My Sister the Bully

(All characters are 18+. This story includes instances of nonconsent.)

My sister Jenna and I never really got along. We were close enough in age to be constantly stepping on each others' toes all through grade school. Always competing for grades, never sharing friends. We were always fighting, for as long as I could remember.

When Jenna went away for college, a year ahead of me, it was a blissful reprieve. I quickly got very used to being effectively an only child. Not having to negotiate who would get the car. Not having to fight for food at the dinner table. Generally having a lot more privacy.

My senior year of high school ended, and over the summer, I had a part time internship in an office that was mostly men, and entirely over forty, other than me. I was looking forward to starting college in the fall. My hometown was starting to feel small.

Jenna came home from college over her summer break. The peace and quiet at home was ruined. She would talk loudly on the phone at all hours, play video games without headphones. Many nights, she had friends to catch up with, and borrowed the parents' car to do that, effectively nixing most of my social life. She was supposed to be a year more mature than me, but she was still a petty tyrant to everyone around her.

Around the same time, I was feeling really awkward about still being a virgin. Not just because I wouldn't know what to do if I did get with a girl, but because I was starting to worry that I never would. I went to an all-guys school, I was in the boy scouts, I played sports, all my time was with the guys. Even my summer job. I knew a few girls, but not very well. Mostly other guys' girlfriends. If I were gay, I could've had all sorts of fun. But I was still a virgin. Maybe that would change in college, but I would still be me, and if that was the problem, it would still be a problem on campus.

While Jenna had been away, I'd gotten used to having time when the parents were out of the house to myself, and spending it with...myself. I got into porn, but it was all way beyond my comprehension. There was a limit to what my imagination could fill in. I couldn't fully relate to what the people on screen were doing, because I had never experienced anything remotely close. And there were questions I wondered about, that porn just couldn't answer for me. What was actually going on, in the parts that a camera couldn't show? What did it actually feel like, on the inside? What did a breast feel like when you held it?

One Saturday morning, the parents left to run errands. I stayed home. Jenna's bedroom door was ajar. I thought this meant she was up and out already, or maybe she hadn't come in at all the night before. I thought I would just go in and poke around in her things. We were always like that. But I had to be careful not to leave a trace, and not get caught in the act. I eased the door open silently, in case she was still around.

She was zonked out on her bed, almost snoring. The smell of booze on her breath was filling the room. She was lying on her side, the sheet wasn't actually covering much of her chest. Apparently she was sleeping in the buff, at least on top. Maybe she didn't close the door because it was hot overnight, or because she was too drunk when she got home.

It was my first time seeing a woman's breasts in real life, maybe since I was a toddler. I had never thought of my sister sexually, of course. Not just because we're related, or because she's obnoxious, though those are both true. It was also because she looked nothing like girls I was into. Between the two of us, she's the one who inherited our dad's height and bulk and frizzy hair and nose. The way she dressed wasn't flattering, but maybe that was the idea, I don't know. She really did look like a younger, female version of dad, with breasts. But I realized in that moment that she did have breasts.

My breath caught, and the blood started rushing to my crotch, taking my common sense with it. I thought to myself, this is my chance. If I'm careful, I could find out what a breast feels like, and nobody would be the wiser, except me. No harm done, right? I was looking at it almost as an academic question, and not thinking about how the breast I was going to fondle was my sister's. It was a breast, and that was all that mattered to me in that moment.

I crept towards the bed. It was like a heist. Go in, cop a feel, and get out before the alarms go off. She was pretty well under, her eyelids didn't even flutter. Moving very slowly, I reached down and very gently let my hand come to rest on the skin. I was watching her face closely, my legs tensed to sprint away.

I didn't expect what happened next. As soon as my skin touched hers, a little moan escaped her lips, and she unconsciously pressed her chest forward into my grip. It made me feel gross at first, though the tent in my pants throbbed in response. As I stood there, perfectly still, I could feel her nipple firming up against the warmth of my palm.

Skin on skin contact wasn't all I was after though. I wanted to know what the breast itself was like. What was the consistency of it? I waited until I was sure she still wasn't awake, and then I gently squeezed the breast in my hand, testing the composition of it. It was softer than I imagined. Not muscle, but not jelly either.

