I pulled him up and swung him around on the edge of the Jacuzzi and dried him off and he did me, and I walked him back out to my room and we got dressed and he wheeled behind me as we went to the kitchen. My mom greeted us cheerily and innocently asked us if we had fun fooling around this morning. Mikey coughed again and my mom handed me a jar of jam to undo. It was too tight as I tried and Mikey asked me to give it to him. He held the jar and gave a slight tug and undid it without any effort and he looked at me as I raised my eyebrows and said, "what? ". "Well... you did that so easily ". "Yeah I know, my hands do the walking, so to say!". I sat down and asked him to arm wrestle. We locked hands and he put my arm back and forth like he was just waving his hand in the air then slammed it down on the table. "damn, I didn't have a chance! I've never wrestled anybody that strong! ", I whined and he gave me a modest smile. "Want to get a bottle to put your whine in?" he teased. I held my hand up with the middle finger pointing down "Can you hear this? ...No? ...Want me to turn it up?" and grinned at him as I flipped him the bird. Then we gave each other a high five and finished our breakfast. He phoned for the Transit and I bumped him down the stairs to the curb and waited. Floyd saw us and was quite excited as he came bouncing over with a couple of friends, one a little shorter than Floyd with short black hair and the other was as a little taller than me, a little older and was thin with long blond hair. Floyd's shorts were tented out as usual. "Hi guys! How are my favorite sausages this morning? Did you give them a good draining? ", and giggled as Mikey grinned and gave him a high five just as the Transit pulled up. Floyd watched, pulling on his tent, as Bob asked, "Well Mikey, did you get into trouble last night?" and gave Mikey a wink then glanced quickly at Floyd's tent and gave me a sly grin and shook his head slightly. "No more than any guys our age would!" Mikey replied and Bob laughed as Mikey gave me a goodbye high five and he'd see me Monday at school. Floyd and I waved goodbye as the Transit disappeared down a street. "Chad, this is Eddie..." pointing at the smaller boy "...and this big geek is Lenny. I was just getting ready to show them how to whack off when I saw you and Mikey so I thought I would check and see if you wanted to come up and show them how much you can shoot. How about it?" he asked, still pulling on his tent. I told him it sounded like fun and he skipped beside me as we headed into his house with the other two following us. He told me his mom was out for a while and we followed him two steps at a time up to his room. He grabbed the bulge down my pant leg and squeezed, "I'm going to whack him off after I do so to show you how he shoots. He's got a huge cock, feel it ". Eddie looked down and reluctantly gave it a small squeeze, then Lenny reached down and squeezed the base with his thumb and forefinger, then moved down squeezing it till he reached my knob and squeezed it several times. "It feels big "Lenny said anxiously as they both absently rubbed their crotches. "Well I guess we better get started ", Floyd said and peeled his shorts off and his 4 1/2 inch cock stuck up. He pulled his skin back and flicked the shaft with his thumb, sat down on the bed and motioned for them to sit down beside him and they sat and stared at his cock. I sat down on the other side of Eddie and Floyd leaned back and said, "now that's hard, check it out ". Eddie reached out and squeezed it and tried to bend it as Lenny examined his small nuts. Floyd slid his hand onto Eddie's crotch and he flinched at first, putting his knees together, then spread his legs as Floyd felt him up "Feels like you're boned up Eddie ". He fidgeted and then switched with Lenny who examined it closely, watching the knob pop out as he slid the skin back and forth on the shaft while Eddie fondled and pulled on the nut sack underneath. Floyd then slid his hand onto Lenny's crotch, who immediately spread his legs while Floyd felt around, tugging and squeezing and said, "feels like you have some serious wood there Lenny! ". Lenny squirmed as he grinned at Floyd, then went back to Floyd's dick. "Pretty hard, eh?" Floyd said as he sat up, "now I'll show you how to do it ". He wrapped his fist around his hardon and started to pump as he squeezed and tugged on his nuts. He demonstrated as he continued to describe how to do it, "you can wrap your fist around it like this and jerk, or you can use your thumb and forefinger like this, or three fingers like this if you like, or whatever feels good. One guy I watched, put his hand on top, wrapped his fist around it and jerked out like this, but he could bend his cock down more than I can. When you're jerking, you could rub your chest and stomach with one hand, or pull your balls with it. Now who wants to try ", he said as he leaned back on his elbows quite proud of his demonstration. (Man that was quite a dissertation!) Eddie sheepishly reached over and wrapped his small hand around the shaft and started to pump it as he chewed on his lip. Lenny fondled the little nuts hanging down as Eddie tried different finger positions. They switched and Lenny started with his fist, and ended up with his three fingers. Floyd had his head back as Lenny stroked him and suddenly a shiver went through his body and he lifted one knee then dropped it and lifted the other as he sucked his stomach muscles in, let out a low groan as his two friends watched, then he threw his head forward as his whole body tightened. His hips started to bounce and he murmured, " yesss... squeeze... Oh yes... now faster... ahh.. uhhh.. ohh.. OKkk... NOWW... UGH.. UGH!!! ", then sat up and threw his