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. I am about 5’10” and about 170lbs (it was the off season for ultimate Frisbee so I had nothing to keep me busy and I just sit on my ass for work so I was gaining a little too much weight). I have blonde hair and brown eyes and I’ve been told I am handsome but I don’t really see it. I’ve been in a relationship once before but it ended before it ever got intimate, therefore and I’m ashamed to say it, I am a virgin.
Then there is my sister Ashley, she is about 6’1” and about 180lbs (I’m guessing because she has never really told me), however all that weight is pure muscle, it’s the middle of the hockey season and she is in peak physical condition. She has brown eyes and blonde hair as well, but she streaked it with brown highlights. Now on the contrary, my sister is hot hot hot she has large round breasts that she hates because they interfere with her hockey and plus any weight that she actually gains goes strait to her ass which is nice and round and kind of plump, by all standards the perfect kind of ass that guys just drool over. Unlike me she has had several relationships that have all gotten intimate, but for reasons I will soon discover, end shortly thereafter. However she was in between relationships at the moment. She works as a waitress as well so she remains active for most of the year.
However this Saturday morning our parents had taken the weekend to go to Maine for their anniversary, so we were alone together. I was still asleep when Ashley walked into my room turned on the light and ripped the covers off my bed. That woke me up as well as any cold shower ever could and I was only wearing a pair of boxers. She was wearing a white cotton t-shirt and a pair of black and white house pants with the stretchy waistband.
“What the fuck Ash!” I shouted. She ignored me and moved to my windows and opened the shades.
“Timothy,” she sighed “breakfast is ready and waiting.” She deliberately calls me Timothy to piss me off. As she moved past the bed I shot a leg across the space between my bed and the wall and trapped my incredibly hot sister next to the bed. She sighed again and moved to crawl over the bed, when she was directly over me I brought my other leg around and knocked her backwards onto my chest. She was now facing up, laying on my chest, her luscious ass was on my now enlarging cock and her head was next to mine, I wrapped my arms around her chest directly under her large breasts and wrapped my legs around the inside of her calves.
“What is that?” she asked quietly with a hint of annoyance in her voice.
“That my dear sister is morning wood,” I said. “And you will be made to sit on it until it passes.” I planned on holding her like that until she started screaming for me to let her go instead. I had done this when we were younger (except for you know, the sexual innuendo) and it usually ended with me getting in trouble after she screamed for mom.
“Is it now?” she said softly in my ear as she started grinding her ass into my now raging hard-on.
“Ashley…un....what are you doing?” I said as best I could.
“I’m merely helping it pass.” She whispered directly into my ear. Suddenly she hooked her arms under mine and threw them off of her as though they were nothing and quickly spread her own legs forcing me to do an awkward kind of split. She then gracefully rose and pivoted on my crotch which was still stinging from the split and now had 180 some odd pounds of girl rotate on it with clothes in between. She was now straddling my waist facing me with her hands firmly planted on my chest. Before I could react or recover from my aching crotch she had pushed her house pants down to her thighs and had opened my boxers so that my raging cock was exposed to the air.
“Don’t do it Ashley, you know this is wrong!” I was getting nervous now.
“Timothy you’ll never learn otherwise.” She giggled. She widened her eyes and mouth in mock surprise, tilted her head to one side, and shoved her ass backwards right onto my cock burying all 8 inches in her ass in one go. I gasped as my dick was forced into her ass, it was very tight, incredibly warm, and a little wet. She closed her eyes, bit her lip, and moaned softly. I moved my arms to try and throw her off of me but she grabbed my wrists in each of her hands and pinned me to the bed. I started to struggle but the only result seemed to be that she moaned a little louder and that her ass tightened around my cock.
“I am not loosing my virginity to my sister’s ass!” I said struggling some more but eventually resigned to the fact that she had me pinned, so I just lay there and glared at her.
