My Sister Ashley - Cover

My Sister Ashley

Copyright© 2009 by VonArmand

Chapter 7: Progression and Surprises

Fantasy Sex Story: Chapter 7: Progression and Surprises - 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  

My jaw cracked as it dropped, never before had I been this shocked and horrified. Natalia remained by my side as Sasha walked across the room to stand behind the form hanging from the ceiling.

"Ashley." I whispered. My sister hung from the ceiling by a pair of silver handcuffs strung over a large hook screwed into the concrete. A thin streak of dried blood ran from the corner of her mouth. Her toes were about an inch from the ground and she seemed either asleep or unconscious, her naked body hanging limply.

Sasha reached out and ran a hand up my sister's hard stomach, between her large breasts and caressed her face. She said something in what I was now assuming was Russian in my direction and Natalia translated.

"She says your sister is very beautiful, you are a lucky boy." I continued to gaze at Ashley; my chest felt like it was trying to explode from the inside out. What had I gotten her into? This was college for crying out loud, these were supposed to be some of our best years, this shit wasn't supposed to happen! I could feel hot tears running down my face as I struggled to break whatever restrained my hands. Sasha spoke again, her hands sliding back down and squeezing Ashley's large breasts, hard.

"Do not worry boy. I will not hurt your precious sister, only make her feel good." Natalia translated, looking down at me in surprise that I was crying. She touched my face and maneuvered to sit on my lap, I was grateful they had not taken my boxers. Natalia sat down and gently wiped away my tears, looking into my eyes, her red eyes softening slightly. She leaned against me, her skin despite having probably a solid pound of ink in it, was soft and warm. Why was she trying to comfort me?

Sasha stood behind Ashley and pressed in close to her, running her hands over the front of my sister's limp body. Her hands traveled down Ashley's stomach to her inner things where they proceeded to inch farther in, inch by slow inch. Her fingers barely touching skin. I looked closer and I could just make out movement under her eyelids, the corner of her mouth quirked fractionally. Sasha's hands stopped, the fingers of one spread Ashley's pussy open so the fingers of the other could push inside her. Sasha peeked her head around Ashley's side to look at Natalia, she said something.

"Really?" Natalia asked excitedly, springing up from my lap and bouncing over to Sasha. I felt her absence on my lap keenly as the cold seeped back into me. Natalia leaned down and mimicked Sasha by sliding a finger into my sister as well. They looked back at me, jealous looks on their faces.

"It is times like this we wish we were men." Natalia said longingly.

"Why we have these." Sasha grinned, jerking her thumb to one side of the room. I turned my head, my neck was stiff. There was a table against one wall, covered in all kinds of sexual paraphernalia, toys, bondage equipment, objects I couldn't begin to identify. My eyes flicked back to Ashley and I could see that one eye was open peering at the table. Her nervous smile broadened enough for me to see teeth. I guess I shouldn't have been surprised to find that Ashley was aware of what was going on, hell she probably could have gotten out of this if she really wanted to. Her eye swiveled to me and she winked. I felt immediately better, my chest eased and I sighed, smiling back at her.

Sasha had moved to the table and was mindlessly picking through the stuff. She held up a roll of duct tape and asked Natalia something.

"Yes that is possible." She responded. She was on her knees in front of Ashley looking at her pussy, her finger still probing my sister's depths. Sasha ripped off a piece of tape and came back to Ashley, laying it tightly over her mouth. Ashley didn't move. I was being more and more impressed with her. She was barely moving although these two were doing all kinds of things that would drive a normal person crazy. Sasha went back to the table and continued to play around with the stuff there. Natalia had moved closer to Ashley and was laying her head against my sister's thigh, playing with her cunt in an almost loving kind of way.

Ashley was squeezing her eyes shut; I could see her jaw working, grinding her teeth.

"What does she taste like Tim? I know you know." She purred looking back at me. My response was to glare at her in silence. That was the first time she had addressed me by name and it made my skin tingle.

"Well I shall find out." She said before turning back to Ashley. She pushed her face into my sister and I knew that from a girl like Natalia, even Ashley couldn't keep her composure. My eyes were locked on the back of Natalia's head and throat, so I didn't hear Sasha come up to my side.

