Kennedy's Strange Life
Caution: This Drama Sex Story contains strong sexual content, including mt/ft, mt/mt, Romantic, NonConsensual, Rape, Gay, TransGender, Shemale, Brother, Sister, MaleDom, Rough, Light Bond, Torture, First, Oral Sex, Anal Sex, Masturbation, Cream Pie,
Desc: Drama Sex Story: Chapter 1 - Kennedy is in the wrong body. She's supposed to be a girl, but she was born a boy. Everybody seems to understand except her brother Mike. This is the story of her strange life.
I'm in the wrong body.
That might sound weird to you, but it's always been the case with me. I knew from when I was really little. Like my earliest memories are of wanting to be a girl. I was always small too, dainty some people would say.
It's weird too; I'm the only small one in the family. My older brother is huge compared to me, and both my parents were above average too. Anyways, I was the small little girly boy in the family. My parents were always really accepting. For my 7th birthday I asked for a dress and my mom was nice enough to get it for me. Over the years I slowly built up quite the wardrobe of girl clothes. A lot of people in the neighbourhood probably thought that was weird, but nobody ever said anything.
I guess my mom and dad were always looking out for me. Like they'd talk to all the neighbours who I guess talked to their kids, so nobody acted that weird when I started to wear skirts and dresses to school. I was just a regular kid, except for the fact I was the only girl with something between her legs.
That's the other weird thing ... I liked my dick. Like I want to be a girl ... I am a girl, but I didn't want to chop it off or anything. Ever since it was obvious that I was different, my parents had sat me down a bunch of time to talk about puberty, and what I could do to actually become a girl and avoid turning into a boy. I was dead set against that, that's for sure. So ever since I was young we'd make a bunch of trips to the doctor.
The docs talked about pills and things I'd have to take, and they even talked about surgery and stuff, but I was against it ... well part of it. I wanted boobs in the worst way! Here I was a teenager, 14 years old and I had no boobs!
My doctors had started me on a bunch of pills recently, which they said would repress my male hormones and replace them with female ones, or something. I didn't understand all of it, but as long as I turned into a girl and not a boy that was alright with me.
Actually it seemed to be alright with everybody. Sometimes I'd hear snickering or something but I think that's just part of being a kid. Some kids just aren't nice you know? The only person who really wasn't nice to me was my brother Mike. He'd call me Ken instead of my full name – Kennedy. He knew that really bugged me. When nobody was around he'd call me really mean names like faggot or cocksucker which really bugged me. I mean, It's not my fault I'm in the wrong body you know? Mostly he just ignored me though and I could live with that.
Life was good for a long time, I had a bunch of friends, girls mostly, and school came pretty naturally to me. I mean I wasn't the best student, but I was pretty good. I really loved spending my time with my girlfriends. We'd have sleepovers or slumber parties and talk about girl stuff. They'd talk about their boobs growing or whatever and I'd feel kinda sad, but then they'd talk about boys and I loved that.
I've been boy crazy since I was born, I swear. There was this one boy I'd had a crush on since I was like 5. He grew up just down the street and I swear Ryan was the dreamiest guy I ever met. Some girls joked that Ryan is what I coulda looked like. He had the same shining blue eyes I have. I swear his eyes glistened in the sun. He was tall and thin, dusty blonde hair too. I've always had my hair long, but he kept his pretty short. God, I wanted to kiss him so much.
"He doesn't even know I exist," I lamented. My friends tried to cheer me up, they swore he liked me, but I never felt he did. One of my friends told me I should just try talking to him at school. They all kinda ganged up on me one time and made me promise I would talk to him the next time I saw him. I finally gave in and promised.
A few days later I ran into Ryan at school. He was walking down the hall checking something on his phone. I kinda froze in the middle of the hallway, trying to figure out what to say. He was getting closer and closer and I just froze. I had no idea what to say! Is he gonna like me, even though I've got those extra parts? A thousand thoughts kept whirling around in my brain and then wham, he ran into me. Literally! I'd seen him coming the whole way but I guess I zoned out because the next thing I knew I was on my butt and my skirt was way up! Ryan was apologizing and looking down at my underwear and I was mortified!
"I'm so sorry, are you okay?" he asked.
I tried to speak but nothing came out. I was like a mouse, only able to squeak. He gave me his hand and pulled me up.