“Don’t worry...uhnn…this doesn’t have…uh…have to count.” She laughed as best she could, slowly opening her eyes and looking down at me. She still hadn’t moved any more that to shudder a little.
“Like hell it”…SMACK! She let go of one of my wrist for a fraction of a second and slapped me clear across the face before pinning my wrist again.
“Shut up Timothy. No more talking. Eddy (her second boyfriend) got me hooked on this anal stuff and I haven’t been able to get any real relief since he left me.” She said as tears involuntarily formed in my eyes. She then started to move her hips forward and back then left to right as though stirring her ass with my cock. It felt amazing not that I was going to admit it to her, and I found my eyes closing as I tried to push up into her. I hated myself for enjoying it, but realized there was nothing I could do, and gave in to her. I stopped resisting and she let go of my wrists only to clamp onto her own tits, squeezing them and pinching her nipples through her t-shirt. With my arms free I let my hands roam over her hard body and let them rest on the only soft spot available to me, her soft glorious round ass cheeks. She squealed in delight, obviously a source of intense pleasure for her. I smacked her ass a few times as she rotated on my dick, which resulted in her moaning louder.
Then she started riding my cock like it was nobody’s business, slapping her ass up and down onto my thighs with incredible force. She would rise so that my cock would almost slide out of her ass only to slam back down again sending jolts of pleasure shooting throughout my body. She had stopped massaging her tits by now and had placed her hands back on my chest for better support and control, so I reached up and removed her t-shirt revealing her gorgeous tits. She wasn’t wearing a bra and I assumed that she wasn’t wearing any panties either (typical). Her nipples were hard as rocks as I started to tease them tweaking them and pinching them.
“Keep it up Tim,” she gasped. “I’m gonna cum!” And cum she did, she stopped moving and sat there and just before I thought nothing was going to happen she exploded all over my stomach. Warm clear liquid shot everywhere sending me over the edge, I grabbed her hips and shoved my cock as far as it would go into her anal cavity and blew my load. I had no idea I had that much cum in me, it just kept shooting load after load into her tight ass.
“Oh my god……Ash!” I shouted as she bent forward and sealed her lips against mine. Her tongue darted into my mouth and she screamed into my mouth as she came again. We lay there for what seemed like an eternity as she lay breathless on top of me. When my slowly shriveling dick escaped from her ass with an audible squelching sound, my own cum seeped out and flowed down my inner thigh. She lay on top of me for a few more moments before kissing me passionately again and rising from the bed. She made her way to the door after pulling up her pants and grabbing her t-shirt she stopped before exiting my room.
“I’m taking a shower then reheating breakfast because it’s definitely cold now.” She said glancing at the clock on my nightstand. “You probably want to clean this place up a bit.” She added. I looked at the clock and she was right, it was ten o’clock and she had woken me up at around eight. I struggled to sit up and stand after she had left, my hips and thighs would definitely be sore in a while. I replaced all the sheets and tossed the dirty ones in the washing machine for later, and after taking my turn in the shower and getting dressed I made my way to the kitchen still unable to believe what had just occurred. She was sitting at the dining room table eating a Belgian waffle, when she saw me she pushed a second plate across the table to my seat.
“I can’t believe that just happened.” I said sitting down, still shocked.
“What do you mean?” she asked around a mouthful of waffle.
“How can you say that? We just had sex!”
“And we will again.” She mumbled.
“What?” I asked. I hadn’t quite heard her.
“Nothing.” She smiled disarmingly and batted her eyes at me. I narrowed my eyes at her and continued eating my waffle. I finished eating and put my plate in the sink.
“I’m going out for awhile I’ll be back in an hour or so.” I stated, not giving her a chance to respond I snatched my keys from by the door and headed out to my car. I drove on mental autopilot to the mall and bought a DVD that just came out; I didn’t want to go home right away so I sat in the food court for a long time just staring at nothing at all. My cell phone rang and startled me out of my stupor.
“Hello?” I asked.
