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Introduction:

My second and last installment
A few days later she came home looking upset. I’d been planning to mess with her again and see what happened, but one look at her face told me that it’d be a bad idea. She stormed past me up to her room and slammed the door behind her. A little while later I was distracted from the TV by a crashing sound from upstairs. It sounded like Cassie was screaming and throwing things. She’d thrown hissy fits before sometimes, but this one sounded bad.

I wondered what was wrong but I knew better than to bother her then. She would probably just try to bounce a lamp off my head or something. I waited until the noise quieted down, then climbed the stairs and went to her room. I couldn’t hear anything on the other side of the door. I knocked. No answer. I knocked harder.

“Go away,” she answered. Her voice sounded faint and shaky.

Never one to obey orders, I slowly opened the door. Her room was a mess and the mirror over her dresser was busted. I started to worry that she’d hurt herself. She was lying sideways on the bed and clutching a pillow over her face. Her body was shuddering like she was crying, but she wasn’t making a sound.

“Are you ok?” I asked. When she didn’t answer, I made my way through the wreckage and sat down next to her. I stayed there for a few minutes until she stopped crying and looked at me from under the pillow. Her eyes were wet and red.

“I thought I told you to go away,” she said, wiping her cheeks. She didn’t seem to have the strength left to even glare at me.

“Yeah, but I heard a bomb go off and wanted to see if anyone survived.”

“Funny.” Cassie rolled over with her back toward me and curled up into a ball. “Now leave me alone.”

“So are you ok?” It felt like a dumb question, but it was the only one I could think of.

“No.”

“You want to talk or anything?”

“No.”

“Fine.” At least I’d tried. I was sure I’d find out more about it later when mom got home.

She didn’t get in until around midnight. Cassie waited up for her. I was supposed to be asleep, but I snuck out of my room and listened from the top of the stairs as they talked in the kitchen.

Apparently Cassie’s old boyfriend had gotten pissed off for some reason and started blabbing to everyone that Cassie had a dick. A guy came up behind her at lunch and grabbed her crotch to see for himself. I knew she wore an athletic supporter to hide the bulge, but if he’d gotten a good feel it would’ve been easy for him to tell what she had down there. Cassie had elbowed him in the gut, then he’d shoved her and called her a freak. Some other kids stepped in before it went any further, but the asshole and his friends had hounded her all day.

“Now everybody looks at me like I’m a mutant or something,” I heard Cassie say. “I hate this body! I hate it!” She started crying again and I heard mom trying to comfort her. I hadn’t really thought about it much before, but I realized Cassie was pretty unhappy about being different. It pissed me off those guys had messed with her like that. I wished I was older and bigger so I could do something about it.

Whatever mom said to her seemed to help though. They started heading upstairs, so I ran and got back into bed. They talked a little more in Cassie’s room and then said goodnight. I pretended to be asleep as mom came in to check on me. She sat down on the bed next to me and I felt her run her hand over my hair.

“Go easy on your sister, Bobby.’ She told me. “Things are hard for her right now.” I wondered if she knew I was awake. Probably. She always seemed to know. She kissed me goodnight and then left.

I waited until I was sure she’d gone to bed, then I got up and went down the hall. I opened the door to Cassie’s room as quietly as I could and slipped inside. I followed the sound of her soft breathing over to her bed and slid quickly in under the blanket, nestling up against her like I’d used to do when we were little. She tensed up for a second when I put my arms around her, but then relaxed again. It felt really good holding her like that. I hoped it felt nice for her too.

The next thing I knew mom was waking us up for school. She didn’t seem mad that I’d gone to sleep in my sister’s bed. If anything she seemed to think it was cute. Cassie didn’t want to go, but mom reminded her about the talk they had last night and Cassie eventually went. I felt bad for her. I’d had my share of teasing in school and I’d hated it, but what she was going through was probably a million times worse. I hoped we’d still have a house left after she got home that day.