A shudder ran through her, starting in her shoulders, and her legs splayed wider on the mattress, pressing her hips down on it.

Then I saw that her eyes were opened. She hissed, "Get. Out."

I ran for it, and heard some object hit the wall just above my head. I pulled the door shut and ran towards my bedroom. At least I didn't hear her chasing after me, but maybe that was because she was naked at the moment.

I was terrified. Would she tell the parents what I did? Would she beat me up? Both? Anything at all seemed possible.

"Lunch, kids!" our mom called from downstairs. I was freaking out. I hadn't heard them come in. I certainly wouldn't have risked our parents catching me fondling Jenna's boob.

I tried to suppress my shakes when I went downstairs. Fortunately the adrenaline and fear made my erection subside.

Jenna came down, in a t-shirt and pajama pants.

"You aren't going out like that," mom said to her. The "are you?" was implied.

"What's the point?" Jenna said. "It's too hot for a bra, mom."

"What was all that banging?" dad asked, as he put out the lunch spread from their grocery trip.

Jenna was staring daggers at me. I answered, "I went into Jenna's room to borrow some cash."

"You mean steal some cash?" Jenna challenged.

"No, I mean borrow," I said. I was daring her to contradict me, but terrified she would.

"Here," dad said, handing me a twenty. "Now, apologize to your sister."

"Sorry, Jenna," I said. I meant it, more than dad could know.

"You don't know what sorry means," she said, not accepting the apology. The parents didn't meddle any further though.

Later that afternoon, she cornered me in the hallway. "Listen, you little brat. You think what you did is okay?"

"I dunno," I stammered. "I just..."

"Well one of these days, it'll happen to you, and we'll see how you feel about it then."

Sure enough, it was about six in the morning on a Tuesday, a couple weeks later, and I was having a pleasant dream halfway between sleeping and waking. I felt an electric shiver, someone's hand caressing my chest. In the dream, I was dancing with some cute young thing, her fingers teasing the sensitive skin of my abdomen, and then her hand trailed lower, towards my waist.

I surfaced from the dream, realizing that this was real, that the hand was my sister's. But I kept my eyes closed, and tried to hold perfectly still. I thought I would let her take her revenge, but not give her the satisfaction of freaking out.

But I wasn't used to being touched this way. I often awoke hard, but now I was rock solid, every nerve on edge. When her hand got close to my pubic hair, I couldn't contain it anymore. I gasped, my hips involuntarily bucking towards her grasp, my erection grazing her hand.

"What the hell, Jenna?" I said.

"Now we're even," she replied with smug satisfaction. Then she left.

I didn't know what to do with myself. I was shaking, I was aching for release, and yet this erection was something my sister had done to me in my sleep. Did I dare take satisfaction in that? What would it make me, if I did?

I felt like she hadn't just gotten revenge, she had escalated this conflict. I had only cupped her breast in my hand. She had gone below the waist. One part of me knew I should let it go, that it had been a mistake from the start. But another part of me wouldn't let that go. I was tired of capitulating to her on things like this. And the side of me that was curious about the female body saw an opportunity.

Another weekend, another late night out for Jenna. This time she didn't get home until dawn. The parents left early in the morning for a day trip. I slipped into Jenna's room again. The sheet was barely draped down over her buttocks, leaving the backs of her thighs exposed.

While keeping my weight off the mattress, I slid my hand carefully up between those thick thighs. She unconsciously spread her legs further apart as I did. My hand found her pubic hair, and exploring tentatively, I found her slit, already hot and soaking wet. At the first touch, she pressed herself down onto my hand, eager for more. I worried she was awake, and waited until I heard her breath resume.

I couldn't see what I was doing, but I'd seen enough online to know roughly where things were, and found them by touch. Her vulva, her sensitive clit, the soft, tender opening to her pussy's interior, all drenched in a hot, sticky fluid. She was already getting worked up in her sleep, every touch sending ripples through her core.

I couldn't resist pushing my luck further. I eased a finger into her opening, feeling where it went, gently probing the shape of her. This set off her building orgasm, and I felt her clench down on that finger as pleasure rolled through her, leaving her trembling.

