My sister Ashley: Chapter 1

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.