Date: Sun, 22 Jun 2014 19:12:33 -0400 From: Eamonn Bowers Subject: Goodnight, Rupert We had just spent our first Saturday of Summer Vacation at the Theme Park. We spent the whole day there, almost getting on all the rides; some of them twice. We even won one of those huge stuffed animals that were bigger than Rupert and as tall as me. My parents were tired half-way through the day, but we stayed at the park to keep Rupert happy. He's 11, and I'm 16. It wasn't until the park closed that he realized the fun was over and it was time to head home. Once we got settled in the car, Rupert was already nodding off. My mom was in the passenger seat, fast asleep within two minutes. Dad turned on the radio to help him stay awake. With all the things we packed and the prizes we won that day, there wasn't much room left in the backseat, so Rupert had to sit on my lap. I will say that I've always known I was gay, but I wasn't ready to come out yet. I know my parents would still love me, but I just wasn't ready for all the drama yet. I was pretty masculine, with my brown buzzcut, and a soccer player's body. My voice is also quite masculine as well. I don't think too many people would guess that I'm gay. I will say that I'm quite sensitive and I'm a very nice guy. And I only play one sport. But that's all I can think of in terms of what's gay about me, other than having quite a few female friends. My brother kept sliding off my lap. We were both wearing our soccer shorts and it was very slippery. I was holding him with his head resting on my left shoulder and his legs on my right side. Kind of like an overgrown baby. He wasn't very big for his age. To me, he still looked the same as he did when he was 8, but he must have started going through puberty by now. I stared at him as the street lamps illuminated his face every few seconds. He had the palest skin, and the reddest hair of anyone I know, with a patch of freckles on his nose and shoulders. His lips were so cute and if his eyes were open, I'd be staring at his round blue eyes, the same ones I have. I was starting to get hard. I glanced over at my mom who was still sleeping, and then I tried to reach my crotch so I could adjust it in a way that Rupert couldn't feel it. I wasn't trying to be perverted, but I couldn't help it. Thankfully, I adjusted myself and we were home not before long. After we emptied out the car and put everything away, my Dad carried sleeping Rupert to the couch. It was 11pm and my parents were deciding if they had enough energy to go to their friends' party that night. I went upstairs to take a shower. I spent about 20 minutes washing my body, making sure I was completely clean and shaved in all the right spots. I liked to be completely smooth down there and I shaved whatever little hair I had on my behind. After checking myself out in the mirror for a bit and brushing my teeth, I went back downstairs to see what was going on. My parents were at the door. My Dad was ready to go and my Mom was fixing her makeup in the mirror. "We'll be home pretty late. It depends how fun the party is", my Mom said, laughing. "Make sure Rupert goes to his bed , but please don't have him up all night if he wakes up." I told her it would all be taken care of, and they left in a cab when it came. I went into the living room and sat down next to my brother and turned on the T.V. I put on some late night talk show and laughed at a couple things every now and then. It must have woken up Rupert because I heard him laugh too. I looked over to see his adorable smile. I asked him what his favourite part of the day was. "Playing the games", he said. "Where's all the prizes?", he asked. "In your room", I told him. "Mom said you shouldn't stay up too late, so maybe you should go take a bath and get your jammies on". He did a big stretch and made his way upstairs. I heard the water running and could hear that he wasn't running a bath, but he was taking a shower. I flipped through the channels and couldn't find anything good to watch, and was growing bored. I went up to my room where I kept all my movies and put one on my T.V. I went back downstairs to get a snack for the movie. When I got back to my bedroom, I heard Rupert getting out of the shower. He walked past my room with the towel over his shoulders, shivering. "Wanna watch a movie with me?", I shouted. "Okay!", he yelled back. A few moments later he ran into my room wearing his white and blue cotton pyjamas. I was in a fresh pair of soccer shorts and my 'Ireland' t-shirt. He jumped up onto my bed and shuffled up against the headboard next to me. I started the movie, and he rested his back up against my torso, using me as a backrest. I kissed the top of his head, which was still wet. I put my arms around him and rested my hands on his belly. His pyjamas were damp from his wet body. "You didn't dry off very well", I said, laughing at him. "Oh well", he said. I was getting hard again, just like I was earlier in the car. This time, I guess I was being perverted, because I didn't try to hide it. I was getting kind of horny having him sit like that. I was getting curious to see if he would say anything. And he did. He tilted his head back and smiled at me. He sat up and whispered into my ear "You have a boner!" Suddenly embarrassed, I said "No I don't !" He sat up beside me and hit my crotch with his hand. It made my penis wag up and down inside my shorts. "Yes, you do", he said laughing. I gave up and admitted having a boner and tried to take the focus off of me by telling him he had boner too, but he wasn't actually hard. "What! No I don't", and before I could stop him, he shoved down his pyjama pants and underwear and showed me his soft penis to prove he didn't have a boner. The way he did that was so startling, but at the same time, so innocent. I could tell he was just playing around, with no sexual motive. But I couldn't help but look at his little penis with lust. I started quickly thinking