My Sister Ashley
Chapter 9: Back to a better time

Copyright© 2009 by VonArmand

Fantasy Sex Story: Chapter 9: Back to a better time - 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  

"Ashley, please! Tim help! Ehhr ow ouch fuck! That hurts!" Oriana screamed.

"Ashley! Knock it off or I might do something stupid!"

The sounds of struggle stopped and Ashley's laughter replaced it. "Ooohh I'm so scared, what are you going to do? Beat me up?"

I reached into my pocket and pulled out Tish's card, slipping it under the door.

The laughter stopped immediately. "You wouldn't dare!" She said warily.

I took out my cell and quickly changed the settings so when I pushed a button it made a noise. I held it to the door and slowly started pushing random numbers. She could hear it.

"Okay! Okay just stop!" she yelled opening the door in a rush. Oriana lay on her stomach, her pants around her knees, no more than five feet from the door. Her ass was red and ... wet? I glared at my sister.

"What?" she asked innocently. I stepped into her room, shoving her back.

Oriana just laid still, her back hiccupping every few seconds. She was crying! I shoved Ashley again, sending her sprawling on her bed.

"Oriana." I whispered, getting down next to her. She turned her head and looked at me with red, tear streaked eyes. One more glare at my sister, my lip curling. I reached back and tugged up her pants; she winced as they came all the way up. I pulled her to her feet and she instantly latched onto me, still sobbing gently.

I whisked her back to my room and closed the door before Ashley could do anything more. I tried to put her down on my bed but she wouldn't let go, so I readjusted my hold and picked her up completely. I turned and sat down on my bed; no matter how light she was I wasn't going to be able to hold her on my feet forever. She curled her legs up on my lap and wrapped her arms around me tighter, pushing her face into my shirt.

This was so weird; it was unusual to see her like this. Ashley yeah, but she was messed up, I'd come to accept that now. She was sick in the head, she had to be. But Oriana, no, she was rock steady, always. She took on everything with a smile; it wasn't like her to be like this. And even whatever Ashley had done to her just now couldn't have been any worse than what she had done to her back in my sister's heyday. I was totally confused.

"What's wrong? What happened Oriana?" She didn't answer except to squeeze me tighter. "What did my sister do?" I hissed.

"She threw me off! She blew it!" she wailed. "And it's not just that." Her voice was muffled by my shirt. Well that was good, Ashley didn't really hurt her; she just pissed her off.

She broke down again, her body jerking with every sob. This was killing me, freaking me out to be honest.

"Then what." I persisted, my voice reassuring.

She peeled her face from my shirt and looked up at me with one bloodshot eye, her hair obscuring the rest of her face. "I'm scared." She whispered, I barely heard her and as soon as she said it she retreated back into my shirt. This was frustrating, I had told her at least a dozen times how she had nothing to worry about and the fact that she didn't seem to be taking my assurances seriously was ... frustrating.

I sighed. "Ori, listen to me." I soothed, prying her head away from my chest. "What can I say ... no, what can I do to make you unafraid?'

She sniffled, "Hai d-don't kn-nhow."

"Hell if you're that scared you can just stay with me the entire time. It would make my roommate a little jealous and it's not like Natalia would report us." I laughed. She looked at me for a second before the barest hint of a smile started to pluck at her lips.

"That's better." I said, gently clearing the hair from her face. She leaned back against my chest, laying her head against me and playing with one of the buttons on my shirt.

"Thanks Tim." She sniffed and rubbed her eyes before looking up at me with a little smile, "I like it when you call me Ori." And then in a quieter voice like she was talking to herself, "Like Oreo, tee-hee." Absolutely adorable. It made sense too, especially when we first met, what with her very pale skin and very dark hair.

"You just like cute things." I chuckled.

"So what if I do?" she challenged, an impish smile on her face. I leaned in and kissed her lightly on the lips.

"Ashley killed it didn't she?"

"Yeah."

I sighed, "No biggie. You'll never be a five minute drive away from me ever again now will you?" I would have my revenge on Ashley in due time, but I was content as I was now.

