My Sister Ashley - Cover

My Sister Ashley

Copyright© 2009 by VonArmand

Chapter 2: A new character

Fantasy Sex Story: Chapter 2: A new character - My name is Tim Donovan I live in New Hampshire and I'm 18 years old. I live with my mom, dad, and my twin sister Ashley...... All the events that follow this story happen a week or so before Christmas break of last year....follow the misadventures of my sis here....

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   mt/Fa   Fa/Fa   NonConsensual   Reluctant   BiSexual   Fiction   Incest   Brother   Sister   BDSM   DomSub   MaleDom   FemaleDom   Spanking   Rough   Light Bond   Humiliation   Sadistic   Torture   Group Sex   Orgy   First   Safe Sex   Oral Sex   Anal Sex   Masturbation   Sex Toys   Squirting   Exhibitionism   Voyeurism  

I woke up the next morning completely disoriented. Where was I, why did my back ache so badly, and why was Ashley laying behind me with her arm draped over my side? Then the memories of yesterday's activities slowly crept back into my groggy mind. I shot to my feet taking Ashley with me and dumping her onto the floor in a heap.

"Aw Christ Tim!" She growled. Her pink bathrobe had fallen open and I could clearly see that she was naked underneath. I looked at the clock, it was five in the morning and it wasn't yet light outside. I apologized to my sister and helped her to her feet as she refastened her robe. I sighed and walked into the kitchen to get some cereal when my stomach shot into my mouth. My mother's purse was sitting on the kitchen table!

"Ashley!" I whispered.

"What?" she asked groggily, coming into the kitchen.

"Mom and Dad are home!" I said pointing at the purse.

"Shit! We have to clean up my room!" she gasped and hurried down the hall to her bedroom. I followed her but stopped before entering and just gaped at the bedspread. Blood had soaked into the sheets along with other conspicuous fluids forming a series of nasty looking stains. The sheets were rumpled and tossed about in disarray.

"Forget it Ash that stuff doesn't come out without serious work. Just change 'em and we'll see what we can do later." I said as I helped her replace the soiled sheets. We finished and then gave my room the same treatment before we settled down and moved back into the kitchen. I poured myself a bowl of cereal and she fished some pop tarts out of the cabinet. We ate in silence and avoided each others eyes before finishing our breakfast and going back to our rooms to get dressed. I threw on a fresh pair of jeans and a light button up shirt that didn't aggravate my back then made my way into the living room to watch some TV. I lay face down on the couch with my head turned toward the television; I could still smell my sister on the cushions. After a while I heard the sound of feet shuffling on carpet and a pair of tight jeans filled my vision. I let my eyes roam up her body and make their way to her pretty face; she was wearing a white button down collared shirt that clung to her waist and emphasized her broad shoulders and full tits.

"We're still cool, right?" she asked.

"I guess, I don't know," I said trying to see around her full hips, "just sit down somewhere." She sighed and stepped to the side and I thought she was going to leave but she turned and sat down on my ass crushing my crotch into the couch. I grunted but didn't feel like trying to get her off of me.

"Tim I need to know that we are okay. I don't want breakfast to be the way we interact with each other, all silent and awkward like." She said. I couldn't turn my head to look at her so I continued to stare at the television as I spoke.

"Don't worry; I'm just trying to digest what happened yesterday. Besides you just want to keep fuckin' me don't you?" I said. "By the way, how is your pussy doing?"

"Well ... yeah you're my current meat. And its not that bad; I should be fine in a few days. What about your back? Are you ready for the five-stars that you deserve for jumping on me last night?" I could see her out of the corner of my eye slowly raising her hand and spreading all of her fingers as wide as they would go.

"No! Don't you fucking dare!" I started to buck my hips to throw her off and she let herself be thrown onto the floor again, giggling. I stood up and stretched; the bandages she applied last night were still tight and my back was sore.

"At least the male population is safe for a few days while you're laid up." I smirked at her as she sat on the floor in front of me.