"Her record thirty seconds." She whispered in my ear, a tangy chemical scent wafted from her.

"What?"

"Thirty seconds make girl cum from naught." She said, "Best of red roses."

"Red roses?"

She blinked, I think she had said something she shouldn't have, "Nothing." She stood up straight and I saw that she had something in her hands.

When I had first seen my sister's strap-on I was impressed, but this, this was truly massive. One end had to have been ten or eleven inches long and pretty thick, the other end must have been a solid seven. She saw that I was looking and grinned, her lifeless white eyes regarding me with something akin to amusement.

Suddenly I heard loud moaning and jerked my head back to Ashley and Natalia. My sister's eyes were wide open, screaming at the ceiling where her mouth could not. Her body was trembling, sweat making her skin shine as Natalia remained planted between her legs. Ashley squeezed her legs together, forcing Natalia back, gasping for air.

"At least full minute." Sasha chuckled, "You can not handle her." Natalia stood up and turned to face us, glaring at Sasha. Her face was drenched in my sister's juices and absentmindedly she wiped her face with a hand, licking it clean.

"You need a huge fake cock to please her, I have done it with nothing!" she said holding her tattooed arms out and twirling around. I was looking at Ashley as they continued bickering in Russian, she was trembling badly. Her eyes fluttering as she tried to calm down, shifting her legs uncomfortably. She saw me looking at her and I gestured to my left, at Sasha, or more specifically what she was holding. Her eyes went wide and flicked back to me, she was scared now, 'help me'! This wasn't a game anymore.

"I invited you as a courtesy Sasha, do not forget that." Natalia hissed. Well there was one way to get Ashley out of this. Sasha stamped her booted foot in a surprisingly girly act of frustration, stormed over to Ashley and stood in front of her. She slid the large end between her legs, back and forth under her pelvis.

"Where do you want, Ms. Donovan?" she whispered. Ashley's eyes were frantic as she looked from me to Sasha to me again. 'Help me Tim, brother!' Shit! I was sweating and I felt sick, what had I done?

"Natalia." I called quietly. She was standing close to Sasha, hands on hips watching what she was doing with her back to me. When she heard me call her name so quietly, she obviously knew something was up and sharply turned around. I lowered my eyes and said nothing. She gave a little squeak and rushed over to me, practically jumping onto my lap, legs on either side of the chair facing me. I cringed as she ground her hips into me.

"What can I do for you my love?" she cooed. I swallowed hard and looked over her shoulder at Ashley who was trying to squirm away from Sasha's more probing touches.

"What will it take for you to make Sasha leave and let my sister go, so we can be alone?"

"Well, it took you long enough to ask." What!? This was what all this shit was for, I wanted to scream. Natalia said something without turning around and I watched as Sasha whirled around, rage contorting her face. She protested, looking from Ashley to Natalia's back, jabbing the dildo into Ashley's hard abs. Natalia rolled her eyes and injected more force into her voice. Sasha shouted back and stormed to the table, picking up a cell phone and rapidly dialing a number. She walked back over to Ashley and stood in front of her staring up into her eyes as she waited for the other end to pick up.

"Lucky girl." Her voice was full of menace. The other person finally answered and she started speaking rapidly as she waved the strap-on in Ashley's face.

"She is calling her husband." Natalia explained with a giggle, "She wants him to be home in less than an hour and to be ready for her."

"Someone would marry her?" I asked incredulously.

She snorted and called out across the room, before falling into a giggling fit. Sasha slowly turned and glared at me, a vicious smile tearing at her lips.

"Funny." She snarled turning around and lining up the large end of the strap-on with Ashley's pussy, she tossed a look over her shoulder before shoving hard. Ashley screamed into the tape and tried to jerk away but Sasha put her other arm around her waist and held her still as she pushed it all the way in. Her eyes rolled back in her head and her chin sagged into her chest. Sasha gave it a twist and frowned after getting no response. She reached up and gently held my sister's face in her hands as her muffled screams died down to a pathetic whimper, tears streamed from her eyes.