I slipped my hand out from under the sheet, and she whimpered as it withdrew. My fingers were sticky with her juices. Out of academic curiosity, I gave it a sniff and a taste before I went and washed my hands.

I thought I had gotten away with it. Even better, I was now familiar with female genitalia, and I had even brought a woman to orgasm. I was still a virgin, but at least I felt like I was a more prepared one.

A week later, Saturday night, and Jenna made milkshakes. Mostly because she wanted one, but the size of the blender meant that you had to make a few at a time. I was watching a movie, drinking a milkshake, and I started feeling completely exhausted. It hadn't been a hard day or anything, but I just couldn't keep my eyes open. I went to bed early and crashed hard.

When I woke up, I was lying on my back in bed. The sheet was sticking to my lap. I lifted it off, and found that my lap was covered with semen. A lot of it. My cock was halfway hard, but felt sore from use, like when I overdid it jacking off. And I had to piss pretty bad. As I got up to clean myself off, my hand landed on a post-it note.

"You're welcome, asshole!" It was Jenna's writing.

I blinked away the sleep. I knew what I had done to her was messed up, but she had jacked me off while I was unconscious. Multiple times, apparently. My sister had done that.

I remembered the night before, how quickly and completely I had gone to sleep. It was obvious now. She drugged me, gave me some kind of sleeping pill. This was getting way out of hand.

But what could I do about it? Just back down? If I told on her, she could tell on me. We were at a stalemate.

That evening, I wanted to get my mind off her. I put on some porn, but it didn't really help. When I went to jack off like usual, it still felt like squeezing blood from a turnip. She had drained me dry, and let me aching sore. I couldn't even jack off to someone else. It was like she had me trapped in her twisted world.

It didn't help that at this point I knew way too much about my sister's body, that I knew how to get her aroused, had seen her orgasm, made it happen, felt it happen from within her. All things a brother should not know.

At the same time, I was starting to suspect that there was something else to all this. Maybe it wasn't just me taking advantage of her. Maybe her retaliation and escalation was all pursuing another agenda. Something neither of us would dare express out loud. Maybe she was upping the ante on purpose, knowing it would make me follow suit.

Our parents went away for an extended weekend to themselves, leaving on Friday night, coming back on Monday. Our dad warned us to not have parties (as if!), and just make sure the house is still standing when they get back.

I woke up early on Saturday morning, aroused and feverish with desire. I could just jack off in my room, I knew that's what I should do. And yet. There was another idea that I couldn't put out of my mind, because it was such a uniquely bad idea, and yet it had me delirious with temptation. By then I knew what a woman's vagina felt like, but I didn't know what it would feel like to the sensitive part of me that longed for it.

Jenna's door was ajar, and she was sleeping nude again, sleeping peacefully. Yet she had barely made it into the bed, with one leg draped off the side, the sheet barely covering her pudgy midriff.

My mouth was dry as I stepped closer, to where I could feel the heat coming off her. Before all this started, I had never seen her as a female specimen, let alone such a sexual one. Yet now I couldn't help but notice and admire her breasts. She gasped and bit her lip as I took one in my hand. Her legs spread wider, seeking out stimulation for the sensitive spot between them. I traced her curves with my fingers, taking pride and delight at the way it made her writhe in her sleep. I slipped a hand down between her legs again, finding her hot and ready. I should have stopped there, but I had already come this far before.

I lowered my shorts to the floor, freeing up my erection. I didn't think I could get any harder than this. It was aching for something more than I alone could provide. Moving ever so slowly, I knelt down behind her, my weight only half on the bed. It was an awkward angle, but with my hand to guide me, and her slit well-lubricated already, I managed to find my target.

Just the tip slipped into her at first, and I stopped there, making sure it hadn't been enough to wake her. It took a few moments for me to get used to being inside her, to feel and acknowledge all of the sensations acting upon me. At the same time, I could feel her getting used to having me inside, contractions squeezing down on me. When I pushed a little further, her hips pressed back towards me, offering a more accessible angle, eager to take me deeper. But I knew I had to go slow, or not at all.

