22 comments/ 176599 views/ 141 favorites My Sister's Holes By: rjjtest1 After yet another dead job interview, I entered my car feeling a little numb. To say that the last few months had not gone well for me would be a bit of an understatement. 22 years old, unemployed, out of school and out of luck. That was my life right now. Of course, things would be so much easier if I just had a girlfriend. I was a little ashamed to admit it, but I was going through a four year dry-spell and there were no signs of rain on the horizon. Sometimes, I had to wonder if I was completely out of practice. This, of course, did wonders for my self-esteem. And so went my thoughts as I drove home on an overcast day in August. While all my friends had their own places and were out living dreams, I still lived at home and had a hard time grabbing a simple assistant manager post at the local Finish Line. Gosh, it was going to be a good week. I arrived home, parked my car in the garage and went inside. No one seemed to be home. Mom was probably off working, as she had to work later and later now that dad was gone. Kayla, my sister, was probably with some friends. Great, I thought to myself, I don't even have a home cooked dinner to look forward to. I headed up to my room to change. As I glanced in the mirror, I couldn't help but wonder why I was having so many problems with girls. It wasn't as if I was a bad looking guy. Sure, I was no Brad Pitt, but few are. I was average height, average weight, and slim. I looked like a basketball player (my favorite sport, though I never quite got good at it). I thought I had good enough looks to win over at least one girl. Besides, if I allowed myself a moment of arrogance, my personality was dynamite. I switched off the light as I exited my room, with the goal of the kitchen in mind, I glanced over at my sister Kayla's room and noticed that the light was on. Turned out, she was home. I thought I would go say hi since she didn't seem to hear that I had come home. I cracked open the door without knocking, as I was accustomed to, and nearly slammed it again on principle. There was my little sister Kayla in nothing but a bra and panties. And let me tell you, these weren't just any pair of bra and panties - these were sexy. It was a black set of satin panties, with a white polka dot patch covering the crotch. The bra - oh, the bra - was black lace that was practically see through. I didn't glimpse nipples, but it was a tantalizing mystery amongst the lace. Perhaps they were there after all. Simply put, Sister Kayla looked gorgeous. She had just turned eighteen, but it hardly showed. She was small and slight, with what looked to be only a B cup bra size. She had a nice firm ass, as countless hours practicing with the cheerleading squad had given her a toned body. Kayla was beautiful and tanned, a result of our mixed Mexican American heritage (mom was from Cuahuila while dad was from Minnesota). Luckily, she was looking down at the time I opened the door, so, after a glance that lasted a little too long for my comfort, I quietly shut the door. I took a deep breath, and knocked, this time waiting for a response. "Hold on," I heard her say. After some rufflings, the door opened and there was Kayla in her cheer squad sweats and a hoodie. "Oh hey, I didn't know you were home yet. How'd the interview go?' She asked with a smile. "Not good. I don't have enough managerial experience, apparently. Let me ask you something: how am I supposed to get managerial experience if no one will hire me without prior experience?" While my tone implied the mock anger I generally generated when talking about the endless job search, my mind was elsewhere. For some reason (I think I knew which reason it was very well), I couldn't help but look at Kayla. Clothed in baggie sweats, Kayla still managed to look beautiful. Long straight brown hair, adorable dimples, and just the right amount of faint freckles, Kayla looked stunning no matter what. Of course, I couldn't think this. No, Kayla was my little sister and it was my job to be her big brother. I wasn't the overprotective sort - after all, it was her life - but she hadn't exactly had the greatest choice in boyfriends. She had been cheated on more than once. Because of this, I had always been her best friend. I was the guy who she trusted everything with. She could tell me about anything - guys, school, career plans, etc. Mom wasn't around enough to fill that role as confidant, so I had to step up to the plate. Which made my recent thoughts all the more disturbing. I tried to focus on her words as she told me about her day and made us a little dinner. "By the way, did I tell you that Jack bought us a tickets to WE Fest next month?" This jolted me out of my self-reprimand. "You're kidding! You get to go to WE Fest?" WE Fest was the state's largest country music festival. All the big names showed up, everybody partied for four full days, and people came home hungover, high and happy. "Yeah, Jack surprised me with the tickets today! I'm so excited, you have no idea." I had a little bit of an idea, since I had once surprised my last girlfriend, Alex, with similar tickets, but