"You have been deprived of a thousand pleasures and pains; you will never be satisfied until you see me again." She intoned quietly, her English suddenly flawless and her voice deepening. Ashley's eyes glazed over and her body relaxed.

"Sasha that does not work on females, just leave." Natalia said tiredly, still not turning around.

"So you say. I will see you both," she said looking from Ashley to me, "again."

"Go Sasha, I will see you at the club." Natalia said a little more calmly. Sasha pulled on a black hoodie and skirt, before calmly flipping us the bird and slamming open a door directly behind Ashley. It was dark outside the door and as soon as she passed through, disappeared.

"Let me get my sister down and then we can do what you want okay." I said calmly. She grinned and ran a hand through my short hair, reluctantly getting off of me. Sashaying over to the table she picked up a set of keys. She brought them over and unlocked the handcuffs around my wrists and ankles.

I tried to stand but my legs felt like rubber and I half staggered half crawled across the room. I reached up and pulled the tape off Ashley's mouth, her eyes snapped back into focus.

"Ouch! Take it out Tim, Take it out!" she cried. I reached down and grabbed hold of the end, slowly pulling the large device out of her with a wet sucking sound.

"Ohh god." She moaned as a trickle of clear liquid followed it out.

"Keys Natalia!" I demanded, holding out my hand. They were slapped into my palm and I quickly reached up and unlocked one of the cuffs. Ashley dropped to the ground in a heap; I followed her down and cradled her head in my arms as she tried in vain to move her extremities. Natalia took the keys and unlocked the other cuff before bouncing over to the table and putting on her own clothes.

"Are you okay Ashley?" I asked, brushing the hair out of her face.

"No! What the hell is this? Why in the fuck was I chained to the fucking ceiling? And who was that?" she demanded, frustrated. "One minute I'm asleep the next, that white eyed freak punches me in the face, shoots me full of something and then I'm here!"

"Sshh Ashley, I'll tell you later okay."

"Whatever, I just want to go home. Aren't we supposed to go home tomorrow?" she asked shakily. Her skin was cold and I turned to Natalia, now fully dressed and standing beside me looking on with amused red eyes.

"Where are her clothes?"

"She had none but these." She said, holding out a pair of flowered panties, grinning. I snatched them from her hand and attempted to put them on her myself. Ashley angrily slapped away my hands and pulled them the rest of the way up as I stood and helped her to her feet. We were both unsteady and Natalia was having a hard time keeping a straight face. She handed me my clothes and I only put on my shorts, handing my large shirt to Ashley.

"Where are we Natalia?"

"The basement of our dorm building." She responded flatly. I put an arm around Ashley's waist and took some of her weight as we staggered towards the door. We made it out and were confronted by a long hallway and a staircase at our end. The whole hall was poorly lit and after a good deal of tripping we made it up the stairs which ended just a few rooms from Natalia's.

"We're going home for the break." I said letting go off Ashley and moving closer to Natalia, "Then whatever happens, happens." I said. She grinned and bit her lip excitedly, handing me a slip of paper with what looked like her cell number on it.

"Yes, gather your strength." She giggled, breaking off into her room after giving me a broad smile. Ashley had kept going down the hall to her room. I walked to her as she reached her door. When I stopped by her side she leaned her head against the door, I could hear her sniffling.

"Are you sure you're all right?"

"I told you no!" She sobbed.

I put an arm around her shoulder, "I'm so sorry I got you into this Ashley. Is there anything I can do?"

"We're going home tomorrow right?" I nodded, "Then you can keep me company tonight, I don't want to be alone." She said looking at me as tears rolled down her cheeks. I would do whatever she wanted right now.

"Sure Ashley." She gently took my arm and guided me through the door. The room was empty and I assumed Catherine had already left. The clock by Ashley's bed read two o'clock. To my immense relief she kept my shirt on as she climbed onto her bed, though she still managed to practically rip her panties in two bending over. This was going to be difficult.

She flopped down and sighed dejectedly, giving me a gut wrenching look. I felt so bad, as I walked over and sat down next to her. She was practically falling asleep before my eyes, her eyelids drooped and that's why I didn't expect her to grab me around the waist and roll over, dragging me over her to almost slam against the wall. Her arms moved higher and she pulled herself closer, her body pleasantly warm against my back. She pressed her face into my bare shoulder and wiggled herself closer still.