"uh ... thanks," I said.
"No problem. Are you okay? Sorry I was checking out my phone and wasn't watching where I was going."
I was watching you just fine, I thought. I shook my head though, trying to clear the cobwebs and not sound like I was, an obsessed little girl.
"No ... yeah, I mean. I'm fine. It was my fault, I shoulda moved."
I smiled at him. Gave him the best damn smile I could. He kinda looked me up and down a little, I'm not sure if he was checking me out or just confused as to what was wrong with me.
"Well, if you're okay I guess it doesn't matter. Uh, I gotta get to class. I'll see ya later."
And that was it. He walked off to whatever class he had. I just stood there looking at his nice ass, my heart beating a mile a minute. God, I wanted him so bad.
"That was pathetic."
What? I turned around and saw my brother standing there. Mike was having himself a good laugh at my expenses.
"I said, that was pathetic. You really think that guy likes you?" Mike asked.
"Shut up, Mike! Like I'd ever tell you anything!"
God, he made me so mad. Standing there with the smug look on his face. This isn't some joke, this is my life! But to Mike I was just a joke, his little girly brother. He walked up to me, uncomfortably close really. He was so much bigger than me it scared me.
"Nobody is ever gonna like you ... KEN," he sneered. He laughed again and started to walk away.
" ... That's not my name," was all I could manage back. I squeaked it, really. Loud enough though, as Mike spun back around and pushed me by my shoulders back into some lockers.
"What did you say, Ken? I'll call you whatever I damn well please. Nobody is ever going to like you, nobody is ever going to want you. Sure these people are used to you by now, but nobody thinks you're normal. We all think you're crazy, Kennedy, I'm just the only one with the guts to tell you."
He stormed off and all I could do is sink to my knees. Then I started to cry. I hated Mike, I mean really hated. I've never hated anybody else like I hate him. Why did he have to be so mean? I just hugged my legs and cried and cried and that's where a teacher found me. He basically dragged me to the nurses office, and she sent me home for the day. I had just said I didn't feel good, I didn't want to be here anymore. I didn't live far from school so they let me walk back. I ran straight up to my room and got under my covers on my bed. I just cried my eyes out until I finally fell asleep.
I dreamed of being held in Ryans arms. It was warm, we were outside in a forest or something. I gazed up into his beautiful eyes and thought this must be what heaven feels like. I could hear whispering though, all around me. I tried to listen, straining my ears but I couldn't make it out.
I awoke then, all alone in my bed. I could still hear the whispering. It was my mother and my brother talking. She said something about them going out. I don't know, I wasn't really listening. I just wanted to fall back asleep, to get back to Ryan ... even if it was a dream. I kept thinking of him and I started to feel all warm on the inside. I'd think of him kissing me, sliding his tongue inside my mouth and pushing me back onto my bed. I'd imagine him taking off my clothes, one at a time. Kissing my face and neck, before going lower, to lick my breasts. I'd dream they were big, and Ryan loved them. He'd reach lower, while suckling on a nipple. He wrap a hand around my little erection, my girl cock as I called it. He'd slowly squeeze me, sliding his hand up and down the small shaft. Then I would feel a finger, his finger, slide into my ass. I always loved the thought of that.
I opened my eyes and looked down my bed, I hadn't even realized I'd started masturbating. Yet there I was, panties down and around one ankle. My right hand around my cock and my left sticking a finger into my ass. I'd been jerking off for awhile now. I loved my cock, it felt so good, but sometimes I thought something inside my butt felt better. I'd imagine Ryan, or some Hollywood star sticking his dick up my ass and I'd squirt all over myself. I loved those thoughts, I felt so free, so good, while I dreamed those dreams.
It was like nothing could hurt me. I'd feel warm and fuzzy all over, with an imaginary big strong man over my prone body. I'd make love to his cock with my body, any part he wanted. I'd sink to my knees, or onto all fours, and give myself to him.
I was still playing with myself and it was really starting to feel good. I knew I wouldn't last much longer, but I wanted to feel more full, you know, back there. I opened my night table beside my bed, that's where I left him. It was a big rubber vibrator. I'd stolen it from my mom's closet when I was younger, but she had a bunch so I guessed she wouldn't miss it.