"Ha! Who said anything about the male population? You're the one who should watch out. You haven't completely disabled me, you should know that." She smiled sweetly up at me. Damn it! She was so hot, looking up at me like that with a lock of golden hair covering her right eye. She slowly stood and faced me, her one visible eye glittering. I could feel my cock stirring and she must have sensed it too because she slowly slid a hand up her chest and started undoing the buttons of her shirt one by one. I wanted her so badly but knew my parents, even when dead tired were early risers and would be up soon. I reached out both my hands and clasped them over hers to stop her from unfastening any more buttons.

"Not now. They will be up soon, you know that. I'm sorry though maybe tonight or something." I said softly. She pouted and began to refasten her shirt. Damn why were they back so early? They were supposed to be home tomorrow afternoon, I thought to myself.

"Oh and what was that about last night huh?" she asked with a smile on her angelic face.

"What?"

"The 'your cunt is mine whore' thing?" She said with a near perfect imitation of my voice.

"You were asking for it," I laughed. "And besides it is, isn't it?"

"Mhm." She bit her lip and looked me up and down "God I'm so fucking horny right now!" I laughed again and I put my arm around her shoulder and ushered her down the hall to her room.

"Why don't you take care of that problem yourself." I said as I pushed her into her bedroom and closed the door.

"But it's not the same!" she whined from behind the door. I was laughing softly as I walked back to my room to wait for my parents to wake up. I never made it. Right as I was about to open my door, my parents door opened and they both came into the hallway, scaring the shit out of me in the process.

"Oh, hello Tim." My mother said following my dad into the kitchen.

"Mom, dad how's it going, how was your trip?" I stammered.

"Oh fine, fine. The reason why we came home early is because they were expecting a serious snow storm and we didn't want to get trapped up there." My mom said conversationally. "Listen Tim could you come into the kitchen for a second? Your father and I want to talk to you."

"Um sure thing mom." I said and joined them at the table.

"Have you eaten?"

"Oh, yeah I've been up for a while now."

"How come we found you and your sister asleep on the couch last night, watching a movie were you?" Asked my father from the stove where he was making pancakes.

"Yea I just got it yesterday and Ash wanted to see it too so we were watching it together and I guess we just fell asleep." I said truthfully. My parents exchanged glances like 'aw our kids are getting along, finally'.

"But why were you all bandaged up, what happened?" He persisted.

"Oh yea I was rushing around the house trying to find some papers I needed for homework I have to do and I tripped and fell. Cut myself pretty good, Ash patched me up though and I'll be fine." I lied.

"You should be more careful. Do you want me to look at it?" My mother asked.

"No, like I said Ash took care of it. We should send her to med school or something." I joked. My dad snorted and my mom suppressed a smile, Ashley was not known for her study skills. And just like that last night was forgotten.

The day passed by impossibly slow and nearly drove me insane. I spent some time in my room removing the bandages and applying some cream stuff to the ragged scabbed-over cuts, but that was the only real distraction I had. Ashley kept giving me these looks and mouthing 'I want you' at me, fortunately my parents didn't see. It became such that I got a hard-on just looking at her and I had to leave, I had to get out of the house. I called my friend Jimmy and asked him if he wanted to hang out at the mall for a while, he agreed and as I pulled on my coat I saw Ashley in the other room watching me. There was a look in her eyes that was a mix of rage for leaving her alone and disappointment for depriving her of her favorite toy or something. To bad I thought, I have to get out of here. I drove to the mall and met Jimmy in the food court, he bought some BK and I got some pizza. For a long while we just sat there and ate not talking, I think he could sense my mood because he tried to cheer me up with the one subject I was trying to avoid.

"Dude, you know Katrina Toslov right, the Russian chick from math class."

"Yup, she sits behind me right?" I said barely hearing him. He nodded.

"Well you know how I've been laying on the ol' Jimmy magic right?"

"Yeah."

"I forgot to tell you. I asked her out on Friday and she said yes. Dude she is so hot. Though not as hot as your sister I have to say." He said absentmindedly.

"Fuck you." I said and punched him in the arm.

"Ow. But seriously dude, most guys in our school would kill to tap your sister." He said wary of another attack. I guess I am a step ahead of most guys then, I chuckled to myself.

