Whore Sister 1 by Resurgiam

She was a few years older, and when I was a kid I thought Jill was a goddess. I was totally infatuated with her. She was my idea of the perfect woman, my first crush, and yes, in my hormone-ridden years I used to fantasize about her in a less-than-appropriate way. Then, starting shortly after her eighteenth birthday, she began to change. She became more distant, and started fighting with my parents all the time. I barely recognized her anymore, and really wasn’t that surprised when she wound up leaving home. My contact with her became pretty spotty. I think she was homeless for a while, and a couple months after she left I found out that she was pregnant. She wound up having twin daughters.

My parents said that they wanted to help her, but made it sound like she wasn’t receptive to their help. In any event, they were unambiguous that she had made a number of poor decisions, and they didn’t want her to be a bad influence on me. My impression was that drugs and extensive promiscuity were involved in her new life. I was told in no uncertain terms that, unlike her, I needed to focus on my studies and career to avoid penury.

We reconnected a little bit after I graduated college. I got a job working for a VC firm and had myself set up in a pretty good situation. I cared about my sister, and wanted to make sure my nieces were ok, but even after I reached out she remained closed off. Our relationship could never get back to where it was, and frankly I had to agree with my parents that she wasn’t making the best choices. She insisted that she wasn’t on drugs, which I mostly believed, but I was fairly confident that she was making ends meet by working as a prostitute. I know she had worked at a strip club for a while.

When she did get in touch, it was usually to ask for money. At first I didn’t mind. A few hundred dollars here and there didn’t make a huge difference to my life, and if it kept a roof above the girls’ heads then it was worth it. But soon she had racked up a serious debt, and I started to feel less like her brother and more like a piggy bank. To be honest, I got a little resentful. I probably wouldn’t have minded if she hadn’t kept me at such arms length. I offered to try and mediate between her and my parents, and to let her and the girls move in with me (I had the space and would have loved to be more involved in their lives), but all to no avail.

Hence my less-than-enthusiastic feeling when my sister called this afternoon asking if I could swing by her place after work. She wouldn’t say what she needed, but I was confident it wasn’t to pay me back for all the money she’d borrowed over the years. I threw on my handbrake and took a deep breath as I prepared to meet with her.

The lock to to the front door of her building was broken, I noted, and the lobby smelled like human urine. It was covered in detritus. Fortunately the elevator still worked. It was already on its way down as I walked in, and when it’s doors open a man about my age dressed in a slightly disheveled suit and tie ambled out. It was clear he didn’t live there, and as I approached he looked me up and down and then shot me knowing, leering smile. As if we were co-conspirators in some untoward undertaking. His eyes glinted and as we passed each other he addressed me.

“Going to 1410, yeah? You’re in for a good time.”

I was going to 1410, which was my sister’s apartment, but I was fairly sure I wouldn’t have a good time. I snarled at him and he held his hands up, walking away with a laugh.

The hallway to my sister’s apartment was littered with trash and smelled like smoke. A vagrant was asleep just outside the elevator. Her doorbell was broken, so I rapped firmly on the door. Chloe opened it, and I was genuinely happy to see my niece even if the hot pants and tank top she was wearing suggested things I didn’t like.

“Hi Uncle Hank.” She greeted me.

“Hi Chloe. Hi Eve!” I said, yelling slightly and waving to Chloe’s similarly attired sister who was lying on the couch in the living room watching TV. The girls were identical twins, and the spitting image of their mother at her age. I don’t think she knew who the father was, and their looks didn’t give any indication, so completely did they resemble their mother’s side of the family.

“Is your mom around?”

“Yeah, she’s in her room. Come on in. Mom! Uncle Hank is here!” Chloe hollered for my sister as she sauntered through their small kitchen and into their cramped living room. I followed, increasingly uncomfortable with the way her pants clung to her ass. I didn’t have too much time to think about it, as a moment later my sister stumbled out of her bedroom.

“Hi Henry.” She said. My jaw hung agape as I saw her. She was wearing a sheer black babydoll which covered virtually nothing. Small cups barely contained her large breasts, the only opaque material on the thing, and rest of the garment was translucent enough that her entire midriff was completely visible. A thin fringe of fur along the bottom barely reached her thighs and did nothing to obscure her tiny, lacy panties. She’d pulled her hair into a messy bun, though I suspect it had been in much worse shape mere moments before. Her lipstick was smeared irregularly, and mascara ran down to her cheeks. “Can we talk in my room for a sec?”