head back and shuddered as several dry orgasms wracked his body. He slouched, then looked at his friends and smiled, "that was awesome Lenny, you did a good job ". Eddie looked at him with a puzzled look on his face and asked, "what was that?". "Well, Lenny just whacked me off and I came, but I can't shoot yet. Do you want to try it? ". He nodded shyly then stood up and pulled his shorts down and modestly covered himself with both hands. "The shirt too, it will just get in the way ", Floyd ordered and Eddie turned away and peeled off his T-shirt. He turned around covering himself and Floyd moved over as Eddie slid between him and Lenny. He grinned and moved his hands aside and spread his knees. His Dick was about the same size as Floyd's and Floyd grasped it with his thumb and forefinger and started to jerk him as Eddie looked down and watched. I reached down and ran my hand down Lenny's crotch and he quickly spread his legs and I rubbed the hard bulge down the pant leg. It felt pretty big and he moved his hand over and ran it down mine and I spread my legs and started to squeeze as he smiled warmly at me. We played with each other as we watched Floyd stroke Eddie and pinch his little nuts. I took my shirt off and lifted the bottom of Lenny's T-shirt up and undid his fly, slid my hand in his underwear and felt his cock and pulled it out. It was fairly thick and cut, almost 6 in. long and I squeezed his big knob as he pulled off his T-shirt then undid my fly. He ran his hand down my bare pubes and into my briefs and found the base of my shaft and pulled it out of my pant leg and it sprang up. He ran his fingers up and down my shaft then pulled the skin back and pinched my knob. We slowly massaged each other as we watched Floyd and Eddie. Eddie was leaning back on his hands with his ankles crossed and was slowly turning his head back and forth. He let out a gasp and sat up, bent over and dropped his head as he started to rock his hips. He spread his feet and curled his toes and grabbed Floyd's wrist for a moment then let go as he started to groan, "uhh... uuhhh... oh..oohhh... ahhh...ohhh !!", and fell back on his hands, lifted his hips slightly," UGH.. UGH..UGGHH!!", and shuddered several times. He sat up and shook his head "That was incredible Floyd! Now I know why you like to do it!" I stood up and took my pants off and sat back down as Lenny stared at my cock and stood up and took his off. He had a dozen or so scraggly hairs and a big set of balls and his big knob curved back slightly towards his stomach and he sat back down and spread his legs and we played with each others' nuts. Eddie looked over and said, "Your dick is really huge Chad! And you're big too Lenny. You don't have your skin "and ran his fingers down Lenny's bare knob then wrapped his fist around Lenny's shaft and started to stroke it as his own small cock wilted. Floyd shot over and knelt down in front of Lenny and pulled on his nuts. "Your balls are big too Lenny, you might be able to shoot! " Lenny looked down and watched Eddie's little hand pumping his cock while he slowly jerked me. Floyd waited a few moments then took his turn and started furiously stroking it as Eddie fondled Lenny's balls. Lenny let go of me and closed his eyes and dropped his head. " I think he's starting ", Floyd said knowingly as Lenny tipped his head back and started to suck his stomach in and out as he rolled his hips. "eh... eh... ahh... ahhh... eh...", and he bucked his hips,"UGH!", a stream of hot boycum shot up several inches, "UGH.. UGHH", and a couple more dribbled out. Floyd ran his thumb over Lenny's tender knob and Lenny grabbed his wrist. "You shot! You squirted Lenny! ", Floyd said excitedly. "Wow! That was awesome!" Lenny said breathing hard as he relaxed. "Now we'll see a really big load when we whack off Chad" and Eddie ran around and sat on the other side of me while Floyd knelt down in front. Eddie grabbed my cock with his little hand and started to stroke me. "It's really thick ", he said as he bit his lip and flailed away. Floyd was playing with my balls. Lenny took over and started thrashing me rapidly. I gritted my teeth and put my knuckles into the bed as I felt my load starting to rise. I bent my head over and let my load go and it flew up and hit me under the chin. I squeezed my cheeks and shot four more up into the air that tumbled back down onto Lenny's fist. "Wow! " Lenny and Eddie said in unison. "That's a lot of stuff!" Eddie said. "...and it's really sticky" Lenny added as he smeared my fresh boycum around on his fist. Floyd wiped some off the end of my sensitive knob, which made me shiver, and ate it. "What's it taste like?" Eddie asked curiously. "Taste it and see" Floyd replied and Lenny wiped some off my pubes and tasted it while Eddie licked some off his fist and wrinkled his nose with distaste and Lenny wiped some more off and licked his fingers "Well guys what do you think about whacking off? " Floyd asked as he started to dress. They agreed that it was really a lot of fun, "You think we can do it again sometime!" Lenny asked anxiously. "Well I really hope so! And maybe my new friend Mikey will be here, he's really kool! He's got a neat wheelchair because his legs don't work very good, but he's got a big dick that works reeeal good! He can shoot as much as Cody!" Floyd answered proudly and we all had a laugh. Floyd usually gets what he wants! Lenny stared at my swinging dick as we dressed and he smiled at me coyly as they dressed and headed out. Hmmm... Monday morning I waited out front of the school for Mikey. The Transit pulled up and I saw Mikey smiling and waving as it pulled to a stop. Bob got out and said to me, "I have a special delivery Chad, you might want to check it out for any