“Tim, where are you? You said you’d be back in an hour.” She sounded worried. I looked at my watch and realized I’d been sitting there for two hours at least.
“Sorry, I’m at the mall I think I’ll get some lunch here. Do you want me to get anything here for you?” I asked. She asked if I could bring home some Japanese food for her, I said okay and cut the connection. I bought the food and some for myself and drove home. Stepping through the front door I called her name and she responded from the living room. I brought her food to her and then told her I was going to my room. Safely back in my room I noticed it still smelled like sex and I used some aerosol to fix that. Damn her I thought to myself, why did all of this have to happen. I opened my new DVD and started watching it on my TV. I lay on my bed eating my Japanese food and watched the movie, after finishing my food and tossing it into the trash the light was blocked coming from the door and I looked up.
“Well well well,” I sneered. “Look who it is, and what do you want?”
“Guess.” She said with a hint of a smile on her face. I noticed there was a wet spot on the crotch of her pants and as she saw me looking she slid a hand down and started rubbing her pussy through her pants.
“No Ashley! No, don’t you think it’s bad enough as it is?” I exclaimed shooting out of bed and standing next to it. It was a struggle between what my body wanted and what my mind told me was wrong and my body was winning, despite it all my cock was once again straining at my jeans.
“You think you can deny me Timothy?” She hissed. She had stopped rubbing herself as the smile left her face and I could clearly see she was going to get her sex from me one way or the other. It also appeared that the wet spot on her pants was expanding.
“I’ll give you one chance to drop your pants and get on the bed by yourself or I’ll do it for you.” She said her voice full of menace. I didn’t move and I couldn’t believe what was going on. My own sister was going to force me to have sex with her AGAIN!
“Fine have it your way.” She said stepping forward into my room. She covered the distance between us in a few steps and bodily threw me back onto the bed. Then she was on me, she swung a leg over my head and sat directly on my face as she worked furiously to get my jeans off. I couldn’t breathe and the musky smell of her soaking wet pussy invaded my senses. Is she trying to kill me or something I thought to myself, I screamed into her ass but that only made her push harder onto my face. Finally I punched her in the kidneys and she grunted and fell forward lifting her ass off of my face long enough for me to gulp down some fresh pussy scented air.
“Are you trying to kill me or something!” I shouted at her ass seeing as that was the only thing I could see.
“Perhaps.” Was the giggled return I got from my groin area. I felt my belt being cast off and the button and fly being opened and knew she had reached her goal. I was still heaving big breaths of air and was in no condition to resist. Suddenly she had me in her mouth. From that point on speech became impossible for me; the only thing that could come out of my mouth was the occasional grunt and moan and coherent thought became a challenge to maintain as well. She had me now I wasn’t going to resist her any more she was too good and gave me too much pleasure for my body to resist her any more. This must have been what had gotten her so many boyfriends, her skill at blowjobs and her willingness to dispense them.
“Why am I doing all the work Timothy?” She asked from around my cock. I realized she had been wiggling her ass in my face for a few moments now. I reached a hand down underneath her sliding along her smooth skin until I reached the fly of her jeans I quickly undid the snap and fly. I couldn’t pull down her tight jeans however, not with her legs spread like they were. I tugged on the back of her pants for a second until she realized what I wanted and squeezed her legs together on my head. Her legs were like a vice as her squeezed harder and harder until it became painful.
“Ash,” I croaked, “let go!”
“Oh, sorry.” Was the response, completely lacking sincerity. She released my head and raised her legs and I was able to shimmy her pants down around her ankles before she brought her legs down again and shoved her pussy strait onto my face. The smell coming from her wet pussy was intoxicating and I found myself starting to drool a little. I slowly started to lick around the perimeter of her hairless pussy (I wondered if she expected this event to happen or if she always kept it shaved, but I suspect it was the latter reason) teasing her with the light touch of my tongue. I located the little nub of her clit and caressed it ever so slightly with my tongue.
