A Wild Date With My Sister
One night I took a cab to my sister's job after her shift ended so we could get something to eat and catch up on things. This wasn't a common occurrence, actually I don't remember it ever happening, but I figured it would be nice because we hadn't seen each other in about a month. We settled on pizza and after we ate I was in the mood for a drink. It was a Friday in the city and I sometimes went to a bar with my work buddies, so why not with my sister instead?
"Wanna grab a quick drink at that bar across the street?" I asked her.
"Really? Ah, I don't know," she said apprehensively, as if it was inappropriate or something.
"Why, is there some law that a brother and sister can't go to a bar together? Come on bubbaloo" I said teasingly. My sister was older than me (I was 23 and she was 26) and I enjoyed playing the role of the wise ass younger brother, sometimes giving her silly nicknames.
"Maybe I should stop home and change first, look at these clothes." I leaned out around the table so I could check her out, she was wearing her office-like business casual clothes: a knee length black skirt, a light blue, collared shirt, but most importantly, dark stockings. Her legs looked sexy to be honest.
"Why?" I said and laughed, "you look kind of hot."
"Thanks, I think. 'Kind of' hot?" Just 'kind of'?"
"You're lucky you got that, stockings girl. Anyway let's go."
She smiled and relented and we headed over to the bar.
I ordered drinks and we sat in a cozy booth along the wall, facing each other across a wooden table. There was a small crowd but as people got off work it picked up. Sitting face to face with my sister in this atmosphere was interesting, if a bit odd, and our initially sparse, small talk reflected that. Soon the drink loosened us up, and then she did the first thing that made me perk up and take extra notice of her. She pulled the clips out of her long brown hair and shook it around like they do in a shampoo commercial. Wow, I thought, I have a pretty sister. I mean, I knew that already, but this time it occurred to me on a more conscious level.
She bought the next round at the bar and as she walked back to the table I couldn't help but check out her legs again. Shit, was that too noticeable? I thought I stared too long.
"Guys are funny," she said as she sat down.
"In what way?"
"They have all these fetishes, like stockings and feet and things like that. Well, stockings I can understand, they do look nice."
So she did notice.
"Yeah when it comes to girls," I said, "you name it, there are guys out there into it. Like... I don't know, when a girl puts a shoe on her head. There are guys that like that."
She laughed. "Get out of here. I've never heard of that one."
"Yeah, seriously. Shoe on head."
"Do you like that?" she asked.
"I don't know, let's try it out and see."
She looked around the bar then reached down to take off her shoe. Cool, she was playing along. Her shoe was a comfortable slip-on flat. She brought it up by her ear, looked around the bar again, blushing and giggling, then balanced it on her head. It was cute! There's something about it.
"So, what do you think?" she said and did a vogue pose.
"You know, it's actually kinda cute. I get it. I understand it now."
"What about it?" she asked, attempting to try and understand the strange world of men.
"I don't know man, I learned not to questions these things. I still don't even know why I like tits, never mind a shoe on a head."
The shoe fell off. That was a rare occasion when I said "tits" in front of my sister. She gave me a quick 'behave' smirk as she put her shoe back on. She has tits, I said I liked tits, one plus one equals two. But wait, they're my sister's tits so they don't count right? Well, previously that's how it was, but her stature as a sexual being kept growing as the moments passed and the buzz from the drinks swirled their away around my head. The bar became crowded with after-work people and as the ambient volume increased my sister and I fell deeper into our private conversation.
"You know that reminds me, I used to have this boyfriend who loved watching me paint my toenails."
I nodded my head in immediate understanding. I liked that too.
"He told me he liked the way I sat on a chair and did it."
"In what way?" I asked.
"Just that I'd have one foot on the floor and one foot up, with my knee pressed against my chest. I had to wear shorts too, if I wasn't he made me change. He would just sit there and stare at me the whole time. It was funny."
Past images of my sister painting her toenails flashed in my mind, and I remembered experiencing sexual arousal seeing it as a horny teen, particularly the way her raised knee pressed against her boob, her sexy feet, and I recalled sneaking quick glances between her legs. Being uncomfortable about those feelings at the time though, I would quickly move on.
