Date: Sun, 26 Nov 2006 06:01:15 -0800 (PST) From: Will Shakespear Subject: Sissy Brother-20 Revised 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, 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 - 20 I felt like I had been waiting forever for my sixteenth birthday. Dad had been patient as he helped me practice my driving, but I was more than ready to get rid of a parent in the seat next to me. Friday finally arrived and as promised Dad wrote a note that got me out of school two hours early. That gave me enough time to get to the DMV and make my appointment for my driver's license test. The first part was an eye exam. No problem, I aced it! The second part was the written exam. The sixty questions are all on a computer. You can get up to six wrong and still pass. I only got four wrong so I breezed through that part as well. The behind the wheel test was the last part and I managed to get a pretty cool guy that understood I was nervous. He took a couple points off for parallel parking but gave me a passing grade for the rest. Dad paid the $90.00 in fees. Yeah, I know they suck, but for a first time driver I guess its ok. They took the stupid ID photo and I was done. Dad congratulated me and let me drive the Lexus home. I knew it wouldn't happen very often. He already told me to plan on driving Mom's Camry. As I guessed, we had supper at home and my grandparents came over for coffee, cake and ice cream. I scored a couple of hundred bucks in my birthday cards and some decent clothes. As I fell asleep that night, I thought "Pretty nice Birthday!" I felt good all over. I propped my new license up on the bedside table where I could see it, turned out the light and was asleep almost at once. Saturday I slept in late. Trevor finally knocked on the door and woke me up. "Jeremy! I need a ride to Devon's house." He called out and I woke up at once. "Shit!" I giggled. "I get to drive!" I jumped out of bed and pulled some jeans over my boxers and grabbed one of the new shirts grandma had given me. I tucked my license into my back pocket and grabbed a jacket. Mom could easily have taken Trevor over to Devon's house but she knew I would be eager to drive. "Do you mind honey?" she asked as she held out the keys to her car. "Um, no that's ok" I said trying to play cool. "Thanks dear" she smiled and we were headed out. I delivered Trev and then stopped at the store. Mom asked me to get a few groceries and if it meant I got the car keys it was fine with me. I got back home about 12:30 I guess. "There are sandwich things from the deli" Mom hollered as I dropped the keys on the dining table and headed to the kitchen. I put the groceries away and made myself a ham sandwich with lettuce and tomato. Looking at the clock my cock twitched a little as I remembered my date with Josh. "Um, Mom?" I said, as I walked into the living room eating the sandwich and carrying a soda. "Could I borrow the car this afternoon? I want to meet a friend. I'll be back by supper." I half asked and half begged. Mom flashed a knowing smile. "Sure honey!" she said. "But remember, one ticket for bad driving and you'll see a lot of the inside of your room!" I mumbled, my mouth full of food, "Thanks Mom, you're the greatest!" and gave her quick sloppy kiss on the cheek. I finished my lunch and went to my room to get ready. "What do you wear when you're going to meet someone to fuck?" I giggled to myself. I felt the urge in my belly, went to the bathroom, dropped my drawers and sat on the can. I took a pretty good dump, cleaned up and flushed. I stripped and took a quick shower. I paid attention to my dick, balls, and ass. "Earn your clean scout merit badge" I chuckled as I soaped my cock several times and washed deep in my crack. I towel dried and then combed my hair. I used my sports stick deodorant under my arms and threw a little after shave on my face. "Ok" I shrugged and headed to my room. As I stood naked looking into my closet I just couldn't decide what to wear. My stomach felt fluttery and nervous. "Shit! This is worse than my first date with Jennifer" I mumbled. My eyes fell on a cool white shirt that I sometimes wore to church. It had long sleeves and was styled to show off my lean build. I took a pair of black dress pants off the hook and put those on as well. I grabbed dress shoes and dark socks, a black belt, and finally I put on my middle school football ring. I liked the