21 comments/ 176833 views/ 74 favorites Emily's Anal Surprise By: BillyBobBill All characters are 18 years old or older. This story contains incest, anal, and religious themes so if you are offended by these viewer discretion is advised. This story is fantasy and I am in no way promoting this be taken literally. If you like the story tell me and I'll make a part 2 ***** I loosened my tie and set my pencil down next to the keyboard. As I leaned back my head tapped the back wall of my cubicle rather harshly. "Something the matter Bruce?" Inquired Tom, peeking from his cubicle looking down at me. "Nothing, just bumped my head." "Huh, we'll you must've done it pretty hard and half and hour ago because you haven't finished a single document" "Looking at my printer I knew he was right, I needed to reformat and print 30 separate documents yet my printers exit was embarrassingly empty. "Haha I'm just messing with you, sometimes I just need to break in the new guy" "Ah get out of here" I said chuckling, and Tom disappeared behind his cubicle wall. He was right, being only 21 I was defiantly the youngest guy here by at least 20 years. Not many fresh out of college guys can get a high end office job. Truthfully Tom was right. I was distracted and had been distracted for a week now. This is the result of a rather peculiar encounter with my Emily, my younger sister. To understand our relationship one must understand our upbringing. As I've seen from pictures my mom was tall and blonde, but had wrinkles from aging. The kind of model type girl in a mid life crisis at around 40. My dad was much younger, being 21at the time of marriage. He had dark brown hair and was a sort of slouched anti social guy. A provider type. My guess is mom was looking for someone to settle down with. They had two kids together, me and my younger sister Emily. When I had turned 3 and my sister 1 my mom had gotten into a sadly fatal car crash and my dad was crushed. I don't remember my mom and her death all that clearly but what I do regrettably remember is the shit I went through from my dad coping, if you can even call it coping. Dad was crushed and went to alcohol for help. His friends thought it was a coping phase that would pass. By the time it was clear they were wrong dad had no friends left. By the time I was 4 my dad would regularly physically abuse me and I have the scars to prove it. My sister was not exempt from his wrath by any means but I was the majority victim. Eventually Dad's drunken rage got him into a bar fight that wasn't forgiving and he never left at all, the police found him with multiple gunshot wounds in the back of an alley. I don't know who that silent guardian was and I don't care, all I know is things got better after that. We were taken into custody by the police and they found us a nice adopted family. The wife was named June had long jet black hair and was sort of on the chubby size. The father was names Mich and he also had jet black hair, but due to his marine training he was heavily built despite later gaining a beer belly. They are great parents who disciplined us and helped with our education by encouraging us to do our best. But due to our past me and Emily were wary of an adult. As such we had a really close relationship growing up. We did everything together, any one who bullied Emily had to answer to her big brother. June and Mich were both extremely religious so I had the "joy" of going to church every Sunday and an overall indoctrination. Emily on the other hand actually did end up becoming specifically religious and her relationship with June got closer because of this. Due to an early scholarship I got I had been at college for 4 years now. I visited during summer of the first year but all the years after that I never found the time. As I parked I got greeted by my smiling step parents as we chatted about what went on in college. "oh my, look at my big boy!" June said laughing She was right, during college I took up lifting and had gotten my body to where I wanted it to be. I have light blonde hair and stood 6 ft 3, a whole 6 inches taller than when I had left home. "Ah, I see you've been hitting the weights!" Laughed Mitch patting my shoulder. My parents sat in the living room talking. I went upstairs to my room, as I got inside and lowered my bags. I heard a scream from downstairs. "BRUCE!" Shrieked Emily as she came dashing up the stairs. She grabbed me in a tight in brace and I almost fell backwards from the force. "it's been so long!" She said laughing and holding me tightly. "Ha, yeah It has I said softly" patting her on the back, I lowered my aim a bit and my pat grabbed onto her firm backside. My eyes widened. Still in a tight in brace with Emily I felt my cock twitch. Emily had grown a lot in these years I've been gone. She was 5 ft 11 and her light blonde hair reached down to her