"That guy knew what was up," I said. "It's probably a common one, a lot of guys like feet.The smellier the better."
She laughed. "Ew, weirdo."
"Whoa, whoa, wait a minute, it's not like women don't have their own weird things about them."
"Hmm, I don't know, you tell me, you're the woman."
"Let's see." She looked around at the bar patrons and thought about it for a few moments. "Ah! I got one. Okay, this is a pretty big one too. Actually, I don't think I should even tell you. Why are we even talking about this? I shouldn't be talking about things like this with my brother."
"Oh, come on. Don't worry I won't tell anyone, your secret desires will stay between us. Pinky swear."
I reached out my pinky. I did this on purpose to make contact and break the physical barrier between us.
"Okay, first of all," she said as she reached out and hooked my pinky with hers, and even that little skin contact felt good, "I didn't say it was my secret, just some women in general."
"Cool, spit it out girl."
She smirked and shook her head at my wise-assery.
"Alright, some women like to be... how can I put this... like, dominated. They have fantasies where they're taken..." she leaned in and whispered, "...by force."
"By force? There's a word for that you know, it starts with an 'R'."
"No! Not that. Just taken by a good looking stranger, or someone she knows, not some random smelly guy in an alley. Maybe he storms into her bedroom or something, then overpowers her and throws her on the bed against her will."
I chuckled and let her get away with the slippery semantics.
"Yeah, I knew this. So, why do they like that?"
"Um, I think because it's the ultimate expression of desire by the man. Let's be honest, women crave being desired right? So this attractive man desires you so much that he can't help himself and bashes through all civilized conventions, all courtship rituals, and just... takes you. It makes a woman feel sexy to be desired that powerfully. I mean... I guess that's how it is for some women."
She caught herself and stumbled at the end, as if she said too much and was describing her own feelings and not just of other women. My arousal and desire for her were getting stronger as I took in the sight of her long brown hair, moist lips, intelligent dark brown eyes... she looked lovely. I liked the way we were leaning in across the table, looking into each other's eyes and engaging in this provocative conversation. I couldn't believe she was telling this stuff to me, her younger brother. Amazing what a little alcohol and the right atmosphere will do.
"Makes sense," I said. "I knew that some women have, ahem, domination fantasies, but I never really thought too much about why. So that's a good explanation."
"Oh, there's another thing too," she continued, apparently getting more comfortable and stimulated by this taboo subject. "Girls are attracted to masculine men right? So say the guy is very masculine, like an animal," she laughed, "and he rips her clothes off! That's hot, the masculinity of it."
"Interesting... I feel like you just revealed some dark secrets. Make sure the sisterhood doesn't find out you told me this stuff, they'll get pissed."
She smiled and took a big gulp of her drink, then exhaled, looking as if she felt relieved to get that off her chest. I leaned back in my seat with my arms spread out, keeping quiet and cool and soaking in the magnitude of that conversation and the moment, that we were brother and sister and the two of us were sitting in a cozy booth floating in a buzzing haze of sexual energy.
"I'm gonna go to the bathroom, okay?" she told me. "Can you get more drinks? I'll have the same."
She put some money on the table. She even pays for drinks too, does it get any better than this girl? She got up and walked to the bathroom in the back, and what are the chances I didn't stare at her ass the entire time? I wanted my hands on it. I suddenly wanted to fuck my sister. Damn! The thought of that was messed up but also exhilarating. Hopefully it'll pass, because that just can't happen. I rolled our conversation around in my head and thought about my sister having fantasies like that. Fuck me, that is erotic as hell. I thought back to us growing up together and I remembered when we used to wrestle, like brothers and sisters do, and although she had decent strength I'd eventually dominate and end up on top, straddling her and pinning her arms over her head. We would both be breathing heavily...
...and the memory sent a sudden jolt through my body. It was the way my sister looked at me when I was on top of her, she'd have a devious smile and a sensual look in her eyes, appearing glad that I overpowered her and daring me to do something, to take her. Take her. Holy fuck, all this time I never even realized it, or processed it, until now. A few times she even provoked me by saying 'what are you gonna do, huh?'