look of the gold against my hand. "Ready or not!" I shrugged as I made sure my hair was perfect. The drive over to Josh's house wasn't long. I was getting more nervous by the minute and I felt like I had to pee. I parked in front and taking a deep breath started up the steps. Before I could knock the door flew open and Josh welcomed me in. "Hey Jeremy!" He grinned. "I thought maybe you'd change your mind." I managed a weak smile. "Ah, no it's cool" I mumbled as I looked around. I was standing in the entry way of a fucking mansion; well at least I thought so. As I looked stunned Josh explained. "Well you know my Dad is a surgeon" Josh said as I stared at the big living room with baby grand piano, fireplace, and marble topped tables. "Mom is an attorney. She does corporate stuff for a big chemical company." I thought, "Shit! Josh is cute, smart, and fucking rich! How lucky is that?" He continued his little speech, "Its all a little embarrassing" He mumbled as I finally got my wits back. "No, it's cool" I said. Josh showed me around the house. There was a huge kitchen, dining room, and a sun room with lots of windows and plants. There also was a home theater room with a plasma screen and surround sound. "Four chairs?" I asked looking at the theater room. "Yeah, it's me, Mom and Dad and my older brother. He goes to community college. But he's trying for Princeton in the fall." I nodded, "Why the fuck not?" I giggled. We stood quietly for a second. "You look great!" Josh whispered. I blushed. "Want to see my room?" He asked. "Sure!" I said feeling my stomach turn again with butterflies. We went up the stairs and came to a door with a cute gold plated door knocker. It said, "Joshua" on it. Josh groaned as he saw me checking it out. "I thought that was really cool when I was 10" Josh said and his face turned pink. He was so cute when he said that. Inside was a perfect bedroom, something right out of Martha Stewart. "Don't you ever make a mess?" I blurted out and then wished I hadn't said it. Josh giggled. "Yeah, it's usually a real pit in here" he laughed. "But I knew I was going to have company. So I worked most of last night and this morning to clean things up." We both laughed. Josh put an arm around me and moved me toward the bed. It was a king size four poster with a massive quilted comforter. He jumped on and patted the comforter lightly. "Come here" He grinned. I was so nervous that I really did have to pee now. "Um sure." I mumbled a little, but "can I use your bathroom first?" I was embarrassed to ask, but I knew it would be worse if I wet myself. "Oh sure." Josh said and nodded to a connecting door. I went inside, unzipped my slacks and pulled my dick out. I was relieved as I felt the piss leave my bladder and splash into the designer toilet bowl. As I finished, I shook my dick dry. "Nice!" Josh whispered and I turned to see him leaning against the bathroom door staring hungrily at my cock. My dick shrunk a little in my hand. He walked over and gave me a hug. He kissed the back of my ear. "Damn, I've wanted that thing of yours for weeks" He whispered and pushed his crotch against me. We kissed. I felt his tongue dance in my mouth and he playfully teased my tongue as we both moaned a little. My dick started to get harder. Josh kissed me for a bit longer and then went down to his knees and unbuttoned my pants, and tugged them down a little. He grinned up at me then took me into his mouth. "Oh God that's nice" I moaned as I held Josh's head in my hands and he deep throated my cock. I thrust my hips forward gently and fucked his face slowly. Josh pawed my ass cheeks and ran his fingers up and down my crack. "So nice," I moaned as I felt my dick slide down his warm throat. He pulled his mouth off and stood up. He grinned and kissed me. "Your pee tastes nice" he giggled and turned toward his room. I laughed, "That's nasty" I said, and followed him in. As I stood in the center of his room, Josh did a slow strip tease pulling off his shirt, pants, shoes and socks and finally his boxers. Walking slowly over to his stereo he pushed a button and soft music began to play. He made sure to show me his ass and bent over just a little and giggled. In a daze I took off my own clothes and let them drop to the floor. My super hard cock was flying out from my belly. Josh's body is fucking perfect. I can't even describe how perfect he is. Think of the most incredible