lower back. Her breasts were perky and a perfect handful from what I could tell. Her legs were slim and sexy as they began from her perfect firm bubbly behind. Emily was also clearly only wearing a thin material shirt that dropped down past her pelvis. I was in a shock. Never had I had a thought like this about a family member. I mentally slapped my self and let go of Emily. "I can't believe you're back!" She said giggling. Her perfect model face accented by her rosy red blushing cheeks. "Me neither haha! Look at you!" My cock twitched again "Look at me?!" She said in surprise sarcasm, "My baby brother has grown up!" Emily used to always call me baby brother even though I was older than her. She did it to annoy me when I was younger and It stuck. I could see the faint pink outline of her nipples on her shirt and she bounced happily. "We'll I'm going to get changed into something, we have a lot of catching up to do!" She laughed as she went down stairs. Emily was amazing to me, despite what we went through as kids she was so ditzy bubbly and happy. I was shy and reserved but she always had enough friends to pass around. From that moment on me and Emily goofed off like regular siblings. But I always had that thought in the back of my head. I got home from work and sat in the couch. It was still day time. The right of the couch was draped over by a Jesus's face. More precisely a blanket with Jesus's face on it. Emily had gotten it at some Christian festival but Mich had insisted it not be used for anything because in his words "Jesus was no rag". June and Emily were chatting in the kitchen. I listened in. "We shouldn't have to deal with this criticism. We needed to kick her out." June argued "I know right mom! It's like so what? It's not our fault she's not a virgin." Emily stated matter o' factly "We'll it isn't her fault either since she was raped, but I agree." Continued June Emily stated, "We'd lose all our funding if a known non virgin was in our group. I really want our group to grow and I'm not going to risk it for some perv!" June nodded in agreement and walked to the laundry room. I stepped over. Emily was wearing her school outfit with a white buttoned up shirt and a blue skirt. "What's going on?" I Inquired "Nothing," she said, doodling something on a piece of paper. "It doesn't seem like nothing" I teased "We'll you know that girls only church club I'm in?" "Yeah?" "We had a member named Brittany, but apparently a guy had "raped" her while she was unconscious at a party." "Oh my god, is she okay?" I said, kind of surprised my sister would use such words "Huh? Why wouldn't she be?" "You said she was raped." "Yeah. She's no longer a member because her virginity is gone." "Wait what? She was raped, how can she be okay?" I asked confused "What do you mean?" Emily said twirling her pony tail and giggling now, as her brothers confusion has made her mood improve. I paused for a second and thought. Emily's been a devote Christian and has followed some extreme standards her whole life. I think I know what's going on here." "Do you know what rape is?" I asked "It's when you take someone's virginity without asking, duh!" She said giggling, my hand was resting on the counter and she put her hand on mine still giggling. I pushed away any excitement and continued "How do you take someone's virginity?" I asked nonchalantly "You..uh...put their privates in your privates." She said than burst out laughing "My husband will teach me silly." I sighed. We'll she got the basics at hand. It was hard to believe an 18 year old like her in this generation is still fairly naive. Feeling somewhat brave I asked "What if you were raped." She stopped giggling. She put her finger on her lips and said "I guess I would keep it a secret. I don't want to lose my position in the club." Emily walked to the laundry room to talk to June. I went back to sit on the couch and fell asleep from my long day at work. I woke up. It was dark. "What time is it?" I said to myself. The clock said 2:34 a.m. Huh. Glad I don't have work tommorow. I shot up in pain. I opened my zipper and let my penis out as I sat back down. My penis had grown profusely from kegels and other lifting exercises and now stood at 8 inches and with a large blue vein at the side. It was pulsating almost painfully from pent up lust. I was extremely horny for weeks now from refraining from masturbating to the thought of Emily. "She's your sister dammit" I shrieked in my mind. I sighed and turned on the tv lowering the volume. I started switching channels and I got to a comedian. The comedian let out a line and I laughed kicking my feet up. I knocked my bag over, my bag having been on the table in front of me. I changed the channel before picking up my bag. As I got up I noticed something fell out of my bag. It was a cylinder glass container of some clear liquid. Oh