Chapter Text
“Hey Anna, come here for a bit,” my older sister called from the other room.
“Fineee,” I called back, exasperated, but closing my laptop, and getting up regardless. Before leaving, I turned to the stuffed animal she had given me for my birthday, I always felt like one of its eyes had a different quality than the other, but I could never tell for sure. “Oh, Batty, what could she possibly want me to do this time?” I was used to Serena making me do all kinds of things, but somehow, she always managed to surprise me. Turning away from Batty, I left the room, and walked down the hallway to Serena’s room, prepared for just about anything.
As I pushed open the door, she immediately grabbed my arm, pulled me in, and closed the door, locking it. “Wh— Hey!” I protested as she dragged me along. She said nothing, all she did was pull me over to her bed and throw me down on it. “Hey! Have you lost it? What do you think you’re—” She covered my mouth.
“Quiet.” She said, getting on top of me, pinning me down. “I won’t have you being disobedient and letting anyone know about this. And, as insurance, I have the link to your OnlyFans, which I know is free, and if you speak a word of this, I’m sharing your real name with everyone there. Don’t worry, I know all the kinky stuff you get up to, kitten, so be a good little sister, okay?” She threatened, taking her hand off my mouth.
Oh, she’s serious. How the hell did she even get my OF? I wondered as I watched her lean in. I tried to squirm free, but to no avail. Her lips came down on mine. I’m kissing my own sister. Holy shit my biological sister is kissing me. It’d be a little less sketch if we were stepsisters, but this is just messed up. Did hell freeze over? My head was spinning as she kept going, and I thought I was going to faint when her tongue entered my mouth. Fucking hell this is beyond taboo. Her tongue was filling my mouth, and I couldn’t help but whine. I didn’t mean to; it just escaped my mouth.
She broke off the kiss, “Oh, somebody liked that,” she teased. My face felt red hot, and I was too stunned to talk. What the hell was going on? Suddenly, I became very aware of something poking me near my dick. Serena was really hard, and I realized that I was too. I couldn’t take my eyes off of her, off of my older sister. She had this devilish grin on her face, her brown eyes showed just how horny she was, and her straight brown hair hung down, tickling my face. “I have a post for your OnlyFans,” she said, sitting up and fishing my phone out of my skirt’s pocket.
I was too stunned to respond or move. I couldn’t even move my hands from their pinned position, despite the fact that she wasn’t pinning me anymore. I only felt more stunned as she unlocked my phone, somehow knowing the passcode, lifted up my skirt, and took a photo of my bulge. I tended to not wear shorts under my skirt around the house, so that gave her easy access. She turned my phone to me, showing me what I looked like. My face was bright red, my mouth still hung open from the kiss, and my brown eyes looked panicked. My curly brown hair made messy patterns on the bed around my head, and my bangs had flipped up, making my forehead visible. Both of my hands were frozen above my head as if I was being pinned. I couldn’t help but think that it made for a great photo, especially with another girl’s bulge visible in it as well. Another girl? The hell am I thinking! That’s my fucking sister! “Serena what the hell has got—” She smacked me. Hard.
“Hush, kittens don’t talk. All you’re allowed to do is make cat noises, moans, whines, and groans unless I ask you a question, okay?”
“Serena, I’m your sister! What is happening?”
“I know, Annabelle,” she said flatly before smacking me again.
“Hey!”
She smacked me again, “Know your place, kitten. If you don’t start behaving the punishment will get more severe.”
“Serena, I’m not playing around!” Smack. That one really stung but I kept going, “This is wrong! I won’t say anything just let me go!” Smack. My face was starting to hurt.
“It’s wrong, is it? Come on, your girl is so excited, isn’t she?” She paused. “Ugh, fine. I’ll let you go. But you’re dead if you talk about this with anyone,” she said, obviously annoyed. Nonetheless, she got off of me.
I got up in stunned silence, trying to process what just happened. I looked over at Serena, and realized she was still on my phone, “Hey, get off my phone already!”
“Quiet you. Just let me send this photo to myself. God your phone’s organization is so dumb, Jesus. Aaaand done,” she said victoriously, handing my phone back to me.