Her face lit up, "Mmm that's right, isn't it." She crawled off of my lap, to my disappointment, and got herself under my covers. She disappeared under the sheets and when I didn't immediately follow a small hand appeared, opening and closing, beckoning me to her.

Playing dumb, "What?"

If looks could kill, I would be dead ten times over as she pulled the covers back to reveal her pretty face. "Get your ass in here and comfort me." She hissed, a tiny smile trying to force its way onto her lips. I took off my shirt (it was hot) and climbed in with her. Again she latched onto me and wouldn't let go. I could care less; her body against mine was all I could ever hope for.

"I love you Tim." She whispered.

"I love you too." It was late and she was quickly out cold, absolutely exhausted from stress. She loosened her hold on me and started twitching like she was running, not totally un-reminiscent of a sleeping cat. I heard some sounds coming from the kitchen.

I carefully worked my way out from her sleepy clutches and got out of bed, quietly making my way out into the hall. It was dark; my parents had gotten home only recently but had quickly gone to bed. A light was coming from the kitchen and as I stepped into the main area I could make out Ashley's silhouette framed in the light of the refrigerator.

"Midnight binge sis?"

She slowly turned to face me, a piece of leftover ... something, halfway to her mouth.

"What do you want?"

"Oh nothing." I said, shouldering my way past her to get a glass of water.

"So uh Tim." She began, sitting on the counter and kicking her feet happily. "When am I going to get some more attention? I'm a needy girl."

I finished my water and walked halfway out of the kitchen before turning back, "Find yourself a boyfriend Ashley."

There was a thud followed by pounding steps before I was tackled to the ground. Ashley sat on my back and shoved my face into the carpet.

"Take that back." She hissed.

"No." I said calmly, grunting a little under the pressure.

"Suddenly you think you can stop me taking what I want from you tiny Tim?" she had he mouth close to my head as she whispered in my ear.

"No I just don't care; I'm not going to give you what you want anymore. I don't care. I've been through too much because of you to give a damn." I could feel her sit up. She was silent, that had hurt badly, I was sure of that. She stood up and walked past me, down the hall and to her room, silently. Truly, I didn't care anymore.

I picked myself up and walked back to my room and Oriana.

The next morning I was actually surprised to find Oriana curled up next to me; her arm lay over my stomach. Ah this was the best. As if sensing my awareness, she groaned and stretched, yawning widely.

"Hmm I think we should do this kind of thing more often." She smiled, kissing my cheek. I did the same.

"We should, I like waking up with you." She blushed and gave me a little shove.

"I'll be right back." She said a little hurriedly and got up, walking quickly out into the bathroom. I got up and put on some fresh clothes before gathering all the stuff I had brought home with me and a few other things. I brought all that out into the living room; Ashley's stuff was already there. As I walked back down the hall she passed me, not even seeming to notice. This was going to be tough. It was the day before classes would start up again so we didn't have to rush but most everybody else would be getting back today as well.

Oriana was coming out of my room and I almost ran into her. "Hey Tim, do you mind bringing me home for a second so I can get my stuff together?"

"Not a problem."

We did that and returned in short order. I hefted her bag for her and shoved it in the trunk of my dad's car, along with Ashley's and my own. Before we left we got the same tearful farewell from out mother, I fared better because I clung to Oriana like a life vest but Ashley was nearly drowned in sobbing kisses.

As we walked out to the car she made to get in the back like usual but stopped and glared at me, turning and getting in the passenger seat. I tried to ignore her and the feeling that I had done something incredibly wrong, and got in the back with Oriana. Dad tried to talk to Ashley but didn't get very far before he gave up. The ride was so incredibly awkward that I actually started sweating, awful.

We got there after an eternity and we all piled out before he could even shut off the car. Ashley shoved past me with her bag and the only reason I didn't do anything was because Oriana latched onto me just then. She strode purposefully to our dorm and shoved through the doors. I couldn't help but smile as I saw an orange blob go flying out of her way behind the glass.

Oriana and I took our time. She still kept a tight hold on me as if she was afraid I would ditch her. When we reached the doors there was no sign of Natalia or my sister, and for that I was grateful. I accompanied Oriana to her room and made sure she was all set. I even took her roommate aside and asked her to keep a careful eye on her.