When Cassie did get home I was surprised to see that she was in a decent mood. She wasn’t exactly happy, but she seemed more like her normal self. So normal in fact that I couldn’t resist the urge to snap her with a damp rag when we were cleaning up the kitchen. She was leaning over and her ass was just too tempting a target. The cloth impacted against her butt with a startlingly loud crack. She yelped and spun around with murder in her eyes. I ran, laughing like a maniac the whole time.

She cornered me in the living room before I could make the stairs. I tried to fake her out and jump past, but she caught me and tackled me down onto the couch. I did my best to escape, but her wet hands gave her an unfair advantage when grabbing my clothes. They also hurt when she pinned me face down with her knees in my back and started spanking me hard on the butt.

“If you’re gonna act like a brat, you’re gonna get treated like one,” she said, her voice sounding stern though I was sure that she had a huge grin on her face. It wasn’t really a typical spanking either. She rested her hand on my butt for a little while in between smacks, sometimes even squeezing it a bit. It was embarrassing and the spanking part hurt, but the more gentle stuff felt kinda good. After a minute she suddenly reached underneath me and put her hand on my crotch like she was checking to see if I was hard. And if course, I was.

“Perv.” She gave me another hard whack on the ass, then let me up and went back to the kitchen. I followed slowly, my rear end smarting and my dick hard as a rock. I watched Cassie’s butt as she walked, suddenly feeling more horny than I ever had in my life. She went back to the sink and a few seconds later I moved up from behind and grabbed her, my dick pressing against her ass. Even though I hadn’t planned it that way, my hands ended up right on her boobs. They felt warm and heavy and really nice in my palms.

“Stop it.” Cassie pulled my hands off her chest and wriggled away toward the counter.

I was way too turned on to listen. I caught her and put my hands back on her tits, squeezing them a little as I started rubbing against her like I’d done on her bed. I felt like I was going to cum even with our clothes still on. I kept expecting her to stop me again, but she didn’t. She just leaned forward, putting her hands on the counter as I played with her boobs and slowly humped her butt. After only a few minutes I started to cum, feeling a rush of sticky heat fill my underwear. I rested up against her for a bit, feeling her boobs moving slowly up and down in my hands as she breathed. It felt really neat.

Suddenly she turned around and pushed me down on my knees. I watched as she quickly undid her pants, her stiff cock falling out almost right away. I didn’t hesitate. I started sucking it, hearing Cassie groan softly as she flexed her hips toward my mouth. I reached around and started feeling her butt as I sucked on as much of her dick as I could. The look on her face told me that she was really enjoying it, and I started to wonder what having my own sucked would feel like. She put her hand on my head and ran her fingers roughly through my hair, then a few seconds later her cock got even harder and started squirting in my mouth. It didn’t taste as gross as I remembered, and I decided to swallow it and see what would happen. It didn’t kill me. Cassie moaned and leaned back against the countertop, and I kept sucking her gently until she pushed me away. She gave me a weird little smile as I stood up, then smacked me again on the butt.

“Okay,” she said, suddenly looking serious again. “Stop fucking around and finish your chores.”

A month went by. Cassie and I messed around a few more times but we didn’t really do anything different. Then it was my fourteenth birthday. Cassie had hinted earlier that she was going to give me something ‘special.’ Of course with her that could mean anything, so I wasn’t sure if I should be excited or afraid. I ended up forgetting about it entirely until the night of my birthday.

Everyone had gone to bed. I was almost asleep when I heard the quiet noise of someone opening my door. I rolled over on my back to look, and In the dim blue glow from my clock I could see it was Cassie. She didn’t say anything, she just sat down on the edge of the bed and pulled the covers down to my knees. I was wearing only a pair of briefs. She reached out and put her hand flat on my stomach, resting it there for a second before running it slowly down along my thigh. I didn’t know what she was planning, but the way she was touching me was quickly getting me hard. She seemed to notice and moved her hand up over my crotch, rubbing my hardon lightly through my underwear. It felt great.