I snatched it away, put it back in my skirt pocket, and hurried out of Serena’s room. My hand struggled with the lock for a moment, but I got out, closed the door, and tried to walk normally back to my room, when my mom walked up the stairs and turned towards me. I felt so panicked, my face was beet red.
“Hey Anna, is everything okay?” She asked, concerned.
“Mhm, yep, everything is okay, mommy, you don’t need to worry.”
“Are you sure? Your face is all red, and you seem kinda unsteady.”
“Yup! Everything is okay!” I said, walking by her, feeling really awkward. “Serena just needed help moving her dresser!” I lied, “She dropped something behind it and needed my help to move it! It was really heavy so that’s why my face is red and all.”
“Oh, okay honey. Well, as long as you’re okay!”
“Mhm!” I turned away from her and kept walking towards my room without looking back. Upon making it inside, I closed the door and sat on the floor, leaning against it. My mind was racing, struggling to process what was happening. Serena threatening me was normal enough, that I was used to. We used to fight all the time as kids and as we got older, she started to blackmail me to get me to do things that I wouldn’t normally do. The first time I bought a vibrator, I was 16 at the time, she threatened to tell on me to our mom unless I got naked in front of her and her friends. They all laughed at me and teased me since I’m pretty small when I’m not hard. Then I got hard, and that only made them tease me more. I suppose I should’ve seen it coming that she’d end up kissing me like that, but it’s still so wrong.
I found myself stuck on the taste of her lips, and the feeling of her tongue in my mouth. A part of me even regretted having her stop. There was something wrong with me. My body craved more; I was so worked up. Getting up off the floor, I pulled my phone out of my pocket, and unlocked it as I flopped into bed with my stuffed animals. I had almost forgotten about the photo Serena took of me, it made me feel all hot just seeing it pop up on my screen. Without thinking about it, my hand found its way under my panties, and I began touching myself.
I had definitely lost it. I was touching myself to porn my older sister and I had made. As I started getting closer to finishing, I noticed my door start to open, and I snatched my hand out of my panties. Serena pushed my bedroom door all the way open, walked in, shut it, and locked it. Her hair was put up into a ponytail now. My eyes went wide.
“I knew my little sis was into it. I mean, I spy on you all the time. There are hidden cameras in here to make it easier for me.” I knew there was something off about the plushy she gave me for my birthday. Wait, cameras? As in multiple? “I already knew you were a degenerate,” she continued, “but come on. You thought you could lie to me? I know you have that photo pulled up on your phone and I know that your hand was in your pants. You’re not getting away from me, Annabelle.” Shivers ran down my spine, I pushed myself up, and backed into the corner of my bed. I knew she had me trapped. “Such a dirty little kitten. So, about the question that I asked you before, are you ready to be good, or will I have to discipline you?”
“Wait, Serena, please. I. This is messed up.” She stopped walking towards me and turned towards my closet. I decided to continue rather than try to figure out what she was up to, “Like, come on. This is an act of incest for fuck’s sake. Don’t you think we shouldn’t be doing this?” She opened my closet and began rummaging through my drawers, specifically the ones I used for storage, not clothes, and I realized what she was going for: My toy chest. “Hey, wait!” I got up from my bed and began walking towards her, “Dude, this isn’t funny! I’ve tolerated it when you’ve teased and blackmailed me in the past but I’m not doing this!” I reached my hand out to her, but she whipped around, grabbed my hand, and cuffed my right arm.
“Oh, princess, you really couldn’t let this happen the easy way now, could you?” I could see that she was taking delight in all of this; this game that I was trying not to play. I froze, fear in my eyes. Then, just as swiftly and precisely as before, she grabbed my left arm, pulled it back behind me, cuffed it, then connected it to my right, and finally locked me in.
“Girl, what the fuck has come over you? Come on, just let me go! I’ll play whatever game you want so long as you’re not making me commit an act of incest! You don’t even need to blackmail me to get me to do things for your friends! I’ll just do them! Please, Serena.”