After that a week flew by with little to no serious problems. I saw very little of my sister and Oriana only curled up with me once or twice which was nice. Natalia too, was rarely seen, and behaving herself whenever I did see her. I called Tish once, just so that she didn't think I had been kidnapped or whatever, and didn't come busting down doors looking for me. She seemed incredibly enthusiastic when I called; pressing me several times for when we could meet up again. I gave her vague promises that it would be soon and assured her I would call again. All in all things were turning out nicely.

And it just got better the next week. Besides the fact that Oriana was becoming more confident and depending on me less and less, I had seen Ashley with another guy. I was positively beaming when she brought him by and introduced us.

"Mark this is my brother Tim. Tim this is Mark." We shook hands and said our meager hellos. He was about Ashley's size, tall and well built; I doubt she would have had it any other way. With a lantern jaw and a very strong face, he looked like a freaking all American hero in real life. I found out later from JD that he was on the football team, the quarterback no less! Typical of my sister I suppose. And from the look in his eye I could tell he was smitten with her, any guy would kill to get her attention, and he was her boyfriend, a lucky man! I was amazed how I was handling this, I wasn't jealous at all; in fact I think I was proud of her.

I started spending a little more time with my sister and was positively shocked to find she hadn't bedded him yet. Normally, back in her day, she would find a guy and within the week she'd be fucking his brains out. She seemed to be taking this seriously and I was happy for her.

So as it was she brought him by again and this time there was a very familiar look on her face. I was sitting in the common room this time, taking notes out of a book and listening to my music. I smelled her very familiar scent before I felt her touch my shoulder.

"Tim if anyone comes looking for me, I'm busy." She said with a mischievous smirk.

"Oh? Busy huh? 'Bout time." I said quietly, pulling out my earplugs.

"Oh shut up! I'm serious."

"So I noticed. You gonna go back to old Ashley or are you gonna be sweet on him?"

"I haven't decided yet." She said smiling, and giving me a loving peck on the cheek. I stood up and turned around, seeing Mark standing a respectful distance away. She went to him and took his hand before leading him down the hall to her room.

"I like him Ashley! Try not to break him!" I called out after them. Ashley flipped me the finger and poor innocent Mark, gave me a questioning look as my sister dragged him back to her room. Shaking my head with a dumb smile on my face, I went back to my work. It seemed little more than an hour before my nose alerted me to another, more unwanted presence near me.

"Mmm, all alone my sweet?" Natalia's thickly accented voice purred from right next to my ear.

To my credit I didn't flinch, "You're supposed to leave me alone." I said in a tired, patronizing voice.

"Ooo but I can not. You and I have not been together yet." She whined, slipping around my side and trying to sit down on my lap. I roughly pushed her away, sending her to the floor at me feet. She was wearing a simple black t-shirt and jeans.

"Why are you so rough with me Timothy?" she cooed, touching her hands to my feet. I disliked it when anyone called me by my proper name but when she said it is was like, I don't even know what, but it was painful.

"Because I dislike you. It's that simple."

"Oh but I can be nice, yes, very nice. Mmm, it would be fun." Her hands traveled up my legs, holding my knees and trying to spread them apart, unsuccessfully. "I can make you feel so good."

I put my book up in front of my face and spoke from behind it, quietly with as much menace and force as I could muster, "If I could break Tish imagine what I could do to you." I peered around my book and watched her sit there, closing her eyes, a big smile pulling her lips.

"Oh I am imagining." She shivered, one of her hands coming away from my knee to her mouth, where she bit her finger, hard. "Why must you do this to me?" Her voice was a gasped moan now. This was trouble, now she wouldn't let me be, and Ashley wasn't here to take any of the heat. This was bad; I slowly closed my book and put it aside, looking her in the face. She slowly opened her eyes; she was wearing her old contacts now, the aluminum silver ones.

"You are not getting away again." She breathed, lunging up at me. I manage to grab hold of her to keep her from being right on top of me. "Let me, uh, let have it please! Why won't you let me?" She pushed her lips close enough to kiss me. My skin crawled wherever it touched hers.

"Get off of me Natalia!" I grunted, pushing her off of me again and back onto the floor.