I decided not to mention that. "So, is it just you and Jack going, or are his friends coming with as well?" "Just me and him, which I think is perfect" she beamed, and those adorable dimples almost made me sigh. "Well, be careful. You know how it is up there," I cautioned her. There was a reason for this: I didn't like Jack. Jack said all the right things when my mother or I was around, but I had seen him when he didn't think I was looking and let me tell you, this kid was a tool. He thought he knew everything and he didn't treat Kayla too well either. She thought all of his "jokes" were just another form of flirting; I saw them as the precursor to abuse. I had tried to subtly warn Kayla about him, but when somebody doesn't want to hear something, well, they don't hear it. "Yeah, I know," she said, all the sudden looking a little sober. "What is it?" I said, suddenly a tad worried. "Well, you know how Jack and I have, you know, kind of been taking things slow?" Making out every chance you get isn't exactly slow, Kayla, I thought, but I answered with a tentative, "Yeah?" "Well, I was kind of thinking that maybe WE Fest would be our, you know, weekend..." she trailed off with a blush. I was now acutely aware of why my little sister would be using her nights home alone to try on new underwear. The thing is, as far as I knew, Kayla was still a virgin. I did not want her to lose her virginity to a creep like Jack, but things like this had to be handled delicately. "Ohhhhh, I understand. Kayla, do you mind if I ask you a really personal question?" "Of course Dan, ask me anything. You're my big brother," she said with a sweet smile. "Look, I don't know how to put this exactly, but have you ever, um, done it before?" The smile vanished, "Well, uh, no, not exactly. I just wanted my first to be with the right guy. None of the other girls understand it, but I've wanted it to be done right and none of the other guys seemed right to me." She looked nervous all of a sudden. I couldn't believe I was talking with my baby sister about her sex life, but I suppose if dad wasn't around to help out, I had to do the job myself. "Kayla, I want to be honest with you. Sex is a big deal. If you don't feel you're ready to take this step, you don't have to, no matter what Jack says." And then, she looked up at me with those big green eyes and said, "Dan, could you help me out with something? It will really mean a lot to me." I was nervous. All the thoughts that had temporarily popped out of my head returned in full force. The image of Kayla's round ass barely covered in thin satin black rushed in to fill the space between my ears. "Um, okay, but with what?" "Look, just follow me. I need your opinion on something." And with that, she grabbed me by the hand and led me upstairs. We entered her room and I saw what I hadn't before: there, in the corner, almost out of sight, were three Victoria's Secret bags. A feeling of dread and excitement crept over me almost instantaneously. She turned a faced me and, with a great sigh as if to prepare herself, said, "I want to make WE Fest perfect for me and Jack, so I went out shopping the other day with my friends. We got some underwear and I wanted a guy's opinion on which is the sexiest. Do you think you could help me?" She said it all rushed, like she wanted to get it out there before changing her mind. I was stunned and I didn't know how to respond momentarily. My gut instinct was to say no; after all, with my cock stirring at the mere memory of Kayla and a four year drought on my hands, there was no way I wanted to be in the same room as both her and those bags. However, I knew this was hard for Kayla and I knew she just wanted her big brother's help. I couldn't let her down. "Okay, just take them out and I'll tell you which ones I like. But remember: each guy is different. Besides, it's really about the girl wearing the clothes than the clothes themselves." "Great! Oh my god, thank you so much. I hope this isn't too uncomfortable for you." "No, don't worry, I just want to help my sister out, that's all." The contents of the bags were spread out before me. There, on the left, was the black pair I had seen earlier. The set in the middle was a simple red one. The panties were lace until they hit the crotch area, where a solid patch covered everything up. The final set was green with a black trim. I don't think the panties would have covered Kayla's ass at all. Since I had already seen Kayla in the black one, I quickly said, "I like the black set," and turned to leave. "Wait, why this one? I was thinking the green one might be better, since it matches my eyes." Kayla clearly wanted more than a simple vote - she wanted an opinion. I just wanted to get out of there as fast as possible so I could go deal with the problem growing in my gym shorts. "Look, I don't know why - I just like the black set the best." "Are you sure? Why are you so sure?" She looked a little inquisitive. I decided the truth would be the best. "Honestly, sis, the truth is that right before I knocked on your door I opened it without knocking and...I saw you in the black set. I know it looks amazing on you and I know Jack