Cassie tugged my briefs down and leaned over, seeming to look at my dick for a while. Then I held my breath as she suddenly grabbed my cock and lowered her head down to it, sliding it almost all the way into her mouth before she started moving her lips and sucking. Oh. My. God. It felt so warm and wet. My whole body started trembling and I felt my hips pushing up like I was trying to hump her mouth. I hadn’t imagined that anything could feel so good. It only took her a minute or so to make me cum, and all I could do was lay there and gasp as I felt my dick jump and start exploding in her mouth. Cassie slowed down but didn’t stop. I couldn’t tell if she was swallowing it or not, but she didn’t take her mouth away even after I was done. I was still so hard it almost hurt. When it was obvious that I wasn’t going soft she started blowing me again, holding my cock around the base while she rubbed my thigh with her free hand. I watched her head bob up and down, thinking how incredibly hot it was that she was sucking my dick. This time I lasted a lot longer and was able to enjoy it more. When I came in her mouth again it was over with quicker than the first time, but it felt even more intense.

Cassie let go of my cock and sat up, wiping her chin with the back of her hand. She looked at me and grinned as she smacked me lightly on the thigh.

“Happy Birthday, Knob,” she whispered.

“Thanks.” I meant it. That was easily the best present I’d ever gotten. She threw the covers back over me and left. I fell asleep almost immediately.

More time passed. I started becoming friends with a girl I knew at school. Her name was Gail and she was kind of shy and nerdy, but in a cute way. We were hanging out more and even went over to each others' houses a few times, though it still seemed like just a ‘friends’ thing. There were plenty of times when we were alone together but I was too nervous to try anything. I wasn’t sure that she wanted me to anyway.

Then Gail mentioned that her parents were taking a trip and wouldn’t be home all weekend. She seemed even shyer than usual when she asked if I’d like to come over on Friday night after they left. I think I said yes, though my pulse was suddenly pounding so hard that it drowned everything out. My imagination was racing all week long as I wondered what she had in mind. I wasn’t really expecting to get in her pants or anything. Despite what had already happened with Cassie I would’ve been happy just making out with a girl, even though I was worried I’d mess it up somehow.

By Friday afternoon I was so nervous I could barely keep still. I was sitting on my bed watching the clock when a sudden sound from my doorway make me jump. It was Cassie, standing there with a smirk on her face.

“Lemme guess,” she said, “you’re sneaking over to your girlfriend’s house tonight.” My sister leaned up against the door and crossed her arms, the teasing grin never leaving her face. “Want me to buy you some condoms? Lube maybe?”

“We’re just friends, ok?”

“Yeah, right. That’s why your hands are shaking. What, afraid she’s gonna molest you and take your precious virginity?”

I glared at her, hoping her head would melt.

“Well fine,” she said, straighening up and turning to leave. “I *was* going to offer you some advice, but if you’re just gonna be a little douche, forget it.”

I sat there for a few minutes as I fought a painful battle with my ego. When it finally surrendered, I got up and went to Cassie’s room where she was busy folding clothes.

“What advice?” I asked, hoping she wasn’t just messing with my head.

“Oh nothing. I forgot you’re fourteen now. I’m sure you know everything there is to know about girls.”

I bit my tongue before I could say something stupid, like how she wasn’t exactly an absolute expert on girls either, what with her cock and all. “Hey, I know plenty. I just don’t wanna do anything that’ll gross her out. If something does happen, I mean.” I hesitated, feeling lame. “I haven’t exactly made out with a lot of girls or anything.”

Cassie looked at me. “You ever even kiss before?”

I stared at the floor, embarrased.

“Don’t sweat it, Knob. Its not hard. Just do it like they do in the movies.” I looked up and saw a wicked grin slowly spreading over her face. “Help me fold these and maybe I’ll show you a few things.”

I helped. When everything was folded neatly and put away, Cassie sat on the bed and motioned me to sit down next to her. I sat down, wondering exactly what it was that she planned to show me.

“Okay, the main thing is to start off slow.” She said, moving in and pulling my arm around her shoulders. “Don’t get too grabby and stuff, that’ll freak her out. Just get close and the rest kinda takes care of itself.”