"Change the subject Jimmy." I said. He did and we talked for a long time about various things, sports, school, and stuff like that. We were there for several hours before he said he had to get home I followed him out and drove home as well. As I pulled into the driveway I noticed my parents' car was not in the garage. I knew that Ashley would try to take full advantage of this situation; I only hoped she hadn't been waiting for too long, she would be pissed if I ruined this opportunity for her. I entered warily figuring that she would attack me rather than approach me civilly. I didn't see her but I could smell her still lingering scent. I crept to my room and still didn't see her, I opened the door and left it open thinking she could just let herself in when she realized I was home.

"They left about twenty minutes ago. They said they were going to lunch so I figure we have about an hour to ourselves." Came her husky voice, and as she spoke my door slowly creaked closed. She was hiding inside my room behind the door! Hearing her voice I spun around and as I did her naked body collided with mine driving the wind out of my lungs and hurling us both to the floor. She flipped me over and sat on my waist again, her usual position of dominance.

"Hello Timothy." She purred mere inches from my face.

"Oof. Hi Ashley." I replied and leaned up and kissed her hard. We kissed passionately for a few moments before she pulled away and leaned back regarding me over her large tits.

"So, what should we do this time?" She asked, smiling wickedly.

"Oh, you do whatever you want. I'm just gonna sit back and enjoy the ride." I said grinning broadly, I laced my fingers behind my head like a pillow and stared at her expectantly.

"Oh come on Tim, you're going to make me do all the work?" I nodded smugly, "Fine, I'll get you back later." She pouted and shimmied backwards until she was sitting just above my knees. Once there she threw off my belt and undid my pants with such speed it shocked me. After pulling down my boxers and exposing my raging hard-on, she licked her lips and tickled the tip of my cock with her tongue making me groan. (Throughout this entire process she maintained eye contact with me which I found was slightly unsettling). She licked my cock up and down before taking me into her mouth; I arched my back and moaned loudly as she continued to bob her head on my cock slowly. I removed one of my hands from behind my head and gathered a fistful of her silky hair in my hand and yanked her off of my cock only to slam her back down again before pulling her back up, intending to repeat the process.

"Oww, Tim don't ruin this." She hissed at me. As she spoke she grabbed my wrist in a vice like grip and squeezed, forcing me to let go of her hair. She then slammed it down next to her pinning it there. "Am I going to have to tie you up again Timothy?" she glared at me. "Well Tim, I've lost the groove thanks to you. We'll just have to go a different route now." She leaned back down and spit on my cock a few times, still wet from her mouth and rubbed it in a bit before sliding forward again. As she did my dick came in contact with the soaking wet pussy lips and she stopped for a moment and shuddered slightly before continuing until her ass was hovering over my stiff cock. Ever so slowly she lowered herself until the tip of my cock was resting against her tight asshole. She paused there for a few moments as if unsure of herself; the muscles in her thighs bulging from the effort of holding such an awkward position.

"You hurt yourself last time didn't you?" I asked softly. She nodded. "We'll just go slow this time then." I placed my hands on her hips and slowly pushed her down onto my cock. Slowly the head of my cock pushed into her tight hole, she winced slightly and I stopped for a moment before she started to push herself down again until all eight inches of my cock was buried in her ass after a few long minutes. She sat there for a while as she adjusted to having herself filled so thoroughly.

"Ahh, this hurts so good." She whimpered through gritted teeth. Ever so slowly she rose off of my cock and then descended again slowly. The pace was driving me crazy, my cock craved speed but I set my jaw and let her go her own speed. Gradually her pace quickened and soon her gorgeous round ass cheeks were a blur of motion. I left my hands on her hips but didn't push her. I had somehow forgotten how good her ass felt clamped around my cock, I moaned loudly and I could feel my balls start to tighten.

"Oh Tim oh, I'm gonna cum!" She screamed. Her ass spasmed as she came, sending me over the edge. Warm clear girl cum shot onto my waist as I blew my load into her tight ass. "Ahhhhh." She sighed, pleased with the outcome. She remained in place as my cock slowly shriveled inside of her. "Well then, that was enjoyable was it not?" she smiled coyly.

"Meh." I said tilting my hand back and forth, struggling to maintain a strait face. Her jaw dropped and she glared at me. I couldn't take it anymore and burst into laughter; she closed her mouth and narrowed her eyes at me.