picture you have ever scene of a Greek athlete, young, strong, hung, with a magnificent ass. That would be Josh. I crawled on the bed and Josh pulled the comforter back so we could crawl inside toasty and warm. Josh ran his fingers through my hair. We looked at each other for several minutes. Then he smiled, "Ready to fuck?" He asked staring me straight in the eyes. "Yeah!" I whispered, the words sticking in my dry throat. Josh nodded toward the bedside table. "Top drawer" he whispered. I rolled over and opened the drawer and quickly saw the tube of KY. "Get me ready!" Josh said as he turned over and rested on his tummy. I squirted some lube onto my fingers and crawled nearer to Josh. I lay on my side and whispered into his ear as I let my hand make its way toward his butt. "You ready?" I asked as I spread his butt cheeks with a couple of fingers and put the greasy ones to his hole. "Yeah, do it!" He said and grunted a little as the tip of my finger entered his ass. I slid my finger in deep and twisted it around greasing every part of his tunnel. Then I put a second finger alongside the first and both sunk deep into his rectum. "Fuck yes!" Josh moaned in obvious delight. I played with his ass for several minutes opening his rear end and making it ready for my cock. "Now" Josh pleaded and I turned back to the drawer and lubed up my dick. I crawled over Josh's back and he raised his ass up without a word from me. I centered my rock hard dick on his hole. I pushed forward and my prick popped into his ass easily. I let my weight settle on his back and my cock sank slowly into his butt. "Fuck that's nice" I moaned as Josh squeezed my dick with his ass lips. "Do it!" Josh commanded with a throaty sound filled with horny passion. I raised myself up a little on my hands like I was doing a push up. I pulled my cock out and then slammed back into his hole hard and deep. "Yeah, that's it!" Josh grunted as he wiggled around on my dick pushing his ass back to take every thrust. I slammed into him for several minutes that way and then he grunted, "Wait!" I pulled out and he rolled over to face me and spread his legs wide pulling them back to near his ears. "Now!" He grunted and I crawled over him, lowered my cock and took him like a girl missionary style. He wrapped his powerful legs around my waist and pulled his ass up onto my cock. We fucked for ten more minutes and then he wanted another position. We stood in the doorway to his room and I got behind him as he held on to the door frame. I thrust my dick up his ass and he grunted with delight. "That's it! That's it!" He moaned as I fucked him again and again. I was covered in sweat and so was Josh. I pulled out and he crawled up on the bed doggie style. I got behind him and thrust back into his hole with my cock. I knew I was about to cum. I planted my feet on the bed in a squat, and I slammed my dick into Josh's rear end like we were playing leap frog. "Fuck! Fuck! Fuck!" Josh grunted as I reamed his hole with all the energy that I had. He wasn't a timid little sissy boy. This guy craved cock like a man. His powerful body sucked at my dick with power and enthusiasm. I felt his ass grip my cock tightly as he tried to milk me dry. As he squeezed his ass muscles he grunted and moaned in pleasure. "Gonna Cum!" I grunted as I pounded him hard and he moaned in delight. "Do it!" Josh whined as he tried to open his legs wider to give me more of his ass. I felt the sperm boiling in my nuts and finally the orgasm I had been working on for half an hour happened. I ground my cock deep into Josh's bowels and felt the relief of squirt after squirt of cock juice shooting into his fanny. "Oh God" I moaned as my knees weakened and I had trouble staying squatted over Josh. My dick squirted four hard spurts and then I trembled and sagged down behind the kid. I couldn't keep my dick in his ass any longer and pulled out flopping onto my back on the bed. Josh fell forward onto his stomach. "Shit that was nice" Josh finally managed to say as we caught our breath. "Fucking Awesome!" I whispered, totally shagged out. We were quiet for a few minutes. Josh giggled, "So was I the best ass you've ever had?" I thought for a second, "Not quite" I said raising up on an elbow to look at Josh. "Taking my brother Trevor's cherry was the best." I giggled. "But other than that, yeah you win hands down!" We both laughed. We talked for maybe half