damage ", and he chuckled as he lowered the ramp and Mikey rolled out. "Hi Buddy! " I said to him and he gave me a five with a big grin on his face. He had shorts on and his legs were bare. "You've got your shorts on today, that's more comfortable isn't it ". "Yeah, I don't care what anybody thinks, I can't do anything about it ". I grinned inwardly and felt good that he had overcome that hurdle. He wheeled along beside me and I asked him how the weekend went. He replied softly, "I whacked off five more times on Saturday and six yesterday", he said proudly, " and I have a good start on today, because I did it in bed and then in the washroom before I left" and he giggled deviously. I slapped him on the back and told him to keep it up which brought a loud laugh out of him. We went into the room and all the guys said hi to us, hardly noticing Mikey's legs. At recess, we went to the gym and I had him toss shots from the line as I returned the ball. I noticed the small boy again who was a class ahead of us, took art with us and also sat out our Phys Ed class like Mikey. He sat a little further down on the bench Mikey was beside when we practiced and I noticed he always watched and silently clapped every time when Mikey practiced and scored. He was shorter that me, had messy brown hair and wore big glasses, kinda nerdy, and his clothes were shabby and baggy because they were too big for him, like hand-me-downs. A Noon hour came and we went outside and joined some guys to eat our lunch. This was new for Mikey, as he usually ate alone and he felt good when they treated him as one of the boys. One of the guys said, "Hey Mikey, I saw you shooting hoops this morning, you're pretty good " and Mikey blushed slightly and thanked him politely. We finished eating and went back to the gym to practice and the little boy was sitting there and watched as Mikey tossed the ball. He was hitting at least 60%, not bad from the throw line. We stopped and Mikey looked down at his crotch and said, "I've got a boner "and I looked down and his big shaft was pushing up against his shorts "I'd like to whack off. Maybe we can go into the handicapped washroom, what do you think? Are you up for it?" and he giggled. I told him it wasn't a bad idea, that I could do with one too and he chuckled again and I pushed him down the hall and into the handicapped washroom and locked the door. I had never been in it before and it was fairly big. The vanity was higher than usual so he could get his wheelchair under it and the toilet was higher with a bar to pull himself up. He worked his shorts down and his hardon sprang up. "That's better", he said and held it up, "what do you think?". "Looks pretty good to me, but it needs a little work, I'll give you hand" which brought a chuckle "but maybe you better get me ready first" and I stepped up to him. He anxiously undid my fly and dropped my shorts as my semi flopped out. "Well isn't that a nice piece of work ", he stated and pulled the skin back to expose my damp knob and stroked it a couple of times until it was hard. I kicked my shorts off and grabbed some paper towels and laid them over his shorts so he wouldn't spunk all over them and bent over, wrapped my fist around his thick shaft and he held his shirt up as I started to jerk him. "hey, you know those two guys that were with Floyd when he came up to us as the Transit pulled in?" He nodded as I continued working his thick shaft "well Floyd wanted to show them how to whack off and asked me if I wanted to too so they could see what a big load looked like" "No shit! Damn I'm sorry I missed it. How was it and what were their cocks like? Did you help them jack too?" he asked intently as he rolled his balls in his hand. "Yeah, it was kind of fun to see Floyd show them the different ways and they jerked him, and Eddie, the shorter boy, had a dick like Floyd's and couldn't shoot but got off. Lenny's was cut with a big knob and almost as long as ours and he had a pretty good squirt" Mikey closed his eyes half way and dropped his head back as I felt his shaft pulsing in my hand and he groaned, letting loose a stringer about 6 inches in the air and he shuddered as a couple shorter ones sputtered out and ran down on my fist. He relaxed in opened his eyes as he raised his head "Christ, did I ever cum thinking about it! Did they jerk you?" "Oh yeah, I think Lenny enjoyed it the most though and his cock is really nice" "Man, you think they might want to again?" "Oh yeah, they're looking forward to it especially after Floyd told them how big your cock was and how you can shoot" "Really? That's awesome! Now let's get to work on that thing of yours". I was really horny after jerking him and thinking about the little orgy we had. I held my shirt up and stood beside him so I wouldn't hit him and he started to rapidly jerk me as he fondled my balls. I started to rock my hips as my cum started to rise and four loads flew out and made a trail on floor. I relaxed as he squeezed and the last dribbles ran down his hand. "You're such a good shot!" he chuckled as he licked his hand and I picked the towels off his waist, wiped my knob dry, tossed them and we got dressed. "Now that's better than lunch! Maybe we should start a club, you know how they have a camera club and a chess club, well maybe we could have a squirt club and see who could shoot the furthest!" he said giggling and we wheeled out and went back to our room. We had fun during class, making lewd gestures and giggling. At recess, we went to shoot some hoops and I noticed the little boy sitting there. We took a break and I said to Mikey, "look at that kid sitting there; he always seems to be watching us ". "Yeah, I noticed him too, let's go over and talk to him ". ...to be contimued...