"Nya! Fine, I can do that if you wish. I'll be yours! Please just take me!" she cried out.

"Shut up!" I growled, reaching down and clamping my hand over her mouth. "Just shut up." She moaned under my hand, arching her back and worming her body on the floor. I held her down by her mouth for a few minutes before I thought she was calm enough. I slowly took my hand from her mouth and looked at her for a moment, wondering what she would do next.

"Please! Fu..." She practically screamed, before I clamped my hand back down hard over her mouth.

"I never will if you keep this shit up bitch." I hissed, putting my other hand behind her head and lifting up slowly. I pulled her to her feet by her head and walked her down the hall to Ashley's room; she should have been finished by now. I pulled her head down against my chest so I could free my other hand. I knocked twice in quick succession.

"What Tim?" My sister croaked from behind the door.

"Kinda need some help Ash." I said, giving Natalia's head a rough squeeze. Her hands immediately went to my belt and started fumbling around. My free hand slapped them away and held them together, as Ashley opened the door.

"So what, are you gonna kill her now?" She smirked, taking one look at the way I was holding her.

"Can you take her please? She's horny and she wont leave me alone." I whined, smiling. She was wearing just a big t-shirt and her favorite black panties, and I assumed poor Mark was comatose on her bed at the moment.

"I'm busy in case you didn't notice." She said at first. She looked Natalia over for a moment, noticing the way she didn't stop moving and the wild look in her eyes. As if in a trance Ashley reached out a hand and pinched one of Natalia's tits. She moaned loudly into my hand and slumped against me, forcing me to tighten my hold on her head. My sister's face went red and she opened her mouth in a little smile. Apparently Ashley's own arousal overcame her revulsion at the moment. She looked back into her room and her smile broadened; she stepped out into the hall and closed her door behind her.

"I can't believe I'm going to do this." She said, heading off in the direction of Natalia's room with me lugging her along behind.

"So," I said conversationally, "how was Mark?"

"He's bigger than you." She said simply, not even turning around.

"Wow. You sure can pick 'em."

She giggled, "Yeah I know right." We reached Natalia's room and found it was open, pushing in; we closed the door behind us.

"Well, here you go Ashley, have a blast." I said smugly, first handing her Natalia's hands and then her head.

"Oh wait! What about um what about that whole dominated slave for life thing that you blundered into?" Ashley asked, suddenly concerned.

"Good point. Hmm ... just let her be on top or however it goes."

"What!? Yeah right, I am not losing control to this freak." Natalia hung limp in her arms, and for a second I thought we might have smothered her but then I noticed her arms trembling and the strained look on her face, she was trying to get out of Ashley's grip.

"You're clever, you'll figure something out I'm sure." I said, turning on my heel and getting out of there before anything else could happen.

Before I could fully leave I heard, "I think a little payback is in order." Shaking my head, I walked back to the common room and sat down again. I thought for a second then pulled out my phone.

I scrolled through my contacts until I came to Tish's number.

"Yeah?" she answered softly after the second ring.

"Natalia has lost it again." I said evenly. She sighed and I pictured her pinching the bridge of her nose.

"Is it a serious issue at the moment?" she asked in a businesslike manner, I assumed she was on the job doing whatever it is P.I.s do.

"No I took care of it. But she could use another talking to by you if you know what I mean."

She giggled softly, "Hold on a second." She apparently put her cell down and I heard a rapid series of clicks, followed by a triumphant 'ha!' "Um yeah I can be there in about half an hour depending on traffic."

"You know where my school is?" I asked incredulously.

"Of course. I went there. See you in a bit master." She said, practically purring that last part. I smiled; I still wasn't used to her calling me that. And if you are wondering why I wasn't worried about Oriana catching wind of this, it's because she was out on an all day trip with her roommate and some new friends. She was getting used to her new settings faster than I did.

I went back to my work and completed all of it in a surprisingly short period of time. So I put my feet up on a low wooden coffee table and closed my eyes, folding my hands over my stomach. I may have drifted off at one time because I was startled when Ashley collapsed into an overstuffed chair next to me.

"So?" I asked, without opening my eyes.

She didn't answer me right away, I understood why as I listened to her labored breathing.