She absentmindedly checked her nails, 8 of them were sharpened, 2 were short. She didn’t say a word to me, she just turned back to my drawer, and continued rummaging for materials. I was beyond fed up. “Stop this, Serena. I. I don’t know what’s happening and I’m really confused. Fuck, my own sister kissed me today! And then when I was finally back in the safety of my room, convinced it was all over, I started having these weird feelings. It’s so wrong to do any of this, y’know?”
She replied without turning to face me, “Yeah, but it made you excited, didn’t it? To kiss your sister; to commit an act of incest?” She really drew out and accentuated the word “incest.”
My face went red, and I was unable to answer. Maybe a part of me wanted it, but I knew it was wrong. It was beyond wrong. Maybe that’s what was so exciting about it.
I was about to try to answer her when she whipped back around on me and put a collar on my neck. The collar was black and purple, black ribbon as the base, with a smaller purple band of ribbon going around it. It had black lace on the top and bottom of the purple ribbon, and in the center was a bell. On either side of the ring that had the bell, about an inch away, were metal hearts set in place by the purple ribbon. On the same ring as the bell there was a tiara charm, and over the bell there was a purple bow. A leash was already attached to the collar. I had no clue where she got the collar from, as it wasn’t one of mine, though it perfectly matched the kind of collar I liked. Serena must’ve really done her research.
She led me back over to my bed with my crop in her hand. Then she took my glasses off before pushing me face down on the bed and tearing my skirt and panties off. “Alright, kitten, from now on, you’re going to be a good girl, okay? And if you’re not, I’ll punish you. I know you’re a massive painslut, so this should be easy for you. Oh, sorry, this isn’t the punishment yet, it’s just the warmup act.” Smack. I suppressed a grunt. “Kitten, I don’t hear you counting for me.”
I knew I had been beat. None of my words would get through to her. Everything in me wanted to protest, to struggle, but she was just stronger than me. It was hopeless. I remembered all the times she had blackmailed me, and how I had never been able to escape. I couldn’t escape getting naked in front of her and her friends; I couldn’t escape having to go to high school in women’s clothes before I was fully out; I couldn’t escape having to be her servant for a week. I knew it was over, so I gave in and let my horniness wash over me. Submitting to my sister was my only option, and part of me loved knowing that it was her. I loved how taboo it was. My lust overtook me, and I knew there was no going back. “One.” I counted.
“Oh, such a good girl! You’ve finally submitted, haven’t you? You’re so obedient kitten, so easy to manipulate,” Serena cooed. I couldn’t see her, as I was face down on the bed, but, somehow, I just knew that she had that mischievous smile on her face.
Another smack, “Two.” Smack, “Three.” Smack, “Four.” And we kept up this routine. I knew how it went; I’d done it with other partners, and I had a good pain tolerance despite how physically weak I was, so I was sure I could keep it up. As she got into the 10’s, I began grunting or groaning as she smacked. I could practically feel how much she was enjoying this. The numbers went by, the pain kept getting worse.
She paused as I counted number 50, and, naively, I hoped it was over. She only paused to lift my shirt up, giving her access to my back. She raked her sharpened nails down, and I moaned despite myself. The pain just felt too good. “Oh, somebody liked that,” She taunted, and began smacking again.
“Fifty-one.” The routine kept going, except now she’d randomly scratch down my back. As she reached 100, my ass felt like it was on fire, and my back was really starting to hurt too.
Around 120, she put one finger in my mouth, and I tasted my own blood. It tasted way too good, and I greedily sucked it off her finger. By this point, each smack was like I was on fire. I wasn’t one to pussy out though, I’d keep suffering through each and every bit of pain, and I’d fall in love with it.
After about 150, my body had confused pain for pleasure, and I felt myself getting close. My legs started shaking. “Oh my, what do we have here? Is my little sister gonna cum just from me beating the shit out of her ass? I’d love to watch it, come on, princess. Cum for your older sister.” I felt her hand on my back, presumably picking up more of my blood, and then it was in my mouth. The taste of my own blood was always so amazing. “It’s so wrong, isn’t it? Just give in. If you really cum off of this, I’ll let you stop counting. You’ve been so obedient, and I really don’t think you’ll miss a number, anyway. From all my spying, I’ve never seen you miss one. Now, cum for me, kitten!” And it was like a dam broke. I came off of nothing but pain. My body shook and spasmed, and I moaned and whined. I couldn’t even make cum anymore after the years on estrogen, but my whole body felt the orgasm. It was amazing to cum for my older sister and I wanted more. I wanted her to break me more. I knew she was only getting started.