“Ohhhhhh Timmy oohhhhh!” she moaned loudly. I smiled at the reaction she was having to this just before she bit down on my cock. She came like a fire hose onto my face, the amount of liquid that came out of her was amazing. I opened my mouth and tried to catch as much of my sister’s sweet cum as I could. She then went into overdrive sucking my cock, trying to make me cum as well.
“Timmy…mmmfff…..why wont you..mmfff…cum already?” she whined.
“Maybe,” I managed to say, “you’re just bad at this.” She wasn’t by any stretch of the imagination and I was close to blowing my load into her mouth, but I couldn’t pass up the opportunity to taunt her. Her response was to bite down on my cock again this time harder. That did it, the pain coupled with the intense pleasure drove me over the edge. I arched my back and pushed my cock deep into her mouth and to her credit she didn’t gag as I shot my second load of the day strait down her throat. She never missed a drop and swallowed it all before slowly rising and sitting on my face once again with my nose buried in her still soaking wet pussy.
“Well Timothy, I have to say you taste wonderful.” She stated flatly as I started to push on her again for lack of oxygen. She responded by putting all of her weight on my face. I was panicking, she was trying to fucking kill me! I could barely see past her ass and up her back, she was looking down over her shoulder and smiling at me. There wasn’t any hate in her eyes just a look of amusement as she watched the fear in my eyes grow into terror. The edges of my vision started to blacken and my chest heaved trying to draw oxygen where there was none. I soon passed out and my world turned to black.
Slowly I opened my eyes, thank God I was alive, and I thought that crazy bitch was going to kill me. My head hurt but after performing a mental check of my body, that seemed to be the only problem. I went to move my arm but found I couldn’t, I couldn’t move any of my limbs! I rotated my hand and felt cloth rub against my wrist; I looked around and realized that she had tied me to my own fucking bed!
“Ashley!” I shouted my temper flaring.
“What.” Came the response softly, from behind my head. Her face appeared hovering over mine; she was chewing on what looked like a piece of toast, crumbs fell onto my face as she took another bite.
“Why am I tied up and how long have I been out for?” I asked calmly trying not to yell.
“Well,” she said taking another bite as more crumbs fell onto my face, “I was sick of having to restrain you myself when you were struggling before and plus I thought this would be more fun. And you’ve been out for about twenty minutes I think.”
“And why, pray tell, did you find it necessary to suffocate me?” I asked as she finished her toast and rubbed her hands together causing more still crumbs to fall on me.
“Umm I thought it would be fun.” She replied girlishly with a big smile on her face.
“Fun! You thought it would be fun! I thought you were trying to fucking kill me and you thought it would be fun!” I screamed making her jump a little.
“Now now Timothy there’s no need to yell, calm down. Sister Ashley will make it better.” She cooed. She walked around the bed, she was naked and her tits bounced with every step she took, I could feel my cock starting to get hard again just watching her. As she walked around me she dragged her hand along my body ever so gently, I started to develop gooseflesh almost immediately. While her other hand she kept firmly implanted in her pussy. When she came to the left side of the bed she stopped. I eyed her warily not knowing what she would do next. She smiled at me and then got onto the bed and straddled my waist again, she took her fingers out of her pussy and slowly sucked them clean one by one as she eyed me from her position of dominance. She finished cleaning her fingers and bent down and kissed me hard on the lips, I could still taste her pussy in her mouth. She then started licking my face with long wet strokes, removing all the bread crumbs and her dried cum from our previous encounter.
Under normal circumstances I believe I would have found this disturbing, but now it was the most erotic thing I have ever experienced. My cock was raging, and felt like it was burning and about to explode.
“Ash please.” I moaned.
“Huh, you want something from me?” She asked softly, sliding up and down my chest leaving a wet trail of pussy juice along my abdomen.
“Ahhhh please Ash some relief ahhhhh.” I nearly cried.
“So now you’re the one who wants the sex eh?” she said. “Well I think I want to play around a bit longer don’t you?”