god. It's lube. Thinking back I realized, it was most likely from one of my college buds. He had talked about putting sex toys in the bags of people going home in the hope they'd have awkward moments with family or something. I chuckled to myself. Oh mike you scud haha. I put the lube to my side and looked at the tv. I hadn't noticed because of the low volume but there was a sex scene going on. My softening cock shot up. The scene was some muscular hero caressing the heroine. I glanced at the lube. I can't believe I'm doing this. I squirted it on my hand and spread it over my cock, I shuddered from the coldness. "Just one rub out" "just one" I told myself. Glancing back and forth to make sure no one was around. Glancing at the Jesus blanket staring at me I look back down. As I stroked back and forth I imagined her heroine stroking me. Up and down. I saw her soft small hands going up and down. I look up to see her face and I see Emily's rosy cheeks and a naughty smile back at me. "DAMMIT!" I say out loud. I gasp and look around. I don't think anyone heard me. I sigh and slide back on the couch. My cock was softening from the fear I got due to waking someone up. It was still noticeably erect and covered in lube. "Oh Emily I whispered to myself." ---- "GOOD MORNING" I hear scream into my ear. "WHO? WHAT WHO-" I drunkedly yell looking around, On the couch, Jesus blanket at the right. It was morning time. Early it seemed. On my lap sat Emily. Her back facing me. I regain composure and notice . Emily is sitting on my lap with her back facing me. She's wearing a blue bikini with white polka dots. Her ample butt is laying on my lap directly Infront of my crotch. Her legs are folded at my sides. It took a second to register. This is almost reverse cowgirl. Emily laughed "Did I wake you up a little loud oh baby brother of mine?" "Uh y-yeah" I say stuttering. My limp penis begins to grow rapidly as I try to zip it close. The zippers is stuck. "W-what are you doing?" I say breathing heavily "Just wanted to go for a little early morning swim is all and I decided to play with my baby brother here" she giggled again still facing away from me and at the tv. Her bikini bottom was strange. It had a button in the middle that connected the top half to the bottom half. Undoing the button would let them be pulled clean off. My cock continued to grow and I noticed it still has lube on it. Frozen in shock I has stopped paying attention to what my sister was saying as my pulsating erect 8 inch penis was stuck out of my pants pointing at the back of my sister in a Bikini in the middle of the living room. The thought of my parents walking in and seeing me like this should have made me afraid but just made my cock grow another quarter inch. I looked up at my sister. Her light blonde hair had fallen over her shoulders and back. Her tanned legs were naked and sexy with her cute feet and their red bottoms at my sides. Almost by themselves my hands reached and grabbed hold of her bikini bottom button with two fingers. In a fraction of a second my hands undid the button and in one fell stroke pulled her bikini bottom clean off. There was a moment. One moment between what I had done just now and what I was about to do. The moment I knew in my core that what I was about to do would forever change the way I look at the world and the way I know my sister. The moment where my sisters next word did not come out of her mouth and the rush of cold air on her now exposed lower body gave her a blush as her head began to turn in confusion at her brother behind her. That moment was less than a millisecond. It may not have even existed on our physical plane. But it was there. In one impossibly fast swoop my hands pulled her cheeks apart and the tip of my lubed penis pushed apart her pink rosebud. The head of my cock pushed into her anal ring and it was inside. There were stages of what happened next. The shock. The disbelief. The denial. The regret. I had none of these stages. She did. It was impossible for me to imagine ever before that there would be a time like this. Here I am My 18 year old blonde bombshell sister is sitting on my lap with her fully exposed body with the exception of a bikini top. Her buttocks was firm but soft and has a rosy red glow like her cheeks. My penis head was inside of her anal ring. A place where she had never been touched or expected to ever be touched. It was incredible. Like a metal rod sticking out off a cushion. Her glistening tan buttocks with rosy red cheeks had an anal opening being penetrated by her own flesh and blood brother. I put my hands on her legs. Still somehow afraid to violate her buttocks I gently caressed her legs. My hands ended at her feet where I pinched her pinky toe. Unbelievable. Here I was an inch inside of my sisters anus and I was caressing her feet like nothing happened. The realization