I snapped out of my stupor and surveyed the scene at the bar. Had to get the drinks. Before I got up I noticed two cute girls standing there, early twenties, one blonde and one brunette. No guys were talking to them at the moment and they had a 'single and looking' demeanor. I scanned them quickly to get an idea about them and developed a plan.
I walked up, stood next to them and waited for the bartender.
"Excuse me girls, hi."
They turned to face me.
"I was sitting over there and I noticed you two. My name is Castle." I stuck out my hand.
"Castle? Really?" the blonde said as she and her brunette friend put out their hands and shook mine.
"Yeah, seriously, Castle. Screwed up, but kinda cool right?"
They gave me their names and both had confused, eye-rolling looks on their faces, but they were smiling in a friendly way, so that's something. I just needed to keep spitting out random shit for as long as I could, because I wasn't trying to pick up these girls. My main purpose was for my sister to see and get jealous.
After a few minutes of small talk, I decided that I liked the quiet brunette a bit better than the blonde so, naturally, I put my focus on the blonde.
"So, you're the tough one right?" I said to her. "You protect your shy friend here from all the wolves in this place. That's the vibe I'm getting."
"Haha, yep, you don't seem like a wolf though. Yet."
"Oh, I am a wolf, worse than that really." As I said that like an asshole and ordered my drinks, I see my sister emerge from the bathroom. I glanced in her direction and our eyes met as she walked back to our table. She looked surprised and disconcerted, but quickly covered it up with a forced smile.
"Alright girls, it was nice talking to you, but my friend is back in our booth and I don't want to leave the poor girl by her lonesome." I pointed at my sister then leaned into the shy brunette. "You seem nice, put your number in my phone and we'll finish this another time, maybe later this week." I tried to hand her my phone.
She looked at me like I was nuts and laughed. "Um, no? I don't even know you! Is that your girlfriend over there?"
"Nope, just a friend. We almost hooked up awhile ago, but we're better as friends, at least I think so, she doesn't."
She took my phone and started putting her number in!
"What are you doing?" Blondie said in exasperation. "Don't give him your number!"
Brunette ignored her and handed me the phone when she was finished. Damn, I'm good. But wait, not so fast, I looked at my phone and instead of a number she managed to text in "you wish". Clever girl. Oh well, it'll have to do.
"Cool," I said to her. "We'll talk soon. Tell your friend here she needs to work on her skills at protecting you from the wolves, cause she stinks at it."
We all laughed and I walked away back to my sister in the booth. I sat down and she was trying to act naturally, but was obviously fidgety. She had a big blushing smile on her face, but the smile had a mixture of... jealousy?
"Don't tell me you got that girl's number," she said.
"Get out of here. You were only talking to them for a few minutes!"
"I can't believe that. Welp, I gotta say, I'm impressed. I didn't know my brother was Mr. Smooth like that. Must be a dumb ass chick though."
I laughed. "Hey, don't talk about my future girlfriend like that. Listen to this, I told them my name was Castle."
"No clue, I just thought it would be funny."
"I doubt I'd give my number to a guy who told me his name was Castle." She laughed.
"Yeah well, you're a savvy chick."
"Aren't you? Anyway," I continued, "I do know one thing that works on girls, savvy or not. If a girl shows an attraction to you, let's say at a bar, the best thing you can do is suddenly ignore her and talk to other chicks, like I just did."
She eyed me suspiciously for a few moments but it felt like an eternity.
"Wait, you don't think I got jealous do you?" she asked.
"No! Why would I think that? You're my sister."
"You wanna get going?" My sister said that after a few minutes of bumpy small talk, apparently the night took a turn she wasn't expecting and her mood darkened. We called a cab and headed to her apartment to drop her off first. I could sense a tension between us in the back seat during the ride, we were mostly silent. I played it cool but my mind was racing and I wondered if she was going to ask me up, and if she didn't, what was I going to do? Just let the night end with a thud? Maybe I should, I thought, we're brother and sister and this whole night was borderline perverted and inappropriate. The cab arrived at her apartment building and stopped in front.