"Remember when I used to do this when we were little, like when I had a nightmare or there was a thunderstorm or something?" she whispered, her breath tickling the skin of my neck.

"Yes, though I wish it was just a nightmare that put us in this situation."

"Hmm, yeah. Just think, at least we get to go home tomorrow." She said yawning. Oh I was already thinking about it, all I wanted was to be near Oriana, just to hold her in my arms, to kiss her. I was gone.

I could feel her arm over me, her gentle breathing on my neck, the fragrance of her hair. She was all I had ever wanted, and I had her, she was mine and I was hers.

"Are you awake?" I whispered. She was not. Why not wake her up, the pleasant way, muhahaha. I rolled on to my side, her arm still over my shoulder and gazed at her in the dark, she was so beautiful. I slid a stray lock of hair out of the way so I could see her closed eyes, they were rapidly moving under her eyelids, she was dreaming. I gently ran my hand over her face, her skin was flawless. I kept going up over her shoulder and down the graceful swoop of her side to her hip. I let my thumb slide my hand down the inside of her hip over her flat stomach. She moaned in her sleep and rolled over, presenting her back to me. Oh, so that's how it's gonna be eh?

I caressed her supple rear, encountering the frustrating barrier of her panties. I moved my hand farther down and flattened it, slowly slipping it between her soft thighs. I'm sure my tongue was peeking out of the corner of my mouth as I felt around in the dark. I continued on, my fingers walking up her leg and over her buried treasure; damn panties! Hmm she must be having a damn good dream considering the dampness I was feeling. Slowly I let my fingers trace her slit, if this didn't wake her up nothing would. I began adding pressure, sinking my fingers into the soft skin and fabric, she moaned, shifting her legs around my forearm. I split my fingers one running to where I approximated her clit should be and the others remaining as they were, slowly massaging her from behind her panty shield.

"Harder." She breathed, finally awake. She was worming her whole body in concert with my finger's movements trying to work every sensation to the max. I pushed with that finger on her clit; she inhaled sharply and let out a low deep moan. She pushed my hand out of the way and quickly pulled down her panties, I had to readjust but my fingers were quickly back to work. I could hear her breathing start to get heavy; I pushed my fingers deep into her and began the complicated little dance I had created. She instantly reacted, arching her back into me and mashing her hand into mine, trying to push me deeper.

"Uuuhh sooner or later you're gonna have to ... uhn ... fuck me for real." She groaned. What!? I paused, why did she say that?

"Noo, don't stop! Or I swear to god I'll rape you right now." Shit! Now I was awake.

"God damn it Ashley!" I cursed, this was the second time I had dreamt about Oriana and it hadn't been true. I tried to pull my hand away but she clamped her thighs down, trapping me.

"Please," she whispered, "please I'm so close. Make me feel better Tim." I sighed, moving my fingers again. She was bucking her hips while pushing my hand with her own, fucking herself on my fingers.

"Oh god. Oh god, yes UUHHH!" she cried, her voice muffled as she buried her face in a pillow. This had to have been her weakest orgasm to date but you wouldn't have been able to tell by the way she moved. She thrashed around, tossing bed sheets every which way. I yanked my arm free and licked my fingers, she tasted different, must have been that dildo. I quickly rolled over, my back to her, just in case.

"What time is it?" I asked.

"Um four o'clock." She responded, I felt her moving around before an arm snaked over my side and down into my boxers. "We still have time to play. And if you think that was all I needed you're wrong, I need more."

I pulled her hand out and shoved her; she let out a squeak as she rolled off the bed with a satisfying thump. "Uhn I'm Ashley. I want sex! Fuck me, fuck me hard. Put it in my big ass. I'm Ashley. I want sex!" I teased in a whining, snide sort of way.

"You're so mean to me!" responded her tiny voice from the floor.

I laughed, "Mean? How am I mean to you? If I recall correctly you've done all the mean things to me."

"Well I'm allowed to, I'm the girl." She said pointedly, still not rising from the floor which I saw as troubling.