corresponded with a jolt of bravery to me. My hands shifted. I put them on her back and felt her soft blonde hair. Than I put them both lower and slowly had them grasp her rosy butt cheeks. I gently patted than squeezed and rubbed her cheeks back and forth. Her anal opening was tight around the head. I felt it almost squeezing me. A jolt of electricity shot in my head and I remembered exactly what was happening. I stopped moving my hands as they laid still on her butt cheeks and looked with fear at the back of my sisters head. "B-b-b-bru-b-bruce." She said softly as she panted slowly. It was her turn to stutter I than felt her pussy drip on my pant leg. Unbelievable. She was turned on. Trying to focus the feeling to the droplet on my pant I shift slightly inside her. "A-ahh" she gasps quietly Than I see it. I feel her neck turning back at me. She looks me in the eyes. Her beautiful blue eyes glistening. Her blond hair slightly covering her face. Her mouth open slightly revealing a little of her front teeth. Her cheeks flushed and adorably red. Her expression is that of multiple feelings. Fear, confusion, hormones, regret, and shock to seal the deal. Her lips move "B-b-bruce....you're my brother." The realization that this is a shameful incestious act surged through my being. My penis twitched and pre-cum is milked by her ass and is ejected. Her eyes widen with the liquid feeling. I don't know what came over me. But I lean foward and put my hand at her chin. She looked so vulnerable, so needing of protection. I grasp her chin and moving forward I make contact with her lips. It's soft and sweet. I taste cherry lip balm. I push forward with my tounge and twirl inside her mouth. My left over fuzz from not shaving in a while brushes past her chin. She pulls her most back and gasps. I feel her vagina squirt more on my pants. I continue. As I embrace her mouth she starts making slight movements with her tounge. I grasp her shoulders and slowly push my penis foward. As it goes two inches I feel the tight anal walls gripping me. She pulls her mouth back but I pull her chin forward. She moans while my tounge is in her mouth. Emily quickly pulls back "b-Bruce!" She says quietly but somewhat angrily Softening her voice as she sees my up changing expression she continues "Y-your i-in my butt!" Coming to the realization that I am having a conversation with my sister while my penis is 3 inches inside of her ass, my hands are on her butt cheeks, and a trail of spit from my mouth to hers is visible I flex my penis inside her causing more precum to squirt out. She gasps and in that moment I continue my tongue assault. I move down to her neck and start nibbling on her. Her moans escape her while she protests. "Mm-mm B-Bruce I'm y-your siste-Ooh ahh y-you can't be in my b-butt, w-w-what if I t-tell mom" At that mention I pull back. She looks at me innocently like she's almost disappointed and guilty she is. God how did I not think of this. Imagine what would happen if my parents know about this. I pause to think and Emily regains her senses and tries to get up, albeit she goes slowly due to my penis in her rectum, she gets two inches out and I grab hold of her waste and push upward. "I-EE" I quickly cover her mouth to stop her from screaming. My sisters firm ass struggling against me makes my penis pulse harder. I pull my head close to hers and she whispers almost in fear "I-I'll scream for m-mom." I smirk. Emily's expression changes to confusion. "Emily" I say as I rub my index finger along her wet slit She gasps "What exactly is in what right now?" Emily looks in confusion and begins to speak "y-your private in m-" Her eyes widen with the realization. Her mouth opens to respond but before she can I push my pointer finger'd tip into her wet vagina lips. She gasps loudly and I cover her mouth with my hand, the hand that has been caressing her buttocks. "Emily oh Emily, you wouldn't want this virginity issue to get out would you? How would your church group like this news?" I say pulling out of her ass a inch. "T-they wou-Ooh-would k-kick me out" she said, as if telling herself. "Right Emily, good girl" "B-b-but it's my butt, n-not my virg-" I interrupt her by pushing my finger into her soaking vagina breaking her hymen. A trickle of blood falls down. Emily stares in shock. I stare back even more shocked at what I has just done. I had violated my sister in more ways than I could even imagine. I shot back to reality. This was my own flesh and blood sister, it was go damn Emily. I was sitting here with my penis inside of my eon blonde sister Emily's asshole. And my index finger was feeling the wet goodness of her virgin vagina with Jesus's face staring at me from a few feet away. I open my mouth to respond when my parents room door opens and June walks out rubbing her eyes and letting out a loud "Good morning kids!"