"Oh yeah, I almost forgot." A sadistic smile crept onto her face as the smile fell from mine "I owe you some pain." She whispered into my face. She hooked her fingers between the buttons of my shirt and pulled it open with a savage jerk shooting buttons in all directions.

"Wha..." I managed before she pinched both my nipples between her thumb and fore fingers and twisted savagely. I screamed, nothing I had ever felt before had hurt this badly. She giggled girlishly and twisted even more if that was possible, I slapped her hands off reflexively and she let go. She stood, my cock falling out of her ass, she towered over my prone body standing with my waist between her legs. A small amount of cum escaped her ass and plopped onto my waist. Tears formed in my eyes and my nipples felt as if they were on fire. I could only watch as she cupped a hand under her ass to stop the flow and sashayed out of my room as best she could. I heard a door open and then the shower was turned on.

"Fuck!" I gasped and clamped my hands over my abused nipples. I lay there catching my breath and trying to sooth my burning nipples before I struggled to my feet and made my way to the bathroom. I opened the door and quickly shed my clothes and ripped aside the shower curtain. She jumped but didn't say anything as I stepped in front of her and started cleaning myself off. I glanced behind me; she was leaning against the shower wall with her arms crossed staring at me.

"Hey they will be back anytime now and you take to long for us to have separate showers." I said. She didn't do anything so I continued washing and finished shortly thereafter before exiting the shower and making my way to my room to get redressed. Not two minutes after I had gotten dressed I heard the door open and my parents clomp into the kitchen. From then on it was an agonizing wait until night fell and our parents went to bed. We were sitting on the couch with a modest distance between us when they headed to their room telling us not to stay up late because we had school in the morning. As soon as their door closed Ashley practically jumped onto my lap, her legs off to one side like a father with his child. Except this child started grinding her ass into my crotch, stirring my cock into action. She did this for a few more moments before stopping to look down at me, smiling.

"Shall we?" she asked sweetly.

"So I take it I'm forgiven?"

"We all do things we shouldn't. Aren't you going to answer my question?" she said stroking my face with one hand.

"Normally you wouldn't have to ask but we have school tomorrow and I'm not exactly feeling up to it. You understand don't you?" I responded.

"Yeah I guess so," she pouted, "but sometime this week right?" she said perking up a bit, acting like a little girl being promised a trip to the zoo.

"Perhaps." I said with a sly grin on my face.

"Because if you don't fuck me sooner or later on your own, I'll fuck you." She growled menacingly. I couldn't take her seriously not with her sitting on my lap like she was, so I laughed and told her I was going to bed. She stood and allowed me to get to my feet and followed me to my bedroom door where I stopped and let her pass. As she moved past me I shot out a hand and slapped her ass hard and was rewarded with a nice smacking noise. She stopped and turned her head slowly, her hair and the shadows obscured most of her face and I couldn't see her eyes but her full-lipped mouth spread into a grin.

"This week Timmy. Sooner rather than later, your cock had better be in me." She whispered before blowing me and overly dramatic kiss and disappearing into her room. I tried to get her image out of my mind as I prepared to go to sleep; and only thinking of school could chase her sultry image out of my head as I drifted off.

The next morning I awoke at the ungodly hour of 6:00 to my alarm. I mumbled curses as I put on a pair of jeans and a white polo shirt then made my way to the kitchen to find my parents already up and about making breakfast. Ashley stumbled in a few minutes later wearing a tight black t-shirt and tight black pinstripe pants, rubbing the sleep out of her eyes. My mother took one glance at her and shook her head in resignation; she had long ago given up trying to make Ashley dress 'appropriately'. Breakfast was uneventful and soon the time came for us to leave, Ashley and I tugged on our coats and made our way to my car (hers was in the shop for extensive repairs due to an accident) yelling goodbyes back at the house. We sat in silence for the entire drive, only breaking the quiet to chuckle when the radio talk show host made a joke.