will be happy with it. Can I go now?" I was embarrassed. Kayla looked at me a little stunned, "You saw me? Why didn't you say anything?" "I don't know, it was embarrassing for you, and, well, really embarrassing for me." She sat there for a moment in thought and then said, "I don't want any biased opinions. If you saw me in one set, then you need to see me in all. Then you can tell me which one you like best. So go wait in the loft. I'll come out in a bit." Now I was stunned. Without a word (or really even a thought), I exited her room and went to go sit on the couch. What was happening? I looked down at my shorts. If I wasn't careful, things could get a lot more awkward between me and my sister. I grabbed a couch cushion to cover myself up right as I heard her door open again. She came out in the red pair and once again, she looked stunning. Her long, slim legs drew the eyes right to the mysterious covered patch. Her breasts, though small, glistened as they were pushed up ever so slightly. My cock jumped up underneath the pillow. God, four years was a long time. "So, what do you think? Better or worse than the black?" she asked a little awkwardly. I could see she was nervous, so I decided to help her out a little. "Look, if you're going to try to be sexy, it's not just about what you wear. It's about how you wear it. Pretend you're a model and strike a pose. Give me some confidence." I smiled encouragingly at her. She glared at me, but I could tell she immediately relaxed. After all, if I could be relaxed, so could she. She stuck out her hips and strutted towards me. Right as she reached my knees, she swung around, so that the round orb of her ass floated tantalizingly in front of my face. She looked back over her shoulder and with a smirk, said, "Enjoying the view?" "Yeah, but I think I still like the black better. Go put on the green" As she left, I couldn't help but think that this was actually kind of fun. I mean, it's not like we were going to do anything. She is my sister. The door creaked open again and this time she took my breath away. With a sultry look she strutted towards me, chest out, sex in her eyes. My cock shot up. This was way better than anything Alex ever had and I said as much, "Oh my god, Kayla you're gorgeous. That's the one." She smiled and looked down, "You're just saying that." "No, I'm not, I promise," I said as I stood up, which turned out to be a mistake. She was looking right at my fully erect cock as it strained my basketball shorts. "I believe you," she said a little quietly. She turned to go back in her room and I got a beautiful view of her ass. It had nothing more than a thin black strip running across the top of her cheeks and one running down her crack. I couldn't tear my eyes away. I followed her to her door, an act which to this day I cannot explain. "Kayla, whatever expectations Jack has, I promise you, you are going to blow him away." "Thanks Dan," She turned and looked at me all serious all of the sudden, "I don't think he likes me all that much." "Kayla, that's crazy. He just bought you WE Fest tickets! Those things don't come cheap, you know." But she was serious. She looked up at me with her big eyes and I could tell she was afraid. She was afraid of being rejected once again. Those cheating past boyfriends were eating her up right now and I knew I had to be there for her. "Look, sis, you are one of the most beautiful women I have ever seen. If somebody doesn't appreciate that, they have to be one of the stupidest people on this planet. And I'm not just speaking in absolute. Kayla, you remember my old girlfriend Alex? Well, I never saw her in anything that made me feel like what you're wearing does. I promise you that." I took her in my arms and we sat down on the bed. I held her for a moment, my beautiful sister. I had momentarily forgotten about the camping trip in my shorts, but sitting there, holding my nearly naked sister, reminded me quite quickly. "Thanks, Dan," she said with a small smile. She stood up abruptly. I moved to go, figuring she wanted to get changed. "Don't go. Just stay awhile." I was surprised, to say the least. I moved back to the bed, unsure of what to do with myself. Kayla wasn't facing me and she didn't say anything, so I just sat back down. Her hands moved up to the bra clasps and I couldn't believe my eyes. My little sister was getting undressed in front of me. As she popped the bra off, I noticed exactly how sexy a woman's back could be, unhindered by the sight of a bra. Either that, or I was really horny. That's when she turned to look at me. Her breasts were small and firm, with two perfectly round brown nipples staring me directly in the face. "Dan, do you promise that you think I'm beautiful?" I was bewildered. I looked her in the eyes, "Of course Kayla. I would never lie to you." "Prove it." She had such a blazing look in her eye that I moved without thinking. I stood up and I kissed my sister full on the lips. And she kissed me back. Almost immediately, the tension I felt in her body melted away as she pressed herself against me. Her arms encircled me neck as I felt the soft warmth of her tongue push its way into my