A little at a time, I fed myself into her, until I was pressed as far into her as I could get in that position. It didn't really hit home until that moment that this was real. This counted. This wasn't just me satisfying my curiosity about what sex would feel like when I had it, this was it. This was sex. Actual penis-in-vagina sex. I had lost my virginity. I had lost my virginity to my own sister. I took a breath, my first breath as a non-virgin. I expected to feel different, to feel changed, but I didn't. The only change I felt was a lack of reluctance and shame where I knew I was supposed to find some. At least not when I was in the middle of the act, my body flooded with new knowledge and sensations.

My body was telling me to go on, keep pushing, but there was nowhere further to go. My curiosity had been satisfied, but in every other way, I was not. Slowly I pulled away from her, feeling our flesh draw against each other exquisitely as I did so. I should have completely withdrawn and left. But my instincts told me to push back into her, and when I did, she shuddered. I felt her walls spasm around me. I withdrew again and pushed back into her again, feeling her body react even harder each time.

I knew that if she woke, I'd be in real trouble. Everything so far had been tame, compared to this. I knew that if I ejaculated inside her, that would be just as bad, maybe worse. But I thought I could keep going for just a little while, maybe just up to the edge.

I gripped her hips and started thrusting into her. From the way her body was reacting, it seemed like she was quickly approaching her own orgasm. I found that I wanted that. I wanted to bring her to orgasm and feel it play out while I was still inside her.

"What are you doing?" she asked, her face still pressed to the pillow, her voice ragged.

The spell was instantly broken. I had miscalculated, by quite a lot. This was a terrible mistake.

I quickly backed away and ran back to my room. I threw myself on the bed and tried to back up to the wall. I was still naked from the waist down, my cock slick with the evidence of my betrayal. Her heavy footsteps came pounding towards me. She walked in completely naked, but also intimidating. Her face was flushed, her hands trembling.

She tackled me on the bed, pinning me down. I wasn't sure if she was going to strangle me or punch my lights out. I would have deserved either one. I put my arms up to protect my head, but she was straddling my waist. She grabbed my cock, still hard and slick with her juices. I worried she was going to rip it right off. Before I knew what was happening, she lowered herself onto it, taking it back into her. I gasped.

"Jenna?! What are you doing?" I asked this time.

"You're going to finish what you started, brat," she said. There was vitriol in her voice, but also a desperate desire.

"But I...but we...." I said, the objections failing to come out of my mouth. I had already proved how worthless they were.

This was all going very sideways fast. Held down by my sister wasn't at all how I envisioned losing my virginity. I struggled, but she was bigger and stronger. I had inherited our mom's slender, shorter physique.

"You want to fondle a tit? Here you go," she said, taking my hand and pushing it against her breast, holding it there as she rolled her hips back and forth, pushing her pubic mound down on me over and over.

She was fucking me in an aggressive, desperate rhythm. Her sex was squeezing and pushing and pulling on my cock, in a riot of sensation. It was all I could do not to surrender to it, not to let my eyes roll back. As a virgin, I was unprepared for this. It was far too much too fast.

"Stop, I'm gonna..." I said. What was the word? Starts with an "E"? The word was too long for my mind to grab onto in that moment, awash in endorphins and primal urges.

"You...better...not," Jenna said, close to climax herself.

"Seriously...it's about to...I...can't..." I gasped.

"Not now!" she said, and she pinched and twisted the flesh of my side. It hurt, and it nearly sent me over the edge, but it did help me focus for a few more moments.

It still wasn't enough, compared to her grinding down on me, taking me deep within her, her vaginal muscles in constant, frantic motion all around me.

Instinct took over, and I grabbed her hips, driving myself up into her with all I had. A misguided evolutionary imperative guiding me, as my tip sought out something deep within her. She felt it, and the full weight of her fell on me, helping me seek that target.

I knew what happened before I ejaculated, what it felt like at that precipice, how I swelled up at the last second. I could feel that happening, and Jenna moaned as she felt it too.

I felt the first fountain of my seed erupt into her, spreading into her recesses and all around me. Her vaginal muscles worked in time with her choked breaths, squeezing me, drawing it up out of me, into her. With every contraction, I somehow had more to give in this exchange of pleasure and fluids and DNA, the same DNA that my sister already had her own share of. We stayed conjoined like that until every aftershock ran through her into me and back into her.