"Alright," she said, "I'll talk to you soon. I had fun."
"Alright." I leaned over to give her a goodnight kiss on the cheek. Just a harmless brother-sister kiss, no big deal, although uncommon for us. She looked a bit startled when she leaned in to let me kiss her, and the skin contact between my lips and her cheek sent a low hum of electricity through my body.
"You want to come up for coffee or something? Go to the bathroom?" she said.
I accidentally laughed. "Coffee?"
"Never mind. It's getting late," she said.
"No, good idea. I do have to go to the bathroom anyway."
Phew. We paid the cab driver and entered her building. We took an elevator to the fourth floor, dead silent the whole way, and I felt excited but shaky and nervous. We arrived at the door to her place in the quiet hallway, and every little clinking sound her keys made as she unlocked the door sounded sexual to me, I have no idea why. I had only been in my sister's apartment a few times the last three years that she lived there, and it felt strange being there this late at night, about nine o'clock. Add that we were still quite buzzed from the drinks. We entered her dimly lit place and she closed and locked the door behind her, and when she turned around I surprised the shit out of her and put my arm around her legs and swooped her up off the ground, carrying her like a bride.
"What are you doing?!" she said loudly.
I laughed and didn't answer as she squirmed in my arms and arched her eyebrows in confusion, thankfully she was also giggling. I carried her to the living room and laid her down on the couch. I then chickened out and couldn't muster up the courage to do anything else. After giving her outstretched, stockinged legs an obvious going over with my eyes, I walked to the kitchen to get some water.
"Okay, what was that for again?" she said as she sat up and collected herself.
"Nothing, just having fun. Don't be such a tight ass. Well, I know you can't help it, you do have a tight ass, and I mean that in the good way."
"Oh do I? How do you know?" she asked.
"Duh, I can tell by just looking at it."
"Yeah well, you shouldn't be looking at your sister's ass, pervert."
I chuckled and let her get the last word.
"I'm gonna get changed and then I'll put some water on," she said.
I was relieved. Her voice had a flustered tone but she didn't sound mad or freaked out. I sat on the couch and watched the tv that she had turned on, full of anticipation and also a fear that I'd eventually fuck up and cross a line.
She freshened herself up for a good ten minutes and then came out and went to the kitchen. I missed it when she passed so I didn't see what she was wearing, hopefully some sexy lingerie. Yeah, right. I went to the bathroom myself, then walked to the kitchen and leaned on the frame by the entrance. She was standing with her back to me and getting something from a cabinet. She had on snug blue short shorts and a white t-shirt. Damn, her cute little ass looked fine. Besides at the bar earlier, I'd never looked at my own sister's ass with this much desire and the conscious intention to devour it. She turned around and what I saw removed all doubts about her own intentions.
"Do you want coffee or tea?" she asked.
Her white t-shirt was tight and sheer enough to see that she obviously wasn't wearing a bra. I could make out the lovely round form and flesh tone of her tits and her nipples stared at me. Her barely concealed devilish grin and naughty eyes told me that she knew, oh she knew. I glanced at them long enough so she noticed, and she turned around to put the cups on the counter and make the tea. When she was done she walked past me with cup in hand and as she did she pushed my shoulder with her hand.
"Jerk", she said with a smile.
That's it, you're done girl. I waited for her to put her cup down on the coffee table and I grabbed her from behind and wrapped my arms tightly around her body.
She squirmed and tried to get loose, protesting weakly but also laughing and smiling. I held tight and dragged her to the bedroom. I eventually got her on the bed until she was laying on her stomach and I laid on top, smothering her skinny body with my six foot, hundred and ninety pound frame. With all her might she managed to spin her body around until she was laying on her back, but she couldn't get me off, and I grabbed her wrists and pinned her arms above her head. There I was sitting on my sister's hips straddling her, just like the old days when we were teens. I never thought I'd be in that position again. I could feel the heat coming up from her pussy. We were breathing heavily and we stared at each other.
"What are you gonna do tough guy?" she said, taunting me.