mouth. I kissed her and we didn't stop. I stumbled softly back, looking for the bed, all the while glued to my sister's lips. God, it had been awhile. But I pulled back. I couldn't do this, not with my baby sister. I looked at her, not wanting to make her feel bad, and said, "Kayla, I hope that proved it to you. I know you're beautiful. But we can't go any farther. We can't." I don't know why, but I was almost pleading. Kayla smiled at me, a small smile, "You know, I think you're beautiful too. And I don't understand why you've been single all this time." She looked down at my shorts, "Do you mind if I have a look?" She said it shyly, but I could tell - she was excited. "Look, Kayla, I don't think it's a good idea." "Oh no, it's nothing like that!" she said quickly, "It's just that I've never seen one before and I, uh, well, I don't want to be unprepared for Jack." I stared at her, "Are you sure, sis?" She stared at me and the blazing look returned to her eyes, "Yes. I'm sure." I slowly slid my shorts down my legs. I was wearing some plaid cotton boxers and the tip of my cock barely peeked out. I moved to the waistband of my boxers when Kayla said, "Can you take off your shirt first? Please?" I just looked at her. Without a word (I didn't know what to say - what was happening?), I took off my shirt. I wasn't chisled, but I certainly wasn't fat. I had never been embarrassed to take off my shirt, even though I was never one of those guys who took every chance he got to walk around shirtless. Kayla looked at me in my boxers and my socks, with something that looked like hunger in her eyes, "Can I..." she trailed off. I knew what she wanted. She wanted to take off my boxers. She wanted to do it. I simply nodded. I think my tongue was glued to my mouth anyways. I couldn't believe what was happening and somehow all conscious thought flow had simply stopped. I watched my sister, with boobs still hanging out for me to see, kneel down in her pale green panties, and slowly, but determinedly, pull my boxers down around my ankles. My cock nearly poked her in the nose, as if to say a sick sort of hello. She looked up at me, questioningly. Her hands moved up to grip my cock, all six inches of it. I simply nodded. I didn't know what else to do. Her fingers were cold, which made it all the more exciting as, for the first time in four years, I felt someone else feel my shaft. She didn't rub it; she just put her hands on it and on my tip and on my balls. I couldn't contain myself anymore, so I pulled her up from her knees and I kissed her. Hard. I didn't hold back this time. I couldn't. I felt my cock press against her thigh. I felt her breasts against my chest. But most of all, I felt her lips on mine. I knew then: I had lost control. I wanted my baby sister. And the craziest thing? She wanted me. I pulled her down to the bed, never once breaking contact with her lips, and I began to kiss down her body: her neck, her collarbone, her chest, and then, I took her beautiful nipple into my mouth. That nub tasted so sweet. I rolled it around on my tongue before she pulled me up again, back to her mouth. I felt her hand wrap around my cock again and this time she began to rub. Slowly at first, but then faster. Without thought, my hand, at first cupping her gorgeous ass, slipped in between the waistband and her skin. I moved it around front, where I felt no hair. She had shaved. I simply rested it there at first before I felt her legs widen ever so slightly, inviting me in. I tore myself away from her lips. She was down on the bed in front of me, me crouched above her. I gripped her panties with both hands and pulled them down her legs. My sister's beautiful wt pussy stared back at me. I got low, exploring with my fingers her folds. I began to slowly rub her clit with one hand. Her breathing got heavier, "Do it, bro. Please." I rose up and kissed her again before plunging two fingers into her tight pussy. As I plunged them in and out, she stopped kissing me so that she could bite her lip. I had forgotten that she had never done this before with someone else. Little moans began to escape her as I sped up, "Mmmm, mmm, please, mmm." I took her directions to heart. Without further ado, I began to kiss down her torso, every slowly, before arriving at her shaved pussy. I kissed it without slowing the pace of my fingers. My Sister's Holes I kissed her clit and took it into my mouth, rubbing my tongue all over. The sweet scent of her musk filled my nose as I tasted the salt of her juices. I slid my tongue down beside my fingers, lapping at her pussy. Her hips bucked as her moans increased, "Oh bro, oh Danny, oh, oh," her hips now bucking up and down relentlessly. I stuck in a third finger. The effect was instantaneous, "OH GOD!!" she screamed as she came in my mouth. I continued to pump until her orgasm wore out. I slid up beside her on the bed and kissed her once again, "How was it?" I asked. She pulled my fingers out of her pussy and sucked on one of my fingers before answering, "Amazing bro. Now it's your turn." She moved down to my cock, rubbing it slowly at first. Then she gave it a short little peck, so that the precum created a