"You ... owe ... me." She gasped, breathlessly.

"Mhm. Don't I always?" My eyes were still closed. "So. What did you do? Care to share?"

"Nothing you would understand brother." She chuckled. I heard her get up; she touched my shoulder as she passed. "And I still have more work to do. It never ends."

I was still laughing when my cell rang. "Which building are you in master?" Tish asked.

I was in a teasing mood, "Well Miss detective I'm sure you can figure it out, use you're skills."

She laughed for a solid minute. "You know, you shouldn't put your feet up on the table master, it's not polite."

I stood up slowly and turned around, smiling. "And what would you know about polite Patricia, fucking me up against a wall?" She was standing back behind the front doors, closing her cell as I spotted her. I walked casually over and opened the door for her.

She stepped up to me, really close; it had been awhile since I'd seen her. She was much shorter without her big black boots, maybe an inch or two shorter than Ashley but still taller than me. "I could do it again if you wish." She said with a smile, green eyes glittering like emeralds. "Or we could do it the other way around."

I barked out a laugh, "That won't be necessary."

She gave a disappointed sigh and walked down the hall towards Natalia's room, "I'll be right back." I watched her walk away and shook my head, going back to my chair. What was going on with me? My heart was racing, and there was a very, very uncomfortable tightness in my pants. This wasn't supposed to happen, was it? I mean, Tish for fucks sake, Tish! And I was feeling this way?! Why had I even called her? Natalia was taken care of, Ashley saw to that, and yet I had called in this girl that in her own words was like my slave or servant, however you like it. How in the hell did I get involved in this shit?

That, of course, was a dumb question. My sister Ashley, she was the reason for absolutely everything that has happened to me for one reason or another. As I sat there I tried to remember all the stuff I've been through along the way. Strangely I wasn't angry, not that every sexual and non sexual (mostly sexual) experience I've been put through was pleasant, it just was, just a fact. Now why was I thinking so much? Things always looked bleaker when I was thinking.

I heard footfalls and looked down the hall to see Tish striding towards me, a big smile on her face. There was an all too obvious bounce to her step as she sashayed up to my chair and practically threw herself on top of me, sitting in my lap. I was crushed into the chair; my groin feeling like it was destroyed under her weight. The pain must have been clear on my face because she smiled, holding my face in her hands and kissed me deeply.

"I'm light as a feather. Don't give me that look master."

"God oh, I think you broke my dick." I gasped in a surprisingly high pitched voice.

"Aww." She kissed me again, harder, grinding her hips into my sore crotch. "You know, I can make you feel better."

"I have no doubt." I croaked. "So did you talk to Natalia?"

She leaned against me and ran her hands through my hair and over my face. "There wasn't much talking to be done. She was unconscious."

"She was?"

"Mhm. It seems a certain someone had a good time on her." She giggled, poking my stomach.

"Ashley, not me." I mumbled.

"What? Donovan did that?" she asked, shocked. "Your sister is sick, very sick."

"What did she do?" I asked, intrigued.

"Oh she did some stuff, some stuff even I've never done. And let's just leave it at that. Natalia won't be bothering you much anymore."

"Mmm I doubt that." I mused. I sat there for a second, sort of thinking of what I would have to deal with when she woke up, when Tish started to fidget in my lap. She was playing with my shirt and trying to catch my eye when I finally said something.

"What? What's the matter?" I asked, actually concerned that something was wrong.

"Oh nothing." She sighed, leaning against me and trying to put her head on my shoulder. She seemed quite content actually. However, I was not, being crushed into the chair and all. And this caused me to start fidgeting, I shifted my hips uncomfortably which, unfortunately caused some very comfortable contact with the curves of her ass. And of course this couldn't just go unnoticed by her, oh no, she just had to do it!

"Mmm, what's that?" she cooed.

"You know damn well what it is." I said with a slightly pained smile as she ground herself into me, "Stop playing the innocent."

"Oh but master, I am innocent. Just brimming with innocence, innocence that's just waiting to be stripped from me." Of course it was painfully obvious what she wanted but I didn't want to let her have anything without a fight so...

"How did you become a P.I.?" I asked her.