She resumed smacking me with the crop. Somehow, my body felt like it was even more on fire than it was before. Eventually, after around 200 total smacks, she stopped. My back and ass felt like they were gonna die, and the metallic aftertaste of blood still lingered in my mouth. I felt like I was in heaven. She undid my cuffs and stripped me the rest of the way naked before redoing them. Pulling me up by my hair, she whispered in my ear, “Now the punishment begins.” All I could do was whimper. She knew everything about me and had been spying on me for God knows how long. I had no clue what she could possibly be up to.
She turned back to my toy chest, and I was unable to see what she was doing. My head was still fuzzy from all the pain. When she turned back around, she had a bit gag and blindfold in hand. Before I knew it, I was deprived of my sight, and I could no longer speak coherently. I tried to say, “Hey wait!” But all I said was “Hayy waii!” As if I had a lisp that affected every letter of the alphabet. I thought I heard the sound of clothing coming off, but I couldn’t be sure if she was kicking mine around or taking her own off.
“Hush, you’re being such a good girl, all you need to do is purr for me,” She instructed, pushing me face down once again. I couldn’t see anything, but I felt her begin preparing my ass with lube. Then I felt something push inside me. A finger? I moaned through the gag. “Aw, are you enjoying that kitten? Come on, purr for your big sis.”
I complied with her orders; at this point I was fully at her mercy. A deep rumbling sound came from the back of my throat. “Awww such a cute kitty!” Serena cooed, mockingly. I felt my cheeks get hotter. I was confused on where the punishment came in, as she was still doing things I wanted. I didn’t have long to consider before my brain broke, however, as her fingers came out, and I felt something push against my ass. It wasn’t one of my anal vibes, I was sure of that much. It could’ve been a dildo, or Serena’s actual dick. I couldn’t help but moan and attempt to say fuck through the gag.
“Oh, such a good sister!” She said, panting. Now I was sure it was her dick. “You like my dick in you?” She asked, as she pushed herself all the way up against me. She felt big, and all I could do was moan. Feeling her hips hit my ass reminded me of the pain from earlier, and it was like I was on fire all over again. She began fucking me from behind and I felt myself being less and less able to think of anything but the feeling of my own sister inside me.
It didn’t take long for me to get close, and I tried to tell her, but the gag definitely impeded my speech. “Yeah? Are you gonna cum already?” She said between breaths. “You’re so pathetic, you haven’t lasted very long at all.” I made a pathetic whining noise in response. At that, she grabbed my hair and pulled. She really knew all of my weak spots. The fire from my ass, the ache on my back, the pleasure from getting railed, and the sensation of my hair getting pulled had made me get really loud. We were gonna get a noise complaint for sure.
“Cum for me, princess! Cum for your older sister!” She said, picking up her pace. My body began to feel tighter, and I moaned, shook, and convulsed with her still inside me. But she didn’t stop. Even after I was for sure done, she didn’t stop, and horror dawned on me as I realized she was gonna torture me with my own orgasms. I couldn’t even protest with the gag on. I absentmindedly wondered how many orgasms she could get out of me.
Staying at its peak, the pleasure was enough to destroy my brain. My mouth moved on its own, desperately trying to speak against the gag, “Quititquititquititquit. That’senough. Fuckfuckfuckfuck. That’senough.” I begged, and I knew it was completely incoherent. The gag had made sure of that. I knew she wouldn’t stop, and some part of me didn’t want her to, even if it was breaking me.