That was a long time ago and she never said anything so I guess she never noticed. I slid it into my ass, slowly, so very slowly. It was so big and I was so little. Once it was inside me, just a little bit, an inch or so, I turned it on. It began to vibrate, just a little. I kept my other hand firmly wrapped around my cock, it felt so good.
I let me thoughts drift back to Ryan from earlier that day. Imagining he had pushed me into the boys washroom, into a stall. He'd have me sink to my knees as he'd open his pants, revealing his massive member. I'd smile, without saying a word, and slide my tongue down its side, feeling each ridge and loving every second of it. He'd grip the back of my head, just lightly, but enough to guide me to take him into my mouth. I'd open wide and let him inside ... and then I came.
I snapped back to reality, as my cum launched from my girl cock up my lithe body. I squirted all over myself, and I loved it. When it finally stopped I was covered in my goo, panting breathlessly. I giggled, loving the feeling after a good cum. The vibrator was still in my butt, just barely, buzzing away. I took it out, slowly. I was always sensitive afterwards. I turned it off, grabbing a small towel I hid behind my bed to clean all the cum off of me. I hid the towel back again behind my bed and put the vibrator back into my night table. I pulled my panties back up, little red ones with hearts on them. I even got a training bra from another drawer even though I had no boobs to speak of. I put it on, it always made me feel so sexy. I jumped back into bed and pulled up the covers before dozing off. Tomorrow would be a new day.
But tomorrow never came, or more accurately, my night wasn't over. I was sleeping blissfully, dreaming the sexy dreams a girly boy like me dreams. It was late. I heard some sort of noise, loud enough to wake me up. I sat up in my bed, my door was open and the hall light was on. It was blindingly bright and my eyesight was fuzzy. A figure was there. The figure started coming into my room now. It was Mike.
"Huh? What do you want?" I asked groggily. I wiped at my eyes. I looked over at my clock and it was just after 11 p.m.
"Mike? Its after 11, what are you doing up?"
But nothing, my brother said nothing. He walked up, slowly, like he was trying to sneak up on me even though I was talking to him. He walked up to the side of my bed and I just stared at him, or the outline of him anyways. My eyes still hadn't adjusted to the brightness of the hall.
"Hi ... Ken..." my brother half growled. God, why did he have to call me that?
"Get out of here Mike before I go get Mom!" I threatened. I figured that would scare him off.
"Moms not here," he said. "They're both out late, may not be back till after 2 or 3. I'm supposed to make sure you're asleep for school tomorrow. She knows you came home sick today."
"Well, I was asleep. Go away."
I rolled over, giving him my back. God I was tired, I didn't have the energy to put up with Mike. I felt him sit down on the bed next to me. Why couldn't he just leave me alone?
"Go away, Mike," I mumbled
He wasn't sitting; he was on his knees next to me. He grabbed me by my shoulder, spinning me around. I was so small and he so big than I flung onto my other side right away. I landed in his lap and my arms came up instinctively, thinking he was going to hit me. But he didn't hit me. He grabbed my arms, pulling me towards him. He linked my wrists together, quickly tying them together with something. I struggled but it was no use. Once my arms were tied he let go with one hand and grabbed my head. He grabbed my long hair and pulled me into his crotch. He was naked!
I opened my mouth to scream, but he just smacked me in the mouth. I could taste my own blood. He hadn't hit me that hard, just hard enough it seemed. He kept clutching at me and grabbing, trying to position me. I was completely dazed. He grabbed my head again and brought it back to his crotch. I tried to tell him to stop, tell him he was hurting me, but as my mouth opened he just impaled me mouth first on his giant cock. I tried to scream, to breathe, too get away but I couldn't. He was holding me down, using his immense strength to control me. I was choking, I couldn't breathe! Tears started to stain my face as I finally was able to pull away.
"Think you can get away with teasing me, huh?" My brother asked, but I couldn't possibly understand. The room was spinning and I was gulping for air. I couldn't process what was happening. He grabbed my head again and smashed my face into his crotch. He rolled over, with me still getting a mouthful of dick. He straddled my chest and began to thrust wildly into my mouth. I couldn't do anything. My arms were still tied together at the wrists above my head and he held them against my headboard. He just kept fucking my mouth, degrading me with disgusting words as he did so.