She narrowed her eyes and sighed, deflating a little and sagging against me. "I came here for the criminal justice program. I wanted to be a cop, I did well and managed to get into the police academy, graduated that and started in the field but I didn't like it. Too much of a schedule, I wanted to be more free I suppose. And someone told me about this P.I. firm and so here I am." She finished.

"And how did you get involved with that little club of yours?" I asked, more curious with her answer to this question than to the other. I put my arms around her middle and gave her a little squeeze. She sighed, smiling and kissed my cheek before continuing.

"That would be my sister." She said with a slight shake of her head.

"What!? Really? Sarah's involved with them?" I asked incredulously.

She laughed softly and looked me in the eye with her emerald soul gazers. "No, and if I hadn't been for my meddling, you'd have a smaller, less gorgeous me at your beck and call. No, she came home from school one day with this card. She said she got it from a friend who got it from a friend, ect ect." She said waving her hands in the air. "I thought it was a little suspicious when she wouldn't tell me what it meant. So I sort of stole it and checked it out myself. When I found out what it was I was ... um intrigued. I got really involved as you know, and because I'm so aggressive, I rose up pretty fast. Fifth out of like thirty or so last time I checked."

"Aggressive, pfft!" I snorted. "You're meek as a kitten."

She giggled, girlishly for a few moments before turning serious. "Meow." She breathed, before grabbing my head between her hands and mashing our lips together. Well ok so my master plan didn't work out so well, I really didn't care at the moment. The constant pressure on my cock felt surprisingly good and it throbbed against her, to her very obvious enjoyment. She pulled back slightly, biting my lip and pulling it with her. She sighed and let it go, nailing me with her eyes.

Now, as she stared into my own eyes, I wondered why she I hadn't rushed her to my room by now. Well that's what her eyes made me think.

"Please ... master." She whispered, her voice husky with lust. Mentally and physically I collapsed, totally breaking to her, breaking to her eyes. With a hand I had wrapped around her waist I let it slip down between her legs, slowly running my fingers up and down one thigh, barely touching her hard enough to be felt through her jeans. She sighed contentedly and closed her eyes in vast relief. Finally I was released from her gaze and my mind returned to me.

"It must be so ... hard, for you to ask huh? After all this time of just ... taking it from others?" I asked quietly. I was pushing harder with my fingers now, coming closer to the junction of her legs. With one swift movement I crossed from her leg to directly over her pussy, rubbing vigorously over her clit through her pants. She inhaled sharply through clenched teeth and buried her head in my neck, before letting out with a long low moan.

"How do you do that?" she whispered, her mouth still against my neck.

"Practice makes perfect." I said with a short laugh.

"Please ... do it again."

"What if I don't." I asked. She picked her head up and looked at me, her green eyes pleading with every ounce of emotion she could muster.

"It'll kill me." She whimpered before leaning in and kissing me hard, putting her whole body into it. One of her hands now held mine to her pussy, pushing it against herself. I couldn't take it anymore; I was way, way too into it. I couldn't understand what it was that she was doing to me to make me feel this way. It couldn't be right, but it felt just so.

"Fine." I gasped breathlessly, pulling away from her to gulp down a lungful of air. "Natalia's room."

"Uh, why can't we just do it here? I can't possibly walk all that way. Unless you want to carry me." She said with the barest hint of a smile.

I looked at her sternly until she finally broke into a big pearly-white smile. "Jeez I'm sorry, can't you take a joke." She giggled, slowly getting up and pulling me to my feet.

"Not when it involves lugging your ... tonnage." I said as she turned to start walking down the hall. I smacked her ass hard and took off laughing as she stood there shocked. I slowed down to a steady walk as I made my way past my sister's room, running through girl territory was attention grabbing, so I acted like I was just out for a stroll. I made it to Natalia's room and let myself in. I couldn't help but notice it still smelled of sweat and my sister over Natalia's chemical funk. She was laying on the floor, curled up in the fetal position, a jacket covering her respectfully. I assumed that was Tish's doing, as Ashley would have left her as she was. She was breathing evenly and if my eyes weren't deceiving me she had the ghost of a smile on her lips.

 
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