“Nooooo!” I practically screamed. She slid up and down my chest for a few more moments then she leaned down and planted one of her gorgeous tits on my mouth. I took it in greedily, happy for the distraction. She then started pulling away; I bit down hard on her tit not wanting to feel the pain of my unattended to cock. She screamed and ripped her tit out of my mouth.
“You cut me you little fuck!” She shouted, looking down at her tit. There was a small but deep looking gash right above the nipple that was already bleeding. I could taste the blood in my mouth as I ran my tongue along my teeth smearing her blood across the front of my teeth and smiling at her.
“Give me my goddamned sex bitch!” I seethed. She looked from my blood stained face to her tit and back again. She leaned down only inches from my face, “I think not.” She said slowly and got off of me “I think I’ll just leave you two here for a bit while I decide if you are worth my time or not.” She said touching the tip of my cock as she headed for the door.
“Ashley! Don’t do this to me, please!” I was crying now. She left the room and I could hear her opening the door to her room and then closing it again. I couldn’t believe she had left me in that condition with an extremely painful erection that I doubted would go away easily. I struggled against my bond with ever ounce of strength I had. Finally the piece of cloth around my left wrist ripped and I nearly punched myself in the face as my arm came loose. I quickly untied myself and leaped from my bed, it was painful to walk with my cock so incredibly hard. As fast as I could I ran down the hall to my sister’s room and nearly smashed the door down entering. She was lying on her bed, still naked listening to her mp3 player. As I entered a look of astonishment came over her face which only made my cock harder (if that was even possible) obviously she thought she was better with knots than she ought to have been.
“You’re cunt is mine whore!” I screamed as I threw myself onto her knocking the breath from both our lungs and jamming my cock into her hard abs which almost caused me to black out again with pain. Before she could react I scooted down a little and rammed my raging cock into her pussy as hard as I could. Somehow our lungs both found the air to scream. She wrapped her legs around my ass and clawed at my back, I was positive I was bleeding but I didn’t care. I mercilessly pounded her tight pussy until I was sure she was bleeding too. For someone who is very sexually active her pussy was remarkably tight. At first she just lay there holding me with her nails dug into my back and her legs resting on my ass as I pounded her. But then she started meeting my downward thrusts with her own upward ones and pulling my ass down into her with her legs. She also started painfully scraping my back with her nails and I feared that it would look like some wild cat had attack me or something. I could feel the blood running down my sides as she opened me up with her nails. I didn’t care though it felt too good to care. She brought one of her blood stained hands around for me to see, and then she licked her hand clean and smiled.
“Every part of you tastes good doesn’t it Timothy?” she said through bloody lips. I couldn’t respond I was too busy slamming my cock into her cunt. I would completely withdraw from her pussy and then slam it back in hard causing her to cry out. It seemed as though I would never be able to cum even with the intense speed at which I fucked her. Finally after what must have been hours I could feel my balls tighten up and I slid my arms underneath her and squeezed her as hard as I could in a bear hug. I shoved my cock as deep as it would go but still didn’t seem like enough and shot my load deep inside her. I lay there trying to crush her in my grip as I completely emptied myself deep inside her pussy. It seemed to take forever for me to stop cumming and when I did I was spent I loosened my hold on my sister and went limp. I lay on top of her for what felt like hours, in that time I never felt closer to my sister than I did now, of coarse that feeling would most likely fade quickly after this. We were both breathing harder than we ever have before and we were both also bleeding all over the sheets of her bed but we didn’t care in the least. I let my head rest on her soft tits while she stroked my hair.
“We better clean you up.” She whispered into my ear. I moaned into her tits in response and let her push me off of her. She got off of the bed and sort of dragged/carried me to the bathroom. She sat me down on the toilet seat as she started the shower; she looked down at my back and shook her head.
“I tore you up good.” She chuckled.
