sorry about the story set up, I don't like giant walls of text.
“Knock it off already.” Cassie had the remote control firmly entrenched in her hand and was doing her best to keep it out of reach. The TV was stuck on basketball, which sucked. I knew that there had to be some combination of leverage and brute force that would cause my sister’s fingers to open and let me gain command of the remote. Getting up and walking to the TV was simply out of the question.
“Knock what off?,” I replied, making another grab. Cassie just rolled her eyes and pushed me away. Time for a desperation move. I stuck my thumb in my mouth just long enough to let it collect a good amount of spit, then, distracting her with another lunge for the remote, I slid my thumb past her defenses and rubbed it over her left ear.
“Ewww! Fucking gross!” Her grip loosened just enough for me to pry the device from her hand. My victory was sweet, but it was also short.
“Okay, Knob. You asked for it.” She grabbed me by the wrist and deftly twisted it behind my back, using her three-year age lead and height advantage to throw me down on the couch. She pinned me on my stomach and quickly moved into a sitting position on my shoulders, resting her full weight down on me to keep me from escaping. It was pretty much over. I knew what was coming next, and with one final effort I raised my free hand and succeeded in changing the channel before she could wrestle the remote away. Yes! No matter what happened now, she could never take that away from me.
I closed my eyes as I heard her unzip her pants. My embarrassment was unreal as she began whacking me on the back of the head with a blunt, meaty object.
As a boy, it’s not easy growing up with a sister who has a bigger penis than you do.
My family isn’t exactly normal. Cassie’s dad was killed in car crash when she was only a year old. Mom got married again and had me, but my dad ran off with a car show model when I was seven, leaving my mom to take care of us by herself. We’ve been though some rough times, but I think we’re closer because of it. And also weirder.
My sister Cassie is…well, different. When Cassie was born she was what they call ‘intersexed,’ which is the name for what happens when your parts are mixed up between being male and female. They decided to operate and make her into a boy, but as she got older it started to be obvious that she wasn’t supposed to be one. Now at sixteen you couldn’t guess that she was anything other than a slightly tomboyish teenage girl. She looked like a girl, dressed like a girl, and even smelled like a girl. She pretty much *was* a girl in every way except for what she had between her legs. A lot of people seem to think that’s the only place that counts, but living with Cassie has taught me that its what’s in your head that really matters.
It was a little strange growing up with her, but I pretty much got used to the fact that she had a ‘thingy’ like I did. The strangeness increased when she hit puberty and started growing boobs, something that the doctors said was unusual since she hadn’t been taking hormones. They gave her some to try out and her boobs got even bigger. Her hips got wider too and she started getting taller. I was still pretty small for my age and it soon became clear that she could beat me up pretty easily. Not that she ever really did, but anytime we had a wrestling match she would win pretty easily. We usually got along well, but as we both got older things started to get…complicated.
Our mom was working long shifts at the hospital, leaving Cassie in charge at home. I didn’t enjoy being bossed around by my sister, so sometimes I got pretty rebellious. Then Cassie developed her unique way of dealing with me, and I quickly learned that making her mad was a bad idea. That didn’t always stop me, however.
Sometimes she got really irritable. She didn’t seem to have many friends even though she was smart and wasn’t bad looking. She liked guys and even had a boyfriend for a while when she was fourteen, but he’d peeked at her once when she was changing in his parent’s pool house and totally freaked out. He broke up with her right after that and she’d hadn’t had a boyfriend since. She was probably pretty lonely. Sometimes I felt sorry for her, but she could also be a real pain to live with.
She was in one of those moods one night when I suddenly got a hyperactive urge to tempt fate. I crept up behind her as she was laying sidelong on the couch. She was watching basketball again. I waited until one of the players made a three-pointer, then I reached down with lightning speed and snapped her bra as hard as I could.
“He shoots, he scores!” I yelled, then ran for my life. It was the typical kind of foolishly suicidal thing you do when you’re thirteen and bored out of your mind.
She snarled and lunged, but I was already sprinting back upstairs, hoping that I could barricade myself in my room before she caught up. I almost made it. She shoved the door open with her shoulder before I could get it completely closed and jumped on me.
This time I knew I was in trouble. The look on my big sister's face made it clear that I was dead meat. I wasn’t going to give up without a fight though. We crashed onto the bed and wrestled like mad, grunting and growling like a couple of crazy animals. It lasted a few minutes before she distracted me with a Charley horse and pinned me to the mattress. We were both panting for breath and I was suddenly very aware of her boobs pressing against my back as she held me down. It was a good thing I was on my stomach.
The grappling match had left me with a painfully stiff hard-on, embarrassing but not terribly unusual. A gentle breeze could often make me hard those days. Acting tired, I relaxed and pretended to give up. I planned on trying to throw her off when she moved up to administer the standard thwacking, but she stayed laying on top of me and didn’t move.