The time between orgasms began to shorten after the first, and by the fourth my body felt like it was perpetually in orgasm. I couldn’t stop begging for her to stop, and my moans had practically turned into screams. Serena had started to moan too; Her moans were beautiful, and I wanted to hear more of them. Somewhere along the line, I seemed to have forgotten that I was getting fucked by my sister, though, to be fair, I couldn’t see her. On the other hand, I could definitely hear her. My body had reversed the sensation from when she was beating me with the crop somewhere around the 5th orgasm, and I began confusing pleasure for pain. It was so much that I was sure it hurt. By the sixth I felt like I was gonna die, and I really wondered how high her stamina was. The only two things I could hear were her railing me, and our moans. They started blending together, almost like they were forming chords. The rhythm began to overlap into some kind of sexual symphony.
I wasn’t even sure I was processing pleasure anymore. All I could do was moan at the volume of a scream and attempt to beg for it to end. I wasn’t even consciously begging; my mouth was just moving.
The seventh was when I finally felt her cum. As her nails dug into my sides, I heard her moan so loudly that I was sure our mom was gonna hear. Then again, if she hadn’t heard me, she wasn’t gonna hear Serena. I felt her shake, and she stopped fucking me, and I thought it was over. My mind was beyond broken. With my senses diluted, I had lost all sense of time, and I wondered how long she’d been fucking me. She wasn’t pulling out, though, and I realized that she wasn’t done with me. Whenever she blackmailed me in the past, there was always some kind of caveat to whatever she had me do, some way that she prolonged teasing me. Once was never enough for Serena, she always wanted more, and despite how broken my mind was, I wanted more too. Being punished felt too good but being punished by my older sister felt even better.
At length, she continued, and once I hit the eighth orgasm, I was in the same state as I was before she stopped. I resumed my screaming, and my mouth kept moving, attempting to say “Enoughenoughenoughenough. Pleasepleasepleaseplease.” But the gag muffled it. I began sobbing and she only fucked me harder. I was screaming and sobbing and, somehow, I knew it was getting her off. Serena grabbed my hair again, pulling my head up, and tears were streaming down my face. I wasn’t sure if I was in heaven or hell.
After the tenth, I was too broken to moan loudly anymore, mostly I just groaned, panted, and attempted to say “fuck” through the gag. To add insult to injury, she started teasing the head of my dick. I was more sensitive than most trans girls there, and I often couldn’t stand being touched there. All I could think was that I was gonna die. Desperately, I began trying to plead through the gag again, but I couldn’t form words, and Serena simply ignored me. All I could do was shake as I approached the eleventh. Once I hit the eleventh, everything after that melted together.
In total, I think I came around 13 or 14 times, and Serena came three times. After what felt like an eternity, she pulled out, and I felt her flop on the bed next to me. I was still shaking from all the orgasms. She was breathing hard, and after a little while she said, “While I could just leave you there, blindfolded, gagged, and cuffed, you were such a good girl for me, princess, so I’ll help you out.”
She helped me up into a sitting position before reaching up into my hair, and undoing the blindfold, returning my sight to me. Everything was bright, and Serena looked so pretty. Her hair was all messed up, and she looked like she just had a workout. Her shirt and bra had also come off at some point, and her tits were gorgeous; I couldn’t help but stare. Then I watched as her hand reached around, and I felt her undo the bit gag. I realized that my jaw had really started to hurt, so having it come off was a welcome change.
Before the gag was fully out, I felt her scratch behind my ear a couple times, and I couldn’t help but nuzzle my head against her palm. “Aw, such a good kitten,” She cooed, finally pulling her hand away, taking the gag and a line of spit with it. My brain was too broken to speak, and I was still experiencing aftershocks from all the orgasms. Undoing my cuffs, she looked into my eyes, “You were such a good little sister for me, thank you, Annabelle.” And as the other cuff came off, she went back to petting me, and I couldn’t help but lay down in her lap. “From all my spying, I knew you were a kitten, but somehow it just didn’t register that you are the human equivalent of a lazy house cat.” As she continued petting me, I started making purring noises. I was just really happy to be pet, even if it was my sister, and super taboo.
Then my eyes went wide, my body froze, and it dawned on me what I had just done. I looked up at Serena, and she had such an evil smile on her face. Holy fuck what did I get myself into?