Serving My Sister IV: My New Playtoy

Note : This story is completely fictional!

Ever since Eileen finger-fucked me, she had been doing so again and again, every day. Not just once, either. This would occure two to three times before the night was over. Everytime, I would fill my panties with my hot cum. Furthermore, I was not to remove my cum-filled panties until I went to bed that night.

Then suddenly, there was a day when that came to a quick stop. An entire day went by, and nothing had happened. Oh, sure, I still had to wear my panties and bra (Eileen had long ago trashed all my male underwear). She had even 'promoted' me to wearing pantyhose underneath my jeans. Put simply, if she and I didn't still live under our parent's roof, Eileen would never allow me to wear men's clothing again.

To tell you the truth, I was a little disappointed that my sister hadn't come to fuck me at all today, and I wondered if I had done something wrong. The early hour of one in the morning was slowly creeping up, and I was still awake. Eileen had made it clear long ago that I was not to go to bed without instruction to do so. However, I was now able to choose my own sleepwear for the night. That night, I had chose to wear my blue, ankle length nightgown with white lace at the cleavage. Plus, the thing was nearly as tight as a skimpy dress.

I was sitting on my bed, reading, when Eileen snuck into my room. Without a word, she immediately went to my dresser and pulled a few things out of the drawer, tossing them on the bed in front of me. "Get these on," she told me. "Quickly."

"Yes, mistress Eileen," I answered without hesitaion, having come comfortably into my role as her servant. It didn't take long to see what she had me changing into. It was one of my lingerie sets, all black, that included a four-hook garter belt, thigh high stockings with five-inch lace at the top, and a lacy, middrif camisole. Of course, there was panties to go with it, but Eileen kept them from me for now.

"Follow me," she ordered once I was dressed. I followed her out from my room, and into my parent's room. They were both sound asleep, my father snoring softly.

"What exactly are we doing in here?" I asked, feeling more than a little nervous. I had spoken the words softly, though I knew it really wasn't necessary. Once my parents were asleep, they were the heaviest sleepers in the world. Literlly, only their alarm clocks could wake them up.

"All this time," Eileen began, "and you still haven't verbally admitted to wanting me. I've seen how well you've been serving me, obeying with enthusiasm and without question... but it isn't enough yet. And it won't be until you admit to wanting me. Now... fuck mom."

I was speechless. I had seen my parents sleep through a lot, but I wasn't sure about this. On the other hand, I didn't want to disappoint Eileen. "Jeremy, you know she won't wake up. Just be gentle." Before allowing me to move, Eileen reached out and grabbed my cock, slowly stroking it. "Be very... extremely... gentle." She stroked me until I was rock hard, then suddenly stopped.

I was already dripping with pre-cum as I crawled over my mother. Though lying on her back, both of her bent legs were leaning to one side. Carefully I placed my hand underneath her knee, moving her leg away from the other. Once my mother's legs were spread, there was still the matter of lifting her nightgown, and pulling off her panties. Somehow I managed it, getting nothing more than a soft moan from here, as her panties passed her ankles. Surprisingly enough, I didn't lose my erection either.

Slowly, I moved back over my mother. I was hesitant as I put my hard cock to her slumbering pussy. Being asleep, she wasn't even wet. I'd have to work my way slowly into her, risking her waking up with every push.

My mother moaned again as I began to make my way inside. It didn't take long for my mother's body to react to me, and she was soon soaked. My cock had a much easier time now, allowing me to move back and forth without dry-resistance. I couldn't believe how incredible my mother's pussy felt. I even sped up my pace, fucking her as if she were awake and enjoying it--and she never stirred!

"Oh no!" I whispered, feeling my body getting ready to cum.

"Don't you dare pull out, Jeremy!" Eileen ordered me. "Cum! Cum in our mother!"

"Oh my-- oh my-- oh my god!" I said forcefully, nearly screaming as I unleashed myself into my mother. "Oh, mommy!" I moaned.

"Mmm," my mother moaned softly. "Jeremy."

I froze, I freaked. My mother knew I had just fucked her. The only question was, did she conciously know that? Or had she simply moaned my name in her sleep, due to her body reacting to sex, and her ears registering my voice? To this day, I still don't know for certain...