"Bullshit! You're no girl!" I giggled. I turned my head just in time to see her slowly standing up, and wouldn't you know it, she had taken off her shirt and completely removed her panties.

"See this is what I was talking about, you are sooo mean to me." I snorted, rolling my eyes, though I doubt she could see them in the dark. "You won't even have sex with your hot, horny, loving, caring, oh-so-willing sister." As she huskily said those last words she crawled on the bed and got down on top of me, leaning closer and closer with each word until our faces were inches apart.

"I think most normal people don't do that." I said drawing away from her as much as I could. I made a promise; I couldn't do this, not when I was so close. She laid flat on top of me her big beautiful tits squashing against my chest, one hand petting my face while the other snuck down along my side.

"Why won't you fuck me Tim? Don't you want me anymore?" Not this again! "Am I not attractive to you anymore? I try to be appealing; I've tried time and again to put myself in that position. But no! Timothy gets so much pussy he doesn't need his first anymore, his easiest. What about me?" She whined. This was where I appreciated having Ashley as my sister, I could be rough with her and she wasn't likely to get hurt. I grabbed her shoulders and pushed, however she grabbed me at the last second and we tumbled to the floor with a loud bang. I landed on top but bounced off of her onto my back. She recovered and made to grab my wrists but I reached out and caught her hands, making a feeble attempt at holding her off.

Grinning sadistically she pushed my hands painfully to the floor, this was turning out to be a mistake. She leaned down and kissed me deeply while she started moving her hips, mimicking fucking me. Damn her! Despite myself I was already painfully hard and her grinding into me wasn't helping in the least. Wrestling with a naked goddess such as Ashley wasn't exactly conducive to staying calm. I couldn't tell her about the promise I had made to Oriana, she would just try all the harder to spite her. And so I decided to keep trying to get on top, I thought only then would she become placid enough to reason with. I took a deep nose full of air and mustered my strength before slowly, shakily, pushing her arms up. Her eyes opened and looked left then right as her hands slowly started to rise from the ground as she was pushed away from me.

Breaking away she hissed, "Stubborn bastard, let me fuck you." And then after a pause, "You need to work out more." She added more force and as she did I turned and her hand smashed into the floor, I used that to shove with my hip and flip her over. Finally! I quickly pinned her hands to the ground and, gasping for air, lay down on top of her.

Immediately she calmed down and closed her eyes. I don't know if she respected the person on top or she was too ashamed of the fact that she had given it up, whatever the case she was done. She practically deflated under me and turned her head to the side, yup ashamed.

"Oh that's right," I chirped happily, "Ashley doesn't like being on the bottom does she?"

"Fuck you!" she growled.

"Do you want me to use my magic fingers on you again, is that it?" I asked jokingly. She blew the hair out of her eyes and glared at me. There was a small noise and Ashley's eyes flicked past my shoulder, she sighed and turned her head to the side again. I cranked my head around and lo and behold who should be standing there but the devil herself.

"If you two are going to fuck do it quietly, you are going to wake up half of my building." Natalia said stepping into the room and closing the door behind her.

"What do you want?" I asked.

"For one I wish to have the two of you, but I understand you would like to go home first so I will settle for quiet. I have to be up early tomorrow and I can not do that with you two slamming around all night." I nodded and she grinned, looking us over and sighing disappointedly before leaving.

"Do you want me to stay or can I go back to my room?" I asked looking back down at my sister.

"Please stay," she said looking up at me with doe eyes. I swear she should be an actress.

"Fine but you have to put some clothes on. And no nonsense!" I said letting go of her and standing up. I got back onto her bed which was still warm and lay on my back watching as she stood up and went to her closet. I couldn't help but stare at her ass, even after all this time it could still captivate me. She slipped into some sweatpants and a t-shirt before coming back over and laying down next to me.

Almost immediately I started to fall asleep and before the blackness took me to a better place, I felt Ashley wrap her arms around me and lay her head on my shoulder. This was better.