long, sticky thread from her lips to my shaft. She looked beautiful. Then she took in my tip in her beautiful warm mouth, sucking on it like it was a tootsie pop. Then she slid her mouth down my shaft, deeper and deeper until I felt the back of her throat. She pulled out for air, looked at me with a smile, and then went down for the blowjob. It was amazing. I felt every part of her mouth - her cheeks, her throat, her tongue. She bobbed up and down, sucking me at every angle. I could resist. I grabbed her by her hips and pulled her over my face, so that I could eat her pussy while she sucked my cock. She went down so far, I could feel my tip slide down her throat. She may not have been very practiced, but my sister Kayla wanted to deep throat. I started to rock my hips up, slowly face fucking her as I buried my tongue in her pussy. I heard her choke a bit and pulled back, but she was determined. She went down as far as she could, until her nose nearly touched my balls. As she slid up for air, I could feel myself cumming. I tried to tell her, but it was too late; right as she pulled away, I blew my load and it hit her directly in the face, the first spurt hitting right below her nose, the second above her eyes and the third on her chin. My sister was drenched in my sperm. She looked a little shocked at first and then gave a little laugh before heading to the bathroom to wash up. I could believe what I had just done - I had gotten a blowjob from my sister. And it had been amazing. As I laid there, thinking, I was surprised when Kayla came back and immediately positioned herself over me, aiming her wet pussy over my shaft, which was already hardening again. "Sis, are you sure? Do you want your brother to take your virginity?" I was serious. So was she. "Bro, I want you inside of me. I want you in all of my holes. Bro, I need this." And she lowered herself down. I felt the warm folds of her pussy engulf my cock as she slowly pressed herself down. When she was all the way down, she began to come up again, bobbing up and down on my throbbing shaft. It was pure pleasure. I saw my sister's boobs jiggling as she bit her lip once again. "Oh god, yes, oh god, that feels so good!" I grabbed her hand and brought it to her clit so she could rub it. No words were needed. Soon, I had had enough. It was my turn to take control. I lifted her off of my and laid her down, ass up. She wiggled in anticipation. "Oh no, just you wait. This will be my surprise. Alex and I used to do this all the time." I bent down and grabbed the three pairs of panties. I grabbed one leg and tied it to the bed post using her own panties. I did it to her other leg as well. I then grabbed her arms and cuffed them behind her back, tying them together with her own panties. "Dan, are you sure about this?" "Kayla, trust me. You will love this." I positioned myself behind her and slid in, slowly at first, but slowly speeding up, until I was positively slapping against her firm ass. "Oh, oh, oh, oh, oh," she grunted with each blow. As I felt the cum bubble up in me, I knew it was time to switch. I pulled out. Using the juices from her own pussy, I moistened her asshole, "Sis, I just want to let you know that I love you. Are you ready?" "Yeah," was all she could say breathlessly. I poked my tip in, very slowly. I could feel her tighten a bit, but then she relaxed. I pushed in a little farther. She clenched and bit her lip. "Kayla, I can stop anytime." "No, keep going," she said with her eyes closed. I could feel her tight pink ass as I slid in even farther. A tiny whimper escaped her lips. That was as far as I was going. I slid out before pushing back in, slowly. She grunted, but said nothing. Taking a little encouragement from this, I continued a little faster. The grunts were constant now. I raised her up a bit and began to play with her pussy as I moved, steadily, in and out of my sister's ass. I started to go harder, "Oh bro, fuck me, fuck me, fuck me, ohhhh, that feels so good, oh, oh, oh, oh." I started using all my force now, going in and out of her super tight ass. She was screaming now, "OH, OH, OH, OW, OH MMMMM, OH, OH AAGH, OH!" Once again, I felt cum bubbling to the surface. I pulled out. I moved to her face where she was helpless to stop me, thanks to her panties. I stuck my cock between her lips and down her throat and I began to face fuck her. Hard and fast, I could hear her choking ever so slightly, but I knew she was fine. I moved in and out and watched the spit bubble up around the sides. She looked at me eyes wide and I knew that she knew what was coming. "Here I come, sis, take it all!" And I came in her mouth, shooting my second load down the back of her throat. She choked at first, but then I felt her begin to suck. I pulled out when I was done and she showed me that she had caught every last drop, except for the few that dribbled out the corner of her mouth. She grinned and swallowed before I untied her, where we collapsed in each other's arms. "Sis," I said, "I think I'll stay here tonight, with you. What do you say?" She snuggled into my arms, "As long as we get to do it again tomorrow morning," and I couldn't help but smile.