Date: Mon, 18 Sep 2006 07:40:18 -0700 (PDT) From: Will Shakespear Subject: Sissy Brother-5 Disclaimer: This is a work of FICTION. Any similarity between my characters and real people, places, or events is merely a coincidence. This story contains descriptions of imagined sexual activity between teenage boys. If you are not 18 years old or if it is illegal where you live to read material of this kind, please stop here. If this story might offend you please go to another site. Please do not copy or distribute or reproduce this material for anyone or any site, without the author's explicit permission. Everyone please enjoy and feel free to send comments and story ideas to playbuddy123@yahoo.com. Sissy Brother - 5 Friday night football is a big deal in our community. The stands are filled with parents, the kids from school, and people from all over town that love football. I remember that I told you that Devon was a friend of mine, but that's not quite true. He's not just a friend; he's my very best friend. We met my freshman year when I tried out for football. Devon is a year older and so a year ahead of me in school. I play wide receiver and he was trying out for quarterback. He's taller and stronger than I am and practically a god in the eyes of the cheerleaders. Anyway, coach had Devon throwing balls to all the guys and when he threw to me I had like this sixth sense of where it was going to be. Something clicked and we seemed to be a matched set. Devon got the quarterback spot and talked coach into putting me on the team as a backup wide receiver. A few weeks later we were stealing the show as our offense dominated the field. So, back to Friday night! After the game (we won 21-7) we showered and headed out to party. No alcohol of course. "Ya, Right!" It was late like about midnight when we got back to my place. Devon was staying over because his folks had to go out of town for the weekend. We spread two sleeping bags on the top of my bed and both stripped to our boxers. As we crawled into our sleeping bags I thought about how Devon looks like one of those guys in one of those weight training machine commercials. He has a great body and I am totally envious. I left a small table lamp on while we talked. "Nice party" I said rolling on to my side so I could look at Devon. "Ya" Samantha did a great job! Devon yawned. "You get any from her?" I grinned. "Ha!" Devon snorted. "You're so full of shit, why should I tell you? He laughed as he stretched out on his back. "Come on!" I argued. "You can tell me." I urged him on. "Shit!" He finally said, "I suppose you won't leave me alone until I tell you". We both laughed. Devon leaned in a little, "OK, we went upstairs, made out and Samantha tugged on my dick while I licked her boobs and played with her pussy." Devon ran two fingers past his nose giving them a smell, "Sweet!" he said as he grinned. "That's nasty!" I giggled. "So did she get you off?" I laughed. "No!" Dev groaned. Her little brother came into the room and wanted a drink of water. "Damn, I'm so gonna get that little twirp", we both laughed. Devon reached into the sleeping bag and his hand moved down toward his crotch. "Now my balls ache" he groaned. "Blue Balls!" we both said at the exact same time, and broke out laughing. Like I said, we can almost read each other's minds. "I've got some porn" I said as I jumped out of my sleeping bag and headed for my dresser. In my underwear draw I had an old cash box with a lock. I pulled the key from the chain around my neck and unlocked the box and pulled out a DVD. "Josh, that little freshman that wants to be water boy next year, gave me this" I smiled as I headed for the DVD player and turned on the TV. A few minutes later Devon and I were laying on top of our sleeping bags face down looking at three guys doing three girls. "Shit! Devon whispered as one guy with a huge dick slowly penetrated the hairy crotch of a brunette with huge breasts. The sounds of sucking, fucking, and cheap porn music surrounded us as we watched wide eyed. "Damn, I wish I was fucking some pussy!" Devon groaned as he humped the bed a little rubbing his hard cock against the sleeping bag. "Yeah" I agreed as I felt my own meat swell and twitch. We watched for a few more minutes. "Turn it off" Devon said as he rolled onto his back and looked at the ceiling, his hard cock clearly tenting his boxers. "I can't sleep like this" he said with a grin and we both giggled. I debated with myself as I turned off the DVD. Finally I decided and jumped back on the bed. "Promise you won't tell anyone" I said as Devon looked at me. "Huh?" He said as he turned. "I said, 'promise you won't tell anyone'" I repeated. Devon shrugged, "OK, I promise, so what gives?" Devon asked. "You have to swear not to tell another soul, ever!" I emphasized. "OK, OK" Devon said as he was clearly becoming more irritated. "My brother Trevor takes it up the ass" I whispered and