I'm not going to get all flimsy this time, I thought. I forced my knees and legs between hers and it wasn't easy, she put up a healthy but ultimately token resistance, trying to appear as if she were fighting me off. I forced my way into missionary position and I began pushing my hard cock against her sisterly mound with upward trusts, and she kept a mostly neutral, non-sexual look on her face, which motivated me to grind my hips even more firmly in a circular motion. After a few moments her face began to betray her and her eyes got that sensual sex look, and her mouth parted and her breathing intensified. Seeing my sister like that, and pleasuring her, was intoxicating.
"Don't move," I ordered her, doubting she would listen. I slowly let her wrists go and edged my way down to her shorts and unbuttoned them, frequently glancing up at her face to see a reaction if any. She just watched me intently, intrigued, and as I unfastened the button and pulled the zipper down she covered her eyes with her hand. She wasn't wearing panties, naughty girl, and I was pleasantly surprised to see that my sister goes old-school and had a small patch of neatly trimmed hair.
I pulled her shorts off and tossed them on the floor and saw it all now. Laying eyes on my own sister's labia and clit was indescribable; so, so forbidden, a brother is simply not supposed to see these most private of parts. My mouth watered. It was unsettling how quiet she was, still with her hand over her eyes and the other arm still over her head. I hurriedly took my pants and boxers off and kneeled between her legs, hard cock standing straight out, and she finally looked.
"Oh my god," she said, realizing the gravity of what was happening. Before she could develop cold feet I got between her legs and nestled my cock on her wet pussy lips, sliding up and down. The intimate contact sent waves of powerful arousal through me.
"Wait, wait," she whispered loudly. "We can't, you're not even wearing a condom."
"Do you have any condoms?" I asked.
"No, I'm not even taking birth control!"
The moment after those words came out of her mouth I suddenly plunged my steel hard cock straight into her wet and slippery cunt, going in as far as I could and mushing her soft mound. It was the best first-entrance of a pussy I've ever felt. She arched her back violently and let out a yelp.
"Oh my god, what are you doing? We can't," she said almost convincingly.
I ignored her and began pumping in and out of her pussy, and I was ecstatic feeling the skin of my bare cock glide against my sister's naked insides. These parts of our bodies were never supposed to touch each other, ever, and it was wonderful. I grinded and pushed and made love to her until the protestations completely stopped. Our breaths and moans intensified and she took off her t-shirt, and I watched in amazement as her lovely round tits bounced up and down. I grabbed her wrists and pinned them above her head again, holding them tightly and digging my nails in a little. I looked down and marveled at the gentle curve of her mound rising up from her flat stomach, hypnotized by the sight of my cock disappearing in deep when she raised her hips to meet mine half way.
The phone on her night table rang. We both stopped and glanced at it for a moment. Shit, I better keep going before this breaks the momentum, I thought. She didn't move to answer it, which was polite of her, but suddenly I was curious as to who it was. A boyfriend? Hmm. I reached over, picked up the handset and checked the caller ID. It was our father. Oh god, you got to be kidding. I was about to put the handset back down and move on from this unpleasantness, but then my devilish side rose up. I answered it. "Hello? Oh, hey Dad."
My sister went wide-eyed with horror and silently mouthed 'what are you doing?!'
I leaned on one elbow and held the phone with my other hand and resumed fucking my sister's pussy, nice and slow, trying to stifle laughter and keep my sex breaths quiet. My Dad was wondering where I was because he had called my apartment.
"Yeah, we ate at the pizza place after work and then I came over here and she cooked dinner."
Wait, I realized I fucked up there.
"We just had a piece of pizza and we were still hungry. Anyway, we were watching tv. Wanna talk to her?"
My sister's eyes almost popped out of her head. I almost cracked up but managed to cover my mouth and hold it in.
"Hang on Dad."
I handed my sister the phone. Her body collapsed with the resignation that she had an insane brother. She took a deep breath, collected herself, and took the phone from my hand.