“I could say the same.” I said. She looked down and gasped. The was blood all along the inside of her thighs and more dripping strait from her pussy along with a thin but constant stream of cum. She gasped again as she spread her legs to get a better look and a huge blob of cum escaped her pussy and splattered on the floor. Despite the fact that we were both in pain we broke into laughter, not that it was terribly funny but it just had to be done. After a minute or so the shower was ready and she helped me to my feet and escorted me in. The warm water felt incredible but the presence of my sister behind me felt better. I turned so the water hit my back and almost collapsed as it did, fortunately she was there to catch me. She held me to her with one arm and used the other to dab at my back with a wash cloth. I put my chin on her shoulder and ran my hands up and down her slick back. She finished washing my back and asked me to switch positions so she could clean up too and I obliged. She moved in front of me and took off the shower head and directed it at her still bleeding pussy. I was still leaning heavily on her shoulders as my hands roamed up her chest and to her tits.
“That’s not going to get you anywhere now Timmy.” She said not looking back at me but continuing to concentrate on cleaning her pussy. She cautiously inserted a finger into herself apparently assessing the damages I had wrought. I slowly massaged her tits feeling my cock start to get hard again and press between her ass cheeks. She said nothing as I slowly pushed the head of my now engorged cock into the tight ring of flesh known as her ass. She moaned softly as I pushed my cock deeper still and then stopped. I looked down and smiled at the sight of my stiff member betwixed her gorgeous round ass cheeks. She groaned and pushed back against me burying the rest of my cock into her ass and pushing me back into the wall of the shower. I gasped in pain but somehow remained standing as she slowly ground her ass on my cock. She returned the shower head to its socket presumably forgetting about her pussy’s injuries and reached her arms back and grabbed my head between her hands. She started squeezing my head and I could see the muscles in her biceps bulging as she applied more pressure. What was it with her I thought to myself, does she always need to cause pain with pleasure?
“Please hurry Tim I need your cum in my ass!” she said. I needed no more encouragement as I started pounding her faster. Her ass was so incredibly tight that it didn’t take long for me to reach climax. I shot my load in her ass and she finally let got of my head. She then pushed herself off of my cock and moved forward so I could clean off.
“Go into the kitchen and wait for me so I can put some bandages on you. I’m going to clean up some more and then I’ll be right out.” She said, I stepped out of the shower and toweled off gingerly patting down my back. I went into my room and put on some pants and then went into the kitchen and sat down at the table. About ten minutes latter she entered the kitchen wearing her pink bathrobe and carrying the first aid kit. She took out the roll of bandages and the anti-septic spray to ward off any possible infections.
“I can guarantee this will hurt.” She said as she sprayed the wounds on my back. It did and I closed my eyes in pain. When I opened them again her face was inches from mine staring strait into my eyes. I could see in hers that she seemed to be getting pleasure from my pain.
“You’re some kinda sick aren’t you Ash?” I said
“It could be said.” She smiled at me making me shudder slightly. She giggled and tweaked my nipple before moving behind me and starting to wrap the bandages around my chest. She finished and allowed me to stand up the bandages were tight and made it harder to breath but I didn’t care too much. I was still relatively early so I suggested we go into the living room and watch a movie together. She agreed and we made our way to the living room while she popped in a movie I slowly sat down on the couch, almost every move I made seemed to aggravate the cuts on my back. As the movie started she sat down next to me and scooted up next to me so that we were touching. I suddenly felt more tired that I ever had before. I slowly lay myself down with my head in her lap yawning as I did so. She sighed and started to stoke my hair when she too stifled a yawn.
“Love you Ash.” I said falling into a deep sleep shortly there after.
“Love you too Tim.” She yawned, as she too fell asleep. That’s how our parents found us late that night, Ashley in her bathrobe with her head slumped forward and me without my shirt on and bandaged from the waist up with my head cradled in her hands on her lap with the TV still on. They moved Ashley so she was lying down and put a pillow under our heads, they too were bone tired from a long drive and re-consummating their marriage so they simply left us there and went to bed.
More soon