I slid myself over further until her body was pressed snugly against mine, my hand resting on her upper arm. She smelled good. Cassie lifted her face up toward me and closed her eyes, her lips only inches away. I wasn’t sure how far she wanted to take this, but the opportunity was definitely there.

“This is the part where you kiss her, dumbass,” she said quietly.

I leaned in toward her, keeping my eyes open to watch her reaction as I touched my mouth to hers. Her lips felt incredibly soft and warm. She didn’t respond right away, but after a few seconds she started kissing me back. After a minute or so she opened her mouth and I felt her tongue pushing against my lips. I let it in and started chasing it with mine, my dick getting hard almost instantly. Kisses like that had always seemed gross when I saw other people doing it, but my opinion was quickly changing now that it was happening to me.

Cassie was slowly edging herself into my lap as our kissing got hotter. I pulled her closer against me, feeling her tits pressing firmly against my chest. She only kissed me harder and slid her hands around my waist.

It suddenly occurred to me that I was making out with my own sister. My response to that was to slide my hands down and grab her ass firmly with both hands. Cassie moaned and started sucking on my bottom lip. I got the feeling that she wasn’t playing around. I wasn’t exactly sure what was happening here, but I did know that I liked it.

After a few more minutes I let go of her ass and moved my hands up front. She moaned again as I palmed her boobs. I squeezed them and she started grinding herself slowly against my lap. I could feel the bulge of her hardon rubbing up against mine, and for some reason that made me hornier than ever. I broke the kiss and lowered her down onto the bed. I’d seen this part in movies before too, the part where they get naked and fuck like crazy.

Straddling her, I grabbed the hem of her shirt and pulled it up. She surprised me a little by raising her arms and helping me take it off. With that out of the way, I reached under her back with the intent of taking her bra off too, but I couldn’t seem to unhook it for the life of me. Finally Cassie did it, and the second it came loose I caught her naked boobs in my hands and gave them a firm squeeze. It was my first time feeling them without her bra in the way, and they felt great. Warm and soft and firm all at the same time. I leaned in and kissed her again, feeling her nipples getting harder each time they brushed against my fingers. I suddenly wondered what they’d feel like in my mouth, and I decided to find out. I moved from sucking on Cassie’s tongue to sucking on one of her nipples. She gasped and moaned softly as I switched back and forth from one to the other. She seemed to really like what I was doing, but I was too damn horny to concentrate on it for long.

I undid her jeans and pulled them off. Her boxers joined them on the floor a few seconds later. I was a little surprised that she wasn’t trying to stop me. Cassie usually liked to make things difficult, but this time she was just laying there with her eyes closed. Naked. I’d never seen her fully naked before, and I had to stop for a minute just to take it all in. Her big firm boobs were rising and falling quickly with her breathing. I moved my eyes down her flat stomach and over the wide curves of her hips. Her dick was stiff and sticking almost straight up. I ran my hands slowly up and down over her smooth legs, suddenly at a loss for what to do next. She was so sexy that I wanted to touch all of her at once. I also had an incredibly strong urge to fuck her, but I couldn’t. So I did the only thing I could think of. I turned her over and undid my pants. I slid them down and off, then lay on top of her with my body pressed firmly down on hers. My dick nestled right up between the firm cheeks of her ass like it belonged there. Her naked skin felt awesome underneath me as I started humping against her butt.

Cassie was moving too, grinding her big ass up at me in little circles. It felt great, but I still wanted more. Then I got an idea. I gathered up a bunch of my spit and rubbed it over both my dick and the cleft of her ass. When I started moving again, the slipperyness felt much better. After a minute I decided to try something different. I took hold of my dick and started rubbing it up and down firmly over the length of her crack, sometimes poking it in to see what she’d do. She didn’t say anything, though she was breathing really fast and heavy. I applied a little more pressure, really liking how it felt to have the head of my dick wedged firmly between her cheeks.