an hour cuddled under the comforter enjoying the afternoon. Suddenly it occurred to me, "Did you cum?" I asked, embarrassed to have not thought about that sooner. "No" Josh smiled. "I've been saving it." I laughed, "Saving it? For what?" Josh turned to look at me with those deep blue penetrating eyes. "Your ass!" He smiled. My eyes got wide as saucers, "Oh no" I said moving a little bit away. "I don't think so!" I was frightened but also a little excited at the idea. I was also feeling confused with several conflicting emotions. Josh leaned close to me and kissed me softly. "Think about it!" He whispered as he touched my chest and kissed me again. "It would be the perfect end to a perfect afternoon." We kissed some more and my cock thickened a little as Josh stroked me. My mind was in a whirl. I just had the second best sex of my life with an incredible guy. I knew I was straight and would always want girls. But, it also felt great being with guys. "Maybe" I thought, "I'm one of those guys that plays for both teams, Bi." As I was thinking about all that, Josh continued to kiss me, stroke my dick, and played with my crack. I was going to protest but his fingers touching my hole felt nice. When I didn't resist, Josh stopped kissing me and looked at me again. "I'd never hurt you" He whispered as he slowly jerked my dick. "But you're pretty big" I whispered, embarrassed I had even said that much. "I promise I won't hurt you!" Josh said and kissed me gently again. I closed my eyes. Part of me wanted to feel what it was like to get fucked. Part of me however, was still enough of a jock to know that we didn't do gay stuff. Without another word Josh gently pushed me over to my side facing away from him. He crawled over me and I could see his hand reach into the drawer get the lube. I knew I could stop him; all I had to do was say, "No!" But I let him go on. Josh crawled behind me and kissed my neck and ears as he used his lubed fingers to play in my crack. "Here it comes" Josh whispered as he eased a finger through my tight pucker and into my rectum. I grunted. "You ok?" He asked as he held his finger steady but firmly deep in my butt. "Yeah" I whispered concentrating on the feelings he was creating inside me. Josh spent maybe half an hour with me on my side. His finger was in my ass the whole time. He kissed me and slowly fingered me until my cock was hard again. "You're ready Josh finally whispered in my ear as he thrust two fingers into my guts. "Last chance." I thought as Josh reached over me again for the lube. I heard a squishing sound as he wrapped a greasy hand around his dick and lubed it from top to bottom. He kicked the cover off the bed. Lying down on his back he looked at me and rubbed my shoulder. "You on top" he suggested. "It's easier!" I gave it one final thought, and then turning looked at the gorgeous jock lying on his back with his dick standing straight up. I leaned down and kissed Josh gently. "Stop if I say so!" I warned. Josh nodded and smiled sweetly. I straddled Josh's crotch and reaching behind me tucked his hard cock into my crack. Kneeling, I slowly sat down and felt the head of Josh's dick push at my hole. "Oh God" I whimpered as I felt the pain of my tight hole being stretched too far. "Easy" Josh reassured me and touched my tummy and played with my nips. I rose up and sat down several times but not quite getting his thick mushroom head inside. Then, feeling we were close Josh thrust up and his dick popped inside. "Shit!" I cried out as a sudden pain shot through my ass. "God that hurts!" I whimpered, "Take it out! Take the fucker out!" I pleaded. Josh tried to calm me. "Its ok" he said as he tried to soothe me. "It'll get better" He promised. We both stayed in the same position. I resisted the urge to pull off, thinking his big cock head would feel worse coming back out. A few minutes passed and I was got a little more used to the feel of his pole in my ass. I warily started to move up and down a little. The feeling got better as my ass loosened up and Josh's cock rode more easily into and out of my butt. "That's it" Josh whispered as I sat on his cock with my eyes closed feeling so many things at once. He slowly started fucking me and I began to feel the incredible tingling that a cock makes inside a tight ass. We fucked for a few minutes. Then, by accident Josh's cock fell out of me. He gently rolled me over onto my side