When I woke up the next morning it felt like my body was being squeezed in a soft vice. I cracked open my eyes and looked down my body. I was basically encased by my sister, her arms were tightly wrapped around my chest and her legs were linked around my own, there was nary a part of her that wasn't in contact with me. I took a deep breath and felt her arms tighten, trying to kill me in her sleep no doubt. I turned, looking at the clock, Christ it was already nine o'clock! Our father was going to be here in less than an hour. I tried to spread my arms but she only squeezed tighter, tighter, okay painful.

"Ashley! Ashley wake ... uhhh ... wake up!"

"I am awake." She purred, raising her head and smiling sweetly.

"You're a bitch, ahhh!"

"That's not very nice Timothy." She was slowly crushing me, I grunted in pain. "Oh does this hurt Tim? Because this is what I feel like when you keep rejecting me, maybe now you understand why I am so damn persistent!"

"Okay! Okay!" I gasped. She let go and I sucked in a huge breath of air, my chest heaving.

"Oh why look Tim! Mom and Dad will be here anytime now! You best go get dressed unless you want people to get ideas." She said as she got up and went back over to her closet. I got up holding my chest and left, heading for my own room. The building was a virtual ghost town; everybody had either gone home last night or early this morning. I knew JD was gone so I strolled into my room and changed, putting some clothes I hadn't washed yet and a few other things into a duffle bag and left my room. I turned left, heading for the main door when something stopped me.

"Oh my, am I getting careless in my excitement?" a distinctively accented voice breezed past me from behind. I slowly turned and sighed, seeing Natalia leaning up against the wall next to my door.

"I guess so." I shrugged turning to go.

"Try not to waste too much energy on your little girlfriend." She chuckled, coming up alongside me. We stopped in front of the glass entrance doors. I could see Ashley already outside sitting on a wall that ran the length of the building, kicking her feet happily whilst looking from the front door to the parking lot. She saw where I was looking, "Or your sister for that matter." I smirked, patting the top of her head, making sure to crush the well made spikes of orange hair she had going.

"Do not fear tiny terror, you'll get your chance." I said mimicking her accent, and walking through the door into the chilly air.

"I had better!" she called after me, trying in vain to resurrect her hair. I snuck up behind my sister and poked her in the side with a finger, making her jump.

"My chest still hurts."

"So does mine." She retorted acidly. I was saved from anymore icy comments by our father's car pulling into the parking lot. Déjà vu! It was just Dad and already he had popped the trunk in anticipation. I threw my stuff in and got in the back, Ashley did the same. I noticed with a tiny smile that Ashley still wasn't walking normally. He knew better than to ask us any questions that would undoubtedly be asked an hour later by our mother and so he spent most of the ride filling us in on what was going on with the two of them.

When we finally pulled into the driveway he told us to get in there quick and get it over with, while he got our stuff out of the car. After the customary hour or so interrogation from Mom we went our separate ways, Ashley to her room and me to my car. I was going to pick up Oriana from the train station as per our agreement, and I couldn't be happier. Her college had a direct rail line to a station not ten minutes away. It took me five to get there.

The train wasn't due for another five minutes and I had all that time to figure out what I was going to do when she stepped off. I grinned, I wanted to play a little game, payback for that promise she had me make. I looked down the tracks and could just make out the headlight off in the distance.

Scanning the area I found a little corner where I could stand unnoticed but still observe the entire platform. As the train thundered in a crowd started to form, parents and siblings, business people, and your everyday traveler crowded onto the platform. I worried for a second that I would not be able to see her in the press of people; however my fears were alleviated when the doors opened and her black framed face peered out the door before she dropped to the platform. I quickly made my way close to the train, maneuvering behind her. She had a very large duffle bag clasped in both hands and was standing on the tips of her toes trying to see over the crowd, looking for me I suppose.

I deepened my voice, "Lookin' for somebody miss?"

"Yeah, my boyfriend is supposed to be picking me up." She responded without turning around.

"Shame he hasn't shown up yet, sweet little thing like you shouldn't be all by yourself around here." That made her turn around right quick.

"Tim!" she shrieked, leaping into my arms, her duffle bag thudding to the ground forgotten. I put a hand on her lower back to hold her up, though I doubt she needed the help considering the death grip her arms had around my neck. I almost laughed as she drowned my face in kisses, only managing to kiss her back a few times out of a hundred.

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