I pulled into the parking lot half-full of sleepy eyed seniors and parked in my usual spot. Before I could fully shut off the car Ashley had gotten out and was striding towards the building, she didn't like walking in with me for some reason. I hurried in after her, not wanting to remain in the freezing New England weather any longer than I had to. Upon entering I climbed the stairs and made my way down the halls to my locker, exchanging greetings, shaking hands, and slapping backs with my friends, I could see Ashley up ahead of me doing pretty much the same thing. My sister and I were two of the most well known people in school, she was the hokey team's star player and I was captain of the Frisbee team one of the biggest sports clubs in school. Everybody knew us and we were friends with almost everyone in our grade, even freshman knew about us within a few days of attending classes. Ashley had a huge pack of friends that would trail her around school and I made it my business to socialize as much as possible, attending almost every party that was thrown. I also organized a few non school related events such as the fat man race, a few paint ball tournaments, and a dodge ball tournament that had become amazingly successful. I finally reached my locker and was greeted by the person I had wanted to see the most.

"Hi Tim!" she nearly shouted, surprising me by coming up behind me. Oriana Bane was the girl who I had been seeing before this whole Ashley fiasco had happened. Oriana was short, only around 5" 4' but made up for it in a personality that was always happy and good-natured. Although she was one of the perkiest girls I knew she was borderline Goth in the way she dressed. She had short jet-black hair cut in a straight line across her forehead and her small slightly pointy ears stuck through her hair, making her look like some sort of elf/nymph child. She wore dark eye shadow around her bright blue eyes which accentuated the features of her pale face. Her nose was slightly turned up at the tip and she was almost always smiling her teeth a dazzling white. She was wearing a loose black shirt with a band logo on it and a pair of baggy black pants with metal studs running down the sides of the legs. Even through her baggy clothing you could easily see her curvaceous form, her tits were large for a girl her size and though not as pronounced and large as my sister's, her ass was tight and of a good size. We were extremely close but we hadn't 'done' anything but make out a few times and only recently at that. I shot to my feet from where I had been kneeling transferring notebooks into my bag, and hit my head on the inside of my locker on the way up. She was laughing hysterically by the time I turned around and faced her.

"God damn it Oriana." I said laughing and rubbing my head at the same time.

"How was your weekend?" She asked managing to get her laughter under control.

"Oh you know, same old same old." I said shrugging. There was a loud bang and I jumped and spun again as Ashley crashed her shoulder into the locker next to mine.

"I bet Miss Ashley had a fun weekend." Oriana said a strange smile on her face.

"Oh yeah lots of fun." Ashley laughed sarcastically but with a serious look in her eyes. Oriana was one of Ashley's best friends, of course I had only found this out after I had committed myself to being with her, or otherwise I might have had second thoughts. My eyes went from my sister to my girlfriend and then back again, they were looking at each other, communicating in that unspoken girl language.

"If you ladies are done we have class in a few minutes." I said shouldering my bag and heading off down the hall. All three of us have most of our classes together, first period today was English, as they fell into step behind me and I could hear them whispering together. I tried to ignore them and focused on what I needed to do today.

English was uneventful as was the rest of the day although very tiring. Every teacher was cramming in tests and homework to get in some grades before the Christmas break. The rest of the week went the same way and due to the work load my teachers had heaped on me I was unable to fulfill my sister's demand, she approached me a few time during the week but always when I was absorbed in my work. Throughout the week she had become increasingly cold towards me when she realized I wasn't going to fuck her any time soon. Then Friday came around.

It was last period gym class; the best time for gym because you could go all out and not worry about reeking during your next class. We were playing dodge ball today; the large gym was divided in two sections with each side pummeling the other with soft 'kid-friendly' dodge balls. Oriana and Ashley were in this class with me as well, although they barely participated; they just stood in one corner of the room and talked. I on the other hand was throwing myself to the floor to avoid neon colored balls hurtling through the air. Two balls rolled near me and I snatched them up and tossed one to a friend of mine.

"Hold on," I told him before he could whip the ball at someone else, "see Ashley and Oriana over there? You take Oriana and I'll take my sister, on three." He nodded and I counted to three before throwing the ball with all my strength (that's what it took to get any distance or accuracy out of the lightweight balls) both balls flew straight at their targets although they lost much of they speed crossing the distance of the gym. The ball I threw impacted my sister square in the left tit; the other struck Oriana in the right shoulder and bounced off in the opposite direction. Oriana just laughed, but my sister glared at me with rage filled eyes. A bright green ball whipped past my head tearing my attention away from my fuming sister. Before I could turn my attention elsewhere, I saw a blue streak heading straight for my crotch. I watched horrified and unable to do anything as it connected squarely with my groin. Even being as soft as they were it still hurt like a bitch and I fell to my knees and keeled over. I looked up and saw Ashley not ten feet away holding another ball in her hand. My friend's face filled my vision, he was laughing so hard he could barely speak.