and getting behind me fitted his cock to my hole again. With me lying in a near fetal position, Josh settled in behind me and entered my rear end slowly and deeply. My eyes were moist from the earlier pain of losing my cherry. Now I felt tears rolling down my cheeks for another reason. "Don't ever stop" I whispered as I felt Josh fuck me lovingly and in a most gentle way. I had never felt so loved in my life. I felt Josh's crotch against my butt and his strong chest against my back. It was perfect. I don't know how virgins feel on their wedding night, but this had to be pretty close. My ass was so tight and Josh had waited so long his nuts were ready to spill after almost the first thrust. He had been in my ass maybe ten minutes and simply couldn't hold back any longer. "Here it comes Jeremy!" Josh whispered as he thrust hard just a couple of times more and got his cock as deep as he could in my ass. I felt a stream of juice shoot into my rear, followed by another and another. Each squirt was hot, sexy, and intimate all at the same time. Like taking an enema, I felt embarrassed at what was happening in my rear end but also somehow excited. "Oh shit, yes!" Josh grunted as he reached orgasm and shot his load. I felt my butt fill up with cream. Josh stayed up my ass for as long as he could but soon his dick softened and he slipped out. Finally, Josh rolled onto his back and I did the same. My hole was sore and I felt it leak cum onto his sheets. "Thanks Jeremy!" Josh whispered as he leaned over and we kissed softly. "My ass is going to be sore for a week and I'll be shitting your cum days." I giggled. "Sorry!" Josh said with concern on his face. "No, it's OK" I smiled and ran my fingers through his hair. "This will be the birthday I'll never forget." We stayed like that cuddled and naked for a long time. Then Josh leaned close and playing with my hair whispered in my ear. "Ever thought of letting your hair grow longer? Like Trevor's?" I thought for a second. "Not really, but yeah that might be nice." Josh kissed me gently again, "Cool, that's my girl!" he said. I made it back home on time. Surprisingly I didn't say much at supper and was ready for bed early. Josh called and we talked on the phone for almost an hour. I played with my cock all the time we chatted. About midnight Trev walked into my room and climbed into bed with me. "You were pretty quiet tonight!" He said as he cuddled close to me. "Yeah, I guess so." I mumbled. "Sup?" Trev asked as he laid a hand on my chest. "I'm not in the mood for sex tonight Trev!" I said, assuming he was trying to get me to play. "Not that!" He said a little hurt. "I want to know what's going on?" I debated about whether or not I should say anything to my little brother. But as I've told you before, we don't have many secrets. "I met this guy from school." I said softly. Trev leaned closer, "And?" I struggled with what to say. "We kind of hooked up!" I said. Trev was quiet. My heart skipped a beat. "You can't tell Mom and Dad" I said quickly. Trev wiggled is fingers on my chest. "That's your stuff" he finally said as I took a breath. I realized I had stopped breathing until he answered. "He's really, really nice Trev" I said gently as I pulled Trev closer. "As nice as Devon is to me?" Trev asked. "Even nicer!" I grinned. It was quiet again. Trev giggled, "I wonder what Mom and Dad are going to say when they find out they have two sissies in the family?" "I'm fucking going to kill you!" I laughed and started to tickle my little brother like we did as kids. "Stop, stop" he giggled. "I'm going to pee!" I stopped and gave Trev a soft kiss on the lips. "Is it ok with you if I have a boy friend and a girlfriend?" Trev thought for a second. Yeah, as long as the girlfriend is me!" We both laughed and growing quiet, we kissed again. then I made gentle love to my little brother in a way we had never done before. "Thanks Jeremy" Trev whispered as he was falling asleep with the feel of my warm cum in his ass. I pulled him closer and wrapped him in my arms. "You're welcome, you little sissy" I said, as I closed my eyes as well. This is the last chapter in this story. If you enjoyed it, please write to me at Playbuddy123@yahoo.com I may have a sequel that will appear in the High School section of Nifty. The working title is Sissy Brother Goes to Soccer Camp. It will be a short series with Trevor and Michael. Thanks for reading.