waited for Devon's response. "He what?" Devon queried not quite sure what he had heard. "My little sissy brother takes it up the ass" I said more slowly. Devon's face scrunched up as he thought a moment, "He's queer?" Devon asked sitting up. "Well, I don't know if he's queer" I whispered, "But he definitely likes to be a girl." The room was quiet as Devon considered what he had just heard. "No shit?" he asked, thinking I was going to say it was all a joke. "No shit!" I said. Devon finally spoke again. "Bullshit!" he said. "You are so full of crap!" and he punched me in the arm. "Am not!" I said rubbing the sore spot he had just made. "I bet if we went to his room right now the little sissy will be wearing girl's panties" I challenged. Devon couldn't be bluffed in cards; I knew he wouldn't take my word for it. "Show me" he said climbing off the bed. We crossed through the connecting bath to my brother's room and saw his TV was still on. Trevor was sound asleep face down on the bed with just a sheet covering him. We walked over and I gently pulled the sheet down. Trevor's thin freshman frame still had a little summer tan. As the sheet came off Devon took in a soft breath. Trevor was wearing the red satin panties with the lace fringe I had given him a few days ago. "Damn!" Devon whispered. "He is a little sissy!" Devon rubbed his crotch. His cock had gotten instantly hard. "He takes it up the ass? Devon asked as he stroked his dick. "Can I have some?" Devon said never taking his eyes off my brother's butt. "I don't know man!" I whispered back, thinking that giving your little brother's ass to a buddy is a little weird. "You can have my jet ski all next weekend" Devon mumbled stroking a little faster. I love Jet Ski weekends but mom and dad don't see the point in spending that kind of money. "We can stay at the cabin and my Jet Ski is yours for the whole time. My conscious tugged at me for about two minutes more, but then my adolescent need for speed won out. "Ok" I said, "but you have to take it easy. I don't you to hurt him" Devon grinned and pulled down his boxers. His dick was flying and super hard. I had seen Devon naked in the showers tons of times, but never hard. He's about 6.5 inches, so he's smaller than me in length. But where my cock is longer it's also thinner. Devon is somewhat thicker. "Wait a minute" I said as I ran to the bathroom and grabbed the jar of Vaseline. "Here" I opened the top so Devon could grease up. As Devon spread grease on his cock I slowly pulled down my brother's red panties. Trevor's cute rear end came into view. "Wow" Devon whispered seeing the tight butt crack and his girlie thighs. "Don't hurt him!" I warned again and lowered my own boxers and stroked myself as Devon straddled Trevor and aimed his dick at my brother's ass crack. I saw Devon's cock slowly spread open Trevor's butt. With one hand guiding his dick he found the hole. "Damn he's tight" Devon grunted as he eased the head of his cock into Trevor's rectum. I saw an inch penetrate my brother's ass before he began to stir. Asleep, Trevor's anus was totally relaxed and did not resist the penetration. But, as he woke up his ass ring clenched down. "Aaaah" Trevor squealed, "My ass" he said as he squirmed beneath Devon. Feeling his bowels being stuffed with cock wasn't a new feeling but it was surprising when your first wake up. "Sshh, be quiet!" I said, quickly getting down on my knees near the bed. I looked in Trevor's eyes, "You're going to wake mom and dad!" I said, putting a hand across my brother's mouth. I could see a little tear drop as Devon grunted and slid his cock another inch up my brother's butt. "I made a deal" I whispered to Trevor my hand still across his mouth. "He gets your ass, and I get his Jet Ski" I whispered. My cock twitched and jerked it was so hard. I watched Devon nail my brother and all I could think about was how sweet it is to fuck freshman ass. Trevor groaned and almost screamed into my hand when Devon slammed the last three inches home. "You got it all" I whispered as Trevor looked at me with a pleading look. "I'm taking my hand away" I warned, "Don't wake mom and dad!" I eased my hand away and Trevor groaned as Devon started to fuck in and out of his butt hole. "Jeremy" Trevor whispered, and grunted again as Devon started fucking faster. "Why didn't you wake me up?" He whined as Devon pounded again and again. "I dunno" I shrugged, "I never thought you'd do it" I said lamely still stroking my own hard dick. Trevor grunted as the air was almost knocked out of him with the pounding of Devon's dick up his ass. "Wait" Trevor commanded and Devon stopped in mid fuck. "Take it out" he ordered and Devon reluctantly withdrew his penis. Trevor moved back a little on the bed and got on his hand and knees doggie style. He swung his head toward me and then the head of the bed. I knew what he wanted. In seconds I was on the bed sitting on the back