Ashley Always Wins

"Take your cock out," said Ashley. "Stroke it while you eat my ass." I obediently pulled down my shorts and began stroking my massive hard-on. With my head comfortably being smothered by Ashley's butt and my cock in my hand, I was in bliss. I couldn't believe how much I was enjoying myself. I stiffened my tongue and worked the tip inside of Ashley's tight pucker. She gasped and furiously began working her clit. I worked my tongue in a small circular motion.

"Cum," said Ashley. Her words were hushed and strained. She could barely manage to get a full sentence out. "Cum.... Cum with me." Her body tensed up and then began to shake. I continued to lick her while her orgasm grew and grew. She squealed as her climax took over her senses. She bucked her hips and rocked herself back against my mouth.

Only when I was completely sure that her orgasm had gained complete control of her did I stand up. With my cock in hand, I stroked myself as fast as I could. I watched Ashley writhing in ecstasy in front of me and I quickly felt my own orgasm begin. I placed a hand on the small of her back to steady myself as I felt a familiar tightness in my balls. Just as Ashley's orgasm was winding down, I began shooting my hot cum onto her ass. She had grown limp with exhaustion as stream after stream of my cum splattered across her ass.

After my orgasm finished, we remained motionless, barely able to keep from collapsing from the aftereffects of our powerful orgasms. Ashley was quite the sight, bent over the net with her pants off, her ass covered with cum. She reached behind her and began rubbing my jizz all over her butt, working it into the soft skin as if it were lotion. She licked her hand clean and found her clothes. She stepped back into her tights and skirt and made sure she had everything on straight. Then she looked at me, smiled and said,

"See you next week."





We continued our weekly challenges for quite some time. I often challenged her for penetration, but she never let me win any of those. I did get more blowjobs, and sometimes she would even get me off even if I lost. I never did get to fuck her though. This led to many, many nights of being kept up fantasizing about Ashley's pussy around my cock... wondering if Ashley was even her real name.