of ways to prolong this. I had never seen him naked before, and I had always been curious to see his privates and compare them to mine. He looked to be about 3.5 inches and his little balls were pretty tight against his body. His sac was so smooth, with only a couple blonde hairs. He was intact just like me, and I wondered if he had a tight foreskin like I did. His penis was clinging to his scrotum from being squished in his tight boy briefs. My dick was rock hard, stretching out the silky fabric of my boxers and shorts. Before it got awkward, I said "Wow, that's pretty big for your age". I wanted to say something a brother should say in a situation like that. I didn't want him to know I was sexually attracted to him. He smiled and asked "Can you pull down your pants and show me yours?" The way he asked so sheepishly was enough to make me want to grab him and rip all of his clothes off right there. "Okay". I lifted my butt of the bed, and took my shorts and boxers all the way off. I was hoping he would do the same if I did it first, but instead he let go of the waist of his pants and the elastic snapped back, covering up his penis. He knelt over just a little bit to get a good look at mine. I'm about 7 inches hard, with a smooth tight ball sac, and a very tight foreskin that is very red when I get hard. I can't pull the skin back and it gives me so much pleasure having the sensitive head so tightly covered by my foreskin. It's part of the reason I get erections so easily. Rupert didn't say anything this time. I think he was actually a bit nervous compared to how he was when he showed me his. "It's okay, buddy" I said. I swung it around to see if he would laugh. And he did. He told me it looked like his but way bigger. It was true. "Well let me see you hard then", I said as nonchalantly as I could. He sat back and put his legs in the air. He struggled a bit, so I got up on my knees and helped him out by yanking them off and throwing them behind me. There he was, laying before me with only his pyjama shirt on. My dick was pointing straight up at this point. I quickly wiped my precum away with his pants so that I didn't scare him. He looked up at me and let his legs dangle outwardly, giving me full access to his penis. He seemed a bit nervous, but still smiled. I don't think he realized, but his hole was in view as well. I didn't say anything but I did enjoy the sight of it. His whole body was blushing, the way your cheeks do when your shy or embarrassed. His scrotum had a tinge of pink, as well as the tip of his foreskin and his nipples were red and hard. I could see he had goosebumps. "Alright, let's see it hard then", I said feeling so perverted. He slowly reached down and played with his little dick. All he did was move it around in his hand, kind of the same movement as strumming a guitar. So innocent. Sometimes I forgot he was 11, his mannerisms are so childish. Slowly I saw his penis was starting to get a bit plumper and his foreskin wasn't as loose. It was getting hard. I reached down and caressed his scrotum ever so gently to see if that would help him get a boner faster. It was the softest feeling ever. I stopped as he looked up at me, when a wave of guilt came over me. He was finally completely erect. The penis was completely parallel to his body as it was so small it couldn't weigh itself down. His balls were so tight and small, they almost weren't even there. His penis was probably 4 icnhes long and the width of the base of my pinky finger. He was mindlessly playing with it; picking it up and making it point to the ceiling and letting it go, making a light slapping sound on his pubic area. Every time he made the tip face me, I caught a glimpse of his head under his tight foreskin. I could tell he had phimosis as well. The skin was so snug on his head that you could only see a the tiniest bright red dot on the tip of his stark white boy dick. He had a hint of pink and blue veins crawling up his shaft if you looked really close. I wanted him like this forever. I cuddled up beside him and put my arm oh his belly. He still played with his boner glanced over at mine every now and then. "What are you thinking?" I asked him. "Can I touch yours?", he asked me. I nodded at him and sat up again. I told him to sit up on his knees like I was and he reached out and gently put his hand around my hard dick. His touch made it pulse and it gave him kind of a scare. He laughed a bit and tried to make his penis bob the way I did. I took my shirt off to show him the rest of my body. I was pretty pale too, but with no freckles. I had a soft look to me, all my features were innocent and boyish, but I did have nice abs and a developed chest. I was quite thin, but not too skinny. His hand cupped my testicles and I could tell he was probably the most intrigued by the weight of a more developed ball sac. He didn't say anything, just caressed me and was innocently curious about his big brother's body. As his hand slid over my hard pink nipples, I shivered. He was turning me on so much, I had to take this a bit further. I reached down and fondled his little package before lifting his shirt over his head and tossing it on the floor. His frame was so delicate and childish. Everything on him was so undeveloped, like a little boy. His chest was flat and his belly was so smooth. The smell of his freshly bathed body was another thing that was driving me crazy. His colouring was perfect. He was my pink ginger boy. I knew I was in love with him now. And I could tell he loved me. He trusted me so much that he felt comfortable showing me all of his most private parts. I caressed him and traced my fingers so gently over his body that he too shivered and leaned in for a hug. My dick pressed against his tummy, and I cupped his bum in my one hand. After enjoying that moment for what seemed like forever, I laid back against the headboard and invited him to come sit between my legs and rest his head on