Suddenly, I felt a sensation like something pushing back against the tip of my cock. I eased off a little and then pressed in again. Cassie groaned softly and something seemed to nip at the head of my dick. It took me a second to realize what it was. Her butthole. I froze for a moment. I knew that you could have sex that way too, but it was something I never imagined myself doing. A weird thrill shot through me, and I just had to see what would happen if I pushed a little more. She groaned again and I felt the pressure against the head of my cock increase.

“Wait…” Cassie said, her voice sounding unusually husky. “Top drawer…Vaseline.”

I jumped up and went to her dresser. Sure enough, there was a tube of vaseline in there. It was actually some kid of lotion, but it was good enough for me. My hands were shaking a little as I squirted some out and rubbed it all over my dick. I rubbed some more into the crack of her butt and quickly got back on top of her. I found the spot again and pushed slowly, this time feeling the pressure slowly spread around the head of my dick. It was going in. Then she clamped down on me and I almost came right there. After a second she relaxed again, and I felt my cock pushing a little deeper inside. It felt completely awesome. Her butthole kept clenching at my dick like it didn’t want it there. Cassie was gasping and digging her fingers into the sheets. For a second I wondered if it hurt, but then I felt my pubic bone come to rest against the soft skin of her butt and realized that I was all the way inside. Balls deep in her ass.

Instinct took over, and I grabbed her by the shoulders and started fucking her. It was so intense that I forgot about being gentle or anything else, the only thought in my head was the feeling of her butt squeezing down around my cock. Cassie squealed and squirmed underneath me, her voice alternating from low grunts to high-pitched squeaks. She might have been trying to push me off her, but by then I was too far gone. I felt her ass grabbing at my dick and her body shuddering underneath me, and with a final thrust I pushed in deep and started cumming harder than I ever had before in my life.

I shuddered, my cock jerking spastically in the tight grip of her butt. As the last pulses faded I fell limp on top of her body, my head spinning. She was panting and groaning softly, the muscles in her ass still trying to push me out. I started feeling guilty at how I’d lost control and pulled out of her as gingerly as I could. I checked my dick, feeling relieved when I didn’t find any blood or poop on it. I wiped it off with my underwear and sat down next to my sister. She hadn’t moved much. I wondered if she was ok. I started rubbing her back a little, hoping she wouldn’t hate me. After a few seconds she suddenly rolled over and punched me hard on the arm.

“Ow,“ I replied.

“Well that’s what you get. That hurt!”

“Sorry.” Looking more closely, I saw that the sheet underneath her and the middle of her stomach were all wet with cum. There was lot of it, and it sure wasn’t mine. “Doesn’t seem like it hurt *too* bad though.”

She realized what I was looking at and punched me again, but not as hard this time. She got up and grabbed a towel, seeming embarrassed as she wrapped it around herself and headed for the bathroom. I gathered up my clothes and left, still dazed by what just happened. I had another hour left before I was supposed to go over to Gail’s, but I definitely wasn’t feeling nervous anymore. When Cassie was done in the bathroom I went in to take a shower. A minute later she opened the door and poked her head in.

“Just don’t expect all your dates to go like that, Knob. You’re not even close to being that smooth.” She left before I could think of a witty response. Anyway she was probably right.

After my shower I went back to my room and got ready. I was still looking forward to seeing Gail, but I was nowhere near as excited as I’d been earlier. I’d just had sex with my sister. Real sex. In the butt. Anything else that happened that day was bound to be a letdown.
52 comments

Anonymous readerReport

2014-12-12 19:35:29
would love to see more of this story, just one thing I would change is more dialog during the sexual encounters

Anonymous readerReport

2014-11-30 22:27:57
more please

Anonymous readerReport

2014-10-05 09:16:33
Those were so sexy and I'd loved how they only did things at a slow speed

Anonymous readerReport

2014-09-12 20:08:24
Please keep it going!

Anonymous readerReport

2014-08-02 10:41:12
Great story. I love the steady progression of their sexual encounters, as well as addressing the emotional issues of growing up transgendered that is so often left out gives it a very genuine feel. Bringing in new characters while further developing the relationship between the siblings would make this a site favorite.

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