I followed, trying not to stare as I learned that her panties were, in fact, a thong, and that the cheeks of her ass peeking out from below her babydoll were bright red. She’d lit a scented candle in the room, but it didn’t fully masked the acrid aroma permeating it. Her bed was a mess, and final confirmation came as my eyes darted to her trash can and saw a used condom sitting on top of its wrapper.

I thought about the guy I had met in the lobby, and for one vivid moment the image of him slapping my sister’s ass as he railed her doggy-style on the bed was seared into my mind.

Jill sat on the edge of her bed and crossed her legs. Her shoulders were slumped and she didn’t make eye contact. She reminded me of a beaten dog. “I hate to do this Henry, but is there any way I can get some money? Just a hundred bucks to make rent. Please? We really need it.”

The words that came tumbling out of my mouth surprised even me. “Did you not make enough off of that lawyer or banker or whatever the fuck I met downstairs?” My voice was shaking, full of rancor I didn’t even know I had. “Fuck Jill, at least he got something for it. How much have I given you over the years? And nothing to show for it. How much do you cost anyway?”

Jill looked at me for the first time, eyes wide. “What the fuck are you saying Henry?”

“Oh don’t try to deny it.” I replied, “Mom and Dad were right, you’re a fucking whore. You’re in here giving your used up cunt to strangers while your daughters sit there in the other room listening. Some fucking role model. And now here I am, meeting my sister’s fucking Johns before she hits me up for money. So she’s not even an expensive fucking whore. My sister is a cheap, washed up hooker who doesn’t even suck and fuck well enough that she can be financially independent. So how much? How much do you cost?”

Jill looked down and muttered something. I cupped my hand to my ear. “What was that?”

“I said it depends on what you want.” She said, looking at me again eyes blazing with a certain fierceness. “Why, you buying, you fucking pig? I remember how you used to look at me back in the day.”

I wasn’t going to back down. There was venom in my voice. “Why the fuck not? If everyone else is going to enjoy my whore sister why shouldn’t I? Make you work for my money for once in your worthless life. So, what can I get for $100?”

Her shoulders were squared and tense, but she didn’t break eye contact. “For $100? 30 minutes of hand stuff, 15 minutes of mouth stuff, or ten minutes of fucking my tits. That includes the friends and family discount, pervert. You don’t have to be gentle, but you do have to wear a condom, otherwise it costs extra. So what’ll you have?”

“Apparently you know my admiration for your tits, but if I’m going to pay for a woman I’m going to get into a fucking hole. 15 minutes, and the blowjob better be good.” I slapped a wad of twenties onto her dresser and glanced up at the clock.

“Well, get started. Whore.”

My competitive instinct wouldn’t let me back down, but I didn’t actually expect my sister to do it. I think mostly I wanted to rattle her. I stood stalk still, shoulders back waiting for her to break. She slid off the bed and walked over to her night stand. Opening it up she pulled out a condom, which she removed from its packaging as she walked over to me.

Any minute now she’d back down. She came within a hairs breadth of me, and looked into my eyes. What I saw in her frightened me, but I stayed calm. Slowly, she sank to her knees in front of me without breaking eye contact. Pinching the tip of the condom she put it between her lips. Her hand reached out in slow motion.

Any minute now she’d back down. Her hand reached the fly of my slacks. They were bulging. It was only at this moment that I realized I had a raging erection. My sister seemed to realize this at the exact same time as she looked at my crotch then back up into my eyes with a strange expression on her face.

Any minute now she’d back down.

Then, suddenly, my fly was down and my throbbing cock was out of my pants. In a single fluid, practiced motion my sister brought it to her mouth, unrolling the condom onto it as she took it all the way to the back of her throat.

“Oh fuck that feels so good!” I exclaimed involuntarily. And it did.

If I had any doubts that my sister was a professional at this they were quickly dispelled. This was a woman who knew her way around a cock. I leaned back, bracing myself against her dresser with my arms and spreading my knees to give her access to my shaft. My eyes rolled into the back of my head as she bobbed up and down on my cock. Her right hand jerked my shaft as she sloppily inhaled my member, but even so I could feel the tip of my dick hitting the back of her throat every few strokes.