I quietly and slowly but powerfully continued fucking her sopping wet cunt, burying my cock in deep, watching her strain herself trying to keep it together. She was doing well so far, like a trooper. Little did my father know that his son was banging his angel of a daughter, and not only that, but without a condom, without any protection at all! I don't know what inspired me to enjoy that fact, maybe to get him back for something in the past. But why, we had a good relationship. Who knows. I felt guilty but the raunchiness and danger was exhilarating.
As they talked I began fucking her faster until you could hear the sticky sex noises. She meekly tried to get up but the incredible sensations of having her brother's cock inside her made her collapse back down. I gave one big powerful thrust and smashed her mound, and she let out a short but audible exhale. She quickly covered her mouth in horror, but as mortified as she was, she was also loving this! I think deep down talking to her father while being fucked was just as thrilling for her as it was for me. Who would've thought my sister was such a perverted, incestuous girl. To intensify the situation I quickly climbed down and put my head between her legs. I flicked her clit with my tongue at lightning speed, and she abruptly stopped right in the middle of saying something about her job and opened her mouth and arched her back in overwhelming pleasure. Oh come on, my Dad must have noticed the sudden pauses! This was crazy.
I jammed my finger in her cunt hole to lube it up, and moved it down to her asshole. Her head perked up and she gave me a surprised look but she continued stringing my Dad along with conversational sound bites, including a hilarious "what's mom doing?" I slowly sunk my finger into her glorious anal tightness and slid my tongue up and down the center of her soaking mess of a vagina, concentrating on the unique texture of her labia and the delicious taste of her pussy cum.
It was getting more difficult for her to maintain calm, steady breaths, always on the edge of breaking down and letting out a moan. I picked up the pace and finger fucked her asshole rapidly and forcefully, managed to also slip a finger in her cunt, and continued licking her clit. She was getting it from all angles and she squirmed around wildly and only give my Dad weak 'yeahs' and 'uh huhs'. It appeared as if she was going to come, her body tightened and she opened her mouth wide and had the most powerful, but at the same time quietest orgasm I've ever seen and heard, right with her mouth close to the mouthpiece of the phone. Dad, your daughter just came in your face and you didn't even know. Amazing.
She finally ended the conversation and hung up, and although she held up fairly well, I'd be shocked if my Dad didn't suspect that something strange went on here. He's not an idiot and he's not deaf. I guess we'll find out, I said to myself.
"Oh my god," she said and covered her face with both hands, taking deep breaths to recover. I wasn't done with her yet, though, and I went to the bathroom and found what I needed and on the bedroom floor saw my other required item. Before she could relax and get herself together, I picked her up off the bed and carried her naked and spent body to the kitchen. I plopped her little ass down on the counter and she went with the flow, resigned to her fate but curious as well.
"Here, put this on your head." I handed her the shoe I retrieved from her room, it had an elegant open-toe design and about a two-inch heel. She smiled, took it from me and held it on top of her head. Very cute. I lubed up my cock with the vaseline and lifted up and spread her legs so I could get access to her asshole. The counter was a bit high but I lifted myself and jammed my rigid cock inside her, not being delicate about it, and she moaned loudly. She was tight as hell and I fucked my sister's ass with ferocity, but what put it over the top was the raunchy, dirty act contrasted with the adorable sight of her holding a shoe on her head. I was going to come already and I felt the powerful incestuous orgasm building up in my entire body. My cock throbbed and I pushed in to get my hot cum as deeply inside her ass as possible.
I came inside my beautiful sister, and it was a transcendent experience. I put my hands under her arms and lifted her up off the counter. I gave her a little kiss on the lips.
After we cleaned ourselves up I got ready to leave. She wanted me to stay, however, and it was an easy decision, I wanted to be with her. We laid in her bed together hugging, cuddling, and barely exchanging any words. There was nothing to say, the wild night spoke for itself. In the quiet darkness as we were about to fall into a much needed sleep, my sister spoke up.
"So, are you gonna call that girl?" she asked with a vulnerable tone. Aw.
"Maybe. I don't think "you wish" is an actual phone number though."
"What do you mean?"
"Never mind. I might call her, we'll see. I want to be fucking you while I talk to her though."
She didn't want to laugh, but she couldn't help it, and our quiet breathy chuckles turned into a few minutes of hysterical laughter.