Afraid that she was thinking up some new and even worse punishment, I quickly flipped myself over on the bed and almost succeeded at knocking her to the floor. She squealed and shoved me back down, hopping up to sit on my chest with her thighs locked around my head. Her leg had brushed against my crotch as she moved up, and to my surprise she suddenly reached back and grabbed my dick through my pants.
“I thought I felt a little pin-prick,’ she said, grinning evilly down at me.
“Shut up,” was my witty comeback.
I struggled to push her off but her knees had a death grip on my head, squeezing down around it like a nutcracker. Still grinning, she reached down and started unbuttoning her fly.
“I think you need to see what a real one looks like,” she said, her voice quieter but no less malevolent.
I winced, afraid to look as she pulled out her cock.
This was *soooo* not right. I could already imagine the many years of therapy that were lying in wait for me. Still, I couldn’t help but look. She had some trouble getting it out, and when she finally succeeded it was obvious why. She was just as hard as I was. Seeing a rigid penis sticking out from the fly of a teenage girl sitting on your chest is an experience that’s not easy to describe, especially when that girl is your sister and you realize that her dick is bigger than your own. I found myself staring up at it in in a state of mild shock. It wasn’t bad as far as penises go I guess; it was maybe five inches long and looked really smooth and clean. It was also, though I hate to admit it, almost *cute.*
She pinned my hands to the bed and looked down at me with a wicked gleam in her eyes. Her cheeks were turning a hot red color like she was blushing. I expected her to slap me with it or something, but she just sat there with her dick pointing slightly down at my face. My heart was hammering in my chest, and I suddenly realized that I was getting really turned on. There were so many things wrong here that it was hard to keep track. And it was about to get even worse.
Cassie’s grin had faded, replaced with an expression of…I wasn’t sure what. Her face was suddenly serious and her boobs were rising and falling with her breathing. Her cock hung stiffly only a few inches away, aiming almost direcly for my mouth.
“Suck it,” she said quietly, almost in a whisper.
I stared at her dick for a moment, not sure exactly what I wanted to do. I’d never even thought about trying something like this before, but...
Without even fully realizing I was doing it, I lifted my head up and gave her cock a little lick. It smelled like the body wash she used and didn’t really taste like anything. Not bad so far. I took the head between my lips and gave it a few experimental sucks. It felt warm and very stiff. Cassie gasped and leaned down over me, pushing herself further into my mouth. I started sucking harder and took as much as I could, feeling it twitch every time the head nudged against my throat. I wasn’t sure if I was doing it right, but the way she was gasping and panting led me to believe that she liked it.
She was gripping my hands so tight it almost hurt. Suddenly her whole body tensed up, and before I knew what was happening there was a sudden gush of warm, salty liquid in my mouth. She let out a low groan as her cock jumped again, pumping out more of her stuff. It tasted kinda gross. I guess I could have pulled my head away, but I think I was too stunned to move. For some reason I hadn’t expected her to cum the same way a boy did.
After a few more squirts, Cassie’s body relaxed and she slowly rolled off me. She sat at the edge of the bed and looked at me for a second, then suddenly stood up and ran out of the room. Not sure what else to do, I went to the bathroom to spit the stuff out. I rinsed my mouth, feeling ashamed as I realized I was still hard as a rock. It was all very confusing. Did this mean I was gay? I walked to Cassie’s room and stopped outside the door. I could hear the sound of quiet sobbing from inside. I didn’t know what I should do. I wasn’t even sure why she was crying. The situation was just too fucking weird. I went back to my room to fire up my Xbox and tried to forget about it for a while.
Cassie avoided me for almost a week. I didn’t know if she was disgusted with me or just ashamed of what had happened. I wasn’t sure how I felt about it, but I knew that I didn’t want things to stay weird between us forever. That weekend I waited until mom had gone to bed and then went down the hall to Cassie’s room. I could see a faint light coming from underneath the door so I knew she was probably awake. I knocked softly.
There was a moment of silence. “Yeah?”
“Can I come in?”
Another pause, but shorter this time. “Okay.”
I went in and closed the door behind me. Cassie was sitting on the edge of the bed wearing only a bra and a pair of boxers. It looked like she’d been reading a book. My eyes immediately locked on her boobs. They were pretty big and were pushing out of the top of her bra like she was starting to outgrow it. I forced myself to look up at her eyes, but she wasn’t looking at me. Neither of us said anything for a few moments.
“Uh, I just wanted to say I’m sorry for, um…” I trailed off, not sure how I should finish. There wasn’t exactly a Hallmark message for this kind of thing.
Cassie finally looked up at me, looking shocked. “*You’re* sorry? Jesus.” She got up and gave me an awkward hug. It was my turn to feel a bit surprised. She hadn’t hugged me in years. I’d been more expecting her to scream and maybe throw something. I could feel her boobs pushing firmly against my chest, and it was starting to have an effect on me. My shorts suddenly felt much tighter.
“It wasn’t your fault. I made you do it.” She said, her head resting lightly on my shoulder. “Do you hate me?”