"You okay Tim?" He managed. No sooner had the words left his mouth before the ball my sister had been holding crashed into his jaw. He fell to the ground next to me and we both broke into laughter. Out of the corner of my eye I saw Ashley striding over to us completely ignoring the rules of the game, as she crossed the boundaries that separated the two teams. Her big basketball shorts and loose t-shirt swished as she walked.

"You're done Timothy, when we get home watch your back." She growled. She walked back to her own side and continued talking with Oriana.

"What was that about?" My friend asked from beside me as he got back to his feet. "I bet that didn't even hurt that much."

"Dude, you don't want to know." I said, as I struggled to my feet I was struck two more times. Just then the bell rang and we hurried to the locker room to change and head home. I changed quickly and made my way to the car, where I waited for what felt like forever for Ashley to show up. When she did she still looked pissed so the ride home was silent and incredibly awkward. When we got home I was getting nervous, we both knew that our parents were still at work and weren't going to be home for another couple of hours. This time I got out of the car first and scurried into the house before Ashley had even unbuckled herself. Once inside I tossed my bag on the kitchen table and before I could do anything else I heard the door open and close. I spun around and found myself facing a furious sister.

"Ash l-let me explain..." I stammered before her fist slammed into my stomach. I went to double over but she held me up by one shoulder and punched me twice more in the exact same place. I hit the hardwood floor hard, headfirst; the last thing I saw before I passed out (yes clearly I pass out easily) was Ashley taking out her cell phone.

When I woke up I couldn't see! I tried to open my eyes and felt my eyelashes brush something, a blindfold! I tried to stand but my hands were bound behind my back and it felt like there was a knife in my stomach. I lay there and tried to recover, my forehead was throbbing from where it collided with the floor. I could also hear muffled voices, perhaps coming from down the hall. I groaned and rolled to my knees, pain shot throughout my body and I cried out but held my position. The voices stopped and I heard footsteps coming down the hall.

"Well well well, look who finally woke up." My sister's silky voice pushed through my headache.

"You're gonna kill me one of these days Ashley!" I screamed.

"That's the plan, but not until you are thoroughly used." She gave a throaty chuckle.

"Fuck"

"That's the idea." There was a giggle from further down the hall that sounded familiar but before I could search my memory for its owner, strong hands picked me up by my shoulders and marched me down the hall and into what I assumed was Ashley's room. Suddenly I was pushed and the backs of my legs hit the side of her bed and I toppled backwards landing painfully on my bound hands. Before I could do anything else a great weight landed on my chest driving the breath from my lungs as strong legs gripped my waist.

"Now listen Timothy, you were supposed to fuck me before the end of the week and you didn't." Ashley breathed mere inches from my face her hot breath caressing my cheek.

"It's only Friday and I've been busy... !" I gasped before I was silenced by a firm slap to the face.

"Shut up Timothy! Now, I have a new deal for you. You can either be my little fuck toy..." Something large, rubbery, and smelling faintly like my sister's pussy smacked me in the forehead sending a spike of pain shooting into my skull from where my head hit the floor. "Or, I can rape you 'till you bleed with my little friend here." She giggled like a little girl as I lay there, horrified, blindfolded, and still trying to catch my breath.

"No!" I said firmly.

"No? No to what Timothy?" she cooed.

"Everything."

"Aww too bad then, it would have been fun." Ever so slowly the rubber object made its way down my body. It stopped at my crotch and I felt my pants being undone, then slipped off along with my boxers. Ashley had gotten off of me by now and I was about to try and get to my feet before I was roughly flipped over onto my stomach and held down by one hand of the back of my head. The object was now placed on my lower back and slowly slid down between my ass cheeks. I was freaking out now; she was actually going to do this, shit! Just before she started adding pressure on my asshole I screamed for her to wait.

"Fine you bitch. I'll be you fucking sex toy. Just get that thing away from my ass!"

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