my chest. We began watching the movie again, not caring that we've missed the beginning. I stared down at his crotch which was still super hard. His foreskin looked really red from being stretched out by his erection. I wanted to make my baby brother cum. I made a bold move and lifted Rupert so that he was sitting up a bit more, but still leaning his head on my shoulder. I reached down in front of us and grasped his scrotum between my thumb and fingers. I rubbed him there to see if I could feel his balls inside of him. They were so tiny that it made me wonder if mine were ever that small. I don't remember. I used my index finger and my thumb to hold his little pecker. The stiffness of his penis was actually impressive and I knew he could shoot pretty easily in this state. I kissed him on the cheek and said in a nervous but lustful voice "Can I make you cum?" He didn't say anything, but scooted in even closer with his legs spread. I took that as a reluctant 'yes". I took hold of him. I braced him with my left hand on his torso and my right hand on his stiffy. I held him as close as possible and I adjusted my penis so that it poked up beneath his testicles. The hardness of my cock put a lot of pressure on his sensitive balls and he let out a yelp of pleasure. I started gently tugging on his foreskin to get him even more aroused. When the tip became so red that it looked like it might, burst, I then began to stroke his little shaft between my fingers. He moaned again. I started humping him through his legs, making my dick rub up against his sac. He was in pure heaven, making noises I've never heard him make before. He gulped and grunted quietly as I wanked him. I kissed him on his neck and could feel heat radiating from his chest as I held him in place. The parts of his body that blushed had now become so red, it looked like he was might have a rash, but I knew it was pure arousal. I moved my left hand from his chest, down to his little pouch and pressed his nuts even more into his body out of curiousity. He yelped again. I aksed if that hurt and he said no. "Please play with me", he begged in a whimpering voice. I was still humping him, making his body writh. I granted his request and continued to roughly play with his boy balls. I tried fishing them out from within him, but was unsuccessful. As soon as I got a hold of a ball, I would almost get it into his sac where it belonged, but it would pop out of my grasp and hide back inside him. I sped up my tossing action on his winky and I knew it would cause him to squirt his load if I kept going. I sniffed and kissed at his neck and whispered nice things into his ear to get him going. He reached down and took hold of my hooded dick. "Such a good boy, Rupert". "I love touching you, Buddy", I would say as I got closer to finishing him off. "I love you, Tommy", he managed to say in a very obviously lustful manner. "I love you too, Rupert". I tightened my grip on his little prick, which was completely bulging and swollen by now. I thrust my hips so violently that he was basically bouncing in the air, so I held him in place again with my left hand. My dick was rubbing up against his crotch so much that I was on the verge of cumming. I needed to see him spray. I used all that was in me to pump his as fast as I could and get this boy to unload. Rupert began to heave, trying to catch his breathe and verbally notified me that he was about to ejaculate. He let out one more loud yelp. I could feel his balls stirring against my penis. I stared down at his cock, still tugging away. His body went limp before he came and his semen jetted out of his little pee hole at a million miles per hour. One squirt after the other. He laid there and grunted with each squirt. He nuzzled me and stretched his legs in the air as his orgasm came to a close. His dick let out a couple more little spurts before he took a deep breathe in and sighed. It wasn't over yet. I quickly flipped the cummy boy on the bed and straddled him. Our scrotums gently but firmly pressed against each other's and i held his still-hard cock in between my finger. I tugged away at my raging boner and told Rupert I was gonna blast my load all over his tummy. I lifted up his legs to get another look at that pink hole. He was a bit confused, but I was too horny to care. I bent down and gave his ass a quick sniff and a little lick. I then rubbed his hole for a minute to get a good feel just to send me over the edge. I put his legs back down, leaned over him with our balls touching once again. I kissed Rupert all over and ended up on his lips, making out with him. I looked down at our boners and couldn't get enough of the site. His tiny little dicklet rubbing against my big brother dick was too much. I roared "Rupert, I'm gonna explode!" He looked really excited to see what was about to happen. He stared right at the opening of my foreskin. I tugged it back as far as possible to show him how it comes out of the piss slit, but it wouldn't pull back far enough. The head was the darkest shade of red I've ever seen before. I humped his scrotum as hard as I could and let my cum blast out of me. It made a loud splashing sound as it hit his chin and his chest. I probably squirted about 10 jets of cum all over my baby brother, the last few spills landed on his penis and balls. I took his little boner in my mouth as well as his balls. I gave it one good suck as if to kiss it goodbye. I laid back down and picked Rupert up to lay on top of me. It was the first good view of his blushing bum. The cutest one I'd ever seen. I traced my fingers along his back and his behind, and kissed his short ginger hair. We laid like that for what seemed like all night. He fell asleep in this position. I gently carried him to his bed and dressed him back up in his jammies after wiping him clean with a damp cloth. He opened his eyes and said in a very soft voice "That was my favourite part of the day". "Goodnight, Rupert".