“No.” I didn’t. In fact, hugging her like this was making me feel warm and lightheaded.
“Good.” She pulled away with a smile, but her smile quickly faded as she looked down and noticed my hard-on though my shorts.
“God, you are such a perv.” She punched me on the chest and walked back to her bed.
“Yeah, well, so are you.” I said, then as she turned back to glare at me I quickly lunged in and yanked her boxers down around her knees. Cassie shrieked and tried to hide herself as she reached to pull them up. I was still able to get a pretty good look. She didn’t have much hair on her crotch. Her penis was semi-hard and I could see that she had a small set of balls hanging down below it. It was pretty weird seeing a package on the body of a sixteen year old girl, but I was starting to get used to weird things.
“You are *so* dead!” She growled.
I decided to make a preemptive strike while she was still dealing with her underwear. I tackled her backwards onto the bed, managing to gain the upper hand as she kicked and growled at me. After a quick but frenzied struggle I was able to flip her onto her stomach and pin her hands.
Resting my weight on top of her, I started wondering what I could do to embarrass her and pay her back a little. The fact that I’d managed to pin her on her own bed while she was half-naked was probably pretty humiliating by itself. I wasn’t in much of a hurry to decide. Rare victories like this needed to be savored. Also, her butt was rubbing against me as she tried to push me off, and it felt kinda good.
“Let go!” She twisted underneath me and I felt my dick slip between the cheeks of her ass. It lay trapped between us, pointed up at the small of her back.
Sometimes I called her ‘Assie’ because her rear end was kinda big, but mostly just because the name pissed her off. Right now though it was nothing to joke about. Her boxers were only covering her ass halfway and the warmth and softness of her butt was feeling really good even through my shorts. I had an idea that I shouldn’t be doing this…it seemed almost like rape. It was the only position I could keep her down in though, and I knew that the second I let up she would kill me.
Just then I noticed that she’d mostly stopped struggling. She was still twisting around a little but it didn’t seem like she was trying very hard to knock me off. Mostly it was just making my dick rub against her ass even more. After a few moments it dawned on me that she might be doing it on purpose. I’m normally a bit quicker on the uptake, but the idea that Cassie could somehow *want* me to dry hump her butt just seemed crazy.
Crazy or not, it was starting to feel pretty damn nice. I decided to risk seeing if I could make it even better. She didn’t move as I let one of her hands go and worked my shorts open. I pulled her boxers down a little more, then moved back into place with my dick laying on her naked butt. I noticed quickly that the feel of skin on skin was much, much better. I moved my hips a little so that my cock rubbed slowly back and forth on the crack of her ass. I didn’t know if this was what actual sex was like, but it felt awesome.
I got so lost in the sensations of pushing against her butt that I didn’t realize I was about to cum until it was already happening. I couldn’t move, or even think as my stuff started launching out all over her back. I’d played with myself plenty of times, but this was the most intense cum I’d ever had. I moved off of her when it finally stopped, suddenly feeling ashamed of myself. Cassie’s back and shoulders were streaked and messy with my sperm. Not seeing anything else to clean up with, I used my shorts to mop it up. She was still laying there quietly like she had been the whole time. The only way I knew she was even alive was from her steady breathing.
I sat back on the bed, unable to keep from staring at her butt. There was just something about the curves of her hips and ass that was really hot. If I hadn’t already known she was ‘different,’ there would have been no way to tell from this angle. Acting on a sudden urge, I reached over and gently squeezed her ass with both hands. I kinda expected her to yell at me, but all I heard was something that sounded like a quiet moan. Wondering how far she would let me explore, I slowly pushed her cheeks apart until I could see her little pink butthole.
It looked clean and was glistening slightly with sweat. Feeling strangely drawn to it, I moved my hand down and rubbed it lightly with my thumb. She gasped and I felt her jump a little, but she didn’t say anything or push me away. I rubbed it again, then took my hand away and stood up. Maybe she liked me touching her butt, but I had no idea what I was supposed to do down there.
Cassie rolled over on her back and looked at me. Her dick was very stiff and lying back against her stomach, the tip all shiny and wet-looking. I could see the shapes of her nipples poking against her bra. She just laid there watching me as I sat down next to her and put my hand around her cock.
I started moving my hand slowly up and down, noticing how soft the skin felt despite how stiff it was. Even her dick seemed girly. I was thinking about sucking it a little when she suddenly moaned and raised her hips. I instinctively pumped a little harder as I saw a thick white jet of cum shoot out over my hand and land on her stomach. She kept flexing her hips as a few more spurts came out, then she fell limp with a long sigh. The sight of her cumming had made my own cock fully hard again. She saw it sticking up as I stood to wipe off my hand and her stomach. She groaned and rolled her eyes.
“Go to bed, Knob,” she said, tugging her boxers back up. “Just remember that I owe you a beating.” She grinned evilly and I made a hasty exit before she decided to make good on it.