of my legs cock thrust out, holding myself up with my arms behind me. "Ok" Trevor said as he lowered his mouth over my knob and wiggled his ass. Devon crawled up behind him, aimed his dick at Trev's hole and entered his butt once again. Trevor was taking cock from both ends and loving it. He bobbed his head up and down over my cock as I thrust my hips up and tried to fuck his mouth. Devon was a mad man fucking his dick into Trev's rear, panting with each thrust. "Fuck, fuck" Devon groaned as he twisted his cock sideways up Trev's butt. Ten minutes of teen fucking, grunting, and sucking made the place smell like a locker room. "Gonna nut!" I moaned. Trev used his tongue on my dick, stroked my shaft, and sucked. Devon panted and pounded away at Trev's crack. The sound of my friend's cock slurping in and out of my brother's tight ass hole really turned me on. My dick grew stiffer and I knew I was close, "Swallow it" I groaned as my cock pulsed and I shot three longs spurts of jizm into my brother's mouth. I grabbed his hair and pulled his head down tight feeling my cock touch the back of his throat as I dumped my load. Trevor coughed, choked a little, and pulled back as my slime slid down his throat to his belly. Devon had his hands on Trevor's waist and was pulling his ass toward his dick as he fucked. Sweat poured off both boys as they were consumed by sex. Devon moaned and finally slammed in hard one last time. Trevor grunted, "Oh God, shoot it up my butt" as he spread his legs to take more cock. "Deeper, deeper" He pleaded, "Fuck my butt!" Devon finished with a jarring slam. "Here it comes Trevor" Devon moaned as his nut sac tightened and he shot a river of juice out of his dick and into my brother's rear end. "Oh God, Oh God," Devon groaned, "Shit!" He grunted as his ass muscles flexed and he filled Trev's bottom with cum. "Uh,Uh,Uh," Devon panted as he shot his stuff up Trevor's butt like a hot sperm enema. At last, Devon collapsed on Trevor's back and both fell forward onto the bed. I sat with my wilting dick inches from Trevor's mouth. He raised his head up and licked the last of the cream off my cock. Devon rolled off and we all lay exhausted. Trevor rolled on to his back and his dick stood tall. "What about me?" he whispered as Devon and I looked at the little guy's cock. Devon shook his head no. I shrugged and crawled over to Trevor's side and gently grasped his pole. "Just a jerk" I said lamely as Devon wondered what I was going to do. I gave my brother's hard dick a couple of strokes and Trevor was on his way to an orgasm. "My butt" he moaned, "do my butt" he said as he spread his legs. I looked down as he put his hands behind his knees and pulled his legs back toward his chest exposing his cum filled hole. With one hand on his cock I moved the other across his bottom. I slid my finger around his hole, teasing him. "Inside!" he pleaded, "Put it inside" I pushed my middle finger into his rear end and felt the tight, hot tunnel grab hold. Trevor moaned and I slowly finger fucked him as I stroked his cock. His breathing increased and his tummy began to rise and fall more quickly. He wiggled on my finger and tried to fuck my hand. He urgently raised his hips up and off the bed, moaning "Shit! Shit!" and then he brushed my hand off his cock and grabbed it himself. "Fuck me, fuck me!" he panted as he jerked himself and I fingered his ass. In a few minutes his hand was a blur. He grunted and I saw his cock twitch as rope after rope of cum shot out of his dick and against his chest. His asshole tightened around my finger like a vice as he spasmed and shot his load. Four long shots of sperm creamed his chest and messed his hand. He lowered his hips back to the bed and I gently pulled my finger out of his butt. "Jesus" Trevor finally managed to say as I continued to tickle his hole. Slowly his breathing returned to normal. The room was silent except for our breathing as we all settled down. Some minutes went by, then Trev cut a nasty sounding fart. "Dude" Devon laughed as he moved away so as to not have to smell the result. "You put it there!" Trevor giggled and rolled over pointing his ass at Devon. "That's nasty!" Devon grunted and stood grabbing for his boxers. I lightly slapped Trevor on the ass. "Night bro" I grinned." Thanks for the fun". I winked and headed for my room. "Can I get some sleep now?" He asked with a grin. "Ya" I said, if we need a girlfriend again I'll let you know." Trev crawled back under the covers and stuck out his tongue. "Better ask next time!" he said. I flipped him the finger and left the room. Devon and I went straight to bed and never talked about what happened. We know we are straight and like girls. My sissy brother just happens to be some ass we can nail when we need it. At least that's what we keep telling ourselves. If you liked this story, please let me know. Send to playbuddy123@yahoo.com with story ideas or comments.