"Fuck, you bitch, you whore. Take it!"
I tried to spit him out, but I couldn't. I was choking again when he finally pulled out. I coughed and almost threw up. I had never felt so disgusting in all my life. I begged, pleaded, for him to stop.
"Let me go ... please ... let me go..."
But he seemed crazed, like he couldn't even hear me. He reached behind my bed and pulled out the towel I'd used to clean myself and threw it down next to my head.
"Don't pretend like you don't like it, you slut," he said.
I tried to protest but he threw me back again. He leaned in, shoving his tongue into my mouth. I froze, not even knowing what to do or think. He stopped quickly, throwing me back onto my front. He ripped my panties off me then. Before holding me face down into my pillow.
"Now I'm going to finally get what I deserve."
He grabbed the towel and jammed it into my mouth. It was still wet from earlier. I was eating my own cum and clearly my brother knew it. He knee walked down my bed, while still being big enough to hold my head down into the pillow. I could breathe threw my nose at least, even if my mouth was full. I struggled with my arms, but behind my head and tied together I didn't stand a chance. He seated himself between my legs as I prayed for god to kill me.
That's when it happened. I wasn't even aware of it, hadn't thought of it, before he did it. He split my cheeks apart with one hand, and smashed his dick into my asshole. I've never felt pain like that, I doubt many have. I screamed but was muffled by the towel in my mouth. Then he pushed again, slowly forcing my sphincter to pull apart. I felt like a rubber band being stretched too far, like I was going to break. He thrust again and again while I cried and screamed, but nothing was going to stop him.
He finally got all the way inside me. It felt like he jammed a baseball bat into me. I was in so much pain I had started to go numb. The corners of my vision was blurry as I breathed hard through my nose. I felt like I was dying. He kept thrusting into my tiny asshole, saying disgusting things to me while he raped me of my virginity and dignity. Sometimes he would thrust in as deep as he could and hold himself there. I think he was trying to hold out a little longer, like he didn't want to cum to fast. He'd wiggle around, stretch the sidewalls of my anus as he did so and touching something deep inside me. When he did that it started to feel really good, and that was maybe worse.
Here I was, face down on my bed, my mouth stuffed with a towel covered in my own girlcum, as my brother raped himself in and out of my ass ... and at times, I liked it. He pushed so hard, so fast, I swear I could feel something tear down there. I could feel it start to get slippery and I couldn't know if that was his pre cum or my blood ... or both.
And then he'd hold himself again, growling at me as he held me down, and I would feel amazing. I don't know why he bothered to hold me at all, he had broken me. My heart, my soul, was shattered into a million pieces. I'd just lie there, ignoring my girl cock the strained for some release. My chest burned as my training bra dug into me. I cursed my body for betraying me as he began to hammer into my too small ass yet again.
He was loving it, dripping drool across my back as he thrust into me like an animal. He was a man possessed, driven to find his relief in his baby sister.
"Fuck Kennedy, you feel so good, I can't last much longer."
I tried to find solace in that, that this ordeal would soon be over. But it wasn't to be. He slowed down again, grinding my insides, when the unthinkable happened. I came. My little girl cock sprayed my stomach with my cum as I wept at my bodies betrayal. My whole body tensed with it and my brother felt it.
"Oh fuck," was all he could say, as he sprayed my insides with his seed. He came. My brother fucked me ... and came inside me. I felt beyond worthless. I wanted to die. He thrust as deep as he could as we both blew our loads together. I begged my body to stop but it felt so soothing to feel his cream pushing deeper up my rectum. Finally he stopped and I stopped and my tears continued to flow. He caught his breath, looking down at me, as I curled into a ball. He still was up my ass, though slowly deflating. I could feel him looking down at me but I couldn't look at him, couldn't open my eyes.
He pulled the towel out of my mouth, and I slowly began breathing as normal. I couldn't open my eyes though. He pulled his dick out of my ass and I could feel his slime already beginning to run down my thigh. He seemed to linger a moment, before he got up and left without a word.
He closed the door softly, dropping my room back into darkness. I finally opened my eyes to check to made sure he was gone. I saw my clock, barely 15 minutes had passed.
15 minutes was all it took to change my life forever.
15 minutes was all it took.
And I began to cry again, before sleep finally took me.