Suddenly, she pulled my dick from her mouth with a pop and inhaled deeply. I moaned.

“Yeah, you like that little brother?” She said, furiously rubbing my shaft, “You like your whore sister sucking your fat fucking cock? This what you’ve been thinking about while masturbating all these years, you fucking degenerate scum?”

I looked down as she leaned over and began licking my hefty nuts. My rigid purple member slapped onto her face as she pulled both my tight balls into her mouth and swirled around them with her tongue. The sight of my dick lying across her face as she sucked my balls nearly made me bust, a risk only increased when she opened her eyes and made direct eye contact with me as she did it.

A quick swipe of my taint with her tongue and then she was back to working my head and shaft. I groaned appreciatively and let her continue working her magic. I was on the edge, but could feel deep in my loins that this wasn’t enough to finish me off. Reaching out, I put my hands on either side of her head to guide her. When this met with no resistance, I firmed the grip of my fingers in her auburn hair and began thrusting with my hips as I moved her head. Suddenly, my sister started making a gagging noise, and tears welled up in the corner of her eyes.

I let go of her head and she slid off my dick coughing. Part of me wanted to see if she was alright. A different part of me wanted to make sure this cheap whore knew she needed to earn her money. That part won out.

“What’s the matter?” I said, chuckling like when I used to taunt her when we were younger, “I thought you said I didn’t have to be gentle?”

She glowered up at me, “You don’t. I’m a fucking professional, I’ll tap out if you take it too far.”

“Good.” I said, grabbing a fistful of her hair and shoving my dick back into her mouth. Her whimper indicated that she wasn’t expecting me to take her at her word, but to her credit she didn’t fight as I started really abusing her throat hole. The force of my thrusts pushed her off her knees onto her ass, and I was treated to the sight of her ample tits flopping out of her scant babydoll as I used her mouth like a pussy.

No, not like a pussy. Say what you will about me, but when I fuck a woman I typically try to make a good impression. I fucked my sister’s facehole like it was a simple masturbation aid. Holding her head firmly between both hands so that her cheeks smushed together together, I relentlessly crammed my cock in and out of her warm, wet mouth. Her lips latched onto my dick and she did her best to use her tongue to improve my pleasure as I practically dragged her across the room with the force of my face-fucking.

Eventually, she was backed up against her own bed so her head couldn’t even move back as I did my very best to shove my girth into her esophagus. A glance at the clock told me I only had a few minutes left, so I redoubled my efforts. I looked down at her face, red from lack of oxygen, the veins in her distended neck sticking out, eyes rolled back, tears and mascara streaming down her face, frothing fluid flowing from her mouth, generous tits with hard nipples bouncing as I relentlessly thrust in and out of her pretty throat.

Suddenly, as I withdrew my cock I caught sight of her hands. They were between her legs, under her lacy thong, rubbing her clit as fast as they could. This sent me over the edge. Leaning my hips forward I trapped her head between my pelvis and the mattress. I groaned as my balls pressed into her chin and several inches of my dick went down past her uvula. I gasped in relief as the tightness of my balls released, relished the feeling of my cum shooting up my dick and emptying into the condom’s reservoir deep inside her throat. My sister made a strange gargling noise as the suction on my dick suddenly increased. My orgasm subsided as her face started turning blue, and with some amount of regret I pulled my deflating cock from her mouth and fell back on my heels.

As I sat on the floor breathing heavily, my sister gasped desperately for air with several ragged inhalations. As the color returned to her cheeks she grabbed her trashcan and wretched into it, before leaning back against the bed, legs spread, totally disheveled. I pulled the lipstick stained condom off my now flaccid dick and threw it into the trashcan. Adjusting my pants I stood, the cold reality of what I had done sinking into me as I looked at my gasping, barely conscious sister sitting glassy eyed on the ground, silent tears streaming down her cheeks.

I didn’t know what to say, so I simply patted the money I had left on the dresser and walked out, making sure to close the door tightly behind me. I made some inarticulate noise at my twin nieces, who were still sitting on the couch, by way of goodbye. They just giggled knowingly at one another and said “Bye Uncle Hank!” I walked back to my car in a daze, and drove home on autopilot. What the fuck had I done?